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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.