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981: Using AI to Enhance Your Reading, Notes, Memory, and Decisions with Kwame Christian

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Fellow podcaster Kwame Christian giggles with Pete as he shares his insights and lessons learned on a novel notetaking approach.

You’ll Learn

  1. How to listen and understand audio at 3X speed 
  2. How notetaking improves your decision-making 
  3. How AI can make a fun soundtrack for your life 

About Kwame

Kwame Christian is a best-selling author, business lawyer and CEO of the American Negotiation Institute (ANI). 

Following the viral success of his TedxDayton talk, Kwame released his best-seller Finding Confidence in Conflict: How to Negotiate Anything and Live Your Best Life in 2018. He’s also a regular Contributor for Forbes and the host of the number one negotiation podcast in the world, Negotiate Anything – which currently has over 5 million downloads worldwide. Under Kwame’s leadership, ANI has coached and trained several Fortune 500 companies on applying the fundamentals of negotiation to corporate success. 

Kwame was the recipient of the John Glenn College of Public Affairs Young Alumni Achievement Award in 2020 and the Moritz College of Law Outstanding Recent Alumnus Award 2021. He is the only person in the history of The Ohio State University to win alumni awards in consecutive years from the law school and the masters of public affairs program. That said, Kwame’s proudest achievement is his family. He’s married to Dr. Whitney Christian, and they have two lovely sons, Kai and Dominic.

Resources Mentioned

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Kwame Christian Interview Transcript

Pete Mockaitis
Kwame, welcome back.

Kwame Christian
Hey, thanks for having me, buddy.

Pete Mockaitis
Well, this is fun. We are not going to talk about negotiation, or persuasion, or psychology directly, or diversity. We’re talking about taking notes, and we both are so excited.

Kwame Christian
So excited. So excited because we’ve been friends now for like five, six, seven years, and one of the things that brought us together is our nerdiness. And so, this is an opportunity for us to talk about this stuff we talk about all the time offline, so I’m pumped about this.

Pete Mockaitis
Well, yeah, so you told us something that blew our minds in our podcast mastermind group, we got together. You were playing a text-to-speech audio on your phone at super high speeds, such that a couple of us said, “There is no way you understand what is being said there.” And you said, “I absolutely do.” And we’re like, “What? What is the story?” So, tell us, you started doing a note-taking thing. First of all, why? What were you trying to accomplish by doing that? And then we’ll walk into a little bit of the details of what you’re doing.

Kwame Christian
Yeah, man, it’s a fascinating story because it goes all the way back to undergrad. I had a friend who was blind, and he became blind in undergrad. So, he had to learn how to be blind, which was a really tough thing for him. And so, he was shadowing another lawyer, and instead of reading using Braille, she was reading using text-to-voice. And he said it was so fast that he wasn’t even able to identify that text, that voice as words. It was that fast.

And so, what I learned from him telling me that story is that you’re processing speed is a skill. With time, you can get it faster and faster and faster. So, from undergrad, I’ve been training myself to go from listening to things in regular speed to 1.25 to 1.5, and now, on Audible, it’s up to, I think, 3.5. That’s the max. But then, with the note-taking apps that I use, you can go up to, like, 600 words per minute.

And so, for me, the reason why I do this is because I’m an avid note-taker. When I read books, I take tons of notes, like 20, 30, and sometimes up to 60 pages of notes, size 12, single space. But I recognize that reading is nothing without retention. So, I want to make sure that I’m reviewing those notes with regularity, but I want to do it quickly. And so, this helps me to really not just consume a lot of information, but also retain a lot of information because I can review it really quickly.

Pete Mockaitis
Wow, so 600 words per minute, I think you said, which is about 4x, if we’re thinking about 150 words per minute as a typical speaking rate. And so, first of all, it just sounds amazing, like for a superhuman ability. So, you are telling, you’re going on the record, this is, as you know, being recorded, that you can understand words played at 600 words per minute.

Kwame Christian
Yes, and let me put a little caveat here, because you will, for sure, miss a couple of words every sentence. So, if it’s a text I’m completely unfamiliar with, with zero context, I won’t be able to do it. But, if it’s notes that I’m somewhat familiar with, and that I have some idea of what it is that we’re talking about, then I can follow it enough to retain the meat of the information. And if you want, I can pull it out and show listeners kind of what it sounds like. You want to do that?

Pete Mockaitis
Yeah, let’s do it.

Kwame Christian
You want to?

Pete Mockaitis
Yes, I do. I do.

Kwame Christian
Okay, cool. Let’s see. Ah, philosophical articles. Great. And let me make sure the tempo is at the right thing. This is 605 words per minute.

Pete Mockaitis
Okay. All right now, Kwame, what did he just say? Or she, I can’t tell.

Kwame Christian
You can’t tell. So, he was talking about Socrates and his philosophical approach, and then going deeper into other philosophical like ideologies, mindsets, thought process, things like that. And so, for me, it’s like, “All right, I read that previously, and so I just want to make sure I’m getting refreshers so I can keep it top of mind because I know that memory decays after time.” So, I know for the things that I really want to retain, I need to revisit them with regularity in order for it to really become encoded in.

So, for me, I know that this is something that I have visited before. So, this is me revisiting these notes, and so for me, memory is nothing without retention. So, I want to make sure that I’m going over these things with regularity so it becomes encoded in my memory at a deeper level.

Because, for me, as a content creator, so as a podcaster, it’s helpful to be able to go back and talk about studies and different methodologies for negotiation, and then also as a speaker too, and a recovering lawyer, I feel the need to cite my sources. So, if I’m talking about different perspectives and different approaches, I can say, “Well, this person approaches it this way, but on this topic, another person approaches it this way. And here’s a book reference for each of those so you can go deeper if you want to.”

Pete Mockaitis
Yes, and I think that really is distinctive in terms of making content great, so that’s super cool. So, if anyone’s in disbelief about the speed thing, I have been playing. So, you use the, I believe, Voice Dream Reader app, and there’s a few I’ve seen out there. This one has a lot of history and a lot of street cred, it sounds like, with the blind community from the reviews I was gathering.

And so, I started doing it in terms of reading books, which it can do as well, and I was fascinated to see it didn’t take years to develop the skill of being able to understand rapid speech, but rather I was able to crank it up pretty good, like over 400, sometimes 500, so well over 3X, and understand what was happening. And it was fun for me, I was training that skill by also looking at the text because it highlights the text as you move down at the same time.

So, what I found interesting was it’s almost like when you can ride a bike in different gears and go faster depending on how much energy and oomph you’re ready to put into that thing. And so, too, I found, “Hey, my brain is ready to go. Let’s do this thing. I can go fast.” And I actually appreciate going fast. Like, it matches my state, and I’m not bored by what I’m reading. Instead, it’s like, “Hold on tight. Here we go.” And it’s cool.

Or other times, it’s like, “You know what? That just seems overwhelming right now. I don’t want to go there. That’s fine. We’ll slow it down to something a little bit more reasonable,” which still might be like 2x, 300 words per minute. So, that was eye-opening for me, just playing around with that a little bit and feeling like, if your brain is tempted to distraction, which mine certainly is, when you’re reading and you start thinking of something else, like, “Oh, wait, what did I just read?”

When I’m looking, the line is being highlighted and I’m hearing the audio, it’s like we’re not deviating from this text, and it’s very effective when you don’t want to read something, it’s like, “No, no, we are powering through this, every line right now.”

Kwame Christian
Oh, that’s smart. I’ve never thought about looking at it as I go, but I think that multimodal form of digesting would lead to greater retention, too.

Pete Mockaitis
Yeah, I think so. I think it has and I dig it. So, okay, we know it’s possible to listen at rapid speeds. You’ve done it. I’m kind of doing it. Blind people have done it for a long time, and it’s been helpful for you to retain stuff. So, give us a picture for like how is life different as a result of you having this as a regular practice? You take a lot of notes and you listen to review those notes at rapid speed. Is this just another Kwame quirk? Or to what extent is this truly enriching you and how?

Kwame Christian
Well, I think, like I said, the retention is big but it allows me to consume more information more quickly. So, I’ve shifted from not just doing audiobooks in this way, but also doing everything. Like, when we hung out in Washington, a couple months ago, you heard me reading my emails that quickly, and so it allows me to consume more information just in general, because now I’m putting everything through a program like that.

But the other thing that I found was an interesting side effect is that I feel like it helps me to be a better listener because, for me, I can listen and still be fully engaged with that person while thinking of what a follow-up question could be. And a lot of times, when people are acting like they’re listening but not really listening, they’re thinking about what’s going to come next, but now I’ve found that I can actually wholeheartedly engage with what the person is saying while anticipating what might be coming and then coming up with a follow-up question.

So, it’s made me a better podcaster because it feels like everybody is talking in slow motion. It’s really, really fascinating. And so, that also comes with a little comical downside, too. It also makes me incredibly impatient with content that is not accelerated. If something is just in one-time speed, I’m like, “I am wasting so much time here. Can you please go faster?” But in everyday life, when you’re actually engaging with people, it really does feel like a superpower, because listening feels less effortful.

Pete Mockaitis
That’s really cool. Let’s hear more about the potential downsides. So, you’re irritated by 1x content sometimes. That happens. What about just like the potential toll? I’m wondering, if feels like if you’re reading fast or listening to things fast, like you’re demanding more of the machine that is your body and nervous system and brain.

It’s almost like you’ve had a huge workout and you’re maybe fatigued afterwards. Is that a thing you’re noticing, in terms of like, “Whoa, more of my energy was sapped in that hour because I consumed more words in that hour,” much like more of your energy would be sapped on a fast bike ride of an hour than a slow bike ride of an hour?

Kwame Christian
Pete, I wish we would have had this conversation years ago because that was an element that I never considered. But this last Christmas break, every Christmas break, I take time to review my notes in 500 times speed and think through everything that I’ve done because I don’t just take notes from the books that I’ve read and the articles that I’ve read. I am kind of like my life stenographer. I’m sitting here just writing down every thought that I care to revisit, anything that I’ve learned that I want to retain, any insight.

So, I’m constantly taking notes, dictating notes into my phone, and then listening to them later. So, every month it can be over 100,000 words of Kwame notes that I’ve created. And then I started to realize a pattern. I started to realize that there was a pretty consistent cycle of burnout that was occurring at predictable times.

And so, for me, as a keynote speaker, constantly traveling, that takes a toll, and I started to recognize that I wasn’t recovering from those trips as quickly as possible. So, I need to reschedule the way that I do things, like making the days afterwards to have a little bit more space. So that helped with burnout. But I was realizing there’s still something else that’s taking a toll. I couldn’t figure out what it was, and I realized that it was this pace that I was keeping with reading and retention.

And so, for the past few years, my goal has been to read – I use audiobooks, so I’m using the term reading loosely here – consume a book every week, taking those notes, and in the morning before I go to the gym, I would listen to those notes, I would review the book notes from the previous books that I’ve read, and during the day I’m listening to the book and taking notes, so it’s a lot on my brain, and I did not fully appreciate the toll it was taking. And to the point where, this year I’ve actually decided to pull back on the amounts of books that I’m reading because it was becoming just too much for me to do while still being well.

So, I’ve found that my mental health has improved as I’ve scaled back a little bit. So now I do it as I need to spot-learn specific things at specific times, but not really forcing myself to keep that pace. One book a week, reviewing the notes in the morning, it was just too much to keep up with, and it was leading to burnout. So, fatigue is real with this, because it does take a lot more to consume information in this way.

Pete Mockaitis
So that’s good to know, and you have that set of options then. You could choose to listen at a variety of speeds based upon your energy and other demands for the day, for the week, and you got that going for you. So that’s pretty nifty. With regard to your note-taking, can you get a little bit precise with regard to, Voice Dream Reader is how we’re listening to or hearing the notes, but you say you’re dictating them to capture them? Or, what’s the capture side look like?

Kwame Christian
Capture side is pretty basic, just the iPhone Notes app. So, I would put it in the iPhone Notes app and then I would just copy and paste it into Voice Dream. And, actually, it might be helpful to go into the types of notes that I’m taking, because I talked about a couple of those things, but I can go a little bit deeper too.

Pete Mockaitis
Oh, yeah, so it’s any thought you might care to revisit, and stuff from books that it was good. That’s what we got so far.

Kwame Christian
Yes, so those are the things, and then also decision-making. That’s been a big focus for me, because, for me, my philosophy, I believe that we just live life decision to decision, and so the quality of our life is going to be contingent upon the quality of the decisions that we make. So, if I can learn how to make better decisions, then I will have a better life. Pretty simple.

So, I would read a lot of books on decision-making, but then I recognized that those books are great and they have a lot of studies that study other people but there’s nobody studying me. That’s my job now. So, any decision that I make, Pete, like any decision that I make that was suboptimal, I write that down.

Pete Mockaitis
Well, now we got here some juicy examples, Kwame, suboptimal decisions.

Kwame Christian
Everything. And, listeners, as well, this is how you know that I know Pete, because I know Pete likes to optimize. And when I used the term suboptimal, I know that word to be your fancy, okay. So, this is great. So, I’ll give an example. It goes down to the most mundane decisions. So, I was doing a keynote in Vegas earlier this year, and I was going down to breakfast, and I was closing the door to my room, and I said, “Ah, I forgot my Chapstick. It’s okay. I feel fine.”

I go down, I eat breakfast, and now my lips are dry because we’re in the desert, and I said, “I should have unlocked that door, opened it, and got the Chapstick because now I’m going to waste five minutes getting back upstairs in this massive hotel. I will never make this mistake again.” So, when I’m talking about every decision, that’s an example of how mundane these decisions go.

But then I think about business decisions, and I think about mistakes that I’ve made in the past, and then, you know, hindsight is 20/20, and I look back, and I say, “How did I not see this coming because it seems obvious to me?” But then when I review the notes, I recognize the emotions that were going through my mind, that were in my body as I was going through this process. I think about how I was feeling, I write down what I’m thinking and what led to the decision. What I was feeling, what led to the decision, who I talked to and how I felt before that conversation, and how I felt after the conversation.

And then I started to recognize patterns. I’m saying, “Okay, this was a bad decision, and I recognize that even though I had the data to make the right decision, I made the wrong decision based on emotionality. Why? Oh, in this situation, I had a conversation with this person, and then they complimented me. I’m recognizing I have a vulnerability, where if somebody compliments me, it makes it hard for me to make a decision subsequently that is not in their favor.”

And so, now I’m more mentally prepared to protect myself to separate the decision from the compliment. So, I’ll put more space between a decision if I feel particularly good about a conversation that I had about a person. And so, like those are the type of decision-making patterns that I want to pay attention to, because once you start to identify those patterns, you can start to anticipate when a bad decision will come, and then you can start to force yourself to put yourself in a better mental and emotional position to make a better decision in the future.

Pete Mockaitis
That is very beautiful. And I’m thinking, even the minute ones can pack big insights. I’m thinking about a time that I had a friend, and there was a bachelor party fun, woo, going on, and I remember I was kind of thirsty, and I thought, “Oh, I should go get some water from the bartender there.” But then I thought, “Oh, no, I don’t want to inconvenience them with just water, which is free and doesn’t produce any income for them or their establishment, or tip for them, and so I just won’t bother them. You know, I can make do and just drink some water later anyway.”

So, the next morning I was feeling very not great. Dehydrated plus, if you will, and I was thinking about, “Boy, I really should have just asked to get the water.” And I was like, “What’s that about? Why am I not doing that?” And then you realize, “Oh, here’s a pattern for me.” It’s like, “I really, really, really feel uncomfortable about putting people out, having them feel inconvenienced for the sake of my needs and preferences.”

And so, that’s good information and to really have at the fore when you’re making a subsequent decision, it’s like, “I feel not comfortable. I feel uncomfortable about this.” It’s like, “Well, maybe that’s because you’ve got this weird hang-up associated with inconveniencing other people to meet your needs, as in not asking the bartender for some water.”

And so, that kind of reflection and note-taking is handy to surface those things. It could be a tiny stimulus or prompt – Chapstick, cup of water from a bartender – and yet have a huge insight on the other side of it that has ripple implications for many decisions.

Kwame Christian
Absolutely. And that’s when it becomes really fun, when you start to see these hidden patterns, and that’s the type of information that you can only get from evaluating and investigating yourself on a deep level. Because we can read all of these books, you and I both have podcasts, so we can talk to these incredible people who have incredible insights. But imagine if one of those incredible people was solely dedicated to investigating your life and trying to make it better.

And I recognize that has to be our responsibility because the ripple effects of these small things can be significant, and a lot of times you might not recognize it until you take the time to investigate it. And one of the things that’s really funny to me is when I sometimes go back to journal entries from years ago, like 2017, 2018, sometimes I will see the original thoughts that led to something that I do with regularity that I take for granted right now.

And that’s always really insightful because it shows me how you are with every decision, everything that we learn and then subsequently put into practice, we are really shaping who we are and changing our identity. So, right now, Kwame of 2024, I can listen to this and I can say to myself, “Yeah, this is how I see the world. This is how I navigate it. Obviously, why wouldn’t I?”

But then I forget how much time it took for me to build this part of myself up to make this a regular type of thing. And sometimes it takes multiple entries and multiple attempts to learn and put these things into place for it to become part of you, but I recognize that the more intentional I am about investigating things, the better I can be when it comes to making tough decisions.

So let me give a tangible example. So, for me, as an entrepreneur, I recognize that sometimes there are going to be times where, if I’m running a company, I want to have the best team possible, and that might require me to have to change the dynamics of my team by removing somebody from my team. And I remember the first time, we’ve been in a mastermind group for like five years, so you were seeing me go through this. It was like an existential crisis having to fire somebody because I had this belief that relationships should last forever. It’s an indictment on me as a leader to not be able to have this person with me till the very end.

And I recognize, through talking with you and the guys and lots of journaling, that it’s a problematic belief. It’s not true. I can overcome this. But I recognize that it took a lot of time and thought and intentionality to really evaluate those underlying beliefs that were leading me to feel the way that I’m feeling now. And so, now fast forward to this year, I had to let a couple people go. And each person, there’s a different emotional thing that was holding me back from making that decision.

And so, I was able to make, to do that evaluation much quicker, and, at the same time, at a much deeper level through this process to recognize those patterns of thinking that led me to make bad decisions in the past, to this time make the right decision. It was still very, very emotionally challenging, but I was able to get to that conclusion faster because of this process of self-evaluation.

Pete Mockaitis
Yeah, that’s powerful. And those are definitely tricky emotional matters. And it’s funny, thinking about some of the mastermind group conversations, that’s often the case in terms of there’s a thing that we’re mostly sure should probably happen or not happen, and yet there is a little bit of uncertainty, but a lot of discomfort, and so we just stall for so long in terms of like launching this thing or shutting something down, and it goes way longer than it needs to because we are rational, cognitive creatures and also emotional creatures.

And it’s so helpful to, well, one, hey, I recommend mastermind groups for everybody, just as a general thought, as well as journaling and self-reflection. These are some of the top tools by which you can see what’s going on and, in fact, have a look in the past and see, “Oh, that’s pretty cool how much I’ve grown, how far I’ve come,” because in the day in, day out, you may not even realize it, just as you said, it seems like, “This is just how I operate. This is how I’ve always been.” No, it’s not.

Kwame Christian
Nope. Yeah, it’s powerful, man, and it’s very exciting, too. I think one of the things that was really helpful when it came to making better decisions, especially those emotionally heart-wrenching decisions, is I would journal how I would feel leading up to the decision, I would journal how I felt as I was making the decision, and then I would journal how I felt immediately after, and then as time passed. And so, it’s so interesting. It’s almost like watching a little kid jump into a pool for the first time, “I don’t want to do it. I don’t want to do it. I’m so scared. I’m so scared. Okay, I’m going to do it. Oh, that was scary. That wasn’t that bad. No, I feel really good now. Why didn’t I do that before?” And so, for me, one of the most empowering things is how I feel after the bad, the good decision. And I recognize that my emotions will lead me to make bad decisions that might feel good in the moment but feel bad for a very long time, and then I can set myself free with a good decision.

Now, the good decision will feel bad in the moment but will feel good after the fact. And so, when I see that freedom afterwards, I’m saying, “I’m not going to focus so much on the decision as I am going to focus on the future feeling of freedom after making the good decision.” And so, I’m like, “I want to make future Kwame happy. What would make future Kwame happy? I know Kwame in the present will feel really bad as he’s making this tough decision, but the future version of myself will appreciate it.”

And so, when I think about it through the lens of making future Kwame happy, that also helps me to have the right perspective, because I’m trying to play the long game. Usually, when it comes to good decision-making, it really comes down to prioritizing long-term benefits over short-term rewards. And when I continuously remember that, and I can see evidence of that throughout my life in this journal, then it helps me to feel confident in the decision, even if I don’t feel like doing the right thing in the moment.

Pete Mockaitis
Wisdom. Wisdom. So, you’re taking these notes, and I’m curious about the nuts and bolts here. Are they tagged by these categories? Or is it just one giant chronological situation? How do you find the relevant stuff from months past? What’s kind of the system that makes it work? We know how that gets captured. We know how it gets reviewed at rapid speed. How does it get organized such that it’s workable for you?

Kwame Christian
All right. Now, Pete, be ready to be disappointed because the organization is not strong. It is just a big old blob of notes, and that’s really what it is. But what I’ve started to do with time is categorize it by month. So, what month am I in, so I could go back into specific months now, but before it was, I would just put all of these notes into one iPhone notes document until the note became so big that the note wasn’t functioning anymore.

Pete Mockaitis
Oh, wow, I’ve never gotten there before.

Kwame Christian
And then I would say, “Oh, okay, time to start a new one.” And so, the last year, I think it was eight different notes, like journal entries that were big, and each of them was probably and listening at, because I was listening at it for a long period of time so I was at like 400 or 500 words per minute as I’m reviewing that during Christmas break. Each one is about 10 to 12 hours long, so it’s a substantial amount of notes.

And so, I did the word count for the last year, it was over a million words of notes that I took. But this year I’m trying something new that’s been really helpful, and it was categorizing by month and giving every month a theme. So, what is the theme? And so, February, I had to let some folks go, so it was red February.

I had to make some really tough decisions, so I’m like, “Listen, okay, so I need to make these tough decisions in my company. What other tough decisions do I need to make in my life? What other things do I need to let go of?” So, I was focusing on some bad habits, some other things. I’m like, “All right, cool. I’m going to make some cuts this month.” And then I realized, red February hurts a lot. So, I said, “March is all about mindset. It’s mindset March. What can I do to be well again, to be more at peace?”

And so, I started to try to approach business as a meditation, approach life as a meditation, “How can I focus on my breathing through all of the decisions that I’m making, through all of the activities that I’m taking? And the worse that I’m feeling, the more I’m going to focus on my breathing. Can I turn life into a meditation?” And so that’s what March was about.

And then we were launching a program, Negotiate Anything Premium, and so April was all about just focusing on revenue. So how can I focus on making decisions that are geared towards revenue? Because going through the notes, I recognized that a lot of the decisions that I was making, they were about status. They were about image. They look good from the outside but the revenue really wasn’t there to substantiate the continuation of a lot of those strategies.

So, I’m like, “Let me evaluate this from a really focused business perspective. What can I do to focus on increasing revenue and increasing impact that we make with that revenue?” And so, that was the focus. So going through these months thematically has been really, really helpful because it’s not just an evaluation of what is occurring, it’s also helping me to make decisions in a way that help me to move my life in a specific direction with more intentionality.

Pete Mockaitis
That’s phenomenal. And so, then when you look back on things, it sounds like you just periodically are just listening kind of like often. But if you’ve got something from 18 months ago, you’re probably not going to listen to that, are you? You’re probably listening to the things you had one or two or three months ago. Is that accurate?

Kwame Christian
Yeah, 100%, because there’s limited utility in going that far back unless, honestly, if I just want to be entertained. But I try to go through it within 12 months, but this year I’ve been trying to go month to month. So, once I finish January, I’m going to review January and February, review February and March and so on. But again, that was leading to a lot of exhaustion, and so I’ve been actually challenging myself to make fewer notes and listen to the notes less. So, I’m still listening to it, but just trying to be in the moment.

Because part of what I discovered about myself in March is that a lot of times I can get so in my head about these things, it’s led to some overthinking in places where I should be in flow. So, when you think about just the psychology of flow, when you’re in that flow state, you’re not actively, really consciously, logically thinking about things. Your body and mind, they’re just kind of responding and reacting, and I know that I’ve consumed enough information, I’ve learned enough through my life that I can flow really well when I let go.

And so, it’s almost like I’m at this point where I’m trying to balance that depth of thoughts and my analytical thinking with my ability to let go and flow a little bit more. And so, to your point about avoiding burnout, I recognize that I have to kind of slow down with this retention, this process, because it’s been leading to burnout, and flow has been a focus.

So, I’ve actually, the last couple of months, this is going to sound very bizarre, but the last couple of months, I’ve been challenging myself to listen to more music and do less, and that’s actually been more rewarding, because I find, when I’m in conversation, when I’m on stage doing keynotes, when I’m doing podcasts and things like that, even when I’m just playing with my sons Kai and Dominic, I’m more present because I’m not over-analyzing things. So, it’s about finding that balance, because anything done out of proportion can be problematic.

Pete Mockaitis
And I don’t think you’re alone with that music comment. I remember at one point, Apple Music had a podcast advertising campaign, so it was on, they were advertising Apple Music offer when it was newer on Podcasts. And I was like, “Boy, there’s so much talk and noise and stuff going on. Like, boy, you know what’s great? Music.”

And I just thought that was such a novel like, “Wow, do you need to sell us on listening to music? It’s like an ancient human delight.” It’s like, “You know what’s great? Eating food. Give it a shot.” But, no, it’s like they’re meeting them where they’re at, “Hey, regular podcast listener, remember music? That’s a great thing to listen to as well.” So, you’re not alone there, and it’s good to be reminded.

Kwame Christian
Absolutely. And now, Pete, I am not perfect. Now, I don’t think I’ve told you this, this newest nerd move that I’ve been doing. So, I’ve taken the notes that I’ve written, like all, like millions of words, and I’ve put it into ChatGPT, and I said, “Okay,” because there are these new apps that are AI music generators.

And so, I don’t know if you’ve ever used these things. The one that I use is Suno AI, and you can give it lyrics and describe the vibe that you want to create, and then it’ll make the music, just brand-new music just off the cuff. And so, I told ChatGPT to take the themes that come up the most frequently in my journal, “What are the top 10 themes?” It’s like decision-making, family, legacy, business, those type of things, just, “What are the top 10 things? All right. Now I want you to make lyrics for music off of those things.”

So, I take those lyrics and put it into Suno AI, and so now a lot of times, where I’m like, “I’m going to vibe to some music, but I want to make sure my music has a good message, and I’d love it if it was talking about things that are relevant to me. Because, I don’t know, when I’m working out, I’m a family man, I try to help my community, talking about drugs and murder in my music. That’s not really the vibe, but I just like the beat.” But now I can take my journal entries and turn them into cool lyrics. It’s motivating.

Kwame Christian
It’s so powerful, I love those things. And, Pete, if you want to, it takes 60 seconds to make this. You want me to make you something, a song for you real quick? I can do that right now.

Pete Mockaitis
So, yep, let’s roll with it, see what happens. 

Kwame Christian
Yeah. Well, now, this app, it has the integration in there. So, it’ll make it yourself. So now, I’ll give it the inspiration. Let’s do customize. I’ll just give it some lyrics. It’ll randomize it. I’ll just say, “Create an inspirational song for my friend named Pete Mockaitis. He is a family man, a businessman, a hard worker, a deep thinker, always looking to optimize decision-making and life in general, and he loves to help people.”

Pete Mockaitis
Can it be a country song?

Kwame Christian
Oh, yeah.

Kwame Christian
So, I’ll say country song, male vocals, you know, inspirational, you want inspirational?

Pete Mockaitis
Yeah, yeah.

Kwame Christian
A little vibe. Okay, the song title it chose is “Rise and Shine, Pete.”

[Song playing]

♪ Rise and shine, Pete ♪ ♪ Family man, true and sweet ♪ ♪ Hard work in the ground, deep thinker, sharp mind ♪

Kwame Christian
It’s not bad. It’s not bad.

Pete Mockaitis
So, it’s good enough so I want to know what comes next.

Kwame Christian
Exactly.

Pete Mockaitis
I was like, “Why did you pull away from the microphone?”

Well, now you got me thinking about affirmations, like if you could put those to music, that might make it more interesting or more impactful, because that’s, ideally, what music should do. It stirs within you emotion and the human spirit. So, that’s fun. Okay. Wow, Kwame, you’re putting all of us to shame, right? We’re just brushing our teeth in silence, and you’ve got custom AI generated inspiring songs and/or rapid playing notes of brilliance. I just feel honored that I was able to draw you in a game of chess. That’s my greatest achievement with this great mind.

Kwame Christian
That was such a good game. It was a great game, and I think it was the perfect ending too. It was a draw. It was a lot of fun.

Pete Mockaitis
And I think you could’ve beaten me if you really wanted to put in the time, but I’m glad you didn’t. So, anything else we should mention before we hear about another round of your favorite things?

Kwame Christian
Yeah, so check out Negotiate Anything Premium. Of course, we have the podcast Negotiate Anything. It’s the number one negotiation podcast, but we have a premium offering for subscribers who could listen ad-free and some bonuses, “Ask me anything,” so you could ask me questions. I answer your negotiator-related questions. But that’s the main thing that we’re working on right now. We’re really excited about the way it turned out.

Pete Mockaitis
All right. Now, could you share with us a favorite quote?

Kwame Christian
Yes. So, for me, one thing that I’ve been enjoying, and this is a quote I made up, “You don’t get bonus points for not using your resources.” And I feel like a lot of times, when it comes to the difficult situations that we find ourselves in, we almost think that there is some kind of valor in not accepting help from others and not using the resources available. And the people who are the most successful are the people who utilize the resources at their disposal.

Pete Mockaitis
Now, Kwame, that’s really, I love that. That’s hitting me.

Pete Mockaitis
All right. And how about a favorite study?

Kwame Christian
So, my favorite study that I’ve been referring to a lot for my negotiation clients is a study on the principle called anchoring. So, I believe it’s the most powerful negotiation technique at our disposal and it’s really more of a psychological principle. It’s like a priming effect. And so, with anchoring, what you do in negotiation is you start off the negotiation with the most aggressive request that you can reasonably justify with the data available.

And so, what they found is that just having a more aggressive first offer dictates the outcome more than almost anything in negotiation.

Pete Mockaitis
No kidding.

Kwame Christian
I kid you not. And so, well, they did as study in real estate, and so they found that with anchoring, even with experienced realtors, it worked for them. So, what they had them do is go into a home and look at the home, and then there would be a list price. And so, look at the list price and then look at the comps. And then you would make a decision on what you think is a fair price for this home.

And so, in the study, what they did was they said, “All right, the list price is, let’s say, $200,000 in this scenario,” and then in the other scenario, the list price was $250,000. In the other scenario, the list price was $300,000. But the comps were all the same. And so, they’re like, “All right, come up with your estimation for what you’d think is a fair price for this home.” And, not surprisingly, based on the psychology of anchoring, the people who were primed with that anchor of 200 guessed an  average less than the people who were primed with 250, who then guessed an average less than the people who were primed with 300,000.

And so, my favorite anchoring study was actually the Gandhi study. So, what they had them do is they separated people into two different groups, and so they asked them ridiculous questions but they asked them the same question, the same second question. So, the first question they asked to Group A was, “Do you think Gandhi was older than or younger than 13 when he died?” Right? Ridiculous. Every picture we see of Gandhi, he’s very old.

And then the other group, they said, “Do you think Gandhi was older than or younger than 130 when he died?” Again, ridiculous. He was old, but not 130. And then they asked them the same second question, “How old do you think Gandhi was when he died?” And the group that was primed with 13 guessed on average 20 years younger than the group that was primed with 130.

So even when there is not legitimate information to back it up, the priming effect from anchoring still works. And so, that’s why, for me, with my negotiations, this is the simple rule that I follow. If I have as much information or more information than the other side, I’m always going to make the first offer because anchoring is so powerful.

If I have less information than the other side, I don’t have enough information to give a competent anchor because I might undervalue it unwittingly, so I’ll counter in that case. But anchoring is so strong, I always find a way to make the first offer if I have enough information to make a competent first offer.

Pete Mockaitis
Undervalue it unwittingly. Well, I guess if you’re on the purchase side, the buyer side, you would want a lower price.

Kwame Christian
Right.

Pete Mockaitis
So, it’s like, “Hey, this isn’t going to work unless I can get a customer acquisition cost of less than $1,000.” So, that’s a form of anchoring. It’s like, “Okay. Well, hey, we got the impressions and the conversion rates and da-da-da, so you’re exerting the pull.” I’ve heard that even judges who see irrelevant numbers, like a housing street address, different housing street addresses in a document, can, in turn, impact their judgment for what’s an equitable distribution of assets. It has nothing to do with the case at hand, it’s just a number. It got in your brain and then it’s in there.

Kwame Christian
Yup. And, Pete, with these studies, it’s like the researchers almost got playful with it because it seems like they’re saying, “How far can we push this nonsense?” Because they did a study where they anchored with the last four digits of a phone number. So, the people who had nine, eight, and seven, as the first number, they were anchored different from the people who had like 0, 1, 2, or 3, just based on those numbers.

So, back when I was practicing law more frequently, when I was making demand letters, if I was asking for a lot more money, I would write the date out numerically. I would write it with as many numbers as possible. But when I was asking for a lower number, I would just write out the date, and say January 1, you know, and not even put the rest of the date because I’m like, “Everything has an impact. I don’t know what that impact is, but I know what anchoring is going to do, so I’m going to go small numbers if I want a small number, big numbers if I want a big number.”

Pete Mockaitis
“Hey, I know it said 10,000, you were hoping for $50,000? But $10,000 is a lot more than January 1, so, I mean, in a way, it’s a bargain.” Well, yeah, that is wild, and I think a good lesson. And that’s also a good lesson just in preparation, in terms of knowing we are hyper-susceptible to these.

Do your research in advance to determine what is a number you can truly live with so you have that influence inside of you, as opposed to, “Well, you know what, we’re going to take a call and just kind of see what they come up with.” It’s like, “That’s kind of playing a dangerous game. You may find that you accept an unreasonable thing as reasonable just because you didn’t get yourself settled somewhere sensible in advance.”

Kwame Christian
Yeah. And, again, Pete, this gets really deep too because, you know, I like to make jokes every once in a while, but in a negotiation, I might make an anchoring joke, right? So, imagine you’re negotiating for a higher salary, and so you go into your boss and you act all serious, and you know a reasonable price might be, let’s say, $150,000 is reasonable. You’re at $140,000, you’re trying to get to $150,000 that’s a reasonable leap.

And so, you say, “Well, I know this might be a little bit awkward but I wanted to have a conversation about compensation.” “All right. Well, what did you have in mind?” “Well, I was thinking is would I want $653,000? No, I’m just kidding, I’m just kidding. But honestly, what I think is reasonable, if we could get to 155,000, that’s what I’d like.”

So, if you say something ridiculous as a joke, you have a little bit of tension that is diffused with a little silly humor, and then you give the real number, the contrast principle still has an effect, “I’m going to do a fake anchor with a joke, then do the real anchor, base it with data and science and the research.” But then it makes whatever you’re asking a lot more reasonable in content, when you consider the contrast principle there, too.

Pete Mockaitis
Yeah. Well, then that gives you so much leeway with your joke in terms of if you say, “Well, I saw an article about a prompt engineer getting paid $360,000. And I said I know how to talk into, or type into ChatGPT, so that’s kind of what I was hoping for. But the market comp suggests to me…”

Kwame Christian
Exactly. Because you can think about it on the other side. Like, the anxiety, like the adrenaline will start pumping, they’re like, “Are you seriously going to ask? Oh, thank goodness.” And one of the best emotions to feel that’s truly undervalued is relief. Give them that feeling of relief, and now it just changes the whole vibe but also has a significant psychological impact.

Pete Mockaitis
And, you know what’s funny, I’ve also done that with my wife. If I have to deliver some bad news, it’s like, “Okay, so everybody’s safe. There were no injuries. We are financially secure. The structure of the home is still intact. However, I broke this thing and I’m sorry.” It’s like, “Oh, okay.”

Kwame Christian
Exactly. That’s a perfect example. Great example.

Pete Mockaitis
Because it does. It’s like, “Okay.” Because in terms of relief, she’s like, “Everybody’s safe.” “Okay. It must be pretty bad if that’s where we’re starting. Oh, okay. You just broke the dishwasher. Okay, that was dumb. You shouldn’t have broken the dishwasher, but I’m not going to give you a hard time about it because I guess you’re right, in the grand scheme of things, we’re okay.”

Kwame Christian
I love that example. That’s good.

Pete Mockaitis
And a favorite book?

Kwame Christian
Favorite book. Right now, I am really liking Unlearning Silence by Elaine Lin Hering. So, she is a Harvard law grad.

Pete Mockaitis
We had her on the show.

Kwame Christian
Oh, you had her? Oh, great. That’s great. Yeah, Elaine is amazing. And so, with her approach, it’s not just about the negotiation excellence because she has that in spades. It’s also about recognizing that sometimes people don’t feel comfortable standing up and speaking out about the things that are really meaningful for them. So, with that book, she analyzes what could be holding you back and then what you need to do to have that conversation and then how to have it more effectively.

Pete Mockaitis
Okay. And a favorite tool?

Kwame Christian
Favorite tool right now, I mean, it would be hard not to say tools like Voice Dream and Suno AI and ChatGPT after this conversation.

Pete Mockaitis
You got it. And favorite habit?

Kwame Christian
My favorite habit right now is I’m really enjoying going to the gym. That’s something we bond over, too. I’m recognizing that it is a keystone habit for me because, for me, like the gym has been a core source of socialization. And you would love this because I recognize there was a hole in my social game when it came to creating relationships out of thin air. Like, if there’s somebody that I don’t know at all and have no connection with, I didn’t know how to just go up to that person and start a conversation.

So, as I was working out, I was learning how to do that because I read in a book written by a spy, The Code of Trust, Robin Dreeke. He talked about how spies would approach people and start organic conversations out of nothing. And I was like, “No way it’s that easy.” So, I started to hone that skill at the gym. And so, for me, after five years of doing that, because of course I’m keeping track, I have a list now of 306 people that I have met in the gym over the past few years.

Pete Mockaitis
This is one facility, 306 people.

Kwame Christian
It’s two gyms now, two gyms.

Pete Mockaitis
Oh, my gosh. Wow, hardcore.

Kwame Christian
But yeah, that’s still a lot.

Pete Mockaitis
You go to two different gyms for your working out?

Kwame Christian
Well, I moved. So, it’s like 10 minutes away, right? It’s the same gym, different locations, but it’s been great. And what’s been funny, Pete, is that I’ve made some really great relationships there. I’ve had people who became employees of the company. That’s how I closed Chase Bank as a client with just making these relationships from the gym. So, yeah, physically, it’s been great.

It’s been helpful in terms of pushing myself harder in the gym. It helps me to understand how I can push myself harder in life, make these social connections. I feel a lot smarter because I have more energy during the day, and my family and my colleagues at work, they can tell days that I miss the gym. They’re like, “Hmm, something’s off Kwame. Did you go to the gym?” I was like, “No, I didn’t go to the gym today.” Yeah, they can tell. So going to the gym has been really, really helpful, not just for physical health but also mental health.

Pete Mockaitis
Well, now, I’m curious. Well, we got to have you on yet again, because I’m imagining, so let’s just say here I’m filling up a water bottle, and you are also in line to fill up your water bottle, what might you say to me here in this gym situation where we find ourselves in?

Kwame Christian
Ah, yes. Okay, so this is the move. This is the move. What you do is you make an observation that both of you can appreciate or recognize.

Pete Mockaitis
“Water is good, huh?”

Kwame Christian
Yeah, “Water is pretty cold today, right, buddy?”

Pete Mockaitis
But, no, seriously though, it’s kind of tricky, like I can’t. I’m in that situation. Like, maybe you want to talk to somebody for any number of reasons, and that’s what I think come up with is something really lame like, “I sure am thirsty. How about you?” And then I think, “Don’t say that. That’s dumb.” So, what do you come up with?

Kwame Christian
So, sometimes it is as simple as like, “Hey, I’ve seen you in the gym so many times, I feel like I should introduce you myself. Hi, I’m Kwame.”

Pete Mockaitis
That’s it?

Kwame Christian
That usually works. I usually would do that with guys. Approaching a woman is different. Because of the dynamic in the gym, you have to be really mindful of that. But sometimes it’s a unique exercise that they might be doing and it’s just genuine curiosity. None of it is fabricated. I’ll say, “What? I’ve never seen that before. What do you…what do you…what does that…what does that do? Like, why do you do it that way?”

So, I’ll ask for advice, and they say, “Oh, yeah, it works the rotator cuff in that way.” I was like, “Ah, I’ve had shoulder problems. That’s really helpful. My name’s Kwame, by the way.” Or if I see shoes that I’ve never seen before, I’m like, “I really like that pattern. I’ve never seen that color combination.” “Oh, thanks, man. I appreciate it. I got it because of blah, blah, blah.” Start the conversation there. And then just say, “Oh, I’m Kwame, by the way.”

And so, whenever you introduce yourself, then people always reciprocate, and then you just build from there. And so, now it’s just like gym, “Hi’s” turn into, “Hey, how are you doing? Oh, what are you up to?” and then the relationship deepens. But you definitely want to respect people where it’s like, “Oh, you make that introduction, but you can recognize they prefer to be left alone.” You can get that vibe, and I think the background and negotiation and body language can help too because you pay attention to the person’s feet and the orientation of the feet.

So, if their feet are staying square with you, they want to stay engaged in the conversation. If I say see the feet start to shift in the other direction, I recognize they want to leave, and then I say, “Hey, well, listen, let me let you get back to the workout. I just wanted to introduce myself. I hope you have a great day,” and then that’s it. And then you just build from there.

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where do you point them?

Kwame Christian
LinkedIn is the best place. So, if you want to connect, I post on LinkedIn every day. Of course, we have the podcast. The podcast comes out every day, and if you like cute children, follow me on Instagram. That’s another place I frequent, too.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Kwame Christian
Yeah, I would say start thinking about your decision-making process. What is it that really moves you to make decisions? Because a lot of times, you’ll be surprised. Because I used to think, I am a deep thinker, clearly, because of the conversation, but I didn’t recognize how much emotion was my emotions were swaying my decisions, and especially what emotions were swaying my decisions.

Because I often thought about negative emotions swaying decisions negatively, but a lot of my bad decisions were made because of the positive feelings I was feeling at the moment too. So, just start taking notice of the decisions that you’re making, and how you were thinking and feeling, especially feeling leading of that decision, and that’s how you can start to optimize decision-making so you can start to have a better life.

Pete Mockaitis
All right. Kwame, this has been a treat once again. Keep on rocking.

Kwame Christian
Hey, my pleasure. Thanks for having me, buddy. Appreciate it.

957: How to Push Past Discomfort and Expand Your Comfort Zone with Dr. Marc Schoen

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Dr. Marc Schoen discusses the critical role discomfort plays in our lives—and offers powerful techniques for getting better at managing it.

You’ll Learn:

  1. Why we need more—not less—discomfort
  2. Everyday techniques to build your discomfort tolerance 
  3. The 45-second trick that helps you handle stress better 

About Marc

Dr. Marc Schoen is an Assistant Clinical Professor at UCLA’s Geffen School of Medicine where he specializes in Boosting Performance and Decision Making Under Pressure and Mind-Body Medicine. He works extensively with elite athletes, professional and college, as well as, executives and UCLA medical students in strengthening their ability to thrive under pressure, and in competitive and uncomfortable conditions. His method of Discomfort Training and Pilates for the Brain builds hardiness and resilience, by rewiring the fear region of the brain which is responsible for Performance Under Pressure.

Resources Mentioned

Dr. Marc Schoen Interview Transcript

Pete Mockaitis

Marc, welcome!

Marc Schoen

Yes, very fun to be here.

Pete Mockaitis

I’m so excited to dig into your wisdom. I have listened to your book, Your Survival Instinct Is Killing You: Retrain Your Brain to Conquer Fear and Build Resilience twice, partially because I think your voice is so soothing. I guess that’s the hypnotist in you. But I would love to kick us off by hearing what’s a particularly striking, surprising, counterintuitive discovery you’ve made about us humans and how we perform best in your many years of working in mind-body medicine?

Marc Schoen

The biggest discovery, I would say, is that I was trained to believe that performance really had to do with controlling pressure or discomfort. And what I found is that, in reality, that’s not really what it is. It’s that we all should be feeling some amount of discomfort. And it’s not the discomfort alone that impairs performance. It’s that it’s our reaction to discomfort. And I have a great two studies on that, if that’s okay to elaborate on.

One was a great study done right around the start of the Afghanistan War, where they took two groups of people, the general infantry and the Special Forces, and they subjected them to a very intense, grueling workout. And the hypothesis was, is that the general infantry would show much higher signs of stress in the body, while the Special Forces would show very little stress.

Well, what they found out is that the Special Forces actually had a higher stress response than the general infantry, but the difference was they were able to parlay that stress response into productive action and, therefore, bring down the stress response, while the general infantry continued to hover in that higher level.

And that really is something that I have seen in several studies that I’ve done, whereas we can train people to manage discomfort and pressure better. But it doesn’t mean they will report that they’re not stressed, but their physiological response shows that they are managing the stress far superior than those who do not receive that kind of training.

Pete Mockaitis

That’s beautiful. Well, I think we could all use a little bit more of that. Did you say there were two studies?

Marc Schoen

Yeah, that was my main study on it, and then the second study was the Afghanistan study. That was not mine. That was someone else’s study.

So, two studies. The Afghanistan study, and the second study was mine, my own. And that was one where I had people who, in their everyday life, come in, report just the stress levels they’re having at work, and every day took blood measures of them, then trained a group into managing the discomfort and the pressure better, and their blood measures, which were cytokine measures, called Interleukin-6 and tumor necrosis factor, those people that received that kind of training had a far reduced inflammatory response, but they still reported being stressed.

Pete Mockaitis

Okay. Well, we’re going to dig deep into what training consists of but, first, maybe let’s hear the big picture in terms of the big message behind your book Your Survival Instinct Is Killing You: Retrain Your Brain to Conquer Fear and Build Resilience. What’s the core thesis here?

Marc Schoen

The core point of it has to do with discomfort. And I think of it this way, is that here we are in this advanced technological society, and it’s done a great job of really limiting our discomfort in our lives. But the paradox of it all is that, even though we have less discomfort, theoretically, we’ve become far more sensitive to being uncomfortable. So, the premise of the book is, “Okay, how do we learn to manage discomfort without precipitating the fear response, like the fight or flight response?”

Pete Mockaitis

And that is a powerful message and question, and so rich and apt, I think, for our time. I’ve also enjoyed Michael Easter’s book, The Comfort Crisis, which explores some of these bits as well. You’ve got a fun word you use frequently in the book. Can you tell us the definition of agitants? What is that? And tell us a little bit of the story for how it is we’ve come to find ourselves here in this place with greater comforts and yet less resilience to discomforts?

Marc Schoen

Yes, I call it the comfort zone dilemma, is that we all strive to be in our comfort zone. And no doubt, it feels good to be in the comfort zone, to be a non-stressed organism, but the downside is, if we take refuge in this comfort zone, what we end up doing is that actually shrinking our comfort zone because we become more and more uncomfortable with the idea of getting out of it. It’s the effect is a lot today.

I see so much of this today, is that, as this shrunken comfort zone happens, we get many more mental symptoms, particularly phobias: fear of getting on the freeway, fear of flying, fear of closed places, or fear of heights. And so, we want to be challenging our comfort zone. If we just fall back into it, we are setting ourselves up for poor performance and many mental symptoms.

Pete Mockaitis

Okay. And so, what is the concept of agitants?

Marc Schoen

So, agitants comes from the word agitation. And I’m very interested in, as our body gets more and more agitated, or has agitants in it, is that we cause a certain sort of high bar, I think of it, and the more agitants we have that exceeds the high bar, the more we are likely to impair performance and have psychological, physical symptoms. But if we can keep our agitants below that high bar, we tend to perform well and have no symptoms. But the key point of this is not the absence of agitants, but rather the well-management of agitants.

Pete Mockaitis

And so, is agitants the same as stress and agitation? Or what is the distinction or the core of this concept?

Marc Schoen

Well, I think of it more as a warming up of the body, heating it up. So, like, we all are theoretically around 98.6 is our basal temperature, and we do okay if we get into the low 99s, we may feel a tiny bit off. But once we start overheating and getting above 100, then our performance is very much affected. So, I like agitants more as a continuum, rather than thinking of we’re stressed or not stressed.

Pete Mockaitis

Okay, certainly. And so then, and for a given stressor, we may very well experience a different internal agitants response, like whether something gets us really steamed and furious, or a little bit like, “Ah, it’s kind of annoying, but I’ll shrug it off.”

Marc Schoen

Yeah, I just find it better to refer to that because of that continuum, rather than that you either have it or don’t have it.

Pete Mockaitis

All right. Well, can you walk us through the history, the chronology, the narrative of how we found ourselves in this place with lots of comfort, and yet a shrinking comfort zone? And you suggest it’s not just the smartphone but this journey starts much earlier.

Marc Schoen

I really think it starts as prehistoric humans, where humans learned to have an instinct to avoid being uncomfortable because the brain is pretty black and white about this. So, if we start feeling discomfort, then the brain starts experiencing a threat. So, in the early days, obviously, that threat was not enough food, or cold, or a mountain lion, or someone throwing a spear at us.

So, we learn real quickly to become sensitive to any impending discomfort and threat. And those humans that were capable of being able to respond effectively to that, live a whole bunch longer than those who are more tight-beat folks that were, “Oh, I’ll be fine,” and they just didn’t live long enough to propagate. And so, we’re a product of worriers and people that are constantly concerned that something bad will happen.

So, it’s natural that we would evolve more and more as a society to want to limit our discomfort because it just feels so much better. But that’s the ultimate trap, is that by continuing to pursue this path of greater comfort, which has really come significantly with technological advance, we’re losing that discomfort muscle so it atrophies, so we’re less capable of responding to the world.

And here’s, like, I think a wonderful example of this. We are in a world with tremendous amounts of psychological resources. And to help people do well and manage resilience and become hardy, but yet with all of that, and all of these technological advances, we have more mental illness than ever, and our troops are more likely to die from their own hands than they are from enemy fire. So, what’s happened is that we, as a society, have become less hardy, more fearful, and so that’s what’s happened to us.

Pete Mockaitis

Ooh, that’s tricky. And you say that in many ways that the march of technological progress has contributed to that, whether it’s microwaves and fast foods and convenient packaged foods, it’s like we don’t have to sit in even hunger or discomfort for long at all.

Marc Schoen

So true. And look how quickly we can create perfection by just tweaking things on the computer, making ourselves look better, sound better, or edit our responses. And not to mention, this was sort of what you alluded to is the issue of delayed gratification. We don’t have to wait long, do we, for gratification anymore? So, we don’t get uncomfortable in the same way we did in earlier times.

Pete Mockaitis

Well, bringing this to careers, in particular, could you tell us a story of how this scenario we find ourselves in, with a relatively tiny comfort zone, has been harmful to someone’s career, and what they did to turn it around and the cool results they saw on the other side of that training?

Marc Schoen

One great example was, some years ago I was sent a fellow that wanted to be drafted into the NBA. He was a senior year at the university, so he knew this is a make it or break it year.

And so, while he was playing during the year, he was never, by the way, historically a very good free throw maker. He’s always like around 60%, but now here he is in this last season, and many of the games being nationally televised, is that he’d get to the free throw line and freeze. He would push the ball rather than just be relaxed, and then his percentage went from 66% or 68% into the high 30s. So, he was having lots of pressure, and then of course freezing under the pressure.

So, I would go to Pauley Pavilion where he would play, and every time he got to the free throw line, the crowd would go, “Oh, no.” You just hear this large moan of 15,000 to 17,000 people. So, I had him come in, and I asked him questions, “What is your memory?” And this is so important for the bigger question that you’re asking, “What’s your memory of being under pressure?” And his memory was oral reports in school, and getting up to do an oral report and being nervous and shaking, and then the kids teasing him about his inability to talk.

So, now, years later, he goes to the free throw line, it’s like going up there for an oral report, and then when the whole crowd starts moaning, it pushes that old button and he freezes up. So, that’s a good example. So, what the solution was is that we couldn’t stop the pressure that he was feeling. Didn’t want to. What we wanted to do to make it so that the pressure, which is uncomfortable, no longer pushed the fear response.

Pete Mockaitis

And how does one make it such that that occurs?

Marc Schoen

It is possible to create a physical, emotional state in the brain that neutralizes the fear region of the brain, as many of you their listeners know is the amygdala part of the brain. So, what we do is put someone under pressure, when they’re uncomfortable, create this physical state in the brain. Hypnosis is the big way I do it, and it will block the fear response. So, now we’re having someone be uncomfortable, and learned that no fear is associated with it, and that’s how it stops.

Pete Mockaitis

Okay, cool.

Marc Schoen

Neuro-conditioning.

Pete Mockaitis

Neuro-conditioning. Hypnosis. Okay. And you said you had another story.

Marc Schoen

Another story is more directly related to business. I see a lot of folks that are young entrepreneurs, and have come up with a fabulous concept, made a lot of money, and venture capitalists come in to give them more funding for their company. And it was their idea, their intuitions, their hard work that created the success, but now you have the venture capital people, working with someone that’s a lot younger, and the entrepreneurs can get very intimidated by these people with their mathematical models, being older, putting pressure on them, second guessing their decisions.

And so, what happens is they start getting frozen up inside, starts second-guessing themselves, start losing confidence, start basically bowing to the pressure, which isn’t necessarily good because the venture capitalists aren’t the ones that created it, nor the ones that made the money. And so, we get this, again, this dilemma where we have pressure, uncomfortableness, pushing the fear response. And what is the fear response mostly is the area of rejection.

You think about it, when it comes to performance, if you look at “What is the issue?” It’s usually rejection, judgment, worry what other people might think, what they might say. When I asked my medical students, “What’s your biggest fear?” And these are super bright medical students at UCLA, “What’s your biggest fear?” Of saying something and embarrassing themselves.

And so, we get this with these young entrepreneurs and they buckle under that pressure. So, what I do is, again, create the pressure but make it so it does not push the fear response, so they can respond accordingly, express their opinion, stand up for what they believe.

Pete Mockaitis

And in your book, you mentioned that it’s very possible to feel two emotions at the same time. You’d say, “I feel stressed, worried, concerned, anxious, and also I’m safe.” Could you talk about that principle?

Marc Schoen

Yes. And that goes to that early concept of being able to create an emotional, physical state in the brain that blocks the fear, but yet, you can have them feel pressure. So, we have a neutral state or a safe state induced by this type of hypnosis, I like to call it hypno-meditation, and the real-world stress, and I also alluded to that study I gave you, is that, yeah, the people did report plenty of stress in their lives, but physically there was no trace of it. It’s an interesting dynamic. I call it duality, is my term for it.

Pete Mockaitis

All right. So, hypnosis is one way that we can get there. You also lay out 15 strategies to stay cool, calm, and collected. Could you share with us maybe your top three favorites for professionals that do a whole lot for folks, and yet are pretty easy, a big bang for the buck or ROI?

Marc Schoen

Yes, so the overarching goal is not to banish discomfort. The goal is to make it so discomfort does not experience as a threat and, therefore, push the fear response. Okay, so then that’s the goal of any exercise that we want to do. I have a lot of different ones that push the button, that make us uncomfortable, because it again pushes that button of rejection, or being judged, or being embarrassed and so on.

One thing that I’ve done to help train myself in this area was to ask people for favors, and that’s an uncomfortable thing. And the exercise I did was, and remember the goal wasn’t to get the favor granted, the goal was dealing with the uncomfortableness of asking for the favor. So, I would go around and ask people for $100. And, of course, virtually everyone would say no.

Pete Mockaitis

Virtually.

Marc Schoen

I actually had one person say yes.

Pete Mockaitis

Alright.

Marc Schoen

Of course I gave it back, but that’s really uncomfortable for me to ask that, and then justify it, or for people just to say, essentially, “Screw you,” or just ignore me, or walk away. That’s uncomfortable. But I wanted to give myself practice in that, and that’s a great tool.

Now, there’s different degrees of pushing this button. One is you could put yourself out there. Let’s say you’re uncomfortable about dancing in front of other people. You could go take dance lessons. Let’s say you’ve always wanted to sing, but you have a terrible voice. Well, you could take some voice lessons. Or, very simple, it’s so easy for us to just take the same way to drive to work or use our Google Maps. What if we were to try to navigate our way without the help of that? Again, the overarching goal is to feel uncomfortable and learn we can manage it and not get a fear reaction.

Another great way is to approach someone that you think is important or very attractive, and introduce yourself. All of these things really push that button. And so, the goal is to be uncomfortable, but still be able to do it.

Pete Mockaitis

And so, if we are in the midst of it, feeling super uncomfortable, and we’re not sure if we can do it, and we are maybe feeling the fear response getting pushed, what do we do? Do we do some breathing? Or what’s your pro tip to pulling it off?

Marc Schoen

Yeah, I have a breath technique. That’s what I call it. It’s on my website. It’s a free download, and it’s a way that you can really expediently knock down your heartbeat and blood pressure. It really just takes 45 seconds to create a result. So, you can use this as a preface to doing any of these exercises, and all we want to do, we just bring it down below that high bar that I talked about so we’re not so overheated, and then move forward with the task.

Pete Mockaitis

Well, Marc, that sounds like 45 seconds well spent. Could you give us a demo on this breath technique?

Marc Schoen

Yeah, it really is something I developed back in, like, 1983 in a biofeedback room at Cedars-Sinai when I wasn’t allowed to do hypnosis on the medical units so I had to find a way that would rapidly relax people. So, I hooked myself up with all these electrodes and then later ran other people through it, borrowed from here, borrowed from there, took from here to make something really quick.

And what I found is that an inhale through the nose, just a medium inhale, not having to be a big diaphragmatic breath, just medium. I’ll make a sound, but you wouldn’t make the sound. Kind of like this, about that amount. We pause for a second, and then have a pattern of four exhales. But the key part of it is to have no inhale between the exhales.

So, it looks and sounds like this, and the sound of the exhales is important. Here’s the inhale. Hold it for a second or so. Start of the exhales. And the last one, we just release the remaining air, and then we repeat that four times. And it’s remarkable, if you’re measuring someone’s blood pressure or heartbeat, how pronounced of an effect that can have.

Pete Mockaitis

All right. So then, these exhales, it’s like a shh sound, like we’re calming, like telling a child to “Hush up now. Shh.”

Marc Schoen

Exactly. Yeah.

Pete Mockaitis

And then there’s a pause between the shushes. And so, it’s about a medium level of inhale, not like a huge maximum.

Marc Schoen

Through the nose.

Pete Mockaitis

Through the nose. And then is the exhale there then, are we aiming to get mostly out, all of our breath out, or like completely evacuated, or just mostly evacuated, or does it really not matter?

Marc Schoen

Yeah, most of it, but we don’t want to deplete ourselves that we’re gasping for air. So, just a medium amount like that.

Pete Mockaitis

And then do we pause after the fourth exhale before the next inhale?

Marc Schoen

Yeah, a comfortable space between. And as you do this, cycles, you slow it down, so you’re pausing more between the exhales. Oh, and what I learned back in the ‘80s about this is that it’s not the inhale that relaxes us, it’s the power of the exhale.

Pete Mockaitis

That’s cool. That’s cool. All right. So, we’ve got that breathing. And tell me, when it comes to perhaps physical interventions, whether it’s cardiovascular exercises, or resistance strength exercises, or getting in cold water, or walking with a weighted backpack, are there any kind of physical fitness-y things that go a long way in improving our discomfort tolerance?

Marc Schoen

Well, it’s best for us to think about these kinds of techniques that I’m talking about, is that we have both discomfort, physical discomfort and emotional discomfort. And so, it is very important to work on our ability to tolerate both of them, and they both affect each other. So, obviously, if we’re physically less capable, then we’re going to be more emotionally uncomfortable, and vice versa.

So, the more emotionally uncomfortable we are, the less we tolerate physical discomfort. So, it makes sense to work on both. Now, here’s what I like to do, is to challenge myself physically. For example, when I used to run quite a bit, I would run, but meditate on the ability to stay calm and keep my heartbeat at a certain level. Or, when I take a sauna and have the temperature like 175, is to see how long I can keep my body cool from sweating. So, there’s that kind of interplay that we can do.

Pete Mockaitis

That’s great. Well, let’s talk about hypnosis for a moment before we wrap up. And so then, for those unfamiliar with hypnosis, could you maybe first share with us some of the best data or studies suggesting that hypnosis is a real thing that’s useful beyond our stage amusements?

Marc Schoen

Yes, it used to be that we thought hypnosis only changed people’s perceptions, and so it’s just sort of like a surface charge with a battery, that you can charge it a little, but it doesn’t seep into the true fabric of what it is. But as we’ve had more advances, we can truly measure the impact of what it does, and we see that it has a cellular impact and a biochemical impact. I even did one of those studies to show that we can use hypnosis to block the inflammatory response in the body, and that’s by measuring cells.

So, now hypnosis can be seen as having both a psychological and a physical effect. I like it because it’s like the difference between a Scud missile and a Patriot missile. It is precise, direct, and much quicker than going in more globally.

Pete Mockaitis

Okay. Well, for folks who are jazzed about that as a tool for being more awesome at their jobs, I mean, I guess we could schedule a session with a professional like yourself. Or, how can we get a taste of this benefits hypnosis might have to offer us?

Marc Schoen

I would like to offer your listeners a free download where it’s a hypnotic set of suggestions, all geared for job performance based on this whole concept of discomfort, threat, fear, and being able to manage discomfort without threat.

Pete Mockaitis

Oh, thank you. That sounds beautiful. We appreciate that. We’ll make sure to link that in the show notes, etc. Okay, so we got that going for us. And then you mentioned the notion of the precision, like targeting anything. I’ve seen a whole boatload of different hypnosis pieces on YouTube for any number of things. What are your thoughts on those? My guess is that the quality and effectiveness vary. Is there any danger in just trying those out? Or, what are you thinking about these?

Marc Schoen

I certainly wouldn’t try someone’s work that isn’t credentialed and has significant training in it. And so, it should be a mental health professional that’s done it for a while because it’s very powerful and mishandled can create some bad results. So, be careful, selective, as to who you allow to do it. And again, most hypnosis can be seen as just trying to deal with changing people’s thoughts only, and just like cognitive behavioral therapy, it certainly can work.

But, if a lot of our behavior is influenced by fear, then it makes far more sense to deal with that part of the brain where it is centered in this limbic part of the brain. So, I like to use hypnosis to go directly at those limbic areas, such as the fear center, such as the pleasure center, the sleep center, and so on. And so, you can use hypnosis in a superficial way, or you can use it in a much more profound way, because to me, if we don’t deal directly with the fear response, no matter what we tell ourselves consciously, it’s just not going to hold.

Pete Mockaitis

All right. And maybe, I’d love to get your…we’ll do your hot takes. I saw a YouTube video where they quickly said underrated, overrated for all sorts of, like, health and fitness interventions. So, let me get your hot takes here, the good doctor, Marc Schoen in the house. Hypnosis for, if I would like, I’m just going to put out some scenarios and say, could hypnosis be useful for this? Maybe say yes, no, or a little would be the three options if I may. We’ll say, “I crave cigarettes, and I’d like to crave them less.” Is hypnosis useful for that?

Marc Schoen

A little.

Pete Mockaitis

Okay. “I get scared when I’m asking for referrals or feedback, and I’d like to feel less scared”?

Marc Schoen

Very positive. Good.

Pete Mockaitis

Okay. “I’d like to sleep longer and better with less interruption.”

Marc Schoen

Good.

Pete Mockaitis

“I would like to stop eating as many cookies, candies, sweets, and diet more disciplined-ly.”

Marc Schoen

A little.

Pete Mockaitis

“I would like to be more assertive in telling my team my expectations for them and how they can improve.”

Marc Schoen

Good.

Pete Mockaitis

All right. Anything else I should have mentioned, Marc?

Marc Schoen

Well, no, you did a great job. And you noticed where I said just a little tend to be those things which are more addictive in nature, that hypnosis is just a medium, it’s a single, it’s not a triple or a home run for addictions.

Pete Mockaitis

All right. Well, Marc, tell me, anything else you want to make sure to mention before we hear about some of your favorite things?

Marc Schoen

The thing I say is just a summary statement, is that in reality, what a lot of people say, “What doesn’t kill me, strengthens me.” It’s really more this, “It’s not the adversity that makes us stronger. It really is our effective management of adversity that makes us stronger and more resilient.” That is the key part of this.

Pete Mockaitis

Well, that’s good. Thank you. “I often find myself procrastinating and putting off the hard, uncomfortable things, and doing easier tasks like email.”

Marc Schoen

That’s a mixed one. That’s why I have to say a little, but possibly good. It depends what’s the source of the procrastination. A lot of people just come into the world wired as a procrastinator, and those folks, you can slightly modify it. There are groups of people that are procrastinators that’s totally out of fear.

Pete Mockaitis

Okay.

Marc Schoen

That can be modified that way.

Pete Mockaitis

And how about, “I find myself I just get so distracted. I sit down to do a thing and then I find myself around the news or social media or shopping minutes later.”

Marc Schoen

Not necessarily a good one either. Just a little bit of an effect.

Pete Mockaitis

Well, now could you share a favorite quote, something you find inspiring?

Marc Schoen

One I always like was something that Lance Armstrong had said when he was the Olympic athlete. It’s something along the lines like, “Pain is temporary, but quitting is forever.” That was a good one.

And there’s an old time one, God knows if I’m saying it correctly, it was something along the lines, you know, that we really want to judge someone based on the stage or position in life, but rather judge someone on the obstacles they have overcome. I like that one. I don’t know who said that but…

Pete Mockaitis

And a favorite book?

Marc Schoen

I love this book called The Untethered Soul.

Pete Mockaitis

All right. And a favorite habit?

Marc Schoen

I do self-hypnosis meditation once to two times a day. That is such an incredible way to keep our body in the zone. Because as we get older, it would seem like it shouldn’t be this, but as we get older, it takes more work to stay in that zone.

Pete Mockaitis

And I’m curious, within that self-hypnosis, are there a couple key messages or suggestions that you think really hit home and bring a lot of the result?

Marc Schoen

If I had to say a core feeling is a belief, but it’s a feeling, is that when I’ve looked over my life, I have not had an absence of bad or tough things happen, but I’ve been very fortunate, that ultimately, it all resolves favorably with a few exceptions here and there. So, what I get to is a place of trust and faith and confidence, that no matter how tough something is, I will ultimately have the resources to manage it effectively. So, I’m just going to trust and let this feeling of total openness, non-tightness, safety, lightness be the prevailing dominant feeling I’m going to feel in my body. That’s what it is.

Pete Mockaitis

And is there a key nugget you share with folks that really seems to connect and resonate with them, and they quote back to you often?

Marc Schoen

It really is this notion that we have talked about that I can be uncomfortable, I can feel pressure, and nothing bad will happen to me. There’s no danger. And that I can persevere and succeed and that, ultimately, most people will say, my ability to hang in that place of fire is where the greatest results happen.

Pete Mockaitis

All right. And if folks want to learn more or get in touch, where would you point them?

Marc Schoen

I would have folks feel free to look at my website. It’s my name, Marc Schoen, M-A-R-C S-C-H-O-E-N.com. You can find out more about me. I will have the downloads that I’ve referenced already there under the product section. But it’ll give you an overview of my work.

Pete Mockaitis

And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Marc Schoen

I would really, really encourage people to challenge their discomfort zones, to push against that key thing I’ve said about rejection and judgment. And even though our tendency is to want to limit our losses, some people call that the negativity bias, often the probabilities of success are actually higher than the probabilities of failure. And so, so I would recommend really pushing that, and being uncomfortable, going in there and just challenging, “I can hang in here, persevere and succeed.”

Pete Mockaitis

Beautiful. Well, Marc, this is a great time. Thank you. And I wish you the very best.

Marc Schoen

Many thanks. Enjoyed being here.

956: How to Delegate Anything with Dave Kerpen

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Dave Kerpen shows how to get over delegation hangups to tackle your top life priorities and prevent burnout.

You’ll Learn:

  1. How to get over yourself and finally begin delegating
  2. How to become a master delegator in 5 steps
  3. A simple rule to prevent embarrassment when delegating and automating

About Dave

Dave Kerpen is a serial entrepreneur, New York Times bestselling author, and global keynote speaker. He is the co-founder and co-CEO of Apprentice, a platform connecting entrepreneurs with top college students, and is the author of several bestselling books, including The Art of People, Likeable Social Media, and Likeable Business.

He is a popular contributor to Inc.com and a LinkedIn Influencer, and has been featured in many media outlets, including the New York Times, the TODAY show, CBS Early Show, BBC, Financial Times, and more. Additionally, Kerpen is the executive chairman of The Nursing Beat and the cofounder and CEO of Remembering Live. He was previously the founder and chairman of Likeable Local, and was the cofounder and CEO of Likeable Media, which was sold to 10Pearls in April 2021.

Resources Mentioned

Dave Kerpen Interview Transcript

Pete Mockaitis
Dave, welcome.

Dave Kerpen
Thank you so much for having me.

Pete Mockaitis
Well, I’m excited to get into your wisdom about delegation. And I’d love it if you could kick us off with maybe one of your most surprising and fascinating discoveries about us humans and delegation.

Dave Kerpen
Well, the most surprising thing is that the secret to delegating is much less about how to do it and much more about getting over yourself up here, getting through your brain, and dealing with the fear and the distrust issues and the perfectionism issues that are likely holding you back.

Pete Mockaitis
All right. Well, succinctly stated right off the get-go, Dave. Thank you. Appreciate it. All right. So, that’s the scoop. So, that’s funny, if people think I’m having trouble delegating, they may very well say, “I need a model. I need some steps. I need an acronym. I need a mnemonic.” And, Dave, you’re saying, “No, what you probably need first is to get over yourself because you’ve got some emotional stuff that’s hindering this whole process.”

Dave Kerpen
Yeah. And, look, my book has the steps and the acronyms and the models, and I love acronyms. I’m all for models, I’m all for systems and tools, but too many people do it to try a system or tool for anything, but certainly, in this case, for delegation, it doesn’t work, and then they say, “Forget it, this doesn’t work.” And the real answer is, “Let’s do the work on ourselves and deal with the issues, the limiting beliefs, the challenge, the fears that are holding us back.”

And then my model might work well but there’s a lot of other models right, or this software might work well but there’s 15 other software that might work well as well. And it’s less about choosing the software and more about getting the mindset right to be able to delegate.

Pete Mockaitis
I hear that. And so, so maybe if folks are so not over themselves, and they don’t even think it’s possible, Dave, can you paint a picture of hope, maybe share some data or a story?

Dave Kerpen
So, first, I’ll paint a picture of a sadder story and then I’ll tell my story, which, hopefully, is a little less sad. Scott came to me, names have all been changed to protect the guilty, but Scott was a long-time real estate entrepreneur, worked for himself, essentially, but built a nice little practice with having a couple people work for him over the years, made a lot, a lot of money, came to me years and years into his career, sort of mentoring me.

He said, “You know, I made a lot of money over the years. My son just turned 21, and I missed his growing up. I missed basketball games. I missed parent-teacher conferences. I missed an awful lot because I was so focused on building my business. And if I could go back, maybe I wouldn’t care so much about building my business because, yeah, it made me lots of money, but I will never get that time back with my son.” And that story struck me.

So, as I was doing the research for my book, I looked at deathbed research, and researched on what deathbed regrets people had. And perhaps this won’t surprise you at all, but, as you might guess, Pete, a very, very small percentage, under 1% of people regret not working enough hours. People almost always, over 50% of people, on the other hand, regret, when they’re asked for deathbed regrets, regret not having more time with friends and family, not having more time to pursue their passions, not having more time to pursue travel and other key hobbies.

We all get the same amount of time and we only get one shot at it in this lifetime. And the reason I wrote this book is that, sure delegation will make you a more productive employee, delegation will make you a more productive leader, delegation will make you a more successful entrepreneur depending on what it is that you do, but I think the stakes are much higher than that. I think delegation is the single biggest key to unlocking success and happiness in life.

And I will share that there’s many, many things that I’m not good at, but one thing that I’ve been fortunate, you know, the sort of happier story is that I pick up my son from the school bus every day, and shut off my phone, and for those three hours after school, I’m helping him with his homework, and we’re playing baseball, we’re having to catch, playing basketball. I’m getting that all-important family time, that all-important parenting time, that’s my priority.

If you’re listening, that might not be your priority, but then you might want to climb Mount Everest, or you might want to work out three hours a day, or you might want to find the love of your life. Delegation is the biggest tool that allows us to have the freedom to pursue our number one, two, and three priorities in life. And so, for me, that’s something I’m proud of, and I wrote this book to help share that with others.

Pete Mockaitis
All right. Beautiful. So, delegation unlocks all kinds of good possibilities for us. The hangup is that we are stuck believing that, “I don’t trust them. They won’t do it as good as I can. Only I am capable of doing this,” any number of these beliefs, mindsets, etc.

So, Dave, help us out, if we are in that place, like, “Okay, Dave, that sounds really awesome. Maybe you’ve managed to find some great people, but I mean, I’ve got a team of knuckleheads or I’ve been burnt before in terms of trying to delegate, and it didn’t go so well. So, what do I do?”

Dave Kerpen
Well, I mentioned before, maybe you try a tool and it doesn’t work, and then you sort of give up. I think a lot of people delegate poorly and choose poorly the person to delegate to. And when we get into my system, an acronym, and I do believe in such things, like I said, the number one and the most important aspect in the beginning is who you choose. And they choose the wrong person, they choose the person that’s there, the most convenient, cheapest, lots of reasons, but they choose the wrong person. And then, of course, it’s going to fail if you choose the wrong person.

But you got to keep trying until you get it right because the solution can’t be that you do everything. You’ll burn out. You’ll be miserable. You won’t have all that time. So, let’s attack one of those myths that you shared, Pete, “You’re the best person for the job.” Let’s really think about this. If we think about this rationally for a minute, there’s 7 billion people. I said I’m good at delegating. I’m pretty good at marketing, there are so many things I’m not good at.

And for me to think that I am the best person for any given task, virtually anything, let’s say anything actually, because honestly, there’s lots and lots of people that are way better at any possible thing that I could do. It’s frankly narcissistic and somewhat ridiculous of me to really try to convince myself that I am the best person for the job. I am very, very rarely the best person for the job. I might be the only person that knows precisely what’s in my head for how to do something, but I might also be wrong about the best way to do something. In fact, I’m probably wrong about the best way to do something.

Chances are there’s people out there that could get to the finish line much, much better than I can. So, if that’s, in fact, true, then the next challenge that I have is, “Okay, how can I choose the right person and then explain what that finish line looks like in a really clear, concise way that allows that person to be mutually aligned with me on precisely what the outcome looks like?” And then the trust issue comes up, “How can I…?”

This is hard, I get how hard this is, you know, I’ve been there, I’ve managed a lot, I’ve coached a lot of people here that have a tough time trusting others, but there has to be some level of trust that somebody else is going to get, it’s going to make their way to the finish line, and they’re probably not going to do it the same way I would. In fact, it’s very rare that they would do it the same way I would, but they might do it differently, and they might do it better than I would. And if they can get to the finish line, if they can get even to 80% of the finish line the way I would have done it, but allow me the time to do other things and not worry about it, well, then I have won.

Pete Mockaitis
Inspiring, yes. I like the winning and that’s cool. Let’s stay with the myths for a little bit longer. I’m with you. Okay, fair enough, Dave, 7 billion people alive on this Earth. Maybe I am. Maybe I am one in a million. Well, there’s 7,000 people that are as good or better than I am at that thing. So, okay, fair enough.

But in terms of realistically speaking, can I find that person? Will they be available? Can I afford them? In terms of the practical realities, are we thinking that, in fact, it is still the case that I could find someone who will do a thing better than me, even if I’m awesome at that thing, given these real-world constraints?

Dave Kerpen
Well, let me answer that in two ways. First is maybe they won’t do it better than you, but this is where most of us, to one extent or another, are perfectionists, so we have an idea about what we want something to be, and perhaps better than us is not necessary, and perhaps the same as us is not necessary. That’s where I got to that 80-85%. If they can get to 80-85% of what we would want, but relieve us of all the stress and the work and the agita of getting there, then I see that as a good outcome.

The other thing I want to address is this issue of, “How do I find this person, this mythological person? I can’t afford it. I don’t have the resources. I don’t have the money, etc.” That may be the case, but more often than not, when people come to me with this, and I challenge them on it, we get to the heart of it, and it seems like they’re making excuses because they’re afraid or distrustful or maybe truly ignorant.

In this day and age, when I can personally go on Fiverr and hire somebody for $5 to design a flyer for me, or if I’m really looking for high level…so, that’s on the one end, on the basic task, right? And then on the higher end, folks come to me, and say, “Well, I can’t find a CMO. I can’t afford a CMO.”

And to them I say, “Maybe you can’t afford it, maybe you don’t have the cash, but then maybe if you’re an entrepreneur, you can share equity and find a partner here. Find a partner. Much better to have a smaller piece of a bigger pie and find a partner, or a partner or two or three.” I think there are always creative solutions to find folks to delegate. You could be listening to the show, Pete, and you could be an entry-level employee.

If you have a set of tasks, and you’re responsible for getting those tasks done, and you think of a more creative way to get them done than you doing it, like, for instance, hiring somebody on Upwork and Fiverr for X dollars, and you vet the process and manage the process, and you pitch your boss on the business case for getting the job done that way versus you doing data entry, or whatever that tedious work is all day long, I can’t predict what the boss will say.

But I know that if somebody came to me and gave me a good business case for managing something differently and better than I had thought of in the first place, I’d say, “Great, go for it.” So, a lot of the time, it’s a matter of creatively thinking through better ways to divvy up the work than maybe we’re thinking. Maybe we’re too stuck in the box of having to get the work done ourselves.

Pete Mockaitis
Okay. So, we’ve busted one myth. Could you bust another or help us with a general thinking, doing approach for getting over ourselves?

Dave Kerpen
So, Pete, I think the number one thing that holds us back, and the reason Get Over Yourself is really as high as the dual meaning of get over yourself to delegate work, but also get over the mindset issues that get in your way is fear. I think that a lot of us, at all ages and all levels of seniority at companies, have fear of failure, have fear of not getting things right, have fear that other folks won’t get the job done as well as we would, have fear that, maybe if we’re off with our kids or golfing or doing something else, that we’re not doing our job right, even if the work gets done.

There are all these fears that we have, and, ultimately fear, of course, is false evidence appearing real. Fear holds us back. All fear holds us back. And so, in my model, in my vision, in my dream, and in my scenario, and what I try to do, is feel the fear because I’m afraid. I’m afraid of screwing up on your podcast right now. I’m afraid about being valuable for your listeners. I’m afraid of not delivering. But I understand that fear, and then I proceed and act anyway. That’s literally the definition of courage.

And so, instead of, like, trying to push the fear away, when we embrace it and tackle it head on, and say, “It’s okay to be afraid that this person is going to screw up. It’s okay to be afraid that we’re going to lose our jobs. It’s okay to be afraid that we’re going to lose our clients.” And, in the face of that fear, I’m going to take an action and figure out how to best delegate this work so that I don’t lose my mind, so that I don’t burn out, so that I get this job done in a better way than maybe I would have otherwise. And that’s the courage that it takes to get over ourselves in that manner.

Pete Mockaitis
All right. I dig it. Thank you. So, yeah, let’s talk about the model in terms of how, in fact, do we determine what we ought to delegate, and then do so effectively?

Dave Kerpen
So, we’ve got two acronyms. You mentioned the acronyms earlier, and while I said that acronyms are great, I said, “We got to deal with the mindset issues first.” So, we’ve dealt with the mindset issues. We’re through it. We’re having the courage to act. And now what do we actually do and what do we actually delegate?

And so, the model is there’s three things that we should be doing as leaders, managers, individuals with jobs. Those three things have to do with the overall vision and strategy of the goals here. If we’re in a position to hire people, making sure that we have the right people in the right seats, the hiring process, and the resources issue.

Now, resource is a tricky one. If you’re the CEO, yeah, it’s your job to make sure there’s money in the bank. If you manage an apartment, it’s your job to manage up and make sure to your boss that you have the headcount and the resources to get the job done. And if you are managing projects but not people, it is absolutely your job to make sure that you, personally, have the bandwidth and resources, and that, again, you manage up your boss, to say, “This is what I will need to get the job done.” And if that includes an extra $100 to manage a Fiverr project, well, then you’ve got to advocate for that.

So, those three things, strategy and vision, hiring the right people in the right seats, and access to resources and capital to get the job done. After those three things, my belief is that you can delegate nearly all, if not all of the rest. And so, the SHARE model is strategy, hiring, access to capital, and then remind ourselves that, if there’s anything else, we can, E, empower somebody else to do the job.

Pete Mockaitis
All right.

Dave Kerpen
Then we move into the 5Cs model of delegation. The first, and probably most important C, is choosing the right person or resource to delegate to. Again, we may think, listening right now, because I’ve done a bunch of podcasts that I already know, and I’ve done a lot of coaching of people, and I’ve heard all of the complaints, all the excuses already, “I don’t have the resources. I don’t have the money. I don’t have the budget.”

So, let me share that when we’re thinking about choosing the right person, it is not just a full-time employee that you could delegate this work to. It could be an intern, it could be an apprentice, it could be a contractor on Upwork or Fiverr, it could be a virtual assistant, it could be a vendor, a consultant, there are a partner, there are numerous types of folks that you could delegate the work to.

And the biggest mistake folks do is jumping immediately to hiring the wrong person, maybe just the person that’s the closest in proximity, the person that works down the hall from them, the person that is their peer, the person that, “Oh, my goodness, my first company was in the social media space.” Do you know how many people hired their 21-year-old niece or nephew to run social media for their company because they happened to be the 21-year-old?

Pete Mockaitis
“You use Instagram.”

Dave Kerpen
“You’ve been on it. You’ve been on TikTok. You have a TikTok account, don’t you? Make some videos for me.” So, this first big mistake is choosing the wrong person. And if there’s anything that should be the bottleneck – nothing really should be a bottleneck – but if there’s anything that it’s worth taking the most time on, it’s that first piece of choosing the person to delegate to.

The next C is communicating clearly what the intended outcome is. And, note, what I’m talking about is not every step. There are some folks out there that, whether I say it or not, they’re going to micromanage, they’re going to do the standard operating procedures, they’re going to do detailed instructions on precisely how to get to the finish line.

And if that’s really important to you, I’m not here to say you can’t do that, but in my experience when hiring people, folks like autonomy. They like to be able to get to the finish line in their own way, zigzag a little bit, learn a little bit, have some freedom. People aren’t robots. They don’t want to just, like, input in, output out. They don’t want to be robots.

Exception might be GPT and actually delegating to robots. We can get to that in a little while. But when we’re managing people, what I would say is, the key thing here with this C is to communicate clearly the intended outcome, what does success really look like, paint that picture, and then, ideally, empower them to get there the way that they see fit.

The next C is coaching them to success. Way too many people see themselves as managers. Nobody likes managers. Managers are bosses. Managers are in your face. Managers are not there to support you. They’re there to boss you around. Coaches, on the other hand, which is I strongly urge you all to use the word coach instead of manager. Coaches, anyone that’s played sports as a kid has had the experience of having a coach, hopefully, a good coach, somebody that cheers them on, teaches them along the way, supports them when they have challenges. So, by all means, coach your person on to success.

The fourth C is check in on the regular. I personally like weekly 15-minute check-ins, just where I’m there to say, “Any challenges? How can I help you reach your goals, etc.?” And then the final C, which is often also forgotten, is congratulate them. When you get to the finish line, please, by all means, like, celebrate success. Celebrate success together and then, of course, move on to the next project. So, that’s, in a nutshell, the SHARE model for what to delegate, and the 5Cs model for how to delegate when possible.

Pete Mockaitis
Oh, I like that a lot. And, Dave, I’d love it if you could make this come alive for me with an example that I’ve heard is quite tricky. I was chatting with someone who is just excellent at sales, in terms of when he’s having those conversations with a prospect, they are just listening wonderfully, asking great questions, building rapport, being super honest and creative, like, “Hey, these are the solutions we got. This might work for you. This probably won’t. This is what I would try instead, such that it generates referrals and business and great close rates, all sorts of lovely things.”

And yet, the challenge is there’s a whole lot of other responsibilities in the universe of making sales happen beyond talking to a prospect in terms of managing the lists, and the outbounds, and the marketing, and the vetting of the potential prospect, etc. And so, we’ve had some conversations, like, “Boy, it should be great if there’s a way that we could delegate all of that, such that you just had appointment after appointment after appointment, and doing what you’re amazing at, and doing less of what sort of sucks your energy, and is not perhaps the highest and best use of your time. That’d be really cool.”

And he said, “Yes, that would be really cool, but in practice I’ve never actually seen a master salesperson do that effectively because people come in, prospects come in, you want to be quick and responsive to them, like, all the time, before the demo or the meeting, and then have the follow-ups, but the follow-ups are best coming from you and not someone else, because they’re like, ‘Wait, who’s this other person? Am I going to talk to this person? I want to talk to the main salesperson, and not the secondary assistant to the salesperson.’”

And so, these are the sorts of hang-ups that have made this tricky. So, Dave, I’m just going to lay that on you, and say, here’s the trickiest delegation question I’ve bumped into, how do we crack it?

Dave Kerpen
Well, Pete, it’s as if we planned this, and God is my witness, we did not. But the story that I will share is actually precisely the same role, and I didn’t write about this in the book, but perhaps I should have. A very impressive young man, Sam, who was a salesperson for me, who, very similar to what you said, was an excellent salesperson, not so excellent, as frankly probably many salespeople are, not so excellent at the pre-work, the post-work, the putting it into the CRM, all of that administrative stuff.

And he said to me, “Dave, can I have a budget for an assistant?” And I said, “No. So, here’s what I’m going to do. You take the chats. You prove the business model. You hire the assistant out of your commissions. And if it works, I’ll make the budget for you.” I wanted him invested in making it work. And, lo and behold, he took money out of his own commission check to fund an assistant to do all of that, to delegate all of that stuff to. And this is a rare case because in corporate America, you’re not funding a headcount out of your own pocket, right? That’s pretty insane.

But in this small business entrepreneurial environment, he pitched me. I said, “Here’s the deal. You want to do this? Go ahead.” And guess what? It worked, and I created the budget for sales support, for admin support because he was able to prove that there was a business value in delegating all that other stuff, that frankly was not the best use of his time, to somebody else. So, it’s absolutely doable. It is doable.

Pete Mockaitis
Okay, so it is doable, and that’s encouraging. Could you share with us a little bit of the particulars, some of the nitty-gritty for how this vexing delegation problem can actually be cracked in the nuts and bolts?

Dave Kerpen
I mean, he chose, he interviewed a bunch of people. We’ll walk you through with the five C’s model. So, he interviewed a bunch of people. He knew what he was looking for. And for him, while the tasks were important, the fit, the cultural fit, the somebody that he could reach out to and really bounce things off of was probably even more important. So, I’m not him, but as I understand, he interviewed maybe seven or eight people, hired somebody.

Hired AJ. Gave AJ very clear directions over the types of prospects that he wanted him to reach out to. AJ did the prospecting. AJ did the outreach. There were some missteps along the way. People are going to make mistakes, that’s okay, as long as you coach them. So, Sam coached him, “You know, actually, I’d like more prospects like this,” and he did just that.

He adjusted along the way, getting him better prospects. They showed up for the call. Sam did his work. He closed them up, passed them back to AJ, who followed up to do the contracts and do the follow-ups and do all of that administrative work, getting them in the CRMs and doing the contracts and all that stuff. And, ultimately, both people did their jobs. And Sam made a lot more money for himself, and for me, for the company, by delegating that work and see him coaching his assistant through the steps that he needed done.

Pete Mockaitis
Okay. And not to get too much into the weeds here.

Dave Kerpen
Yeah, no, weeds.

Pete Mockaitis
When AJ was reaching out, AJ is reaching out, as AJ in his name and his email to the people, and he’s saying to the prospects, “Oh, let me have you speak with Sam.” And there’s a handoff? Or is AJ stealth being Sam?

Dave Kerpen
No, no, there’s a handoff. I think that authenticity is important. And so, I’m all for delegating, clearly, many, many things, but if you get a LinkedIn message from me, it’s from me. And I might have an assistant, my apprentices are going to write all the messages, they might draft all the messages, they might select all, using whatever criteria, they’ll do all the work in figuring out who to send messages to. But I like to click send. I do think it’s important, at the end of the day, for authenticity of we are who we say we are.

Pete Mockaitis
And I agree. And what’s really funny is, in this particular delegation scenario, and I guess this is a tricky nuance I’m glad we’re discussing, it’s funny because, well, so, Dave, I get a lot of inbound pitches. People want to be on the podcast, and that’s cool. What a great place to be. What a blessing. But what’s really funny is it’s clear that either there are, I don’t know, PR firms or software or automations or something happening, where someone says, “Oh, hey, Peter, I think we could really make a great podcast, blah, blah, blah, blah, blah,”

And I say, “Yes, I agree. In fact, we did make a great podcast four months ago. It was memorable to me. I’m sorry if you’ve already forgotten it.” And I’m just teasing them because I know what’s happening, and they’re like, “Oh, Pete, I’m so sorry. Oh!” you know. Or, I’d be like, “Hey, Justin, I’m getting this message from you, but it feels as though we don’t have a relationship and we haven’t seen each other in person numerous times, and we certainly have.” And he’s like, “Oh, yeah, sorry!”

And so that happens, and I don’t hold it against them, like, “You’re dead to me for this faux pas.” But it does diminish a little bit. It’s not a good feeling, and it could actually, in fact, be more devastating if, in fact, they’re like, “Hey, what the heck, man? We’ve had a long-standing business relationship, and maybe actually things are tense right now in our business relationship, and I’m getting an automated message from ‘you’ that isn’t really from you.” That might be enough to push it over the edge.

I think there’s a lot to it, whether it’s a human or a robot or an automation, that the way you’ve said it is, it’s like, you’re the person who clicks send, because then you can be like, “No, wait a minute, not that person. I’m already friends with that person. They don’t get a message like this.”

Dave Kerpen
That’s right. That’s right. And as much as I think that there are lots and lots of opportunity for delegation to tools and use of software tools when we don’t have, you know, I talk about resources to delegate, sometimes we don’t have individuals, or we don’t think we have individuals to delegate to. There are a lot of great tools to manage a lot of tasks. But when it comes to communication with people, I do think authenticity is an issue.

It’s funny. I told the story in my very first book, now 12 years ago, about I was friends with a State Senator on Facebook and I got a chat, a live chat from him asking me for a donation. And I was like, “Huh? I donated. I feel like I donated recently.” And he replied, “I know but I really need a little bit more.” And something was amiss, so I said, “Wait, this is my State…” I’ll protect the guilty here. I said, “This is my State Senator, X and X name, right?” Pause. And I said, “Please respond.” “Actually, this is an intern. I’m managing the account.”

Like you said, sometimes the stakes are higher than other times. I mean, if I really wanted to blow that person up for using interns to pretend to be them, to ask for money, I mean, it’s a really bad look, I think. So, I think we have to be very cautious about how much we, I’ll say how much we automate, and how much we automate about that final step in the process.

Pete Mockaitis
Certainly. And I’ve heard that said as a general rule of thumb for AI, like, “Have a human in the process so it doesn’t do dumb things, like automatically deny everybody’s health insurance claims.” Like, whoopsie daisy, you know, or a number of the embarrassments that people have managed to get themselves into when they use AI without the human oversight touch.

Dave Kerpen
Yeah, I love, love, love large language models like ChatGPT for drafts, first drafts of articles, of emails, of marketing plans. I mean, there is massive, massive value in the work that a large language model can provide and produce, given the right input. So, the work becomes less about what to produce and more about the inputs, the prompts that you give the models.

But all of that is really wonderful, again, for a first draft, and then I urge you, as a human, to take that first draft and check it over, first of all, like literally, for some obvious ones. We’ve heard some of the horror stories there. But then work with it, use it as a starting point, because what a great starting point. Sometimes folks have come to me super overwhelmed.

Actually, I just had a woman that I invested in say, “I need a marketing plan. I don’t know even where to start.” And I said, “Here’s where to start. Go to ChatGPT, put in your goals, put in your budget, put in your target audience, and ask for a draft of a marketing plan.” She did it, and it produced a six-page marketing plan for her to consider. Now that’s a great first draft, but it took 10 minutes. And years ago, or without me, without that idea, she might have taken 10 hours to come up with that initial starting point.

Pete Mockaitis
Beautiful. Well, Dave, tell me anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Dave Kerpen
I want to give the listeners credit. Sometimes I take for granted that some of this stuff is easy because I’ve been doing it for a while, but I want to recognize that it’s hard. It’s hard to shift the mindset. It’s hard to change. It’s hard to let go of stuff that you’re used to owning and controlling and doing the work on. I want to really take a moment to recognize that and appreciate that. If you’re listening and you’re thinking, “Well, he’s full of S-H, and in the real world, this is hard.”

I hear you and I get it. It is hard stuff and it is worth doing the work on, is my pitch. It’s worth muddling through and challenging oneself, and becoming more self-aware about the limiting beliefs and challenge and fears that are holding us back from delegating more, and the constraints that we think we have that maybe we don’t have as badly as we might think, and then doing the work. And there’s a brighter side on the other side of the rainbow, it really is. It gets easier.

Pete Mockaitis
Lovely. All right. Well, now could you share with us a favorite quote, something you find inspiring?

Dave Kerpen
Sure. My favorite quote is from Seth Godin, who writes, “How dare you settle for less when the world’s made it so easy to be remarkable?” I think so many of us go through life like not being as intentional as we could be, and not doing the work to really stand out, and be amazing. And I think, like Seth says, it’s not that hard to be amazing. Go for it.

Pete Mockaitis
All right. Well, now could you share a favorite study or experiment or bit of research?

Dave Kerpen
Probably Adam Grant’s research. He’s probably my favorite author and I love his research. I’ll go back to his initial research from his first book, Give and Take, that talked about givers, takers, and matchers, and the value of becoming a giver and giving freely. It’s a little tricky to talk about this on a podcast because I get that I’m giving information, but it’s more of a matching situation. I’m expecting to get book promotion. I’m getting that and I’m grateful for it.

But that first book of his that I read really moved me, if I wasn’t a giver already, to become a giver to the extent possible, and the research shows that it pays. It’s ironic because we need to give without the expectation of getting something back, but when we do that, it just comes back to us tenfold in the long run.

Pete Mockaitis
All right. And can you share a favorite tool something that helps you be awesome at your job?

Dave Kerpen
There’s so many that I could talk about, but I want to say that the free, simplest set of tools is Google Suite. Yeah, Google Sheets, Google Docs, and Google Slides. Those three I use nearly every day, and for next to nothing I’m able to do a lot of cool stuff. So, thank you, Google.

Pete Mockaitis
All right. And a favorite habit?

Dave Kerpen
Walking. Walking gets the blood flowing and is a healthy habit. I chuckled because I have a whole bunch of habits that maybe aren’t enjoyable, maybe not as healthy as walking.

Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

Dave Kerpen
With the context of delegation in mind, it’s probably “Hire slow, fire fast.”

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

Dave Kerpen
I would say, first and foremost, I have pro bono office hours. I’ve met with 838 people over the last 10 years on Thursday afternoons. So, anyone that wants to chat with me, get some free coaching, absolutely no strings attached, I never charge for coaching ever, go to ScheduleDave.com, and you can book some free time with me on a Thursday afternoon. Of course, the book Get Over Yourself, and all my books are available on Amazon and bookstores everywhere. And if you’re looking for really awesome college-level talent, ChooseApprentice.com is our website.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Dave Kerpen
Feel the fear. Life is scary. Be courageous. Think of what you can get off of your plate and challenge yourself to say no, say no to more, and then figure out how you can take those no’s and get that work done in one way or the other, either delegating to humans, delegating to ChatGPT, getting that work off your plate so that you can say yes to more, not necessarily at your job, but more of your priorities in your life and with your family.

Pete Mockaitis
Lovely. Dave, this is powerful stuff. Thank you. I wish you many more successful delegations.

Dave Kerpen
Thank you so much for having me, Pete. It’s great to connect.

950: Cal Newport: Slowing Down to Boost Productivity and Ease Stress

By | Podcasts | One Comment

 

Cal Newport shows how to achieve more by doing less.

You’ll Learn:

  1. Why we’re measuring productivity all wrong
  2. The surprising math showing how doing less means achieving more
  3. The trick to eliminating tasks that don’t serve you

About Cal

Cal Newport is a professor of computer science at Georgetown University and a founding member of the Center for Digital Ethics. In addition to his academic work, Newport is a New York Times bestselling author who writes for a general audience about the intersection of technology, productivity, and culture. He is also a contributor to The New Yorker and hosts the popular Deep Questions podcast.

Resources Mentioned

Cal Newport Interview Transcript

Pete Mockaitis
Cal, welcome back.

Cal Newport
Well, thanks for having me. It’s always a pleasure to chat.

Pete Mockaitis
Oh, I have been loving your book Slow Productivity, and I would like it if you could kick us off with any particularly, strikingly, fascinatingly counterintuitive discoveries you made while putting this one together.

Cal Newport
The importance of doing fewer things is something that I think proved to be a pretty rich vein. So, I have this principle that’s in the book, it’s one of the three principles of Slow Productivity is do fewer things. And when most people encounter that for the first time, what they think I’m probably saying is like, “Look, it’s stressful to do a lot of things. You need to go easy on yourself. Stop trying to be so productive. Like, do fewer things and you’re just going to be happier.” But that it’s a sacrifice, right? You’re going to produce less, but you need to because it’s for your own sanity and psychological health.

As I really looked into this, though, one of the big surprises is, “Oh, wait a second. Doing too many things is like this endemic productivity poison. Like, it’s not just making people miserable, it’s an incredibly terrible strategy for trying to produce valuable stuff with your brain. And when you commit to doing fewer things, it doesn’t actually lead you to accomplish fewer things, and these are somehow separate.” And this was a pretty exciting discovery because I was ready for it to be like, “Look, we got to just reconfigure what we think reasonable amount of work is,” and this ended up to be one of these sorts of win-win situations.

Working on fewer things at a once not only makes your life much more sustainable, you’re going to produce more. Like, over the long term, you’re producing more. You’re finishing stuff faster. You’re producing better work. You’ll actually be better at your job in any sort of observable, measurable way if you’re doing fewer things right now.

Pete Mockaitis
So, doing fewer things in a zone of time, like a week or a month, results in more total things done over a longer arc of a year plus.

Cal Newport
Yeah. So, here’s the math on that, and really, let’s think about doing fewer things at once, like concurrently, “What is my count of commitments that I’m actively working on?” That’s the number that I want to reduce. Here’s the math of why this leads to more accomplishment, is that in knowledge work in particular, when you agree to a commitment, especially if it’s a non-trivial sized thing, like a project, it brings with it administrative overhead, like, “I have to send and receive emails about this project. I have to attend meetings about this project.” So, everything you say yes to has administrative overhead that is necessary to support the work, but it’s not the actual work itself.

So, what happens is when you’ve said yes to too many things, the quantity of administrative overhead goes past a threshold where it’s really sustainable, and now what you have is a lot of your day is now dedicated to talking about projects, like the talking to the collaborators, having meetings, sending emails, and these are fragmenting your day as well. So, it’s not just like, “Let’s do our administrative overhead hour this morning and then get to work.” No, no, no. These emails and meetings are spread out throughout your day, which means you really never have any ability to give something a long period of uninterrupted time to really give it your full concentration.

So, now you have a fragmented schedule, a small fraction of which can actually be spent working with real concentration on the actual projects, the rate at which you’re finishing things goes down. And so, by having, let’s say, ten things on your plate at once, the rate at which you’re finishing things is very slow. Like, most of what you’re doing is being in meetings and sending email. If you instead had three things on your plate, you’re going to actually finish those three things real fast because you have huge swaths of your day to actually work on them. And what happens after finish one of these three things? You can bring another thing on.

And so, if you work through this scenario, “How long will it take me to finish ten things if I work on them all at once versus if I just do three of them at a time?” That second scenario, it’s going to take much less overall time to get through those ten things than the first, and it seems counterintuitive because we’re used to thinking of ourselves like a computer or a robot, “This thing takes this much time, that’s just it. Ten things take ten units of time, that’s just it.” But it’s not like that. The overhead matters. So, doing fewer things at once actually moves things through faster and at a higher level of quality.

Pete Mockaitis
That’s beautiful. And not only that, so there’s the administrative overhead situation fragmenting our time and our attention and our energy, and there’s also the psychological factor of, “Oh, hey, I’ve made some great progress today,” or, “Oh, hey, celebrate. That whole thing is done. Feel good.” And then there’s just the market responding.

Like, I remember when I was land-lording, because if I had a unit that was almost ready to go, it did not produce rent. It’s like, “Oh, no, it’s really close!” I could maybe have someone come tour and say, “Now just imagine this, this, and this will be different when you move in.” And that didn’t really work for them, in terms of like, “Yeah, no, I’m ready to go with another option, because that place already looks done and beautiful, and maybe I can imagine what it would look like done but it’s not done now, and it’s not visually appealing,” that’s why they stage homes, you know, all that stuff. So, there’s benefits on numerous dimensions psychologically, and then starting to reap the rewards of what you have sown.

Cal Newport
Well, it’s important to remember busyness doesn’t create revenue. So, just like you don’t get rent for the days you spent painting and working on a unit you owned. You have to do that stuff, but it generates no money. And if you spend more time painting and spend more time rearranging, it doesn’t generate more money. You have to actually rent it. The same thing is true in knowledge work. Emailing about a project doesn’t generate revenue, attending a meeting about the project doesn’t give you revenue. Finishing the project does, right?

And so, what we should care about is, “How quickly am I completing projects? How good are they?” because that’s what actually generates revenue. But in knowledge work, more so than in like renting buildings, it’s also obfuscated and complicated because, “Well, I was working on this but also this, and I have seven different things I kind of do, and other people are involved, and no one really knows what I did.”

In that obfuscation, we get a lot of the problems with modern knowledge work because it’s hard to just say, “You produced nine this year, and last year you produced six and you’re doing better.” Because it’s hard to say that, we tend to fall back on what I call pseudo productivity, which is, “Well, let me just focus on this high granularity activity that’s highly visible, emails, meetings.” I just see you doing stuff and so I assume you’re productive. Like, that’s the core of the knowledge work dilemma, is we’re focusing on visible activity in the moment as opposed to quality accomplishment over time. From that fatal mistake comes like almost everything negative about the current knowledge work experience.

Pete Mockaitis
Cal, this is beautifully articulated. Thank you. We love actionable wisdom here, but let’s go meta and slow down, and say I would love for you to take us through that whole journey of history, philosophy, perspective, principles on this very concept of pseudo-productivity, knowledge, work, and how we have found ourselves in this current state that is kind of jacked up.

Cal Newport
Yeah, I mean, it’s a fascinating story. It’s what the first part of my book delves completely into, is just understanding how we got where we are. Because this is, by the way, just as an aside, it’s a big part of my approach is because I’m also a professor and a founding member of the Center for Digital Ethics at Georgetown. I think a lot about culture, society, and technology and their interactions from the sort of removed of, “How do these systems work?” I think the systems matter.

And there’s a fascinating story when we look at what’s happening in knowledge work that spans from basically Adam Smith to Slack. Okay, so here’s what we get. Before knowledge work emerges as a major economic sector, which is really the mid-20th century, the term “knowledge work” is coined in 1959. Before that occurred, we had a pretty good handle on what we meant by productivity. It goes, “An economic concept that we could measure pretty accurately within specific organizations.” It goes all the way back to Adam Smith.

So, we first get good with measuring productivity in agriculture, and it’s a ratio, “How many bushels of wheat do I produce per acres of land I have under cultivation?” It’s a single number. And we also had in agriculture well-defined production systems, “Here is how I rotate my crops. If I change how I do this, and that number goes up, then I say, ‘Oh, this is a more productive way of doing it.’ And so, what we get here is sort of rapid innovation in cultivation of crops and planting systems because we have a number we can track.

Okay, we go to mills and factories. We could do the same thing, “Now I’m going to measure how many Model Ts are we producing per labor hour I’m paying for,” and that’s a number. And we have a very clearly defined production system, “And if I change something in that, we can see if that number improves.” This is what happened with automobile manufacturing. Henry Ford innovates the continuous motion assembly line with interchangeable parts and that number went up by a factor of 10. They’re like, “Oh, great, this is a much better way to build cars.”

And this sort of quantitative productivity journey was massively successful. The industrial sector, the wealth created by the industrial sector, grew at a staggering rate from the 1800s into the 1900s. Some economists would say, essentially, all of the capital in which the modern Western world was built came from the productivity miracle of being able to measure these ratios, adjust systems, see how those numbers got better.

Then we get knowledge work. None of this works anymore because we’re not producing Model Ts, and we’re not just producing wheat on acres of land. It’s a complicated position where I could be working on a lot of different things that shifts over time. It’s different than what the person right next to me is working on. How we do this work is highly personal. There is no production system we can tweak as an organization. Everyone manages their own work and time internally however they want to do it. So, we have no systems to tweak, no numbers to measure, and this was really a big issue because, “How are we going to manage knowledge workers without these numbers?”

What we introduced was pseudo productivity. A crude heuristic that says, “We can use visible activity as a proxy for useful effort.” So, I see you doing stuff that’s better than not. So, let’s all come to offices where we can have bosses. So, let’s make sure that you’re working all day. And if we really need to get ahead, let’s come in earlier and stay later. We can just increase the window of visible activity. So, we use this crude heuristic.

What happens where this goes awry is when we get to the front office digital IT revolution. So, we introduced computers and networks and then mobile computing and ubiquitous internet. And now suddenly, you can demonstrate visible activity, the thing that pseudo-productivity demands. You can demonstrate this at a very fine granularity, like sending individual email messages anytime, anyplace, and this is where pseudo-productivity begins to go off the rails.

Once I can be engaged in pseudo-productivity and measure pseudo productively anywhere at any time, and it has to be at this really fast, fine-grained granularity where it’s not just, “You saw me in my office during this hour,” but, “How many emails did you send to that hour? How quick were you to reply? How many things are you saying yes or no to?” It’s spun off the rails.

And we see this sharp discontinuity, if you study knowledge work, study how people talk about productivity in knowledge work, study how people talk about what’s good and bad about knowledge work, you get to the early 2000s, there’s a sharp discontinuity where suddenly we become unhappy. Just as email and laptops and then smartphones arrive, we suddenly begin to get much less happy.

Pete Mockaitis
Intriguing. And, Cal, what is the measure of that and what’s our approximate year when we start seeing that go, “Boom,” downhill?

Cal Newport
Well, you can see it in survey data, but where I like to look for this is actually in the tone of productivity books, because I’m a collector of business productivity. Look at the business productivity books from the ‘80s and ‘90s, like what are the big players here? It’s like Stephen Covey.

Pete Mockaitis
Getting Things Done, yeah.

Cal Newport
The 7 Habits of Highly Effective People, First Things First, you know, Eat That Frog. These are very optimistic books. Like, Stephen Covey’s whole thing is, if you’re careful in identifying what’s important to you and what’s urgent and what’s not urgent, you can figure out what to do with your day with the goal of actualizing all of your deepest desires and dreams as like a human, “We’re going to self-actualize you.” What’s the first big business productivity book of the 2000s? David Allen, Getting Things Done.

Pete Mockaitis
Oh, that was 2000, okay.

Cal Newport
And if you look at that, the tone is drastically different.

Pete Mockaitis
We’re overwhelmed. We’re drowning. We need help.

Cal Newport
We’re drowning, yes. I profiled him for The New Yorker. I really went deep on David Allen. It is a nihilistic book. Getting Things Done is like, okay, forget Stephen Covey trying to self-actualize our deepest goals as a human being. What is the goal of Getting Things Done? Can we find a few moments of Zen-like peace amid the chaos of the day?

Pete Mockaitis
After your weekly review, you can, Cal, and then it’ll pass.

Cal Newport
He’s trying to reduce work to this agnostic widget polling, like at least we can find some peace. It’s a very nihilistic book. But what changed between 1994 and 2003? Email. So, we see it. It’s just a change. And then what are all the biggest business productivity books of 2010s? We got Essentialism, The ONE Thing, my own book, Deep Work. All of these are books that are about, “How do we push back against the overload? How do we resist this? How do we find the things that really matter?”

I mean, it’s a complete tone shift where overload, having too much to do, being stressed out, becomes the defining feature of knowledge work once we get to the early 2000s. You don’t pick that up at all in the ’90s, in the ’80s, in the ’70s, and in the ’60s. So, the technology had this huge discontinuity in our experience of this sector.

Pete Mockaitis
Okay. Understood. And so then, when it comes to the measurement has broken down, what is to be done there in terms of like there are, I think in your book you said, we’ve tried some really stupid things, like, “How many lines of code have you written?” or, “How many words have you produced?” And it’s like, “Well, I mean, were those lines of code brilliantly efficient? Were those words tremendously insightful?” or, “Are they kind of like bloated and lame and blah?” So, it’s like those might have a purpose of, “Kind of, if I can constrain them with a quality-paired metric as well.” It’s a real tricky beast, Cal. What is to be done here?

Cal Newport
Well, as long as you’re in the pseudo-productivity mindset, all the solutions are going to be like that. It’s going to be, if activity is what matters, my biggest concern, if I’m a manager, is you’re taking breaks from activities. So, I want to make sure, like, what was the big concern of managers about remote work? It’s like, “Well, what if there’s periods of the day in which the person is not doing things? That’s taking away the bottom line,” because we imagine knowledge workers like they’re on an assembly line, “Hey, if you stop putting the steering wheels on the Model T for an hour, we can’t produce Model Ts for an hour.”  It’s just this very direct.

So, what is the solution? We have to move away from this activity-based notion of productivity towards something that’s more outcome-based. And that allows for a much slower definition of productivity that has a lot more variation, a lot more idiosyncrasies, and is a lot more sustainable and meaningful for the people involved.

Pete Mockaitis
All right. Can you give us some cool examples, or stories, or metrics, or numbers we might use when we talk about outcome-based? I’m thinking, in some fields it seems pretty straightforward, like sales. Like, okay, there’s revenue or gross profit generated from the sales that you’ve made. And that could look very different in terms of you were cultivating a relationship with a multimillion-dollar account for months or years, and you landed it, and we can measure that, and it’s way bigger than you hustling with your cold-calling, your cold-emailing to get dozens of smaller clients. So, there’s one outcome.

Cal Newport
And sales is an interesting example because I just met a salesman from a big tech company at a book event talking about Slow Productivity. And you know what he said? He said, “Look, in our company,” because sales is clear, unlike almost every other knowledge work, you have these metrics, like, “What did you bring in?” And so, it’s an interesting natural experiment. If we take a knowledge worker where there is a clear metric of success, do we see a drift away from pseudo productivity? And we do.

This is what the salesman told me. He said, “Yeah, in our company, the sales staff doesn’t have to go to meetings. Everyone else does. Everyone else. You got to go to meetings. If someone invites you, whatever, everyone in these more ambiguous jobs, yes. But the sales staff, all meetings are optional because they have this number and they want that number to be better. And the sales staff is like, ‘That number is worse if I’m going to meetings.’”

Pete Mockaitis
That’s true, “What you do is so important, we’re not even going to put that at risk for anything.”

Cal Newport
Which shows how important were those meetings in the first place, right? Another place where we’ve seen innovation, like this actually is in software development, because software development, it’s knowledge work in the sense that it’s all your brain, but it’s pretty closely aligned with industrial manufacturing because you’re producing products. So, there’s much more of this notion of, like, “We’re shipping something. How long did it take to ship?” Like, it’s more measurable than other types of knowledge work.

We’ve seen tons of innovation, tons of innovation in software development that try to get away from just this completely generic activity base, because they learn, like, “I don’t care if you’re busy. What I care about is do we get these features added quickly? What’s our turnaround cycle on updates to the software?” Like, they have things to measure. So, what do you see in software development? You see a move towards these agile methodologies where, A, workload management is transparent and centralized. It’s not just, “I have a bunch of junk on my plate.” It’s, “No, no, it’s all on the wall, and this is what you’re working on, and it’s just this one thing.”

You see things like sprinting in software development, “We want you to do nothing but work on this feature until it’s done, and then we’ll talk to you again tomorrow,” because, again, whenever we begin to see adjacency, the actual measurable outcome, all of these tropes of pseudo-productivity that are really killing us in digital age knowledge work, they all begin to shatter and fall away. So, it’s like we have to take that mindset from sales and software development, and we need to move this into more types of jobs, we’d be clear about the workload management, work on fewer things at a time.

Just measuring performance at the scale of the year makes a big difference, “What did you produce this year?” Because when you’re talking at the scale of the year, you don’t talk about meetings or emails or small things you did. You talk about things you finished. So, just having like an annual perspective for thinking about productivity, that makes a difference. So, all of these types of things, we see it in software, we see it in sales, we need to move that to many more jobs.

Pete Mockaitis
I like that a lot, the thought associated with, “What is the time horizon we’re looking at?” Because if it is a day, and I’m looking at, “How many emails did you send?” or, “How many hours were you logged on?” it’s like that tells me very little. If I look at a year, that could tell me a whole lot. And then, I guess, in a way, there’s some art and science right there in terms of evaluating, “What’s the ideal period by which we should be looking at and thinking about these things?” Do you have some perspectives there?

Cal Newport
Well, even allowing people to figure this out on their own can be really effective. Like, you say, “Okay, I want you just to make your pitch to me as your boss, like what you did that was valuable this last quarter or this last year.” Like, you can kind of figure out the timeframe when you write about it, just allowing the individual to report like, “Okay, here’s what I’ve been working on. I completed this and this, and we’re working on this big project, and we made this much progress on it. And I think this is all really important.”

Like, letting someone just describe why they’re valuable, because it’s not going to work if I ask you to describe why you’re valuable. You said, “Look, I just looked up my statistics. I’ve been sending 150 emails a day. I’ve been logging seven hours a day in Teams meetings. I’ve been in a lot of meetings.” Like, it sounds absurd when someone’s asking, “Quantify why you’re valuable.” You think about the big things. You think about it at a bigger time scale.

There are organizations that do this super explicitly. I profiled these in The New Yorker a few years ago, these organizations that had a very hardcore way of doing this, called ROWE, results only workplace environment, where it was all that matters is results, including when you show up to work, when you don’t, what days you don’t work. Everything is up to you, but they’re really, in these environments, they’re really hardcore about what are your results.

And because of this, it really banishes pseudo-productivity culture. If you’re like, “Hey, come to all my meetings,” you’re like, “No, because in the end, I’m going to be measured by these things I’m producing, and that’s going to hurt me. So, no, you’ve got to convince me to come to your meeting. And if it’s not going to be worth the time, I’m not going to do it, because all people care about is what I have produced.”

And they’re really interesting to study because, you see on the positive side, these hardcore results only environments, a lot of pseudo-productivity falls away. On the negative side, it is really difficult for a lot of people to leave the comfort blanket of all the obfuscation you could generate by just sending lots of emails and meetings because you can’t hide anymore. You produce or you don’t.

And there is, I think, a certain segment of knowledge workers, and it should be acknowledged, that do find some comfort or peace in being able to be much more obfuscated about their work, like, “It’s not really clear what I’m doing, but I answer my emails a lot, and I’m in a lot of meetings, and I sort of just, I’m around, and so it feels like I’m being productive.” When that goes away, it gets exciting for a lot of people, but it gets scary for some people as well.

Pete Mockaitis
Yeah, I’ve heard that in particular about the culture at Netflix, in terms of, like, it’s exciting and terrifying for this very reason. I think ROWE could also have some potential downsides with regard to collaboration and team camaraderie culture. It’s like, “I’m out to get my results. Period. So, get out of my way.”

Cal Newport
“Get out of my face.”

Pete Mockaitis
So, it’s tricky to get all the pros without the cons. Well, the security blanket, you might feel secure in the moment, but I would venture to say, “If you’re not clearly creating value in excess of your salary and payroll costs, your security is quite slim come lay-off time.”

Cal Newport
I think that’s right. In the good times, where no one needs to be fired, it prevents you from being noticed in a negative light. Like, “Yeah, I’m not thinking about Pete. Like, I see him a lot. I’m sure that’s why I’m not thinking about them.” But you’re right. When times get tight, “All right, now we have to start reducing staff,” that’s suddenly when people shift their thoughts to not, “Are you doing something bad?” to, “What good are you bringing?” And, right, that’s when things get to be dangerous for you.

So, when times are good, you can just be really active and you’re not going to draw any attention. But when times are bad, ultimately people are going to wonder, “Hey, what do you do? What’s the value? Like, what would happen?”

Pete Mockaitis
“Like, what is it you do here?”

Cal Newport
I would say people, by the way, so my column for The New Yorker during the pandemic was named Office Space, in part because of exactly that reference that there was a lot of people in the pandemic, especially when they were forced to do all their work from home, and they could see like their partners and what their partners were doing for their jobs, and I think a lot of people in knowledge work had that same reaction of like, “What would you say I actually do here? Is it “I’m a professional Zoom meeting attender?” Like, is this really a good use of my graduate degree?” I think a lot of people had that crisis.

But, yeah, back to your point. If you’re producing stuff that’s valuable, not only does that give you security, it begins to give you leverage to slow down your definition of productivity. Because the more you can point towards, “I do this and I do this really well, but that’s also why I’m not just sending emails all day and a bunch of meetings. Hold me accountable for this. But in exchange for that accountability, you’ve got to give me more autonomy.” Like, that’s a fundamental exchange of trying to negotiate for a more sustainable, slower definition of productivity.

Pete Mockaitis
That’s good. And when it comes to this notion of doing fewer things, you mentioned the book The ONE Thing, which I love. And it’s so funny, when I read it, also with Greg McKeown’s Essentialism, it’s so calming to me, and I guess I like productivity books or non-fiction business-y books. But I think it’s also just like, “Oh, I don’t have to do everything. Okay, okay, that’s nice.” So, it’s just sort of reassuring.

But I’d love your perspective on, “How do we really select from a noisy world of thousands of options? What are those few things I’m going to do?” And the number you suggest is it, “It’s probably going to be more than one, but hopefully is less than five?” Is that the range you are shooting for?

Cal Newport
Yeah, for major projects. Yeah.

Pete Mockaitis
Okay. And so, how do I pick and choose, like of hundreds of potentially good things, what really, really, really deserves my one to five?

Cal Newport
Well, there’s two environments here. So, one is you work for someone. So, if you’re in an organization, what really seems to matter is just add constraints, and then you will see pretty naturally like what makes the cut. So, for example, one of the things I recommend if you work within an organization, where you can’t just directly say no to a lot of things, what you do instead is saying, “I’m going to keep a two-tier list of what I’m working on. Tier one is actively working on. Tier two is queued up for me to work on next. And as I finish something in the active tier, I pull in the next thing from the waiting tier, and that becomes something I’m actively working on.”

So, you artificially constrain the number of things you’re actively working on. And the rule is why this works is you say, “Okay, administrative overhead can exist for the things I’m actively working on. If it’s in my queue, then I don’t do administrative overhead. So, if you give me something to do and I put it on my queue, and I make this public, and you can look at it, and it’s a shared document, you can watch it. I can tell you, ‘Watch this march up my queue until it gets to my active work tier.’ Once it’s there, email me about it. We can have meetings about it. You can ask me how it’s going. But until it’s there, the answer is ‘I’m not working on it yet.’ And where is it in my list? You can look at it yourself.”

So, now you’ve restricted the administrative overhead that’s being generated to only a small number of the things that you ultimately have committed to. Once you have those constraints, it leads to better selection because other people are now involved. So, a boss comes in and says, “This thing, I want you to do this thing.” You say, “Great. It’s on my queue, it’s back here.” They’re like, “No, no, I need this. This is way more urgent.”

Well, now you can involve the boss, and be like, “Great. Well, which of these three things that I’m working on now should I swap out?” And now they’re kind of involved. Like, “Actually, you know what? Stop working on that thing. I don’t think that’s as important as I thought it was when we first thought about it. Move this in here instead. And now that I’m looking at your queue, take out these four things as well. That’s not where the priority is.” So, once you have constraints, you begin to get wisdom.

So, another, this is an example from the book, but another place where this began to happen was a division within a large research lab where they had a lot of projects coming at them. And what they did is they centralized this, they said, “Okay, we’ll put every project we want to work on, on an index card and we’re going to put it on the wall under this certain column. These are all things we want to work on. And then here next to it are the ones we’re actively working on now, and we label it with who’s working on it. And so, when someone finishes something, we pull something else in here, we decide together what to do next.”

And they have this heuristic that arose over time, “If something’s been on that left side of the wall for a while, and we keep pulling other things in but we’ve been leaving that alone, that’s probably not that important. You know, let’s take it down.” Like, if you’re on the wall too long and it never moved over to, like, “Let’s work on it actively next,” that was their cue of, “This was exciting when we thought of it, but it’s not that important.” So, once you have constraints, wisdom about what’s important and what’s not, it begins to emerge because you’re thinking about this in a way that you don’t, when all you’re doing is just saying yes to things and trying to keep up with everything at the same time.

Pete Mockaitis
So, if you have the constraints, it’s almost like a forcing mechanism such that it’s not so much like, “Oh, there’s a magical measurement, there’s a magical question, or a magical metric by which we use to measure that answers this question for us.” It sounds like you’re saying, “Yeah, that doesn’t really exist across all industries and types of work but, rather, put the constraints in and you’ll feel the tension, and you’ll see what just really, really has to get done soon and what can wait.”

Cal Newport
Yeah, just being forced to continually make the question of “What next?” forces a lot of wisdom. And I keep having to say, “Okay, what am I going to pull in next? What am I going to pull in next?” And making that decision again and again, what emerges from it is, like, a better understanding of, “Oh, this is the type of stuff that’s important to me. And this stuff I keep leaving over here, and moving other stuff ahead, oh, I guess that’s not really that important to me.” And it’s a lesson that comes out from people who use these two-tier pole systems.

It’s something I talk about often. You build up the muscle of understanding over time what matters and what doesn’t, because you keep making these decisions and keep getting feedback on what stays and what moves. And, then over time, you stop adding the stuff to your “to-work-on-next” list that you know, like that’s never going to be pulled off. And then you become much better at being like, “No, we don’t do that anymore,” because you’re like, “I’ve seen too many things like that type of project that we put on this list or we put on the wall and it sits there for two months that we finally take it down. I have now learned, I’ve gained wisdom, this is not the type of thing that we really need to be working on.”

So, you become much more self-aware of what you can actually do with your limited time and what’s worth doing with your limited time when you’re explicitly and consciously having to make these decisions again and again.

Pete Mockaitis
And when you say “explicitly and consciously,” that reminds me of some of the interviews we’ve had about decision-making with Annie Duke and others who suggest having a decision journal. And I think the practice perhaps of writing out, “What is the rationale by which I’m using to place this in the top tier or not?” And then having that written enables you to kind of reflect on it and say, “Oh, yeah. Well, that was true at the time, but things have shifted,” or, “Yes, this is the pattern I see over and over and over again. Like, it’s really important to a really big client. Okay, that seems to be a prioritization principle that we keep going back to again and again.”

Cal Newport
I love that technique. By the way, yeah, I know Annie talks about it. My friend Dave Epstein from “Range” and “The Sports Gene,” he was on the show recently, and he was telling me about how he does this as well. And part of the reason why I think this technique, like a decision journal, is effective in knowledge work is that we don’t otherwise have clearly defined processes.

One of the defining features of knowledge work is that organizational strategies, processes, how I figure out what to work on or not, how I figure out how to manage my day, all of this is informal and personal, and most people just wing it, it’s like, “Oh, my God, I just got this urgent email, so let me do this. Oh, and there’s a deadline. I’m going to stay up and do this.” When you keep a decision journal, what you’re actually creating over time is process, you’re like, “Oh, this is how I deal with this. This is the right way to figure out what to work on next.” We forget the degree to which, in knowledge work, we just wing it all the time.

It’s not like we have, “Here’s how I build cars. How do I improve that?” It’s the equivalent in knowledge work, if the way we built cars was just put a bunch of tools and parts in a warehouse, threw a bunch of engineers in there like, “Guys, build me some cars. Let’s go.” Everyone was just running around like, “Hey, can I have the wrench?” That’s the way we do knowledge work. So, if in that world, you’re starting to actually think, “How do I figure out what to work on? What didn’t work? What did work?” you start to think about that clearly.

It’s like the one-eyed man in the world of blind people, you’re going to have this huge advantage, you’re like, “Oh, my God, I’m just really…why are people working so hard? Like, I’m really killing it over here, and I’m not even working,” because no one else is doing this. They’re just getting after it with Slack and email in their calendar, and just saying yes to everything, and trying to be busy. So, there’s a huge advantage once you start thinking process-centric within knowledge work.

Pete Mockaitis
That’s beautiful. And to The ONE Thing, that is one of my favorite questions I think about often, “What’s the one thing I can do such that by doing it everything else becomes easier or unnecessary?” And I think that is one handy question. I’ve learned it’s not applicable in all situations, in all domains. But I’m curious, have you discovered any other organizing principles or questions that tend to serve people pretty well, pretty often?

Cal Newport
Well, I mean, first as an aside, have you heard Jeff Bezos’ version of The ONE Thing idea?

Pete Mockaitis
Well, no, until you articulate it. Lay it on me.

Cal Newport
So, this is like the big idea within Amazon when to figure out “What are we going to work on? And what are we not going to work on?” Bezos has this thing, “Is this something that’s going to make our beer taste better? And if it’s not something that makes our beer taste better, we shouldn’t be in that business.” And the case study he’s referring to was when, I guess, German brewers, beer brewers used to generate their own electricity. And then at some point, they plugged into a grid instead of generating their own electricity. There’s a lot of annoyance and logistical overhead with running your own generators and dynamos.

Pete Mockaitis
It sounds tricky.

Cal Newport
It’s tricky, right? And they said, “Oh, we should just plug into the grid.” Why? “Because making our own electricity doesn’t make our beer taste better so let’s not put any energy into that. We want all of the people we hire to have their energy into making our beer taste better.” And so, Bezos brought that over to Amazon, “We should be focusing on the things that makes us money, that our customers really care about. Anything else, if we can outsource it, we should, or just not do it at all.”

And so, I really love that way, like, “What makes our beer taste better?” But that brings me to, I think back to your question, one of the other big principles is obsess over quality. And what this is really doing is, basically, in knowledge work, in some sense, figuring out, “What’s your equivalent of brewing beer?” Like, figuring out, “Me, as an individual employee, what’s the thing I do that’s most valuable? And if there’s nothing really there that’s valuable, what’s something I can learn to do that’s going to be really valuable?”

And once you identify that, you can focus more of your energy in, “My goal is not to be really responsive. My goal is not to make sure that everyone gets everything they need from me as fast as possible. My goal is not to be in every meeting where you need me. No, my goal is to do this thing better. I want to do this better and better because this bottom line helps our organization.” And one of the keys behind this idea is focusing on something that’s really valuable to your company or your organization, is like the foundation on which all radical engagements with slow productivity will eventually be built because it gives you leverage.

It gives you control over your job. It makes your value clear. You’re playing the right game. It allows you to focus on what matters and not these sort of accessibility routines that everyone else is trying to do with their email and with their meetings. And when you really begin to care on making your beer taste better, all of the busyness becomes unnatural to you. So, you say, “I don’t want to be on email or in meetings. That’s getting in the way of getting better at these marketing strategies or at writing this code.”

And so, slowness becomes natural, and as you get better, you get more leverage to make your work slower. So, that idea of figure out like what your equivalent is of brewing beer, what’s the thing you do best and focus on that, that unlocks almost everything else.

Pete Mockaitis
That’s cool. So, if I’m doing marketing, what’s giving me more impressions per dollar, or more purchases per, whatever, what’s boosting my conversion rate, etc. Or if you’re creating products, it’s like the beer tastes better, what will delight the customer all the more, and make them say, “This company rocks. I love their stuff. I would tell more people about their stuff. I’m going to buy more of their stuff.” Very cool.

All right. Well, so we’ve talked about, so we got three principles here. We’ve spent some good time on do fewer things, and we hit the obsess over quality. Can you unpack the third one for us a bit?

Cal Newport
That’s work at a natural pace. And the argument here, it’s a psychological argument, the way that we work in knowledge work, which is all out, all day long, year-round, is really unnatural. It’s unnatural in a sort of literal sense that human beings throughout our whole history as a species are used to having huge variations and intensity of what we’re doing. There’s really intense periods during the day and really quiet periods. Some months are much more intense than other months. In the winter, we’re kind of hunkering down. And in the fall, we’re doing the harvest, and it’s super busy. And we have all this variation, that’s what we’re wired for.

And then we got mills and factories. And in mills and factories, it made more money if people just worked as hard as they could as much as they could. And so, we switched for the first time in human history to just like work hard all day long, but it was very unnatural and very intolerable. We had to invent labor unions and regulatory frameworks just to try to make these jobs survivable, essentially.

When knowledge work emerged in the mid-20th century, we said, “Okay, how are we going to organize this labor?” And we said, “Well, let’s just do the factory thing.” Because that’s what was going on, that’s what was in the air. The core of the economy was industrial manufacturing. So, it’s like, “Great. We’ll just approach knowledge work like we do building Model Ts, eight-hour days, work as hard as you can.” Like, if you’re resting at all during the day, that’s bad. Pseudo-productivity activity matters, and it’s the same all year round.

So, we adopted this way of working. It was actually super unnatural and required all these safety mechanisms. We adopted the same thing without the safety mechanism, and it’s an exhausting way to work. It doesn’t, over time, produce more productive effort even if in the moment it seems more satisfyingly frenetic. So, work at a natural pace says, “You need more variation in your intensity on all sorts of time scales. It shouldn’t all just be all out.”

It also says, “You should take longer to work on your projects, that we make our timelines too small. Give yourself more time so that you have room for these up and down variations.” Like, this is the way all the great thinkers through time past work, up and down in intensity over time until eventually something good came out. That’s how we produce things with our brain, not the Model T model of just, “Clock in and turn that wrench as fast as you can until you clock out.”

Pete Mockaitis
Okay. Well, so then any sense for how do we tune in to knowing if we’re overall too much or overall too little? I know there’s going to be variability, busy seasons, lighter seasons, but any clues that we might focus in on to go, “Ooh, let’s crank it up,” or, “Let’s tone it down”?

Cal Newport
Well, that’s not the hard part. The hard part for people, actually, is just being comfortable with the idea that you shouldn’t always be cranked up. And then once you have that realization, there’s a lot more variation that just becomes natural. So, like a couple of things you can do. One, just start doubling your timelines for everything you agree to do. Instead of doing the typical trick of, “In theory, what’s the fastest possible time I could get this done?” and then falling in love with that timeline, “Oh, my God, that’d be great. If I could get this done before Christmas, this would be great,” and then we commit to this impossible timeline.

Double everything. So, give yourself much more breathing room. And, two, actually engineer seasonality. You don’t have to tell people about this if you work for someone else, but just schedule out your project so that the summer is going to be slower, but you’re really going to be getting after November. You can just start engineering variations in your workload. No one is tracking your workload so carefully.

There’s no graph somewhere in the central office, where they’re like, “I’m looking at Pete’s daily work project touches here, and they’re down in July versus whatever.” People, it’s all just chaos. They don’t know what’s going on. So, take longer and engineer seasonality explicitly into your project flow and your workflows. Just doing that is going to be like taking a deep breath.

Pete Mockaitis
Lovely. Cal, tell me, anything else you really want to make sure to mention before we shift gears and hear about a few of your favorite things?

Cal Newport
Well, I mean, again, I think the key thing to keep in mind is don’t use the word productivity so confidently.

Pete Mockaitis
You live it.

Cal Newport
I mean, there’s a lot of talk where people are like, “I want to be more productive,” or, “Productivity is bad,” but people aren’t really defining their terms, and that’s a big problem. We all just assume we all know what productivity means, but we don’t. Like, when people say, “I want to be more productive,” what they really mean often is, like, “I want to produce more stuff over time.” When people are critiquing productivity, what they’re often doing is critiquing a sort of industrial notion of productivity, like, “The effort per day needs to be large.”

We’re not talking about the same things. Like, let’s define our terms. This is why I think it’s helpful to say pseudo-productivity is what we’re doing. Pseudo-productivity is different than quantitative productivity, which is what we used to do. Slow productivity is itself an alternative. Like, once we get clear about terms, a lot of the absurdity of what we’re doing just becomes self-evident. Like, a lot of this idea of, “I want to do this now instead of that. I’m going to do fewer things. I’m going to have more variation.”

When we realize that’s in contrast to pseudo-productivity, and that’s a part of slow productivity. Just having the terms clear, I think, really makes it better, much easier for us to make progress. So, that’s my final thing I would say is don’t be too confident that you know what people mean when they use the word productivity. I actually push on it, “What specifically are we talking about here?”

Pete Mockaitis
Lovely. Thank you. Now, could you share a favorite quote, something you find inspiring?

Cal Newport
Well, there’s an obvious answer to this question because I actually wrote a book with this quote in the title, so maybe I’m telegraphing I like this. Steve Martin, doing Charlie Rose interview about his memoir, “Born Standing Up.” And Steve Martin says, “People are always asking me, ‘How do you succeed in the entertainment industry?’” And he says, “The answer I give them is never what they want to hear. What they want to hear is, like, ‘Here’s how you find the right agent,’ or, ‘Here’s how you like get onto the writing staff.’”

And he says, “No, what I tell them is, ‘Be so good they can’t ignore you. If you do that, all the other good things will follow.’” I wrote a book called “So Good They Can’t Ignore You” 10 years ago, 12 years ago now that was just inspired by that quote because that’s how important it is to me, because I ultimately think, especially in creative work, that’s what it all comes down to, “Be so good they can’t ignore you. The other stuff will work itself out if that’s where you’re focused.”

Pete Mockaitis
And a favorite study or experiment or bit of research?

Cal Newport
Well, this always shifts, but there’s a new study someone just showed me, which I found very satisfying, because I don’t use social media, and I’ve often argued with people for various reasons why I should. And one of the reasons they give me is, like, “Well, this is how, like, you’re an academic, and this is how people know about you, and know about your work. You have to be yelling at people on Twitter about Trump. And if you’re not, you can’t be a successful academic.”

A new study just came out where they studied the citation count of academics correlated to Twitter engagement, and found Twitter engagement does not lead to more citations. It does not lead to more notice to academics’ work. What does matter? Doing really good important work. And so, I found that study very satisfying. You’re not going to be able to tweet your way into intellectual significance. You just have to do good stuff.

Pete Mockaitis
And a favorite book?

Cal Newport
A book I just read, which I really liked, was Abraham Joshua Heschel’s The Sabbath. It’s a 1950’s-era book by a great Jewish theologian, talking about the Shabbat. But I found a lot of secular resonance in this book because he was looking at the theology of Shabbat, taking a day off of work, like as it said in Genesis, right in the Bible. And he has this really cool argument. I wrote an essay about it.

But he has this argument that’s like, “Look, you take a day off from work. This is not instrumental. This is not you have to take a day off work so that you’ll be able to do work better when you get back. It’s not instrumental. You take a day off of work so that you can appreciate all the other stuff in life that’s important.” In Genesis, it was like God looked at what he had done and said, “It is good.” It’s like gratitude and presence.

I just thought it was, from 70 years ago, looking at something that was written 3,000 years ago, is a really sort of timeless idea that it’s not just, not everything is just the work, and breaks from work is not just about making the work better. It’s about all the other stuff that’s important to you. And it’s a slim book, it’s beautifully written, it has these original woodcut illustrations which are fantastic. A really cool read. I recommend it.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Cal Newport
I recently have gone down the mechanical keyboard rabbit hole.

Pete Mockaitis
Oh, yeah.

Cal Newport
Yeah, because I wore off on my MacBook, I wore all the keys off because I write a lot, and the plastic was cheap in this generation. I wore every key off. You can’t see any key. And so, I got a cover for it with the keys on it, and I wore all those off too. So, I finally bought a nice, a NuPhy, N-U-P-H-Y mechanical keyboard, and, oh, I love it. Just the click and the clack. It’s substantial. I love writing on it. Your fingers spring back up with the keys so that you can type faster. I don’t know, I’ve enjoyed it. I write all the time. I enjoy writing more on this than I did when I was on just the MacBook keyboard, so I love my NuPhy wireless mechanical keyboard.

Pete Mockaitis
Alrighty. And is there a key nugget you share that really seems to connect and resonate with folks; you find it’s quoted back to you often?

Cal Newport
I think people, really, like more recently, one of the things that come back to a lot is this idea that activity doesn’t matter, busyness isn’t monetizable, your email inbox is not going to be remembered 10 years from now, but what you produce that you’re proud of, that’s everything, and just this idea of output over activity. That’s what keeps coming back to me. That’s what people seem to be quoting when they’re talking about this book or calling into my podcast, so I like that. Busyness is maybe satisfying in the moment, but is forgotten in the mist of history.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Cal Newport
Do fewer things. Like, trust this idea that if you cut down the number of things you’re working on right now, you will look back when this year is over and be much more impressed, and proud of what actually got accomplished.

Pete Mockaitis
Cal, this is fantastic stuff. I wish you much fun and slow productivity.

Cal Newport
Thanks, Pete. I’m going to go slowly get some things done.

935: The Five Steps to Winning Every Week with Demir Bentley

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Demir Bentley reveals the five simple steps to successfully plan and execute vastly more satisfying and productive weeks.

You’ll Learn:

  1. Why nobody really plans their week—and how to fix it
  2. The master key to getting ahead of your to-do list
  3. How to transform your calendar into a power tool  

About Demir

Demir Bentley is an executive productivity coach, co-founder of Lifehack Method and WSJ Bestselling author of Winning The Week: How To Plan A Successful Week, Every Week.

He teaches hard-hitting efficiency techniques and proven accountability strategies that have helped clients generate millions in revenue while saving thousands of hours.

In the past eight years, he’s helped more than 70,000 professionals, including executives from Facebook, Google, Uber and PepsiCo, to prevent burnout and create more freedom in their lives.

Resources Mentioned

Demir Bentley Interview Transcript

Pete Mockaitis

Demir, welcome.

Demir Bentley

Good to see you, Pete.

Pete Mockaitis

I am so excited to learn all about Winning the Week and your flavor of productive goodness. And I think I’d like to start with your origin story.

Demir Bentley

Like a comic book.

Pete Mockaitis

Yes, very much, maybe as a radioactive spider but, in your case…

Demir Bentley

It’s close.

Pete Mockaitis

…you’re working at Wall Street, not loving it so much. Take us into the scene.

Demir Bentley

Like a lot of people, I learned to perform for love when I was really young, and I don’t want to get too deep, but I think a lot of people just realized that they just get a little bit more love and attention if they can get those A’s, and if they can exceed. And so, I figured out young, I was like, “Oh, I can do this stuff. I can perform. I can get grades. I can write papers. I can produce things.” And so, I became one of those insecure overachievers who’s really developed a strong juicy core of, “I’m only valuable by what I can do and what I can produce.”

So, obviously, I ended up on Wall Street because that’s where all of the insecure overachievers, the most insecure overachievers go when they really want to prove to themselves that they are somebody. And I really was that “If I can make it here, I can make it anywhere” dreamer. I really felt, “If I could hack it in finance, then maybe that deep hole inside of me would finally truly be filled and I would be somebody.

No, I jest a little bit, but, seriously, there was that juicy core of, “I’ve got to make it in finance.” And I did, I got to a really high level of finance but I did it by working 80 to 100 hours. And my secret sort of sin, or my secret, like, hidden behind-the-scenes was that I was actually really massively unproductive. I just masked that lack of productivity with brute force work and just the deep guilt and shame that kept me coming back to the trough.

And so, I remember thinking, there was an episode where I remember thinking that I was so proud that my boss had come in on the weekend and had seen me there all alone, there was nobody else on the floor, and I was just there. And right after that weekend, he called me, and he said, “You know, this is actually not a good thing. Everybody else can get their work done in 40-50 hours, and you seem to be needing 80 to 90 hours of work to produce what other people are producing in 40-50 hours.”

So, that was my big wakeup call of, like, “Oh, I’ve been wearing this like a badge of pride, like a badge of honor,” the busy badge, I call it. I’ve been awarding myself the busy badge, thinking that I’m just inherently, intrinsically more valuable than other people because I have this ability and this desire to outwork everybody else and come in on nights and weekends, and just realizing that, “Actually, other people saw that as sad and pathetic.”

That didn’t stop me. I wish I could’ve said that that was the moment when I stopped but, actually, I had a health implosion. I was overweight, I was overstressed, I wasn’t sleeping, and I got, like, a mystery illness. After much testing and three surgeries, I was diagnosed with something called salary man sudden death syndrome. It’s not very common in the United States but it’s extremely common in Asia where, otherwise, healthy young person dies from extreme overworking.

And so, although there was no definitive, “You’ve got this condition,” there was a general recognition among my three doctors that if I kept working this hard, I would probably, at some point in the future, die, and that I needed to immediately cut my hours down to 40 hours a week. Now, mind you, I’m doing everything I can to keep my head above water, working 80-100 hours a week, and they’re telling me, “As of next week, you need to bring it down to 40 hours a week.”

And so, that weekend, I talk about a lot in our book, that weekend was this like crisis moment. I felt like my whole world was crashing in. I thought I was going to have to quit my work or I’d certainly get fired. It just felt like there’s just no way that it’s going to happen.

And, yet, there was a series of events that happened over the course of that weekend. I walked in next week, I worked 40 hours, I got everything done in 40 hours, and that was the beginning of this sort of rebirth, this, like, religious awakening that I had, realizing that I suck at this productivity thing, and I realized that so much more was possible. And that was the beginning of my journey in my personal productivity work, and also the beginning of my journey as, ultimately, which is hilariously becoming a productivity coach for other people and showing other people how to have that same transition.

Pete Mockaitis

Wow, this is powerful. You have a chat about productivity, you don’t think it’s going to be life or death but, for you, it literally was.

Demir Bentley

It actually was.

Pete Mockaitis

“Become more productive or die or lose your job.” Like, high stakes stuff. So, I want to dig deep for a moment. You mentioned deep shame there. What were you ashamed of?

Demir Bentley

So, like many people who are unproductive, I’m a very emotional worker. And emotional worker isn’t defined by crying in the corner. That’s not what I’m talking about. Emotional workers are the kind of people that, if they’re feeling it, they can show up in two incredible acts of productivity, incredible feats of productivity, but they can also have incredibly long periods where they can’t motivate themselves, and they’re not feeling it. And in those periods, they can barely bring themselves to lift a pencil. And in those moments, they just feel incredible self-lacerating shame and unworthiness. And they know and think that somebody is going to find them out.

Pete Mockaitis

Well, Demir, lay it on us the way. What were the initial steps you took when you were in the I-can’t-lift-a-pencil mode? And, ultimately, how did you survive by doubling your output per hour, I guess, like cutting your hours in half?

Demir Bentley

The funny thing is what really solved my first tranche of the problem was something that everybody thinks that they know that they should be doing. And I’m going to come back to the word “thinks that they know.” And it’s just planning your week. The problem with this is there’s nothing more dangerous than somebody who thinks that they know something because, then, they approach it with zero curiosity, zero sense that they have anything to learn or anything that they might be doing wrong, and way too much confidence.

And so, we actually ran a survey of 5,000 people, and the survey was only people who manage between five and 50 people, so managers, people who are already very successful, earning a lot. We asked them, “What are the top five things that you can do to be highly productive?” And almost everybody in the top three put, somewhere in the top three put planning their week. So, duh, that’s a duh moment. Almost everybody knows it. Out of 5,000 people, it is common knowledge that you should plan your week.

Then we followed up with the same 5,000 respondents. We said, “Have you planned the last, the four out of the last four weeks?” And out of 5,000 people who had said very confidently, these were people who manage between five and 50 people, making over $100,000, out of those people who confidently said, “Yes, you have to plan your week,” less than 1% of the people had planned their week in the last four weeks.

So, there’s something odd about planning your week. It is something we all know that we should be doing, and less than 1% of us have a consistent practice in doing it. That kicked us off on a sort of curious exploration around why that is. But let me just say, coming back to my story, that borne out of sheer desperation, I looked at my calendar and I did what I call the first planning session of my life, the first real planning session where I took all 40 hours, and I took every task that I needed to get done, and I allocated it a spot in that 40 hours.

And every single 30-minute increment had to fight for its life to be on my calendar. That was the very first real planning session I had. And, lo, and behold, it went from spinning my wheels at 80 hours a week to actually getting everything done 40 hours a week. And so, I will say that my rebirth, my sort of aha moment came a lot earlier than the framework that I built around it. I think I spent a lot of years trying to understand, “What happened to me? What went right? What was the difference? What changed?”

When I finally got that through the course of my coaching, I was able to sort of boil it down into the winning-week method. And now we have a framework where we can explain to people. But, at the time I realized that it was just me being desperate. And in my desperation, I realized “I’ve only got so much time. I need to be excellent with that time.”

Pete Mockaitis

Okay. And so then, you were putting individual tasks onto specific pieces of time, like, “Thursday 4:00 p.m., I answer my emails,” or whatever the thing is. So, it went there, scheduled, appointment style.

Demir Bentley

It’s called calendarization. It’s the idea that you take all of your tasks and actually put it on the calendar. And most people stop short of this. I almost say it, like, calendarization is when Pinocchio becomes a real boy, that’s the magic moment. If you’ve done all of your planning, meaning you’ve reviewed your calendar, and looked at your priorities, and looked at your task list, but you do not take your task and put them in a specific slot in the calendar, what’s happened is you’ve done all of the necessary work but Pinocchio cannot become a real boy now.

It is when you take your tasks and put them on your calendar that you truly become a plan because, now you’re actually allocating. By stopping short, we stay in the realm of wishful thinking. Wishful thinking is sort of we’ve got all of the things that I want to do over here in this bucket, and I’ve got my available time in this bucket, and I’m just sort of vaguely in a wishful thinking way, hoping that by the end of the week they’ll match up.

But by not actualizing them, by not marrying those two markets together, then we never really meet base reality. And this is where a lot of people’s plans fail, and that’s why a lot of people say, “Oh, planning doesn’t work for me,” and that’s why a lot of people stop planning after initial tentative events to plan. It’s because, the truth is, is that the way most people plan doesn’t result in a holy-crap moment where they just kill it in their week, and so they stop doing it because they didn’t feel that magic, they didn’t feel the lift.

You know, the moment in the Tesla when somebody hits the accelerator, and your face sort of gets plastered to the back, and you go, “Oh, that’s power.” That’s what you want to feel in a productivity technique when you try it, to be like, “Oh, this works.”

Pete Mockaitis

I love that, the planning gives you a holy-crap moment, like, “Whoa, this works.” And I feel that way about most interventions that I assess. It’s like, “Hey, is that supplement doing anything for you?” “Well, I mean, I think it might potentially be making a little bit of a difference.” More and more, I don’t really want to mess with much of that in my life. It’s like I want to be like, “Holy schmokes, I feel the difference with fish oil and saffron.” And the rest, I’m like, “Meh, maybe.”

And so, that’s that. Likewise, I think it was Taylor Jacobson, shoutout to Taylor, over at Focusmate.com, which is awesome, who put us in touch, and that’s how I felt about that tool, which is online accountability partners on demand. Very cool. It’s like, “Holy crap, this is making it happen. Wow!” And there’s no maybe squinting about it.

And you’re telling me we can have that experience from the act of planning our week, and if we haven’t felt it, we ain’t been doing it right. Is that fair to say, Demir?

Demir Bentley

Absolutely. People say, “How do you know you’re in love?” It’s like, you know because it hits you like a sledgehammer. “How do I know that my planning worked?” You know because it hits you like a sledgehammer. You have no doubt in your mind that that week, out of 100,000 variations of that week, different alternate realities, imagine 100,000 different realities of the last past week where there were 100,000 versions of you playing out the same scenario, you can look at yourself in the mirror, and say, “That was the best that I could’ve done. In any alternate reality, this one was the best that I could’ve done. I met my challenges with as much resourcefulness and willpower and ingenuity and leverage as I possibly could,” and you just know it.

Pete Mockaitis

Love it. I love it. All right. Well, Demir, lay it on us, calendarization is important. How do we pull this off? How do we, in fact, win the week?

Demir Bentley

So, I’m just going to start with just a tiny bit of setup, which is that a lot of people assume, and I think I totally understand why they would, that if you’re doing a technique right, that it’s going to feel good. Let me just start by foregrounding this that when you’re doing planning right, there is a base amount of fear, anxiety, and stress that is just table stakes.

If you’re doing any planning, and you’re feeling fear, stress, anxiety, you’re doing it right because the essence of planning is pulling forward all of the unmade decisions, worries, potential things that could go wrong in the next seven or 30 days, and you’re pulling that into a 30-minute moment. How do you think that 30 minutes is going to feel? Not amazing.

So, first, let’s let go when we’re going into planning, this idea that it needs to feel good, or that, “I’m doing it wrong if I’m feeling fear, stress, or anxiety.” No, that is the tradeoff. You’re taking a slap in the face on Friday instead of a punch in the teeth on Wednesday.

Pete Mockaitis

Okay, Demir, it’s not going to be one of those Instagram-worthy situations where I’ve got my latte and my multicolored Post-Its, and I’m crafting a beautiful visual of what’s going to happen in my week or month. That’s not what it’s like?

Demir Bentley

So, what we did was we condensed it down into five simple steps. So, step one, actually, I’ll get a little clever. In our book, we talk about step zero. The reason we called it step zero, not to annoy people, is because you only have to do this step once and you’ll never have to do it again. And that is create an environment for your planning that is a reward in and of itself.

My wife and I, we go to a little brunch place, a little like French café experience. It’s like our date. Call us a nerd if you want because we probably deserve it, but this is like our date afternoon. We have babysitting, we go down to this French café, we spend 30 minutes planning, and then we’ll spend the rest of the time, two and a half hours, just connecting because there’s no better way to connect with your spouse than to get resolution on the unresolved things in your relationship.

So, step zero, do this once, you’ll never have to do it again.

On Friday night, go to a wine bar. Saturday morning, go to a café. Create an environment for your planning that you actually look forward to, that’s a reward in and of itself, and that will have help tamp down on that avoidance that people get around planning because you’ll think to yourself, “Oh, this is a treat. I’m making it a treat for myself.” Okay, that’s step zero.

Step one, and this is something you do every single week, learn a lesson from the past week, five minutes. Take five minutes, don’t learn five lessons, not 500 lessons, just skim the cherry right off the top of the cake, “If I had to find one lesson that I could derive from the past week, something that I did really well, something that I didn’t do well, what would that be?” And fold that into the next week, “How can I apply that in the next week?”

This is what we call a learning loop, and this is how people get better, whether it comes to flying an airplane, or playing sports, or playing music. They all have positive learning loops built into their practice where they’re not just practicing, they’re doing what we call positive intentional practice, where they’re focused on, “What did I do well?” or, “What did I do wrong? And how can I use that to get better?” And just five minutes, that’s it. Not 50, not two hours.

Take five minutes and just observe to yourself, one thing you did right that you want to keep doing, that you should do more this week; one thing that you did wrong that you should maybe correct and learn from this week, and then move on, and roll that into your planning. And that might sound small but do that 100 times, 200 times, and, all of a sudden, you’re getting 1% better in an accumulated sort of exponential way.

Pete Mockaitis

And so, the learning could be anything from, “Hey, when I worked in the morning, I felt very energized. Maybe I should try that again.” Like, that kind of a thing?

Demir Bentley

Perfect.

Pete Mockaitis

So, that’s our first step. What’s number two?

Demir Bentley

Step two, choose a leveraged priority, because the number one mistake people make is they’ll either choose too many priorities, which is an oxymoron because the word priority literally means the one thing above all other things. So, when somebody says to you, “I have five priorities.” It’s like you’re misunderstanding what the word priority means. Priority means the order: one, two, three, four, five. So, people tend to conflate multiple priorities instead of having one. Or, they choose a priority that has no leverage in it.

So, I just want to talk about that for a moment. When we choose something that has no leverage, it means that we have to expend a lot of effort to do that thing but it is no easier to do it the next time that we do it. And when we apply leverage to something, we’re doing it in such a way that every time we come back to do that thing, we have made it at least 1% easier to do it the next time, sometimes 50%, sometimes 80%.

And so, leverage is just walking through your world in such a way as you can say, “How do I choose a priority such that the thing that I do this week does not just benefit me this week but it makes every week in the future easier?” This comes from the book The ONE Thing by Gary Keller and Jay Papasan.

Pete Mockaitis
I was going to say, that rings a bell.

Demir Bentley

Yeah, shoutout to Gary Keller and Jay Papasan. I’ve read that book 12 times. It’s a productivity bible for me. If you haven’t read it, and you’re out there listening, it’s a must read.

Pete Mockaitis

It is amazing. Jay has been on the show, and it’s one of my all-time faves.

Demir Bentley

It’s the ultimate. So, ultimately, it’s really just about as you’re going through your planning, let’s choose a leveraged priority for the week, because, ultimately, you don’t have to be perfect. I know this sounds crazy, people think, “I can only be great at productivity if I’m perfect.” No, if you are in there doing things with leverage every single week, everybody else is going linear and you’re going exponential.

And all it takes, and I’ve seen those with clients again and again and again, is when I get them doing that for six weeks, there’s something magic that happens between week four and week six, where the cumulative effect of four weeks of doing something that makes the future easy, by the time they get to week four, five, or six, they start seeing that loop coming back around, and start saying, “Wow, there’s something different about my life now. Things are feeling easier.”

Pete Mockaitis

And can you give us a couple examples of the sorts of things that have reverberating echoing effects for many weeks to come?

Demir Bentley

Yes, so it could be really anything but I’ll just give you a stupid example. So, when we first had our first kid, I had one of those overly-fancy coffee machines where it took, like, 30 minutes to make a cup of coffee, but now we have a newborn, and I just realized, “This is crazy. It’s taking me 30 minutes to make a cup of coffee. If I make two cups of coffee a day, that’s effectively an hour a day that I’m losing to simply getting caffeine into my system.”

So, I basically said, like, “No matter how much I love this coffee, it’s not worth an hour of my day.” I went ahead and created the simplest coffee station. I consolidated everything down. That whole moment, that aha moment, took me 15 minutes. Now, today, it takes me 10 minutes from the moment I walk into the kitchen, to the moment I walk out, it’s 10 minutes to make a cup of coffee. So, what does that mean?

Pete Mockaitis

Well, now, Demir, if I may. What are we talking? Are we talking about a drip? Are we talking about an AeroPress? How was this done?

Demir Bentley

It’s just a button. Slide the thing in.

Pete Mockaitis

Coffee maker button?

Demir Bentley

Like a Nespresso.

Pete Mockaitis

All right, a Nespresso machine.

Demir Bentley

An espresso, slide in the pod, hit the button. There’s a little time for warmup, I’ve got the coffee foamer, and it’s just 10 minutes, in and out, and I’ve got a delicious-tasting coffee that’s 90% as good as the one I made in half an hour but it comes out in 10 minutes or less. And I’m talking about I could really, if I was rushing to it in five or seven minutes, but I’m being generous saying it was 10.

So, think about this in terms of leverage. I did something once that cost me 15 minutes to do in terms of setup. Then every single day now, instead of spending an hour, I’m spending 20 minutes. That means there’s 40 minutes a day, ad infinitum, that I get back into my life.

Pete Mockaitis
Okay. Cool. All right. So, we have steps one and two. What’s three?

Demir Bentley

So, three is interrogate your calendar. Have you ever heard the term review your calendar? “Oh, do a calendar review.” I find that to be so gutless and passive. Review, like, “Oh, okay, I glanced at it, right?” The truth is your calendar is a slippery bastard. There’s so much in there that could screw you up but it doesn’t jump out at you, and say, “Hey, give me a watchout for this, a watchout for this.” It’s there but it’s just sort of buried.

So, I like to think about your calendar, you need to put on the witness stand, and, like one of those procedural shows, or a witness in a movie, you got to sweat your calendar. You got to get in there. You got to hit it from the left, hit it from the right, try to trick it, try to catch it. And so, a lot of people will do a passive calendar review and there are still a lot of landmines hidden in their calendar. It could be that meeting that got rescheduled from noon to 9:00 and you just missed it, but now it’s going to blow you up next week, you’re going to forget it, it’s going to make you look bad.

It could be that you volunteer to take your kids and drive your kids and their friends to a volleyball game, but you forgot about it, you didn’t put in your calendar, another landmine. And when these landmines blow up, it costs us huge amounts of stress and anxiety, you lose social credibility and capital, and you end paying a higher price in terms of your cognitive energy and your actual time to try to fix it in the moment. That’s what I call a landmine.

So, you need to get into your calendar and sweat out those landmines. You need to pour it out and really find them. And the reason why is you need a calendar that you trust more than your instinct. To me, when I look at my calendar now, a lot of people will say, “Well, Demir, you’re supposed to be here next week.” I’m like, “I don’t think so.” And they’ll say, “Your calendar says so.” And I’ll say, “Then you’re absolutely right,” because that’s the kind of effort and attention I give to my calendar. I want my calendar to be the single source of truth in my life when it comes to my time availability and my time supply.

Pete Mockaitis

Okay. Noted.

Pete Mockaitis

So, when we interrogate it, we’re really looking at each thing and ensuring that it’s true, that it’s accurate, it belongs there, and it’s worth the time that you have put for it to be there. That’s what you mean by interrogate?

Demir Bentley

Yeah, I have a series of like nine questions, “What should be there that isn’t? What’s there that shouldn’t be?” because a lot of times people will decide they’re not going to go to that party but they don’t get it off their calendar. It’s like, “Get it off your calendar.” If it’s not actually going to happen, get it off. They also forget the things around the calendar appointment, like if you’re going to go to the dentist, you need to get out the door, get prepared, drive, anticipate traffic. Then you need to get back.

So, typically, people’s calendar is more of a sketch of their time supply than it is a detailed accounting of exactly where their time is going to need to get allocated. I’m not saying there’s no place for blanks in your calendar. In fact, that’s where we’re going to go next when we actually look at our task list, that’s our time demands. So, once we do this, you should end with a calendar that still has some open spots but you feel very confident, “These are the hard-edge commitments that I have in my calendar, and here’s the time that I have available.” This is what I call your time supply.

If you’re running a basic business, if you don’t have a really good sense of supply and demand, like, “How much inventory do I have to sell this week?” If you don’t know how much inventory, you’re liable to oversell your inventory, which is what people do all the time with their time. They commit to too many things and think that they’ve got more time to get thing done, which means they overcommit to doing to many things, which means that they’re either going to have to work nights or weekends to get it all done, or they’re going to suffer a loss of credibility when they invariably have to come back to people, and say, “I’m sorry, I can’t do that for you.”

Pete Mockaitis

Understood.

Demir Bentley

Got it. So, time supply and time demand. So, we just took care of time supply. Go over to the demands. Where do your time-demands live? Look at your task list. And that was weird, like when I call your calendar your time supply, and I call your task list time demands, people have to sort of scratch their head, and be like, “Oh, yeah, I guess I’ve never really thought about it that way.”

Your calendar is not just your calendar. It is a tool to help you understand your supply of time, and your task list is really there to help you understand the demands on your time. These are the bids for your time. And the problem is you don’t have enough supply to meet all the demand. So, what you’re really doing when you’re going with your task list is you’re saying, “What are the best highest quality bids?”

So, if I was selling truffles, I used this example in my book, if you’re selling truffles, there’s always fewer truffles in the world than there are demand for truffles. There’s only the small finite supply. And so, this is really elaborate system for allocating truffles in a way where the highest bidder always gets the truffle. And so, that’s what we need to see our time as, as this highly perishable, incredibly finite thing that needs to go only to the highest bidder. And if you don’t send it to the highest bidder, what’s happening is you’re leaving money on the table and under-utilizing that precious resource.

So, we go to your task list for five minutes, and what I really want you to do is the same thing that you did on your calendar, get rid of the stupid stuff. Come on now. Let’s get rid of all that stuff that you know doesn’t really need to happen. Let’s identify that really high-value leveraged stuff. Let’s get into places where something might be urgent but not important, and let’s start to put it in an order where it’s going from the order of most leverage to least leverage, or at least most urgent to least urgent so that we can really understand and look at that top 20% which is our highest-value bids for our time.

I’ll say one more thing here, if I can plug it in. The nature of the modern world is that you will never, from now on to the day that you die, ever finish the weekend that we can get everything done that you planned for the week. I defy you to have a week, because human nature is that, even if you had one week where you got it all done, next week you would increase the amount that you thought you could get done, and you would, thereby, get back into the cycle.

We are greedy and lusty for life. We want more. We want to do more. We want to live more. We want to be more. It’s great. There’s nothing wrong with it, but you need to understand that the definition of winning your week is not that everything got done this week. The definition of winning your week is that, “I did the right things at the right time in the order of leverage and the right level of completion.” That, my friends, is what David Allen calls the martial art of getting things done.

Let me say it one more time because I said it really quick. It’s doing the right thing at the right time to the right level of completion with the right degree of leverage. If you can get those things right, you can look back and say to that bottom 80% of your task list that didn’t get done, “I’m fine with that. I can live with it because I know I did the right things in the right order to the right level of completion.”

Pete Mockaitis

Beautiful. And the next step?

Demir Bentley

Yeah, and that’s the final step, which is marry the two together. You’ve got this beautiful market, you’ve got time supply, you’ve got time demands, but if you don’t actually marry them together on your calendar, you’ve stopped before Pinocchio becomes a real boy. So, the idea now is to take that top 20% on your task list and actually take it over onto your calendar and give everything a specific time that you’re going to do it. Does that mean it’s written in stone, like the tablets from Moses of old, and God Himself cannot change it? No, it’s just an initial sketch of a plan.

But here’s what happens, and here’s what’s so beautiful. When you start pulling things over, I don’t have one client who will not come back to me after pulling things over and calendarizing, and saying, “Wow, I really don’t have as much time as I thought I had.” But we tend to live in this world of wishful thinking, and there’s nothing that will banish wishful thinking around your calendar and around your capabilities quicker than actually saying, like, “How much of this will fit?” Right?

My grandma used to have a saying, a very religious woman, very pious, so this is the only cussing she ever did, she said, “It’s like 10 pounds of shit in a five-pound bag.” She had this analogy, “That’s like 10 pounds of shit in a five-pound bag.” And what I thought was funny of that was this idea that it’s just you’re trying to put more in here than can possibly fit, and it’s just exploding out. And this is the case with a lot of people’s week, is that by not marrying the two together, they have this idea that they’re going to fit more in than they can. And what ends up happening is that they got a lot of you-know-what sitting all over the place.

Pete Mockaitis

Yeah, that’s graphic, and it makes the point because you are. You’re going to have a big old mess on your hands and it will be…and something is going to get hurt. Maybe it’s your credibility, maybe it’s your sleep, maybe it is your patience with your loved ones. Something is going to get damaged when you have too much stuff that just doesn’t fit with your time supply available.

Demir Bentley

We’re in a crisis right now of commitment debt. This is something people don’t think about. We know about financial debt. We know about the crisis of financial where people are borrowing against their credit card, they’re not really living within their means, but it’s happening so slowly and so insidiously that it’s just building and building, and for a while they’re robbing Peter to pay Paul, and everything is fine, until it’s not fine.

And we’re actually experiencing the same thing with commitment debt, meaning every week for 10 years, we’re just overcommitting a little bit, and we’re just taking what we didn’t do this week, and we’re trying to push it into next week, and we’re robbing Peter to pay Paul, and we’re shifting things around and trying to, oh, apologize here and come up late with some miraculous productivity here.

But you run that for a decade or two decades and there’s a point at which you can’t rob Peter to pay Paul anymore, the whole Ponzi scheme comes falling down, and you realize, “I am way overcommitted,” and that comes from not being clearly anchored in living within your means. And it’s not just that you can live within your means financially, you can live within your means from a commitment perspective, “Am I actually making commitments that I have enough or more than enough time to satisfy?” And I would tell you most of my clients come to me and they’re in severe amounts of commitment debt.

Pete Mockaitis

Okay. Understood. And what’s our next step?

Demir Bentley

Yeah, that’s it. You allocate time supply to time demand, and you meet those two together. Now you’ve got a plan for the week that actually matches base reality. And I can tell you, do that the first week, you’re going to experience something different. And it’s not because there’s anything so amazing or magical about our coaching. It’s just because you’ve covered every single important base.

You have looked at your time supply, you’ve looked at your time demand, you’ve understood where your leveraged priority is, so you have what I call the holy trinity of planning your week. Look at your time supply, your time demand, and your priorities. You’ve covered off on each of those bases, that is better than 99.9% of people do. Most people don’t plan the week at all. The people who do plan the week, they’ll do maybe one of those of three, two of those three. It’s incredibly rare that you’ll see somebody do all three of those and make sure that it fits into the allocated time in the calendar.

The funny thing is it feels magical when you do it. It feels like one of those aha moments where it becomes advanced common sense where once you do it, you’re like, “Well, I can’t really unthink this, I can’t really unlearn this because it has to be like this. It just makes sense.” But then you look back, and say, “Yeah, well, it can’t have made that much sense because I wasn’t doing it for years.” So, it’s just a simple way to cover off on every base.

When most people can actually just plan their week correctly in the right way, they’re going to see that they’re winning more weeks.

And just like investing, you don’t have to win on every investment. You just have to win more investments than you lose to make money. Well, you don’t have to win every week. You just have to win more than you lose with leverage to see yourself in a much better position next year than you are this year.

Pete Mockaitis

And winning, so we do the planning, what is winning, just like executing most of the plan, or how do we define winning?

Demir Bentley

Well, that’s why I defined the leveraged priority. To me, winning is if I can achieve my leveraged priority, I have won for the week, and most of the time, I can do that by Tuesday. So, if I can do something every single week that has leverage on it, I’ve won because I’ve done something this week that makes next week and every week thereafter easier.

Now, that’s probably 5% of my time. Five percent of my working hours is my leveraged priority, not even close to the majority. Again, perfection not needed, not required here. You don’t need to spend 50% of your time working on a leveraged priority. If you could just allocate 5% of your working hours to do something that has a little bit of leverage in it, that means that you’re planting a seed every single week that’s going to benefit all the weeks thereafter.

So, that, to me, is the definition of winning. If I can get my leveraged priority done every week, I’ve won. And then, thereafter, I’m just scoring extra credit bonus points.

To win the week is not, “I’ve got everything done.” Win the week is, “I’ve got the big thing done and I made the biggest possible dent I could in the rest.”

Pete Mockaitis

Beautiful. Demir, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Demir Bentley

I would just say that I wrote the book Winning the Week because I think that we need to be more humane in our conception of how we treat ourselves in the productivity world. There’s a strong undercurrent right now of, like, “Be more disciplined. Be more excellent. Get up at 4:00. Do all of the things. Do the perfect habits. Do everything right. Don’t lose a day.”

And I just feel like that doesn’t match up with the thousands and thousands and thousands of clients I’ve had. Human beings have good days, we have bad days. It’s a mix. Every day in every week, we’re sort of meeting ourselves at a different level. Sometimes we wake up, we’ve got more energy, more desire to do something. Sometimes a little bit less.

The thing I love about playing the game in a week-long increment is you can have a bad day or two and still win the week. And this is sort of the message I want to get out to people. You can feel that you got your butt kicked five days out of the week, and yet still look back and look at what you did that week, and realize that you won the week.

So, I don’t want people trying to connect themselves to this idea that, “I need to be perfect every day. I need to crush it every day.” Actually, no, you can get your butt kicked five days out of the week. And if you did it with the right level of intention, and you chose the right leveraged points, you can actually look back on a week that you really felt like took you to the cleaners, and realize that you won the week.

Pete Mockaitis

Fantastic. Well, now can you tell us a favorite quote, something you find inspiring?

Demir Bentley

We came up with The ONE Thing when we were talking earlier. I think that book is a productivity bible. There are so many quotes and amazing things from that book. So, although I don’t have a quote, I’ll put in everything in the book The ONE Thing. That book is just amazing.

Pete Mockaitis

All right. And a favorite study or experiment or bit of research?

Demir Bentley

I think the best one, his name is Czechoslovakian. It’s so hard. It’s Czecemensky or Zemensky or something like that.

Pete Mockaitis

Mihaly Csikszentmihalyi?

Demir Bentley

There we go. Thank you, yeah. He did a study that, basically, said, it proved that when we walk away from a task that’s incomplete, our brain continues trying to problem-solve around it, unless, and this was the important part of the study that really intrigued me, unless you actually gave yourself a breadcrumb trail to come back to it. So, that when we actually terminated something midway, meaning we hadn’t completed it, if we actually created a specific plan for when we were going to come back to it, and what we were going to do when we came back to it, they found that your brain actually didn’t spin around it.

I think the reason I love that so much is because the truth is that we still have to live as human beings in the midst of our productivity journey. There’s always going to be moments where you’re deep in the middle of something, you’re knee-deep in it, and you need to step away, whether that’s the weekend where we all have to step away every five days, or whether it’s a crisis in your personal life and you need to step away from something.

I think there’s something so beautiful about being able to sort of recognize, “If I don’t give myself a specific time and plan when I’m going to come back to this, I’m going to be spinning on it and burning a lot of cognitive energy that’s going to keep me from enjoying my weekend, that’s going to keep me from being present in this moment where I need to be present. But if I actually just say, ‘This is the plan, and this is where I’m coming back to it,’ I can actually put it down and know that my brain isn’t burning and losing cognitive energy as I’m facing this thing that I need to face in my personal life.”

Pete Mockaitis

All right. And a favorite tool?

Demir Bentley

I think my favorite tool is Asana. And the reason my favorite tool is Asana, or choose your flavor, it could be Monday.com, is because I think it represents a paradigm shift in how we think about productivity and communication, and that’s a different podcast. But I think Asana is more than a technology. I think it’s a paradigm shift.

Pete Mockaitis

Okay. And is there a key nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

Demir Bentley

I say all the time, I say perfection not required.

Pete Mockaitis

All right. Thank you. If folks want to learn more or get in touch, where would you point them?

Demir Bentley

Yeah, check us out at WinningTheWeek.com or you can check us out at LifeHackMethod.com. That points to over our different socials, and we’re everywhere. We’re on Insta, and we’re on YouTube. It’s got some cool trainings. So, if you want to sample a little of the goods, we’ve got a lot of free trainings on YouTube and different places you can check us out.

Pete Mockaitis

All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Demir Bentley

Yeah, I’ll just say do less than you think. Just like working out, people think, “I got to get in the gym. I’ve got to become this warrior. I’m going to lose all this weight.” And, really, what you should be doing is getting out and getting up to 10,000 steps. The difference between 7,000 steps and 10,000 steps is huge when it comes to your health. And the difference between planning your week for 30 minutes versus not is tremendous in your productivity.

So, stop trying to be a weekend warrior, and get in there, and be Rambo, and just blow the competition away, and start thinking about really, really small things that can have huge disproportion effects for your productivity.

Pete Mockaitis

Fantastic. Demir, this is awesome. I wish you much winning of many weeks.

Demir Bentley

Thank you so much. It’s a pleasure, man.