This Podcast Will Help You Flourish At Work

Each week, I grill thought-leaders and results-getters to discover specific, actionable insights that boost work performance.

937: Speaking the Hidden Language of Connection with Charles Duhigg

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Charles Duhigg shares the simple secret that helps you build powerful connections with anyone.

You’ll Learn:

  1. What supercommunicators know that others don’t 
  2. How to ask questions that deepen and enrich relationships 
  3. How one sentence can dramatically ease workplace conflict 

About Charles

Charles Duhigg is a Pulitzer Prize–winning investigative journalist and the author of The Power of Habit and Smarter Faster Better. A graduate of Harvard Business School and Yale College, he is a winner of the National Academies of Sciences, National Journalism, and George Polk awards. He writes for The New Yorker and other publications, was previously a senior editor at The New York Times, and occasionally hosts the podcast How To!

Resources Mentioned

Charles Duhigg Interview Transcript

Pete Mockaitis

Charles, welcome to How to be Awesome at Your Job.

Charles Duhigg

Thanks for having me on. I appreciate it.

Pete Mockaitis

Well, I’m excited to be chatting. I read your prior book The Power of Habit many years ago, and you got a fresh one, Supercommunicators coming out here. I can’t wait to dig into your wisdom. But first, I got to hear, so in addition to being a Pulitzer Prize-winning investigative journalist and graduating from impressive places, you’ve also served as bike messenger. Tell us this tale.

Charles Duhigg

Yeah, so before I went to business school, I was living in San Francisco and didn’t have a real job. And so, I was like, “You know what I could do, I could become a bike messenger.” And this was back in the late ‘90s when bike messengers were super cool. And so, I signed up for it, and I lasted, literally, one day. I actually got pneumonia from being a bike messenger for one day because San Francisco, of course, was filled with hills, and I was not physically ready to be a bike messenger.

It was interesting though because I would say probably about half, I mean, I did spend time with the other bike messengers, and probably about half of them were more active drug users and had some real serious health issues going on. And I do remember there was this one guy, I took the bus over with him in the morning, and we were driving over the bridge on the way to San Francisco, past the IKEA, and someone was like, “I hate IKEA. IKEA is corporate awfulness.”

And he’s like, “No, bro, IKEA is the best. They got that play area for kids. Me and the wife sometimes will just bring our daughter there, and then we just take off for like six or seven hours, man. It’s amazing.” And I was like, “Okay, this is bike messenger life.”

Pete Mockaitis

Bike messenger life. Well, I’m thinking you have to be in great shape. If they’re using drugs, which drugs are we talking about?

Charles Duhigg

I don’t know. I did not really ask. There seemed to be a lot of conversation about the various drugs, which, of course, I knew nothing about. No, they’re in great shape. Like, if you ride your bike all day long all over San Francisco, you’re in pretty good shape. The other thing is I just didn’t know how to navigate San Francisco, and it’s a hard city. There are ways around the hills and I knew zero of them.

Pete Mockaitis

All right. Well, you lived to tell the tale, and I would be most terrified of getting hit by cars.

Charles Duhigg

Yes, I was terrified of a lot of things. That was definitely one of them.

Pete Mockaitis
But if you’ve got the cool bag, the bike messenger bags are the coolest. Like, the seatbelt buckle and that material.

Charles Duhigg

And at the end of that one day that I spent as a bike messenger, when I was on the bike coming home, I felt like the coolest thing on earth, I was like, “Yeah, I’m a bike messenger. Just, like, messaging stuff,” and then I got pneumonia.

Pete Mockaitis
Mercy. Well, I’m glad you’ve recovered and I’m glad we’re here now chatting about Supercommunicators. It’s a great title and a great premise, and you were something of a supercommunicator in your world, although I think you’ll tell us times that maybe that was not as much the case. But before we get into all that, can you maybe kick us off with anything particularly startling or surprising that you discovered as you’re researching and putting this together?

Charles Duhigg

Yeah, absolutely. This has really changed how I communicate. And you mentioned that I’m a supercommunicator. Actually, the truth is all of us are supercommunicators at various times. We all sometimes walk into the meeting and we know exactly the right thing to say, or a friend calls and they’re upset, we know exactly how to make them feel better.

And the point is that, actually, we all have this talent. In fact, it’s actually hardwired into our brains, it’s how we evolved but sometimes we can forget it. And so, the goal of this book is actually to remind people or teach them how to think about communication so that it’s easier to remember what to do to be a supercommunicator.

And, for me, this really started when I was talking to these marriage therapists, and one of them described the situation that I’ve had a lot in my own life, which is sometimes I would come home from work after a long and hard day, and I would start complaining to my wife. I’d be like, “My boss is a jerk, and my coworkers don’t appreciate me, and blah, blah, blah.” And my wife, very, very wisely, would offer some practical advice. She’d say something like, “Why don’t you take your boss out to lunch, and you guys can get to know each other better?”

And instead of hearing what she was saying, I, of course, would like explode, and be like, “Why aren’t you supporting me? I want you to be outraged on my behalf.” And so, when I was talking to these therapists, I was like, “What is going on here? We’re both bringing sort of our best selves in this conversation, we’re both bringing good intentions.”

And they said, “Look,” and this is the big insight of the core of the book. They said, “Look, most of us think about discussions as just being one thing, it’s a discussion about one topic but that’s totally wrong. Every discussion is actually made up of multiple kinds of conversations.” And, in particular, there’s these three buckets that most conversations fall into.

There are practical conversations, “Why don’t you take your boss out to lunch? Here’s a problem, let’s solve it. We need to make a plan for how we’re going to get to my mom’s for vacation.” Then there are emotional conversations. And in an emotional conversation, I do not want you to solve my problem. I want you, literally, to just kind of give me encouragement and validate how I’m feeling.

And then, finally, there’s also social conversations. And social conversations are about how we relate to each other, how other people see us, how sort of we exist within society. And, oftentimes, when we’re having a conversation, we will move, or having a discussion, we’ll move from conversation to conversation. But if we’re not having the same kind of conversation at the same moment, we really won’t be able to connect. And that was what’s happening.

Pete Mockaitis

We, meaning, like, party A and party B, both on the same page, the same style and level of conversation.

Charles Duhigg

Exactly. When I came home and I was upset, I was having an emotional conversation and my wife replied with a practical conversation, and so I could not hear what she was saying and she got frustrated by what I was saying because we weren’t, what’s known within psychology as the matching principle, we weren’t having the same kind of conversation at the same moment.

Pete Mockaitis

Understood. And so, when you say, to complexify, often the conversation is not just one, it’s multiples.

Charles Duhigg

Oh, absolutely.

Pete Mockaitis

Sort of simultaneously, or weaving back and forth, or all those things.

Charles Duhigg

Yeah, absolutely. You’re usually moving from emotional conversation, to practical conversation, to social conversation, and then back to emotional. And what’s important is just that everyone who’s in that conversation, whether it’s two people or many people, that we look for the clues about what kind of conversation is happening, and we match others, and we invite them to match us.

So, when someone says something really emotional and they’re sending us a signal about, like, “Look, we need to talk about how we feel. This is not about solving the problem. This is about airing out why the problem exists,” our ability to pick up on that and then match them, and then, after that, invite them to move to solutions, to move to a practical conversation, that’s really powerful. That’s how you connect with, really, anyone.

Pete Mockaitis

Certainly. Well, that sounds powerful. I suppose, if I may be so bold, can you prove it? Can you tell me, really, what’s at stake or what’s unlocked if we upgrade our super communication frequency from once in a while when I’m on fire to fairly regularly?

Charles Duhigg

It’s hugely powerful. Think about at work how many conversations you have that if the conversation goes well, things get so much better, and if the conversation does not go well, things don’t get better. Like, let me ask you. So, just think about the last week, what’s the most meaningful conversation you had in the last week?

Pete Mockaitis

Well, I’m in the process of buying a company, so we had a meeting with the buyer-seller accountants, so I think that seemed important from just a dollars and cents perspective.

Charles Duhigg

That seems really meaningful. And I’m sure that that’s like taking up a bunch. Now, my guess is that a lot of those conversations are practical, but buying a company also brings up a lot of emotions. Like, it can be scary, it can be exciting, you can have partners who are saying, “I think we’re moving too fast,” or, “We’re not moving fast enough.”

A big transaction like that, have you found that some of the conversations you’ve had with your spouse, or with your partners, or anyone else that they’ve been emotional instead of just purely practical?

Pete Mockaitis

They have been emotional in that you see emotions are there but it hasn’t been super intensely emotional in either way.

Charles Duhigg

That’s fine.

Pete Mockaitis

Well, maybe between my partner and I, like, “Oh wow! This will be such a cool opportunity if we did this, or this, or this, or this. This will unlock this,” so there’s that. But never have we been super intensely emotional in terms of, like, angry, or, “You’re screwing me over,” which is great. None of us feel that.

Charles Duhigg

Which is great. And, by the way, most emotional conversations are not super emotional, they’re not super intense. We all have those conversations sometimes, and knowing how to navigate them is really important but most of the conversations we have every day are at a lower temperature, and that’s fantastic.

But if your business partner came, and he’s like, “I’m so excited. This is going to be amazing,” and you didn’t engage with that excitement at all, you didn’t sort of invite him to share that excitement, it’d be hard going forward. And then if you came in super practical-minded, and you’re like, “Look, I don’t care how excited you are, we got to figure out the dollars and cents on this,” and all he talked about was like the excitement and how he feels, it’d be super frustrating for you.

But just helping us recognize what kind of conversation is happening, that helps us figure out how to communicate.

Pete Mockaitis

It does. And what’s intriguing, though, is the interconnectedness. Like, let’s say, “I’m super excited about this specific possibility of integrating some staff here over there,” and they go, “Oh.” And so then, in some ways, the optimal response, for me at least in that moment, is not so much, “Yeah, that’s really cool,” although that’s not bad. I mean, I wouldn’t shun that, I’ll take it.

But I think, for me, I guess maybe next level stuff is hitting both, which is like, “Oh, my gosh, that is really exciting, and it will be so easy to just do this.” It’s like we hit the emotion and extended the practical at the same time.

Charles Duhigg

Exactly. So, the book is filled with stories of sort of supercommunicators who are just normal people who sort of figure something out about a particular conversation. And one of them is about the CIA officer in his early 30s, he’s just been hired, and his job is to go recruit spies overseas. So, they send them to Europe, and they’re like, “Come back with some spies.”

And this guy, his name is Jim Lawler, he’s a great guy, he spends, like, a year trying and just strikes out again and again and again, and he is terrible at this job. He can’t make a real connection with anyone he’s trying to recruit. And then he meets this woman Yasmin who, she’s in town, she works in foreign ministry in her home country in the Middle East, she’s like the perfect, perfect candidate.

And he goes, and he “bumps” into her at lunch, and then invites her to lunch next day, tells her he’s an oil speculator, and eventually they get to know each other, and they kind of start investing in each other a little bit. And then, at one point, he’s like, “Look, I lied to you. I’m not an oil speculator. I work for the Central Intelligence Agency. Will you help us by telling us what’s going on inside your ministry because we want the same things you do? We want to stop the repression of women. We want to bring down this theocracy that’s ruling your country.”

And she just looks at him and starts crying, and she’s like, “They kill people for that,” and she just bolts out. And so, this guy, Jim Lawler, he’s told his bosses already that he’s recruiting Yasmin, and when he goes and he tells them, like, “I tried to close the deal and she ran away,” his boss was like, “You’re going to get fired. You’ve been here a year, she’s your only possible recruitment, and you just screwed it up.”

So, Lawler knows that he has one more opportunity, one more meal that he can ask Yasmin to have with him. And so, he takes her to the meal, and she’s really depressed, and she’s depressed because she’s about to go back to her home country, and she’s kind of depressed in herself. She’s depressed that she hasn’t changed more on this vacation, and he tries to cheer her up. He tries to tell her stories about when they were sightseeing, and it just doesn’t work.

And then towards the end of the meal, he just decides, like, “You know what, this isn’t going to happen. I’ve screwed this up.” And so, he just gets honest with Yasmin, and he says, “Look, I know that you’re disappointed in yourself. I’m super disappointed in myself. Like, I thought I was going to be a great CIA officer, and it turns out I’m terrible at this. And I see other guys who got hired with me, and women who got hired with me, and they’re doing so much better. They all have this confidence I don’t have.”

And he just starts talking about how he’s going to have to go back to Texas, and work for his dad. And his brother is a better salesman than he is. And while he’s describing all this, he’s just being as honest as he can, matching Yasmin, unintentionally she was glum and wanted to talk about how she felt, and now, finally, he is also talking about how he feels, she starts crying. And Lawler reaches across the table, he said, “I didn’t mean to make you cry,” and she goes, “No, no, what you want is important. We can do this together.”

And she becomes one of the best assets in the Middle East over the next 30 years, and Lawler actually goes on to be one of the top recruiters in the CIA. But I think the point here is that, unless we know how to look for what’s happening in a conversation, unless we are a little bit conscious, and it’s not hard to get conscious of this, a little bit conscious about how to match someone, we can totally miss what they need, and they can miss what we’re asking them for.

Pete Mockaitis

Well, yes, thank you, that’s a lovely tale. And so, let’s just go ahead and do more, please, Charles. So, that’s a demonstration of the emotional vibe, like, “What’s up?” And so, in that instance, there’s crying, there are some dramatics. So, give us more of the tale showing how that unfolds marvelously in the practical flavor and the social flavor?

Charles Duhigg

Well, okay, and I would actually say that conversation, there are emotional aspects but there’s also practical aspects because she’s agreeing to become a spy for him. So, one of the things that we know is that when researchers have looked at people who are consistently supercommunicators, they found that these kinds of people, on average, ask 10 to 20 times as many questions than other people.

Pete Mockaitis

Oh, no kidding?

Charles Duhigg

But we’re oftentimes not aware of it because the questions are like, “Hey, that’s interesting. What do you think about that?” or like, “Huh, what did you do next?” or just little things that make it easier for us to enter a conversation. And there’s actually an experiment I like to do. So, think for a second, if you were having, like a really bad day, like just a terrible day, who would you call that you know would make you feel better?

Pete Mockaitis

Oh, we got a few options.

Charles Duhigg

Sure, but I don’t know, who comes to mind first?

Pete Mockaitis

I’d say my wife.

Charles Duhigg

Okay. Now, let me ask you this, is your wife, like, the funniest person you know, like standup comedian funny, like just kills it every time?

Pete Mockaitis

She is among the funniest people I know.

Charles Duhigg

Okay. Okay. But you described her as a wife, you don’t describe her as, like, my comedian wife.

Pete Mockaitis

Yeah.

Charles Duhigg

What about is she the most successful person you know, like earns the most money?

Pete Mockaitis

Well, depending on how we measure success, yes. From an income-generation perspective, she is not.

Charles Duhigg

Okay. And what’s interesting is the audience probably thought of someone that they telephone to make them feel better. And that person probably is not their funniest friend, or their smartest friend, or their most successful friend, so why telephone that person? What’s that person doing that makes us feel so good?

And the answer is what they’re doing is they are inviting us to share who we are, and then they’re proving to us that they are listening. So, you asked for an example of how this happens in the everyday world. There’s a guy named Nicholas Epley who’s a professor at the University of Chicago, and one of the things that he’s done a lot of work on is trying to figure out, “What kinds of questions can we ask that make people feel closer to each other, almost like without it being obvious?”

And what he found is that there’s this category of question known as a deep question. And what a deep question is that it’s something that asks you about your values, or your beliefs, or your past experiences in a way that invites you to open up and explain who you are. So, an example of this is to say to someone, like, “Where do you work?” and then they say, “I’m a lawyer.” You say, “Oh, have you always wanted to be a lawyer? Like, do you love practicing the law?” Those are deep questions.

Now, they don’t seem like overly intrusive or awkward but they’re deep questions because they invite the other person to expose something a little bit that’s vulnerable. And if when we hear that vulnerability, if we reciprocate that vulnerability, that other person will feel closer to us. So, my guess is that a lot of the conversations you have with your wife, and tell me if I’m getting this wrong, involved you asking her the deeper question rather than the surface question, her telling you something that’s real, and then you responding with something real yourself, and that you probably feel closer as a result. Is that fair?

Pete Mockaitis

Oh, yeah, sure, that happens.

Charles Duhigg

Yeah. But we don’t think about asking deep questions, and yet it’s something that we know helps us figure out what the other person wants to talk about, it helps us align.

Pete Mockaitis

So, let’s hear some more examples of these deep questions. So, “Have you always wanted to be a lawyer? Do you love practicing law?” What are some other examples here?

Charles Duhigg
Really, I mean, anything. Like, where did you grow up?

Pete Mockaitis

Danville, Illinois.

Charles Duhigg

Okay. Like, what was the best part of growing up there?

Pete Mockaitis

Well, what’s deep is that I have to think for a while. There’s a lot of good things.

Charles Duhigg

That’s a good sign though.

Pete Mockaitis

It’s so funny. When I hear questions, I really like to answer them masterfully or accurately. But, in some ways, I could say any great thing about growing up in Danville. So, I’ll say. I just had a lot of fun meeting so many different folks. And it’s almost like divisions of, in my experience, like divisions of race or class or whatever didn’t even matter. It was just like, “Oh, well, Ruhini’s parents have a huge house. That’s kind of cool,” and that’s that. And then onto the next. It doesn’t matter.

Charles Duhigg

So, here’s what’s interesting about the answer you just gave me. First of all, you’re telling me a little bit about what it was like to grow up in this place. And so, you’re telling me about your experiences. You also told me about your values, like you value people who are kind, you value kindness. It sounds like you value kindness more than financial success or professional success.

It sounds like you’ve had some experiences where, like, you’ve had friends who are more wealthy than you and probably friends who are less wealthy than you but you found something really meaningful in creating friendships that aren’t defined by demographic lines. That’s a pretty easy question for me to ask, like, “What’s your favorite part of growing up there?” And yet, when you answered that question, I now know so much more about you, and you also told me something kind of intimate.

Now, in the language of psychology, you’ve exposed a vulnerability. Like, you put me in a place where I can judge you. You might not care what my judgment is, and you probably don’t, like if I was, “Oh, man, that sounds like a terrible place to grow up,” you wouldn’t care because I’m some idiot that you just met.

But the fact that you opened yourself up and exposed little bit of vulnerability means that you’re ready to feel closer to me, and if I reciprocate with vulnerability, if I tell you that I grew up in New Mexico, Albuquerque, which is true, I’m going there pretty soon, and one of the things that I loved most about it was that it was a place, like my high school was on 89% Hispanic or Native American. And that’s true of a lot of New Mexico and to grow up as a white guy, to get a chance to feel like a minority is really powerful and it creates empathy.

Like, A, I’ve told you something about myself by answering the question that I asked you, but, B, by reciprocating your vulnerability, we feel closer to each other. We can’t help but feel closer to each other. Literally, our brains are hardwired to feel closer to each other.

Pete Mockaitis

Yeah, and what’s interesting is, as we super-communicate with each other, is that it’s funny how the monkey mind just has all these associations, in like, where it just might naturally want to go. So, you say Albuquerque, I’m thinking, “I love the show Breaking Bad,” and so I have a desire to say something about “Breaking Bad.” But, really, from a connecting perspective, that doesn’t really do much for us here.

Charles Duhigg

So, here’s a good example here. I said I’m from Albuquerque, you definitely could’ve broken in and been like, “Oh, my God, I love Breaking Bad. That’s the best show ever.” But because you are a good communicator, you intuit it, like, that would actually disrupt the flow of this conversation. That’s a fun conversation, maybe a practical conversation, and I’m revealing something about who I am. It’s an emotional conversation or social conversation. And so, instead of interrupting me and stealing the spotlight in saying, “Man, I love Breaking Bad. Do you like Breaking Bad?” you knew to match the kind of conversation I was having.

Now, think of how many times we sometimes get this wrong. Like, I get this wrong with my kids all the time. Like, if my kids come to me with something they want to talk about, they’re upset about something, or they want to talk about the social scene at their school, and instead of listening, and asking questions, and matching them, and meeting them where they are, I start trying to solve their problems, like I have all these lessons in my head that I want to shove into their head.

And, of course, they’re like, “Whatever, dad.” It’s like you breaking and being like, “I love Breaking Bad.” It’s me being like, “Well, here’s a lesson that you can learn.” I do this all the time. I still make this mistake but the more we become conscious of it, the more that we’re aware of listening for what kind of conversation is happening, matching other people, inviting them to match us, the more we end up having those special moments.

Pete Mockaitis

And it’s funny, I think if we weren’t primed in the world of, I’m thinking about deep questions and matching, and practical versus emotional versus social, I might very well have just let her rip with “Breaking Bad is awesome.”

Charles Duhigg

Yeah. Or, I might’ve like talked about growing up in Albuquerque. I mean, this is something that definitely happens, someone says. My dad passed away about five years ago, and I found that when I came back, I was living in New York at the time. When I came back to New York after the funeral, it’s the most interesting thing that had happened to me that year. It’s sad and it’s hard but it’s also just interesting and complicated.

And one of two things would happen. I would tell people that I was just back from my dad’s funeral, and they would say, “I’m sorry,” and then change the topic. And they’d usually change it to something that’s totally unrelated or totally different emotional attitude, or they would just not respond. That happened all the time. And what I really wanted was I wanted people to be, like, “What was it like? What was your dad like? Tell me about your dad.” That’s amazing when someone has passed away and someone else asks you what they’re like, you love describing them.

And I think that, to your point, oftentimes during the most meaningful conversations, we have this instinct to do that, “Hey, Breaking Bad, I love Breaking Bad” because we feel so uncertain, we feel so unsure of ourselves in the conversation. But the more that we can recognize how the conversation works, what this other person is asking for, the more certain and comfortable we become in giving it to them. And that can be incredibly powerful.

Pete Mockaitis

It is. And I think there’s uncertainty or fear or trepidation, whatever the vibe is, in that moment. It’s like the risk is really, I think, lower than what we perceive it to be emotionally.

Charles Duhigg

Oh, absolutely.

Pete Mockaitis

Because if I were to say, “Oh, man, I’m sorry. That must’ve been really hard. Tell me what are some of your favorite memories of your dad that came to mind.” I’m thinking, like, at worst, you might say, “I’m really just not comfortable telling you about that.” You’re not going to scream at me or assault me. You might just shut that down if it’s like, “Dude, I barely know you. I don’t feel like crying in front of you at this moment. It’s been a day. I’m just going to terminate the conversation.”

Charles Duhigg

And, by the way, it’s been five years, and so when I bump into other people who have been to the funeral, I ask them, like, “Tell me a little bit about your dad or your mom.” Literally, not once has someone ever said, “I don’t feel like talking about it right now.” People love talking about it. It’s like literally this thing that just happened to them. It’d be like if you got married and none of your friends asked you about the wedding, like when you get married, you want to talk about the wedding, “It was overwhelming.”

And, honestly, like going to a funeral for a parent is just as overwhelming, and sad instead of happy, but you still want to talk about it. And I think that you’re right. I think that people perceive a risk that not only is overblown, oftentimes it actually isn’t even there.

Pete Mockaitis

That’s good. Well, so then social, who are we, this category, it sounds like we’ve touched upon it in terms of it’s unveiling values and what we’re about.

Charles Duhigg

It’s a little bit different. So, when we’re having a social conversation, what we’re really talking about is, “How do I relate to other people? How do they relate to me? How do I see other people? How do I think other people see me?” So, think about, for instance, there’s a story in the book about Netflix. So, Netflix had an executive who, about five years ago, he used the N-word in a meeting, and he used it in a kind of benign way.

He was trying to describe something but many people in the meeting, for good reason, were offended. He ended up getting fired because of this, but it set off this whole controversy within Netflix. And they hired someone to come who was a supercommunicator, understood how communication works. Her name is Verna Myers, she’s amazing.

She kind of transformed how the conversation, across the entire company, thousands and thousands of people. She transformed how the conversation is happening to help people understand, “It is okay to say to someone, ‘I see something differently than you because of my background, and that doesn’t mean either of us are wrong or right.’”

If I’m a black parent, I might very well see cops differently than a white parent. And that doesn’t necessarily mean I’m wrong or I’m right. It also doesn’t mean we have to agree with each other. But understanding that difference, that’s a social conversation. It’s a conversation about identities, and how identities shape how we see things. That’s actually a huge part of understanding. And if we’re comfortable having that conversation, then it makes it a lot easier to come together.

Secondarily, as part of that conversation is this emphasis on belonging, that every single person has the right to participate in a social conversation and to have an identity. Everyone has had a racial experience, a gender experience, whether you’re black or white or man or female or nonbinary. We all have these experiences that shape who we are. And sharing that with other people, it feels really good. That’s a social conversation.

A social conversation is sharing how we see ourselves in an attempt to align how others see us with our self-image, and to hear how they see themselves and how that might differ from how see them.

Pete Mockaitis

Can you give us some more examples here?

Charles Duhigg

Yeah. Well, so a lot of social conversations are like office gossip. There are actually these really interesting studies on gossip. And what they find is that gossip is really important within companies because gossip is how we not only learn information, it’s how we establish moral and social norms without having to be overbearing about it.

So, if someone is, like, “Oh, my God, Jim got so drunk at that party last night,” and they seem critical of it, then we know, actually, drunkenness is not a norm that’s accepted at this company. And it gets even down to smaller things. And once you start thinking about these kinds of conversations and the powerful role that they play, you can begin thinking about how to make them better.

So, there was a study that was done of an investment bank, and this investment bank was like a place for people who are at each other’s throats all day long. They were competing for deals, they were competing for bonuses, they would have these screaming fights on a regular basis during meetings.

So, these researchers come in, and they tell everyone, “Okay, look, before every meeting, for the next week, what we want you to do is we’re going to give you some notecards. Before every meeting, just write down, literally, one sentence on the notecard, and write down what you hope to accomplish in this meeting, your goal, and what kind of tone or mood you hope the meeting will have. And then when you start the meeting, if you want, you can read it, you can share it with other people, or you don’t have to.” Most people didn’t.

And what they found is that, when they looked at the cards people wrote, what people would write were things like, “I want to ask Maria if she wants to come on vacation with me but I want to make it easy for her to say no,” or, “I want us to figure out the budget for next year…” a pretty practical conversation, “…but I want everyone to get everything off their chest because there’s been some tension.”

Just by asking people to write that sentence before each meeting, the incidence of conflict went down 80% within the firm that week. Now that did not mean that people agreed with each other, it did not mean they stopped fighting, it did not mean that they were less competitive, but because everyone knew what they wanted out of that meeting, and because they knew what kind of mood they were looking for, they were able to signal that much more easily to other people, and we pick up on those signals.

Pete Mockaitis

Yeah. Well, that’s my favorite kind of thing, Charles. We have a minor intervention with a huge result, that’s cool. So, we’re writing that down, and, in so doing, that gets to the “Who are we?” in terms of, I guess, “Who are we?” in that moment in terms of how we’re showing up right then and there.

Charles Duhigg

Yeah, absolutely. We’re coming together and we’re working for this firm together. We are all here trying to remind ourselves that we are on the same team as opposed to on different teams. And if I’m talking to you in a meeting, and I’m saying, like, “I want to discuss the budget but I want to give everyone a chance to get things off their chest,” then what I’m saying to the other people is, “I understand you’re frustrated. I’m your boss. I could tell you we’re just going to do the budget. It’s my way or the highway. But I’m signaling to you, in a social context, I understand you are frustrated. I understand that you don’t feel like I am being the boss I ought to be right now.”

“And once we have that conversation out in the open, then we can start talking about how do we resolve it? Are there things about how we run the social organization that is this company, that we run it in ways that make it hard for people to speak up or to bring their best selves to work? If we’re having conversations with someone else, and we’re talking about ‘How does Jim see this?’ or, ‘I have a problem. Here’s my solution.’ That’s a practical conversation. “Now let’s think about how the rest of the firm is going to react when I bring up this solution.”

That’s a social conversation because the way that other people react will not be based entirely on pragmatics and practicality. It won’t be based entirely on emotions. It might be based on power differentials or on structural issues. But once we sit down, and we’re like, “Look, let’s talk about how this is going to play out at the company from a social perspective,” then suddenly we’re having a slightly different conversation than an emotional conversation or a practical conversation. We’re trying to anticipate how other people see themselves and how that shapes what they believe.

Pete Mockaitis

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

Charles Duhigg

No, the thing I would say is the book is filled with stories, and the reason why it’s filled with stories, there are stories about there’s this awesome study called the 36 questions that lead to love. It’s known as the Fast Friends procedure, and it was this study that try and make strangers into friends, and it worked. It worked by getting them to ask each other deep questions.

There are stories about conflict, like, “What do we do when we’re in conflict with someone?” And the answer there, and that story takes place in part online in Facebook. It’s this group that was put together of gun rights advocates and gun control advocates. And what we found is that, in conflict, it’s even more important to prove that we’re listening.

And one of the ways we can prove that we’re listening is by this thing called looping for understanding, which is pretty instinctual. It’s, ask someone a question, repeat back to them what they just told you in your own words. And then the third step, and this is the step that most people forget but it’s the most important, ask them if you got it right.

If you do that and you continue looping until they agree that you’ve gotten it right, it’s almost impossible for people to be angry at each other no matter how big their difference is. And that doesn’t mean that you have to agree with each other but it means you can take anger out of the equation. And so, my goal with these stories is, and there’s a lot of practical tips.

There are sorts of the bullet points after each chapter, but my goal is to give people these skills that they can use to become better communicators because, as I mentioned, all of us are supercommunicators. Sometimes we just do it by instinct, sometimes we’re just lucky and it comes out, but if we learn the skills then we can do it whenever we want. And for the most meaningful conversations, we can really connect with someone else.

Pete Mockaitis

Just a follow-up on the looping point, I understand you’ve also got some research associated with the asking of a follow-up question is another super powerful thing that people did.

Charles Duhigg

Absolutely. And that’s actually a form of looping. Like, sometimes if I ask you a follow-up question, it’s proving to you that I was listening to what you were saying, and that’s really important.

Pete Mockaitis

Certainly. And so then, the good follow-up questions do just that. They prove that you were listening to what we’re saying as opposed to, “So, tell me more about that” which still is a decent question when you got nothing else. But, ideally, for a follow-up question, we want to have some content. I sort of think about it like when I’m getting emails, it’s like, “Was this a mass email sent to the whole world or was it sent specifically to me, Pete Mockaitis?”

And there are little indicators of that in the note. And so, too, with the question, one would have to have listened and shared some bits, like, “Oh, you said you think guns are a great way for teachers to prevent violence if they were all armed. Is that right?” “Yeah, that’s what I said.” It’s like, “Well, are you aware of some incidences in which folks armed up the teachers, and they saw the desired results?” So, there’s a follow-up question that shows I was listening.

Charles Duhigg

Yeah, that’s a question where you are presupposing the answer, so I would say one thing that’s important is…

Pete Mockaitis

Oh, I really wasn’t. I was like “Do we have that information?” “I’ll tell them and then no more problems.”

Charles Duhigg

Yeah, if you’re genuinely and curiously asking, that’s the key to ask curious questions. But you had said something like, the generic question is like “Tell me more about that.” But, again, getting back to deep questions, instead of saying, “Tell me more about that” like an easy way response, if you’re not certain what to say, is to say, “What did you make of that? You just told me about this thing. Why was it important to you?”

And that’s a deep question. It doesn’t appear deep. It doesn’t appear intrusive or it doesn’t appear overly intimate but, again, it’s asking me to explain about my values, or my beliefs, or my experiences. It’s giving me a chance to tell you about how I see the world. And I guarantee you that once you hear that, the follow-up questions are going to be almost automatic.

Pete Mockaitis

All right. Well, now let’s hear about some of your favorite things. Can you tell us about a favorite quote, something you find inspiring?

Charles Duhigg

I think the quote that I use most with my kids is, “It’s only a mistake if you don’t learn something from it.” And I realize this is kind of a cheesy quote. But honestly, I make mistakes all the time, we all make mistakes all the time, and it’s so easy to get down on yourself, that if you tell yourself, “It’s only a mistake if I don’t learn from it,” then it stops being a mistake. It starts being an experiment. And not all experiments are supposed to go right.

Pete Mockaitis

Okay. And a favorite study or experiment or bit of research?

Charles Duhigg

Actually, I mentioned the 36 questions. This is an awesome, awesome study. So, what they did, it’s these two researchers at the University of Rhode Island, they took all these people in pairs, and they put them in a room, total strangers, and they would have them ask these 36 questions back and forth. And they designed the questions to be deep questions without appearing…many of them didn’t appear very deep, particularly at first.

And then they send everyone home, it only takes an hour, they send everyone home. This is pre-internet, by the way. And then seven weeks later, they tracked down everyone who’d been in that study, and they asked them one question, “Did you ever seek out the person that you had that conversation with?”

Now, they had not given them any information on how to find each other. There was no exchange of business cards or anything like that, so finding the person you had the conversation with was actually kind of hard. They found that 70% of people who had engaged in those conversations had sought out their conversational partner. They’d go out to beers and movies together. Three people ended up getting married to the person that they had the conversation with.

And it’s because of this emotional reciprocity, it’s because if we ask deep questions, and then we answer them, we feel close to the other person. And so, I just think it’s a wonderful study.

Pete Mockaitis

It is. I actually went through that list of questions on a date.

Charles Duhigg

Oh, yeah?

Pete Mockaitis

We didn’t end up getting married.

Charles Duhigg

It’s okay. It’s okay.

Pete Mockaitis

But, in a way, it was a good outcome, and then I think we…I don’t know how much that exercise contributed to things but I think we parted on good terms not too long thereafter.

Charles Duhigg

Excellent.

Pete Mockaitis

And I guess we knew some new things. And a favorite book?

Charles Duhigg

I used to always say The Varieties of Religious Experience by William James, which is just one of my favorite books. And for anyone who hasn’t read it, there’s a chapter on the religion of happy-mindedness. William James, of course, is like the father of American psychology. And the religion of happy-mindedness is about people who are just happy. Like, why are they happy? And what did they know that we don’t?

But the other book that I love, that I’ll make a plug for, it’s actually a novel. It’s by Jennifer Egan, and it’s called A Visit from the Goon Squad. And very similarly, I think it’s about how we create happiness in life, and how we recognize it and sometimes fail to recognize it even when it’s right in front of us. So, it’s a wonderful book.

Pete Mockaitis

Okay. Thank you. And a favorite tool, something you use to be awesome at your job?

Charles Duhigg

So, I just read an article about AI for The New Yorker, and part of it is about Microsoft’s Copilots that are coming out. And so, I’ve been using all the different AI products, and I will say, like, I don’t think that it’s making me more productive. It’s just super fun though. Like, I sent out an email this morning, and I made an image on Midjourney for it. So, I would say, right now, AI is the tool that I’m enjoying very much.

Pete Mockaitis

Well, so lay it on us, ChatGPT, Midjourney, what else is cool and interesting?

Charles Duhigg

Oh, the Copilots. There’s going to be an explosion of Copilots over the next couple of years. And Microsoft is releasing them right now, but every company is going to be creating agents or copilots. So, in three or four years, this is totally feasible. We will wear a device that records every single conversation, and that conversation will be digitized. It will all be our data. No one else will have it.

And then 10 years from now, you’ll be like, “You know, I was once doing a podcast, and this guy talked about AI, and I can’t remember who he was, but he mentioned Midjourney. Go find that conversation.” And the AI will be able to find it. It’s what large language models index and search very, very efficiently with even vague guidance.

And so, if you think about it, our conversations are a huge corpus of knowledge, it’s a huge database, and it basically only exists between two people, or if you happen to be recording it, it exists between two people and whoever is listening to the conversation, but it’s hard to remember and you don’t know exactly who said what. And once we’re able to unlock the database of conversations, it’s going to be awesome.

Pete Mockaitis

Okay. And you are a habit master. Tell us your favorite habit?

Charles Duhigg

So, in The Power of Habit, there’s this whole thing about keystone habits, which are habits that set off chain reactions of other behavior changes. So, for me, I would say my keystone habit is definitely exercising in the morning. And I really dislike exercising, so what I do is I sign up for half marathons. And, by the way, I hate races. There’s nothing I enjoy about it.

But I sign up for half marathons because I’m so scared about how bad it will hurt to run that half marathon if I haven’t trained. And that gets me to go train every morning. And then after I train, I’m like, “Oh, man, I feel great. This is really good.” So, I would say my big keystone habit is trying to exercise at least once each day.

Pete Mockaitis

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

Charles Duhigg

As I’ve been working on Supercommunicators, the story with my wife, I think, is something that really resonates with people, because I think we’ve all experienced that. Like, someone comes to us with a problem, and we try and solve it for them, and then they’re frustrated, and then we’re frustrated. And so, I find that explaining, “Oh, it’s actually two different kinds of conversations are happening here,” that that’s been really powerful for a lot of people.

Pete Mockaitis

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

Charles Duhigg

If you Google me, I’m at CharlesDuhigg.com. If you just type Supercommunicators into your Google browser, I’ll probably come up, or Power of Habit. And then my email address is charles@duhigg.com, and I read every single email I get from listeners and from readers, and I respond to every single one, so feel free to drop me a note, and I will definitely respond to you.

Pete Mockaitis

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

Charles Duhigg

I think that, here’s the thing that I would say, is think about your job right now, and think about where you’re not communicating as well as you can. Maybe it’s with a coworker, maybe it’s with your boss, maybe it’s with a client, maybe it’s when you’re doing pitches. There are some times in your life where you wish that you could be an effortless supercommunicator, and it’s not happening on a consistent basis for you.

And my guess is, as a result, you’re shying away from that opportunity because you’re worried that it’s not going to go as well as you want it to go. So, just break it down. Try and think about the last conversation you had where it didn’t go as well as you wanted it to go, and try and figure out, “Were we having the same kind of conversation? Was I asking enough questions? Was I asking the right kinds of questions? Was I proving to this person that I was listening to them? Were they responding to me and inviting me to match them?”

If you do that, you’ll find that there’s this part of your work life that you probably don’t like as much as you should, but it is an absolutely solvable problem. Nobody is born a great communicator. It’s just a set of skills that anyone can learn.

Pete Mockaitis

All right, Charles. Thank you. I wish you much luck and super communications.

Charles Duhigg

Thank you so much.

936: The 8 Super Powers that Unlock Gravitas with Lisa Sun

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Lisa Sun shares her tools for building true, lasting confidence.

You’ll Learn:

 

  1. What gravitas really means
  2. The Six Forces ruining your confidence
  3. How to discover your “confidence language”

About Lisa

Lisa Sun is the founder and CEO of GRAVITAS, a company on a mission to catalyze confidence. GRAVITAS offers innovative size-inclusive apparel, styling solutions, and content designed to make over women from the inside out.

Prior to founding GRAVITAS, Sun spent 11 years at McKinsey & Company, where she advised leading luxury fashion and beauty brands and retailers in the U.S., Asia, Europe, and Latin America on strategic and operational issues. Her first collection was featured in O, The Oprah Magazine, People, and the Today Show in the same month.

Sun and GRAVITAS have been featured on CNN and in Forbes, Fast Company, New York Magazine, Elle, Marie Claire, InStyle, and more. GRAVITAS includes among its activities a commitment to AAPI causes and New York City’s Garment District. Often called the “dress whisperer,” Lisa is also a highly sought-after public speaker who likes to impart her hard-won knowledge on gravitas and how to best harness it to other women. 

Resources Mentioned

Lisa Sun Interview Transcript

Pete Mockaitis

Lisa, welcome.

Lisa Sun

Thank you so much for having me, Pete.

Pete Mockaitis

Well, I’m excited to dig into the wisdom you’ve captured and put together in your book, Gravitas: The 8 Strengths That Redefine Confidence, because confidence is something our listeners often say, “Yeah, I want more of that,” and I can dig it. So, in your fashion business, you are on a mission to catalyze confidence. I did look that up in the dictionary, it meant what I thought it meant, to, like, accelerate like with a catalyst.

So, just if anyone else was wondering, but could you give us a tale from your own career story in which you had catalyzed some confidence, what went down, and what did you do?

Lisa Sun
So, I was at McKinsey and Co., the management consulting firm for 11 years, and after a year of being there, I had my first annual performance review.

Pete Mockaitis

Oh, boy.

Lisa Sun

And the opening line was, “Lisa comes across as young and overly enthusiastic at times. She should seek to have more gravitas.” I think we have all been told at some point in our career to be more confident, essentially, they were saying that. And when I asked my boss, “How do you get gravitas?” she said, “Go buy a new dress, wear big jewelry, and great shoes.”

That is the most offensive piece of feedback you can give to a 23-year-old, making $43,000 a year, size 18-20 to go buy new clothes. And when I asked her why, she said, “Okay, really, it’s not about clothes. Every morning you wake up and you’re the first person you have to look at in the mirror, and you have to like yourself, I can teach you how to be good at this job but I can’t teach you how to like yourself.” So, I put on a dress, it reminds me I can do this job. So, she said, “Dumbo did not need a feather to fly. It reminded him that he could.”

And so, what we have done, and why our mission is to catalyze confidence, is, “How do we, as adults, create reminders every day of our talents and gifts?” And so, that’s really the origin story of my company, of the book, and I know we’re going to dive deeper into what we’ve learned, but I do think that we’ve got to reframe confidence, gravitas, not as a behavior but as a choice and a mindset.

Pete Mockaitis

Oh, already you’re dropping actual wisdom on us. Thank you, Lisa. We had a really cool chat with Dr. Srini Pillay back in the day. We’ve got a link in the show notes. And he used a cool term, psychological Halloweenism to mean just that, like, there are ways you can dress up, like in a Halloween costume that impact you psychologically.

And so, for her, it was the dress. Sometimes I put on a blazer jacket, it’s in my office corner, just like, “No, Pete, you’ve got to get serious and be Mr. Executive right now. Let’s put that on.” And it makes an impact. And so, it’s not about the clothes itself but it can be prop that helps get in the right mindset, like Dumbo and his feather.

Lisa Sun

And I think the reason is, and this is really what we dive deep into, is if you look up the word confident in the dictionary, it has nothing to do with bravado, swagger, or performance. If someone tells you be more confident, you’re like, “Oh, I’m going to speak up, I’m going to be assertive, I’m going to stand on the stage.” It’s very behavioral.

If you look it up in the dictionary, it’s an understanding of, appreciation of, and trust in your own talents and abilities. And so, that actually shifts the entire way you think about it. And the reason we, as adults, need reminders is we are born fully self-confident. Ask any five-year-old what they’re the best at in the world, and they’ll tell you right away. You don’t have to have kids but you know this feeling, “I’m the best at soccer,” “I’m the best at hugs,” “I’m the best at everything.” They’ll run off a long list of their accomplishments at five.

But what we found is in your adolescence, between the ages of 8 and 12, there are six forces that hold you back. They actually appear on the ages of 8 and 12, it’s chapter 2 of my book. And so, it’s not our fault that we have an inner critic. Think about your adolescence, it’s all about starting to be doubting yourself, self-consciousness. And when those forces appear, to break out of them, we actually, as adults, have to make a conscious choice, and we have to channel a different mindset.

And reminders, like a dress or a blazer, they remind us to believe in ourselves again. And it’s really, if you were five years old, you don’t need the blazer, but as an adult, because you’ve had setback, disappointment, you’ve experienced fear, insecurity, self-doubt, that’s why we need these little tokens in our life to break ourselves out of it.

Pete Mockaitis
Now, I want to hear about the six forces soon but, first, let’s just make sure we conclude the thread. So, you had the conversation, it’s not about the clothes, but the clothes can help be a reminder. And what, ultimately, did you do in your McKinsey days to boost that confidence and get superior reviews?

Lisa Sun

Well, to be clear, I wish I could go back in time to give myself this book. I feel like you write the book you most need to read yourself. I wish I could get in the DeLorean and go back to that 23-year-old person. What I did is not what I would tell people to do today. Like, I wish I could go back and tell my 23-year-old-self something quite differently.

Well, parts of it. The one part I would still do is I always say the mentor chooses you; you don’t choose the mentor. Make yourself mentor-able. So, one thing I was really good about was saying, “Hey, what’s one thing I could do differently?” I really think people are bad at giving feedback, and also asking for it. It’s like browsing in a store, “Can I help you? Do you have any feedback for me?” “No, I’m just browsing,” “Oh, no, keep doing what you’re doing. You’re doing well.”

So, one thing I do is I took ownership of it, and I said, “Okay, what’s one thing I could do differently? What’s one thing I could do differently?” And over time, I enlisted a lot of people that have fingerprints on my journey, everyone from McKinsey offered me a speech coach. So, I was one of the few associates that, every Friday, was in front of Judy Marcus, saying, “Let’s practice my presentation.”

But I think what we did over the course of 11 years is we corrected the behavior but I don’t know if I ever fully corrected the mindset. So, to give you an example, someone at a book reading in DC said to me, “I’m going to call BS on this whole thing. I always thought of you as a very confident 20-year-old or 30-year-old.” And I said, “I was faking it. I was performing. I was actually still deeply insecure, overachieving, beating myself up, tons of self-loathing, but I learned how to play the game. I learned how to pretend to be assertive, and outspoken, extroversion, charisma.”

And so, I think that I was able to do it because I played into what the mold asked me to, but it wasn’t enjoyable. I don’t think I really liked myself during the process.

Pete Mockaitis

Okay. And so then, how did you get to the place where you authentically had that internal deep wellspring of true confidence?

Lisa Sun

Well, I left McKinsey in 2011, I took a full year off, and went around the world by myself with my BlackBerry. I don’t know if any of your listeners still miss their BlackBerry. I miss my BlackBerry. That thing never died or cracked. And one of the things that I realized was the fundamental difference between our society and Asian cultures, or even other cultures, is our culture really celebrates extroversion and charisma.

Pete Mockaitis

We’re talking about US business culture?

Lisa Sun

US Western. I would just say Western culture, North American culture. And, for example, Kelly Shue at Yale, she’s a professor, she studied 30,000 employee records, and she found that men were consistently rated highest on promotability but lowest on actual performance and results, and women were the opposite. Women were very good at delivering results and performance but not promotion potential.

And when she double-clicked on promotion potential, it was extroversion, charisma, and outgoingness, like being outgoing. And so, she said, “This explains a huge part of the gender pay gap related to promotion,” which is we’re scoring things that you can see but not actual results. It’s like why Janet Yellen was told in 2013 she didn’t have the gravitas to lead the Federal Reserve.

And Ezra Klein at The Washington Post said, “It’s because the pervasive view of gravitas is not stretched to include her. She’s self-spoken, collaborative. By the way, the most qualified person for the job. Why is it we only label confident people as extroverted?” And so, that was the first unlock, as in my travels, as I was reflecting on this after leaving McKinsey, it really started to make me think that, “Are we talking about confidence in the right way? Are we really helping people be their strongest versions of themselves?”

And so, when I started my own company over a decade ago, I said, “Look, this is not about asking people to fake it to make it. This is about creating products, services, and content that really help people turn the mirror on the inside and see how valuable and strong they are.” Things don’t get easier, we get stronger, and I don’t think we, as adults, acknowledge those strengths actively. We can tell you what we’re working on, our opportunities, our deficits, things that aren’t going well.

But when I ask you and put you on the spot, Pete, and say, “What are you the best at in the world? Tell it to me like a five-year-old,” you’re going to sit down and go, “Huh, I need to think about that question a little bit.”

Pete Mockaitis

Yeah, it’s funny, and when you say that, I do need to think about it, and it’s like, “I guess I’d have to combine. If I’m number one in the world, I have to combine like six things that I’m top 1% at so as, probabilistically multiplying them that makes me top dog out of eight billion.” That’s how I’m thinking about it.

Lisa Sun

You can’t benchmark yourself. No, Pete, that’s my whole point. Like, you automatically went to benchmarking it. It’s not measurable. It’s how you feel about yourself. It’s the iceberg model of consciousness. Ten percent of the iceberg is visible. It’s the behavior we can see. Ninety percent is below the water line, and it’s thoughts, values, feelings, wants, needs about ourselves.

So, I can tell you pretty confidently, because I’ve written a book about it, I can tell you now what I’m the best at in the world because, guess what, you’ll never be able to measure it. It’s in my own head, it’s what I think I’m the best at in the world.

Pete Mockaitis

Well, tell us, what is that thing, Lisa?

Lisa Sun

So, I always share two. I’m the world’s best plus one. Please invite me to a party. I will fetch your drinks. I won’t hover.And I’m the world’s best positivity mirror. So, when we spend time together, I will see something in you that you may not even see in yourself, and I will take a moment and I will reflect it back onto you so that you know that I saw you, and I value you, and I heard you.

Pete Mockaitis

And as you’re thinking about this world’s best piece, the focus is not so much that that it is factually, demonstratively, empirically, provably, truthfully correct in, like, a scientific or journalistic sense of the word, but rather that your innermost depths of being are vibing with that as true. Is that accurate?

Lisa Sun

Yup, because mindset drives behavior. Carol Dweck, at Stanford, wrote this great book called Mindset, and she’s proven over and over again that if you can reset your mindset, you can change your behavior. I’ll give you a very clear example that I think some of your listeners will appreciate. I own a women’s wear company. We make $100 to $300 dollar workwear, and I still dress hundreds of women a year, and you can book a 30-minute appointment with me. And, Pete, I’m about to give all your male listeners an insight into what every woman feels. You’re welcome.

Pete Mockaitis

All right. We’ll take it.

Lisa Sun

Every woman comes into a dressing room with the worst self-loathing, the most negative mindset she sets herself up to fail, even before all those six forces that we’re going to dive into, she brings all six forces of her inner critic into that dressing room. She tells me, “I hate my arms. I hate my thighs. I’m going to lose 10 pounds.” Like a mirror inside a dressing room, as soon as she undresses, she doesn’t feel like trying on clothes.

And for 10 minutes out of those 30 minutes, I don’t let her talk about her body or her clothes. I ask her three questions, “What are you most proud of in the last year of your life? If your best friend was standing here, what would they tell me about you? What are you the best at in the world?” And, by the way, no woman wants to answer these questions but I always say, “If we can’t reset the chemistry of this room to a place of positivity, we are going to fail today.”

And so, as she starts answering the questions, I’m like a velvet knife, you don’t feel like it’s happening, I’m starting to dress her, and we start laughing and smiling, and she comes out of the dressing room, all of our mirrors on the outside so you only get to see yourself when you’re fully dress, and she’ll say, “This is a skinny mirror.” I’m like, “Nope, it’s from Bed, Bath & Beyond. Rest in peace, Bed, Bath & Beyond. It’s 1995, I can’t trick you.”

She goes, “What did you do?” I said, “We made a choice that this was going to work. We changed your mindset from a place of negativity to a positive place where you start to tell me all the things you love about your life, and then you let me do the work. I’m a dress whisperer. I get it right on the first time.” And so, I use the dressing room as an analogy of how most of us wake up. Most of us wake up in a deficit mindset, focused on what’s missing in our life, or what the weaknesses are, versus focusing on the abundance we have, the talents we bring, our superpowers.

And if you reset that for yourself every day, by the way, I still, I woke up with all six forces in my head today. I still have to reset it. But if you can do that, that drives the behaviors and outcomes you want in life.

Pete Mockaitis

All right. Yeah, I really dig that. It’s associated with needing to do a reset in the morning. And I’ll tell you, what’s been most effective for me is straight up dunking into cold water. It’s like my brain is not capable of having many other thoughts, but they’re like, “Oh, oh, oh, that’s cold.” And then I’m kind of rejuvenated, I was like, “All right.” And so, it’s almost like I wash away that stuff. Now, that is…

Lisa Sun
And maybe that’s your little black dress. That’s your little black dress, right? You don’t need a blazer this morning. You’re just going to dunk yourself in cold water. The thing is as I’m putting on my clothes for the day, and I have to wear gravitas every day, we literally have the word gravitas sewn into the back of the clothing, it’s the clothing label.

And so, that’s literally a ritual for me of I woke up with all six forces focused on the weaknesses in my life, and as I’m dressing, I’m like, “Okay, I’m the gravitas woman. All right.” I validate myself. I tell myself what I’m proud of from the previous day. I really go through this ritual. And I think that’s what we’re trying to help people do is reset their minds before they take on the day.

Pete Mockaitis

Yes, let’s hear about the array of rituals that you’ve seen in your work and discovered are effective for people. So, I mentioned cold water, you’re talking about a great dress, some validation. Show us, what does this look like in practice? And what are some different flavors of it?

Lisa Sun

And maybe I take away from rituals and more about the approach we built, but I always say confidence is not a state of being; it’s a total approach because every single day you’re going to face setback, disappointment, fear, insecurity. And so, it’s really about creating an approach in your life. The three parts of the approach is, one, identify which of the six forces you’re feeling.

And I know we’re going to go into them but I think it’s really important, before you diagnose insecurity or fear, to know what’s driving it. It’s like why you don’t ask kids if they’re sad. You say, “What happened?” You double-click on it. So, I feel like we need to do a better work in having conversations with our inner critic, like, “What is driving me feeling this way?”

The second part is I always say you’ve got to be able to take a self-affirming inventory of your strengths and talents. And in our work, we identified eight superpowers, most of us have two or three. My mom who is my guru has all eight, she’s like, “I take your quiz. I have all eight of them.” So, you can take a free quiz from us and discover what your superpowers are.

But then the third part, and I think this is the really important one, is really believing in those superpowers, connecting them to real-life events, starting to really understand and advocate for your talents, but also decide where you have gaps. A lot of people take our quiz and they’ll say, “Okay, I have three of them but there’s ones I don’t have.” I’m like, “Well, first of all, love the three you have. It’s not like Pokemon. You don’t need to catch them all.”

But of the five you don’t have, what do you want in life, and which of those five do you want to cultivate? So, you take real ownership. As people progress and climb the ladder, they go from having two superpowers to four or more. And we found that in our longitudinal quantitative data over the course of five years.

So, if I step back from it, it’s like diagnose what’s driving insecurity and fear in your life, be able to create a self-affirming inventory of your strengths and talents. And then the third thing is, take ownership of what capabilities you want to grow and advocate for and own over time.

Pete Mockaitis

All right. Well, let’s dig into it, these three pieces of approach in some depth. What are these six forces? And how do we identify them?

Lisa Sun

So, the six forces, the first is called the deficit mindset. This is where you view weakness or what’s missing over your potential and your strengths. The easiest way to diagnose this one is when you look in the mirror, “Do you look for the wrinkles or your beautiful eyes?”

The second one is called shrinking effect. This is where you shortchange yourself or underestimate your own abilities versus others or a standard. The example I use here is this is why people say sorry all the time without actually being sorry because they just think they must be in the wrong. Or, this is why women will only apply for a job if they’re 100% qualified, whereas men will often apply if they’re only 60% qualified, “Ah, that’s good enough.” But if you have shrinking effect, you’re like, “I have to be perfect to sit in that seat.” You shortchange what you’re offering to the world.

The third force is called satisfaction conundrum. This is where you tie your self-worth or happiness to an external marker of success, “I’ll be happy when I lose 10 pounds,” “I’ll be happy when I get that promotion,” “I’ll be happy when I get that car.” The problem is, when you tie your self-worth, it doesn’t mean we shouldn’t have goals and ambitions, but when you tie all of your self-worth to a single marker, if you get it, you just chase the next one, “Oh, I lost 10 pounds. I think I could lose five more.” It’s a treadmill.

Or, if you don’t get it, you beat yourself up for not getting it. And so, every time I didn’t make partner at McKinsey, I literally took it out on myself. I had this brass ring that I tied all of my happiness to when I should’ve stepped back and said, “You know what, I’m really creating value, I have a lot going on in my life. This one thing didn’t happen for me. Okay, I need to figure out all the other gifts I bring to the table.”

The fourth we call superhero façade. This is where you go, “Ahh, I got this. Every part of my life is perfect.” Then you try tell the world that you’re a superhero. The problem with that approach is the most successful people in life will say, “You know what, whenever you see me succeeding over here, I promise you I’m failing somewhere else.” And when you can talk about where you’re failing, you invite people to have fingerprints on the journey, and to help you, and make you even more successful. So, the most confident people in the world do not tell you they’re perfect or they’re superheroes. They’ll, in fact, tell you the reverse.

The fifth force is we call setback spiral. This is where a negative moment of criticism, a disappointment, spirals to expound all parts of your life, “So, this person gave me a piece of criticism. That must mean I’m a terrible sister, daughter, friend.” You start to say, “Okay, all parts of my life are off even though this is squarely just in one part of it.”

And the sixth force is systemic bias. This is where there are asymmetrical structures of power at work, where the rules were not created by you or for you. So, it took me twice as long to get to the same markers of leadership as my male colleagues. Well, reflecting back on that, I would say when I joined McKinsey in September of 2000, only 13% of the global partnership were women. There weren’t that many people that looked like me. So, maybe part of this wasn’t me. This was the system wasn’t built to see someone like me yet.

And my favorite article from Harvard Business Review the last four years, written by my two friends, Ruchika Tulshyan and Jodi-Ann Burey, is, “Stop Telling Women They Have Imposter Syndrome,” because it implies we’re criminals or unwell, when, in fact, a lot of it was driven by systemic bias, that the roles just weren’t created by us or for us.

But, in total, these six forces allow you to have a vocabulary to say, “Okay, right now, the way I’m feeling, oh, it’s satisfaction conundrum. I’m tying so much of my happiness to this one marker. Okay, Lisa, how do I go fix that now?” But I think it’s really important to diagnose which one you’re feeling. Maybe all six.

Pete Mockaitis

Well, yes, that is handy for sure because when you, like a good consultant knows, when you properly segment the problem, you’ll see there are very different solutions, whether it’s a factor one versus factor four. So, tell us, once we zero in on that, what do we do about it?

Lisa Sun

Well, then what you do is, I always say, “Okay, now you’ve had a conversation with your inner critic. You’ve explored why you’re feeling this way, what the worst-case scenario could be, and now you can drown it out with the megaphone of your superpowers,” because when you know your strengths and talents, it changes the solution space. You can focus on what you do have and what you can bring to the table. You have gas in the tank to keep going.

And so, for us, we did launch a quantitative study, and you can take the quiz at MyConfidenceLanguage.com for free, and you can discover, of the eight superpowers you’ve identified, which ones you have, and lean into those. So, I’m happy to walk through those eight and then give you an example of how that changed my life, if that helps, Pete. Do you want to go there?

Pete Mockaitis

Let’s do it. Yes, please, let’s hear it.

Lisa Sun

Okay, so let’s do it. So, the eight superpowers. Leading, “I set direction, I’m in charge, I inspire followership.” Performing, that’s what you and I are doing together right now. We’re on center stage, extroversion, charisma, the exchange of energy between two people. Those two superpowers are the most written about and talked about. Less than 20% of people in America have them.

So, the six that cover 80%, and, by the way, if we let them perform all day, nothing would get done. The other ones are achieving and knowing, “I get things done with a winner’s mindset. I love goals and I love meeting, exceeding them.” It’s being an athlete. Knowing? “I’m the smartest, the most well-researched, most process-oriented person in the room.” You want to build IKEA furniture with someone who has knowing as their superpower.

The best example of this is the three black women from the movie “Hidden Figures.” How do three black women have the gravitas to send a man into space at NASA? They weren’t the leaders. They weren’t the performers. They were the achievers and the knowers. The next two are giving and believing, “I support others. I’m empathetic.” Believing, “I’m optimistic. I see the best in everyone.” The best example of these forms of confidence, Ted Lasso.

Ted Lasso actually says, “I was underestimated my whole life because I’m not a commander, I’m not a leader. I’m here to help everyone become the best versions of themselves. I’m not here to win or lose. I’m here to believe.” And so, that’s a unique form of confidence that is undervalued and underestimated in the workplace.

The last two are creating and self-sustaining. Creating is my number one, “I can believe in things before I see them. I love the future ideas. I create something from nothing.” And self-sustaining, this is the hardest one for most people to get, “I like myself. I don’t need to impress you. I don’t need external validation.” It’s the quality most needed to ask for a raise, a favor, or overcome criticism.

But together, all eight of them, start to create a different inventory for your life. So, for example, my confidence language is creating. I’m the daughter of immigrants, I know what it takes to create something from nothing. Immigrants believe in things before they can see them. Performing, that’s what we’re doing now. Leading, being in charge. And giving.

And so, I know that those are the four I have. By the way, my team has opposite languages because my language doesn’t get anything done. Most of my team is achieving, giving, knowing, believing. They get things done. They stay organized. They keep everyone motivated. And so, you’ve got to have that language.

And the reason why that’s so important, I make women’s workwear, in March of 2020, when the pandemic started, our sales were not zero. They were negative. We had to refund people because we have a 30-day return policy. If you just bought a dress to go to the office from us, you send it back to us. And so, what we did is we did not let those six forces hold us. We didn’t focus on what we didn’t have.

I could’ve spiraled. I could’ve had deficit mindset. What I did is I said, “Team, what are superpowers? What do we have right now that no one else has?” I put on LinkedIn, and this is my performing and creating superpower at work, I said, “The sales of my company were negative.” No superhero façade. “If you need hospital gowns or face masks, we can get them to you. DM me.”

And Uwe Voss, the CEO of HelloFresh, DM’d me and said, “We need 2500 face masks in Newark right away. How can we help?” And so, we pivoted our business for 72 days during the pandemic to making personal protective equipment. And that was only possible because we focused on our superpowers and our strengths, not our deficits and our weaknesses.

My team’s confidence language, they got it done, they organized the spreadsheets, they got people to come in and work. It’s really about focusing on your strengths and having that growth-based mindset instead of deficit mindset.

Pete Mockaitis

That’s really cool. Really cool. And so now, I’m thinking here. So, we identify the forces that aren’t working for us so much, as well as identifying our superpower. How does that knowledge then translate into the feeling of, “Alright, in my innermost depths, I’m confident and ready to rock”? How do I make that leap from the knowing to the feeling?

Lisa Sun

Well, so once you’ve discovered your superpowers, I always say you’ve made the unconscious conscious. So, the good news is you now have words attached to your talents. And the quiz is not wrong. A lot of people take our quiz, and they go, “Whoa, I have five out of the eight.” I’m like, “Are you surprised?” They’re like, “Yes.” I said, “You’ve been underestimating or underleveraging yourself your whole life. You’ve got a lot.”

Or, “These are the ones, I don’t have them.” I’m like, “Don’t focus on those. Focus on the ones you have.” To own it though, I always tell people, take a moment you’re really proud of in life, and deconstruct it through the lens of your superpowers. Why did your superpowers drive that outcome? Connect it to a specific memory.

It’s like that movie “Inside Out” from Pixar. Your brain can only remember core memories. I can’t remember what I had for lunch yesterday but it has these little core memories that form the basis of your character. So, take one of those core memories and say, “Huh, I have five superpowers. What is it about me that made that happen?” because we’re so focused on looking at the summit that we don’t turn back around to see how much we’ve accomplished.

By doing that, you start to believe in it. It’s one thing to take a quiz, it’s another thing to actually believe in the results. After that, then you can start to say, “Okay, how am I going to advocate for that? How can I show up? How can I make sure I get credit for my talents? And where are the places I want to add to my superpower portfolio?”

So, the example I just shared with you of pivoting my company to making personal protective equipment for 72 days, I can connect that to my four superpowers. I can say, “This is why I got us here. By the way, these are my team’s superpowers and how they contributed.” So, I really believe in my confidence language.

If I tie it back to what I’m the best at in the world, I’m really high on performing. So, that doesn’t surprise you when I tell you I’m the world’s best plus one. When I tell you I’m the world’s best positivity mirror, that’s giving. You can actually start to see all these things come together.

Pete Mockaitis

Oh, lovely. Could you share with us another story of someone else who had things come together in terms of they worked through these approaches, and where did they start, what did they discover, and where did they land?

Lisa Sun

So, I’ll give you an example. In chapter one of my book, I talk about a woman named Suzanne, and she is in finance, and she came to me, and she said, “Ugh, my boss just told me I didn’t have gravitas.” And this is one of the funny things I always think, when you tell people to be more confident, it’s anxiety-inducing, it’s ambiguous. I kind of want to say, “Which of these eight superpowers do you want me to embody?”

And I said, “Okay, I know he can’t take the quiz, but which of these eight superpowers is your boss, is your CEO?” And she said, “Okay, he came up through sales. He’s probably performing, he’s leading, and he’s achieving.” “Okay, got it.” I said, “Let’s have you take the quiz,” and she goes, “Oh, my gosh, I’m knowing, achieving, and giving. We overlap on the achievement, like I always had a number, but I’m not extroverted so I don’t have performing. I don’t have leading.”

And she goes, “Huh, so when he says I don’t have gravitas, it means I’m not leading/performing.” And I said, “Okay, but are you getting credit for being giving and knowing?” She goes, “You know what, that’s not in his style.” And I said, “But you take care of everyone, you’re the smartest person driving the process, you’re VP of finance.”

And I said, “It’s actually a double-edged sword. Number one, when you do your weekly check-ins, make sure you’re taking credit for the things that he’s not seeing, the way in which you build relationships, take care of others on the team, the way you built up process, the way you think about numbers. You need to make sure you get credit for being achieving, knowing, and giving.”

“At the same time, you can say to him, ‘Hey, to get to the next level of leadership, I think what you’re saying is I need to work my leading and performing skills.’” And she did that, and she goes, “He said yes. He said, ‘That’s what I mean by gravitas. I need you to speak up more in meetings. I need you to be seen as setting direction more actively, but you’re right, I have not acknowledged that you are the most collaborative and empathetic person in the team.’”

And it’s funny, McKinsey did a report that said women are the reason why companies made it through the pandemic but the ideas of collaboration, empathy, care, they’re not on the traditional HR scorecard because women didn’t write the scorecard to begin with, so how do we give them credit for those things?

And, ultimately, what happened is she got promoted to CFO after two years because she got recognition for the qualities that she brought to the table, but she added superpowers. She actually retook the quiz, and she said, “I have four and a half superpowers now. That is so different than two years ago when I only had three. Thank you so much. I feel stronger that I can advocate for myself in this environment.” But she was promoted to the C-suite in less than two years.

Pete Mockaitis

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

Lisa Sun

Thank you, Pete. No, I love that this is How to be Awesome at Your Job, and I think being awesome starts with recognizing how powerful you really are.

Pete Mockaitis

Okay. Well, now could you share with us a favorite quote, something you find inspiring?

Lisa Sun

My favorite one is my best friend Jane Park, who is the founder of Tokki. She always says, “Life doesn’t get easier. We get stronger.” And what I love about that is it focuses on the fact that there are no regrets, only learnings in life, and that the more we view every single moment of our life as an opportunity to get stronger, the stronger we get.

Pete Mockaitis

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

Lisa Sun

I really think Kelly Shue at Yale did a phenomenal job with her study. I’m going to give her a shoutout. It was awesome.

Pete Mockaitis

All right. And a favorite book?

Lisa Sun

My favorite book is Dale Carnegie’s How to Win Friends & Influence Others. And it’s ironic because he focuses mostly on extroversion and charisma: smile, shake hands, be engaged. And a hundred years ago, that book was formative in terms of changing the way in which we relate to each other.

But the real reason it’s my favorite book, because I think what we’ve done is we’ve expanded it. I hope Dale Carnegie, if he were still alive today, would love the expansion we’ve done on his work about adding more qualities and superpowers to the equation. But when I was 12 years old, I was a freshman in high school, and my parents realized they could not afford the education that I wanted, or they wanted for me.

Let’s be clear. I went to a fancy college. It was $28,000 to go to an Ivy League college in 1996. And so, my dad went around town, and he asked, “How can I help my kid make $28,000 a year to send her to college?” And this is before endowments were releasing financial aid left and right. And the local Toastmasters chapter said, “Hey, the Rotary Club, the Lion’s Club, they have these student-speaking competitions. Your kid could win $5,000, $10,000, $15,000. We will train her to become a public speaker.”

And so, I got to join Toastmasters at the age of 12. And when you join, the founder of the chapter that I joined in California gave me a copy of Dale Carnegie’s book. I still have it. It says 99 cents, and he said, “This is the first book you’re going to read,” because, think about it, a Taiwanese immigrant’s daughter had to learn how to operate in Western culture. And the Toastmasters and Dale Carnegie taught me how to show up that way.

So, I ended up winning $20,000 in speaking money to pay for my first year of college, and then had another scholarship for year two. But that book, I still love that book mostly because of the memory and the way it changed my life so early on.

Pete Mockaitis

Yeah, that’s beautiful. We had Joe Hart, who’s the CEO of Dale Carnegie Organization currently, on the show, and we stay in touch. So, I will let him know.

Lisa Sun

Will you tell him? I’m obsessed with the book and him. I have a personal connection to Dale Carnegie’s teachings.

Pete Mockaitis

All right. And now how about a favorite tool, something that you use to be awesome at your job?

Lisa Sun

So, my favorite tool, I still own a Levenger.

Pete Mockaitis

Oh, yeah.

Lisa Sun

Old-school Levenger. I still write out every day my priorities, and I block out time on my calendar to think. So, I still use a Levenger. I’m old school.

Pete Mockaitis

And those who are not in the know, these are those handy notebooks with the disk so that you can remove pages then put them back in, right?

Lisa Sun

Yes

Pete Mockaitis

And a favorite habit, something you do that helps you be awesome at your job?

Lisa Sun

So, I do two things. One is I am a hip-hop dancer, so I dance in a dance class five days a week at Anna Kaiser Studios, and I really love the power of dance. So, that’s one thing that I do. The second thing is once a week, I turn off my phone for eight hours, and it’s usually on a Saturday. And of those eight hours, I will go to a museum. I’m lucky I live in New York City, so I recognize that’s not for everyone, and I will just let my brain turn off for an hour or two just looking at beautiful art or something that I want to learn about.

But I find that, because we’re always in response mode, that we don’t give our brainwaves the chance to amplify and lengthen. And I actually turn off. It’s not like “Do not disturb” because you can still see if text messages are coming in. I literally turn it off for eight hours.

Pete Mockaitis

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

Lisa Sun

Oh, the one that I get quoted most often is self-confidence is a choice and a mindset before it becomes a behavior.

Pete Mockaitis

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

Lisa Sun

Well, I would say, first, make sure you take the quiz at MyConfidenceLanguage.com. It’s really fun. @lisalsun at Gravitas New York on all social media platforms. And if it’s LinkedIn, I really am responsive on LinkedIn messenger more so than email.

Pete Mockaitis

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

Lisa Sun

How to be awesome at your job, I think, starts at recognizing how awesome you are first.

Pete Mockaitis

All right. Cool. We got it. All right. Lisa, this has been a lot of fun, and I wish you all the best and much gravitas and confidence in your adventures.

Lisa Sun

Thank you so much, Pete. Thanks for having me.

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.

934: Building Confidence by Facing Fears with Michelle Poler

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Michelle Poler shares her epic story and strategies for facing fears head-on.

You’ll Learn:

  1. How to instantly flip your fear perspective
  2. Why to dare being disliked
  3. The distinction between being brave versus fearless

About Michelle

As the Founder of Hello Fears, Michelle Poler has created a social movement empowering millions to step outside of their comfort zone and tap into their full potential. She has inspired some of the world’s most influential organizations including Google, Facebook, Microsoft and many more. Poler is also the creator of the project 100 Days Without Fear and her work has been featured on CBS, CNN and Buzzfeed, among many others. 

Resources Mentioned

Michelle Poler Interview Transcript

Pete Mockaitis

Michelle, welcome.

Michelle Poler

Hello. Thank you for having me.

Pete Mockaitis
I’m excited to hear so much of your story and your pro tips. Could you kick us off by giving us the whole scoop on the 100 Days Without Fear project?

Michelle Poler

Yeah, where should I start? This is 2015, I moved to New York to do a Master’s in Branding at the School of Visual Arts, and I realized that I was not living life to the fullest, that I was living inside of my comfort zone. And, suddenly, at the Master’s that I was doing, they asked us to do a 100-day project of our choice. And while a lot of the students kind of picked a project that could fit their lifestyle, I adopted my lifestyle to the project when I decided that I was going to go outside of my comfort zone for 100 days in a row. Basically, I faced one fear a day.

Pete Mockaitis

Okay. Well, lay it on us, so what was the first fear you tackled? And what was the most dramatic? Can we hear a few tales on the frontlines?

Michelle Poler

So, the first fear was to actually accept this project, to say yes to facing my fears. I spent my entire life living inside of my comfort zone, so it was like 26 years saying no to things that made me uncomfortable, and, suddenly, saying yes to all of them at the same time, so that was really scary, just saying yes to this project, committing to changing my life from one day to the other. So, that was the first fear.

And then I started slowly taking risks, doing things that are outside of my comfort zone, but that are not too risky or dangerous. For example, fear number two was, I think, eating an oyster, something I avoided for a really long time. Fear number three was getting a piercing in my ear. Like, those small things that I avoided for 26 years, and, suddenly, I’m like, “Let’s do this. I’ve been thinking about this for so long, but I didn’t have the courage. Now, I’m going to try it out.”

And then, little by little, I started, like, escalating on the level of, I guess, I don’t know, the fears that I was facing, until the project went viral around day 40. And then, even though I got a lot of love and new followers, and people being very inspired to go after their own fears, I also got criticism, as you could imagine, and people saying things like, “You’re doing things that I do on my day-to-day life.”

I was doing things like getting a Brazilian wax, or driving at night, or flying by myself, eating by myself in a restaurant, doing all these things that I just avoided for a long time. And I was like, “This is my time to step it up,” and that’s when I started facing bigger fears, doing things like skydiving, posing nude for an art class, holding a tarantula or a snake, doing standup comedy, things that people don’t do on their day-to-day.

Pete Mockaitis

Well, there’s so much in there right there, and it’s unfortunate when you hear the haters, or the critiques, because that’s sort of the whole idea, like, “Yeah, they were my fears, not yours.”

Michelle Poler
Yeah, it’s very personal.

Pete Mockaitis

And I think, if we’re honest with ourselves, all us probably have some fears that it seems like “normal people,” or everybody else is just fine with. I’m thinking about maybe there’s some, like, home improvement projects, like, “I don’t know if I really want to get down and dirty with, like, the saw, and the drywall.” And it’s like, “Oh, it’s no problem.”

And so, I think that’s dead-on. It’s sort of unique for each individual, and so maybe there’s an implication right there. It’s like who are you going to share this with? Some folks will support you, and some folks will just do the opposite.

Michelle Poler

That’s why people hide their fears because they’re afraid to be judged, I guess, and say, “Am I the only one afraid of this?” And then that’s why I think the project went viral because I was, I guess, brave enough to be very vocal about my own fears, even though they’re like super simple, some of them, but still scary to me.

Pete Mockaitis

Well, could you paint a picture for us for one particular that was pretty hard, and what the scene was like, and what you were feeling, and how it unfolded?

Michelle Poler

Well, so many come to my mind, it’s so hard to choose one. But let’s talk about posing nude in front of an art class…

Pete Mockaitis

Oh, let’s.

Michelle Poler

…which was really scary.

Pete Mockaitis

Lay it on us.

Michelle Poler

First of all, I didn’t come up with that fear. A friend of mine suggested that fear. Actually, I only came up with 20 fears. The rest, like all the other 80 fears, people suggested to me, and those that I can relate to, and I was like, “Yes, that is definitely outside of my comfort zone I would tackle.”

So, a friend suggested this, and she’s like, “Why don’t you pose nude for an art class?” And I’m like, “Why did you put that idea in my mind? Now I can’t say no because I’m in this process of facing my fears but I definitely don’t want to do that, but how can I say no to that now?” And so, okay, so I signed up for a class as a model, I talked to, I think it was, like, a school of art in New York, and I thought, I was so self-aware, so self-conscious that I went waxing.

So, I was like, “I don’t want any hair in my body,” and I starved like the entire day because I was like, “I want to look good,” which was a huge mistake, both decisions were big mistakes because when I got to the place, before it was my turn to model, the models that were there, they had, like, curves and a lot of hair.

And that’s when I realized, “What am I doing?” I was only thinking about myself. I was not thinking about the students. And the students need something to draw, they need more hair and curves and all these things, and I was so self-aware that I was removing all of that. And so, at the beginning when I undressed, I went to the room, immediately I turned around, I gave my back to the students because I was so afraid to look at their faces. And then the professor was like, “Okay, Michelle, can you turn around now?” It was like quick 5-minute poses.

So, after five minutes, she was like, “Please turn around,” and I was dying. I was like so embarrassed but, at the same time, I had this really interesting change of thought where I went from thinking about me, and how I look, and how I’m being perceived, to thinking about them and what they need in their class to succeed. And then, at that moment, I started bending myself and finding interesting shapes to give them something to draw. And it was really interesting having that transformative, I guess, thoughts in that moment.

Pete Mockaitis

That’s cool. And then how did it wrap up?

Michelle Poler

So, they all knew that I was facing a fear, that I don’t normally do this, and they were like really supportive at that point, and then they were clapping and cheering, and they showed me their drawings.

Pete Mockaitis

All right, so there you have it. And so, you have one sort of master key right there, was shifting the focus away from yourself onto others and being of service. That’s pretty cool.

Michelle Poler

I realized no one is judging us in the same way that we judge ourselves. I was judging myself so much, I was the only one judging myself, and that thought, that, I guess, aha moment stays with me every single time that I’m afraid to put myself out there.

Pete Mockaitis

That is powerful. And so, you share that and many other such insights in your book Hello, Fears: Crush Your Comfort Zone and Become Who You’re Meant to Be. Can you lay it on us, what are some of the master principles that you’ve unearthed here?

Michelle Poler

Well, I divided the book into 10 chapters, and they’re all the 10 different fears that stops us from becoming who we’re meant to be from fulfilling our potential. And some of the main aha moments that I share in the book are related to the fear of rejection and failure. Those, at the end of the day, are the biggest fears that hold us back from pursuing what we actually want to go after, and fulfilling our own definition of success.

At the end of the day, it’s not about skydiving or holding tarantulas. It’s about what we tell ourselves in that moment where we’re about to take a risk, a risk that is aligned to our dreams. That’s the most important thing because it’s not about facing any fears, it’s not about facing a hundred fears. I’m not here to tell you to do that. It’s about facing the right fears, the ones that are holding you back from the life that you actually want to live.

And so, one of the things that I share in there is one of the most powerful tools that I have, and that have changed the lives of so many people is that, you know, the typical question that, I don’t know, why on earth we are used to asking ourselves or other people around us when we’re about to face a fear, and it’s, “What’s the worst that can happen?” Have you ever asked yourself that question or somebody else?

Pete Mockaitis

Certainly.

Michelle Poler

That’s a really terrible question. Because when you think about what’s the worst that could happen, immediately your mind goes to the risk, and that’s not helpful when you’re trying to face a fear. And even though I know the intention of the question is to help us understand that we’re not going to die, but we might get rejected, we might get fired, we might be embarrassed. There are other things that might happen if we take certain risks.

So, instead of asking ourselves, “What’s the worst that can happen?” I started asking myself, “What’s the best that can happen?” That question brings your mind to focus on the reward instead of the risks. And that is the main reason why we, in the first place, decide to face a fear because we want something, we desire something, so let’s focus on that instead of the risk that that may bring.

And it’s not that I’m telling you do not consider the risk. We’re human and that is the first thing that we’ll consider anyways, but we forget to consider the reward. And that is why, so often, we stay in our comfort zones. So, next time you’re about to do something scary, something that is worth it but that’s outside of your comfort zone, ask yourself, “What’s the best that can happen?” Try to put yourself, your mind, in that scenario, and that is the one thing that will encourage you to take action.

Pete Mockaitis

Oh, that’s handy. Thank you.

And, Michelle, you’ve also got a strategy for, specifically, dealing with impostor syndrome. What’s that?

Michelle Poler

Well, impostor syndrome is the one thing that keeps us from really going after the things that we want to do because we tell ourselves that we don’t deserve that, that we’re not worthy of, and we ask ourselves, “Why me? Why would people listen to me, my message? Who am I to be someone to be heard?”

And I ask people to ask themselves, “Why not me?” That is a question I ask myself before doing this project, and putting it out there, because I was like, “Why would people follow me? Like, why would I talk about fear? Who am I?” And then I’m like, “Why not me? Am I not passionate enough? Am I not creative enough? Am I not intelligent enough? Do I don’t want this enough? I do.” So, it’s about betting on yourself.

And one question, like a different question I always ask myself, and this really also helps with impostor syndrome, is, “What is everybody else doing? And how can I be more me?” I don’t have anything against Google, but people Google too many things, and they Google how to dress up for conferences, how to speak in public, how to do all these things.

And I never Google anything, unless it’s an address or something like that, or a recipe, but before going to Google, I always ask myself, “How would I do this? How would I speak in public? How would I dress for a conference? How would I do an icebreaker?” Like, anything, I always ask myself, “How would I do it?” before I research other people. I actually avoid researching other people because I want to make sure that anything I do comes from me.

If I’m going to do research, I’m going to do it myself, I’m going to do my own research. When we own who we are, and our authentic selves, we are not going to have to deal with the impostor syndrome. The impostor syndrome is when we’re trying to be somebody else to fit in, to be accepted, to be liked. But if you’re just really trying to be yourself because you like who you are, you accept who you are, you give yourself permission to just be you, there will not be any impostor syndrome that can stop you.

Pete Mockaitis

Well, that’s really a fun perspective in terms of if I am not trying to fit into a mold or a role, then the impostor syndrome goes away because the comparison goes away. It’s like, “Oh, I’m not a big shot like these people who are doing these things in this way,” because you didn’t even bring that up in the first place. It’s like, “I’m just going to do how I do…I’m just going to do this thing the way I imagine it ought to be done,” as opposed to trying to fit another set of expectations, which I may very well fail to meet because they’re not mine.

Michelle Poler

That’s why I encourage people, instead of comparing yourself, contrast. I’ve been practicing that for so many years already. Like, since I was little, I didn’t want to be like anybody else. I think this was, I have to thank my mom for this, in that she, in the first place, she called me Michelle because she was like, “I don’t know any Michelle in the world, so then I won’t have any expectations. I just want you to be who you are,” since the beginning, and she was always very curious about who I am, and always listening to me.

And I always felt like I had a voice, and I’m really grateful for that. And that is what I want to encourage people now to see that they have a voice, that it matters, that that’s their own, and that’s all we want. We don’t want a copycat. We don’t want more of what we already know and have. We want real people with real problems, real solutions, real ideas.

Pete Mockaitis

And then, to that end, I suppose as you’re doing you and living your life and approaching things the way you want to, you’re going to get some criticisms, you’re going to have of those haters. What are your favorite approaches for dealing with this kind of stuff that comes your way?

Michelle Poler

The first thing is that it’s so important to understand that we are not here to be liked by everybody, and that is okay. I’d rather be loved by a few than liked by everybody. And the more you want to be liked by everybody, the more generic you will sound, and the less you will connect with people. The more you are daring to be disliked by others, the more true to yourself you’ll be, and the more you’ll connect with the right audience. And, for me, that’s priceless.

And I’ve heard a lot of people that they don’t like me, and they say, “Michelle, I can’t stand you. I can’t stand your voice or how self-confident you are,” because I am very self-confident, and people don’t like that. But then there’s another group of people that really admire that, and that they want to be like this, and they want to learn from me so they buy my programs, and they buy my books, and they listen to my talks. And they actually get really inspired to change their own lives. And, to me, that’s enough.

Pete Mockaitis

That’s cool. Well, so that’s a great perspective, that we’re not trying to be liked by everybody. We’re just loved by a few, and that’s enough. And so, help us, if we’re there intellectually, and we’re like, “Yeah, that makes sense. I agree. That checks out,” and yet emotionally we’re not there, how do you recommend we get there?

Michelle Poler

So, I want to ask you something. Do you like everybody? If you have a party at your house, would you like everybody to be there? Or, can you think of a few people that you’re like, “I’d rather not have him in my house. I’d rather not hang out with that person”? And every time, for example, on social media, if I lose followers, I don’t think, “Oh, they don’t like me.” I’m like, “Maybe I don’t even like them either. Like, we’re just not a match, and that’s okay.”

Like I was saying, we’re not here to be liked by everybody, just like you don’t like everybody. It’s okay if people don’t like you. But those people you don’t like, they’re loved by other people, and that’s fine too. I think we’re not supposed to be a match for everybody in anything in life, in love, in jobs, as influencers, as anything, and I’m okay with that.

Pete Mockaitis

That’s cool. And then when you’re in the midst of doing something you’re afraid of, do you have any specific mantras, self-talk, pump-up rituals, any tactical things you do when you are about to enter into the fearful place, and you want to make sure that you go forward instead of running away?

Michelle Poler

Yeah, sure. So, like I told you at the beginning of this conversation, I spent my entire life avoiding fear, avoiding discomfort because every single time that I experience that feeling in my body, when you’re about to do something scary and your stomach starts telling you, “Stop it! I don’t want to go that route. Like, it’s not safe.”

I used to interpret that feeling as a sign of my body telling me, “Don’t go that way. It’s dangerous and it’s a sign that you shouldn’t do that.” It’s my intuition trying to protect me. And I realized that that feeling is also growth. That, for me, was a huge realization because I thought, “Oh, my body is protecting me,” and I realized now that my body was protecting me from growth, from opportunity. And growth feels like that. It feels uncomfortable.

So, every time now that I experience that feeling in my body of, “I am uncomfortable. My stomach is telling me not to go that way,” I understand that there’s an opportunity there. And now, instead of avoiding it, I choose that.

Pete Mockaitis

Okay. So, through practice, repetitions, you’ve just made the connection that, “Oh, doing this thing that I’m afraid of is what makes for growth. So, this fear feeling is really just the pre-growth feeling, and that’s that.”

Michelle Poler

Yes, it was over and over again, as I was doing the project, every single day, if you ask me, you haven’t asked me this, but everybody asks me the same question, “What’s the biggest fear that you faced?” And the biggest fear is the one you haven’t faced. It’s so hard for me to tell you and answer for that question now because I already faced them.

Every single day of the project, I thought, “Okay, this was not that bad. Tomorrow I’m going to die. I can’t.” It’s going to be the worst one because I haven’t done it, because the fear is the unknown, but after I did it, every single day would be like, “Okay, that wasn’t that bad. Tomorrow is the worst one.” So, I can’t even think which one was the worst one because after I did all of them, none of them was as bad as what I thought they were going to be.

Pete Mockaitis
Well, that’s a huge lesson right there in terms of, “Hey, take it from Michelle. She’s done this a hundred times, plus a hundred document of times and then more that each time it wasn’t as bad as you feared it would be.” And I’m curious, so that was the experience over and over and over again, “Oh, I’m really scared of this thing. Oh, that wasn’t so bad. I’m really scared of the next thing. Oh, that wasn’t so bad.” So, I’m curious, somewhere along the line after 50 days or 70 days, did you come to think that the next day wasn’t going to be so bad?

Michelle Poler

No.

Pete Mockaitis

No? Okay.

Michelle Poler

And I’m still a fearful person. People think that I’m fearless now, they’re like, “Oh, my fearless friend, you faced so many fears. I want to be fearless like you.” I’m quite the opposite. And, actually, being called fearless is like a disservice to what I actually am. It’s actually the opposite of brave. Fearless is doing the things that don’t scare you.

So, what’s the courage in there? Why would I be proud of being fearless? I’m more proud of being brave. That means that I was definitely afraid every single time that I faced a fear and still I conquered that fear, like I still showed up. And I think that is more powerful, more valuable, more inspiring than being fearless.

Pete Mockaitis

So, now you have the perception, “Oh, this fear feeling equals that I’m about to grow.” So, you know and understand that at a deep level but you still feel the full fear and think it’s going to be terrible before you embark on the thing?

Michelle Poler

Yes, and I try to avoid it at the beginning, I go through the entire process just like the first time because we’re human, and new fears come up every single day, and a fear means that it’s something that you haven’t done before, but, also, it’s really interesting to understand that if you do something and you don’t like it, it’s very fair that you don’t want to do it again, not because you’re afraid but because you don’t like it, generally, because you tried it.

My entire life, I just said, “I don’t like this,” or, “I’m afraid of this,” but I never tried those things. Like, I would say, “I don’t like oysters.” “Have you ever tried an oyster?” “No.” “So, how can you know?” So, it was so important for me to just expose myself to all these fears, try all these things, and now I can tell you with all certainty that I do not rollercoasters. I tried them and I don’t like them, and I don’t want to try them again. But I could if I need to, but I don’t want to, but I tried them.

Pete Mockaitis
Yeah, that’s a good distinction right there. Okay. So, maybe, Michelle, if we could zoom right into now, today, is there something that you are experiencing fear and avoidance of right now? And how are you talking to yourself or planning to approach it?

Michelle Poler

Well, for the first time in my life, I am experiencing fear of success. When I heard about fear of success years ago, I was like, “That makes no sense. Why would somebody be afraid of reaching their goals? It makes no sense.” But now, as a mom, and understanding how limited time is, I am afraid of success. So, I’m at that point where I’m, like, “Should I grow more? Should I stay where I am?” Like, that is one of the fears I am right now dealing with, and also the fear of having another baby. Like, we are thinking about it but, at the same time, brings a lot of fear because now we know what it is to be parents.

Pete Mockaitis

So, with the fear of success, what are you doing with that?

Michelle Poler
I guess the most important thing is to understand what is your definition of success first. And understanding also that it can change over the years, because my definition of success was to be New York Times’ bestseller, speak as much as possible, like be on the road as much as possible, be on all these shows and surround myself with these people.

And, suddenly, what if my definition of success changed to also have more free time, be more at home, have more quality time with my family? So, it’s understanding that and being at peace with what your definition of success is today, and stop pursuing an old definition of success that you had in the past, or worse yet, pursuing other people’s definition of success.

Pete Mockaitis

Okay. Well, so I guess what I’m thinking here is, with this fear of success, it doesn’t so much seem as much as the others as something that you’re just going to just go do it, but rather maybe it seems like there’s some thinking, some distinguishing, some sorting out, that prioritizing, soul-searching, values to finding clarifying action that’s happening with this fear.

Michelle Poler

I think what’s important here is to identify if you’re not pursuing something because it is no longer part of your definition of success, or is it because of fear? If the answer is fear, then my recommendation is to never make decisions based on fear. If only fear is what’s holding you back, then you definitely have to go for it. Find the best way to do it. If you need therapy, whatever you need, but go for it. Do not allow fear to hold you back.

But if it’s just that your definition of success changed, then that’s something that you have to adapt. So, in this point, that’s what I’m trying to figure out, “Am I not growing because of fear? Or is it because my definition changed in this moment?” And it can always change back in the future but that’s what I’m trying to understand right now. So, it’s a lot about just looking inside and being really honest with yourself, and do not ask other people what the answer is. We love asking other people, “What do you think I should do?” And people don’t know. Only you know. The answer is always inside of you.

Pete Mockaitis

And as you do this self-inquiry, having these conversations with yourself, and you land at…and sometimes it’s really trick to reach that point of clarity, that, “Oh, it’s only fear that’s holding me back,” because a lot of times, fear can masquerade as, or rationalize some things, like, “No, really, there’s a strong chance something terrible will happen if you do that thing.” So, I guess we can call that risk. Do you have some perspective on how you distinguish between this emotion of fear versus valid risks that need to be prudently considered?

Michelle Poler

That’s a really good question. I think it’s like having that honest conversation with yourself. Like, if I’m thinking about it, what I told you about the fear of success, I think it’s more aligned to I actually want to spend more time with my family, I actually want to feel more at peace and less rushed and less things to do, and all of that.

But when I talked about having another baby, that is actually fear, that’s not my definition of success. That is, I know what it takes now to have another baby, and fear is the one thing that’s holding me back but it’s something I want. So, if I determined that fear is the only thing in my way then I’m not going to let it come in the way of something I want.

Pete Mockaitis

Okay. Understood. Well, now zooming into the workplace in particular, what are some of the top fears you’ve observed people have at work, and how you recommend we tackle them?

Michelle Poler

One of the main fears people have at work is they don’t want to be themselves. They want to be who they’re expected to be. So, I’m at work, I’m expected to behave like this, to talk like this, to send emails like this. And I want to encourage people to be their true selves at all times with whoever, with your boss, with your team, with your in-laws, with anybody. I think that that is the definition of living an authentic life, and people say, “Well, at my work, they wouldn’t like my real self.” Then maybe you’re not at the right job, that’s what I would say.

I think that we only have one life. I’m very mindful about that. And one of my purposes in life is to live life to the fullest, is to really enjoy my life, is to feel that every day counts, and I want to be happy. And there is a huge difference between being comfortable and being happy. And people, without realizing it, they’re pursuing comfort, not happiness. And I feel like it’s one of my missions to make people see this and understand that comfort will not lead to happiness.

And we’re told this since we’re little. Since we’re little, it’s like, “You need to find the right job. You need to have stability. You need to find a partner. You need to have all these things.” And when you check all the boxes, and you ask yourself, “Is this what happiness is about?” If you’re not truly happy, it means that you’re checking other people’s boxes, and you should check your own boxes. That’s what will lead you to your own happiness and not comfort.

Pete Mockaitis

Okay. And now let’s hear about, at work, folks have a fear of speaking up in a meeting or asking for what they really want and need. Any tips on how we can tackle those in particular?

Michelle Poler

For me, the best strategy is if you really believe that you deserve something, you’re certain about that, you’re not just being entitled, or you want it because somebody else got it, you feel like, “I deserve this. They’re not recognizing me and I have to speak up for myself,” first, you have to do it. If not, you’re betraying yourself and you are rejecting yourself. Because of the fear of rejection that you’re getting, you have that fear, “I don’t want to be rejected. I don’t want to get a no,” you are rejecting yourself. And I think that’s the worst thing that we could do.

So, first of all, encouraging people here to speak up and ask for what they know they deserve. And the strategy I would use, again, is asking myself, “What’s the best that can happen if I do this, if I ask for it?” What if you get a yes? We’re so afraid of getting a no and being judged that we stay where we are. Every time that we choose comfort over growth, we feel like we’re staying where we are but we’re actually moving backwards.

Every single time we’re choosing comfort, we’re moving backwards because the rest of the world is moving forward. And I think it’s also, like, our duty to speak up for ourselves. And if you know you deserve this, you ask for it and you don’t get it, maybe you’re at a place that they don’t appreciate you enough.

Pete Mockaitis

Okay. Now, could you share a favorite quote, something you find inspiring?

Michelle Poler

This quote is by Steven Pressfield, and this is the quote that inspired me to put my 100 Day project out there.

So, it says, “Are you born a writer? Were you put on earth to be a painter, a scientist, an apostle of peace? In the end, the question can only be answered by action. Do it or don’t do it. If you were meant to cure cancer, or write a symphony, or crack cold fusion, and you don’t do it, you not only hurt yourself. You hurt your children. You hurt me. You hurt the planet. Creative work is not a selfish act or a bid for attention on the part of the actor. It’s a gift to the world and every being in it. Don’t cheat us of your contribution. Give us what you’ve got.”

Pete Mockaitis

Oh, beautiful. Thank you. And a favorite study or experiment or bit of research?

Michelle Poler

Well, I’m a big fan of Brene Brown. All of her research that she’s done about empathy, about language, about vulnerability, anything that is in her books, I’m a huge fan of those. I learned so much from her.

Pete Mockaitis

All right. And a favorite book?

Michelle Poler

I would say The War of Art by Steven Pressfield from the quote that I read. That book is very simple and very life-changing. Well, also, a kids’ book.

Pete Mockaitis

Oh, sure.

Michelle Poler

Can I say a kids’ book that I feel every adult should read. It’s called Maybe by Kobi Yamada.

Pete Mockaitis

Okay. And a favorite tool, something you use to be awesome at your job?

Michelle Poler

Favorite tool, Videoleap. That’s where I edit all my reels. So easy to create a reel and find the perfect music and everything through Videoleap. So, I’m a big fan.

Pete Mockaitis

All right. And a favorite habit?

Michelle Poler

Dancing before any phone call, any important phone call, like with clients, or doing a podcast interview. Before coming to this podcast, I danced by myself in my office. It just gets me in the right mood.

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

Michelle Poler

The question, “What’s the best that can happen?” It’s the one that I get the most quoted on. And if I can share another one, is when you believe in yourself so much, you make others believe in you as well.

Pete Mockaitis

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

Michelle Poler

You can go to my website, MichellePoler.com, or if you want to watch me embarrass myself facing all 100 fears, you can go to 100DaysWithoutFear.com, or follow me on Instagram @hellofears.

Pete Mockaitis

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

Michelle Poler

I would say the final challenge would be find the right place for you. Don’t settle. Don’t settle for anything in life, not for a job, not for a partner, not for a city, not for a home, not for a dog. Find what feels right for you.

Pete Mockaitis

All right. Michelle, thank you. This was a ton of fun. And I wish you many adventures and fun times crushing more fears.

Michelle Poler

Thank you. Thank you for having me.

933: How Building a Habit of Bravery Transforms Everything with Todd Henry

By | Podcasts | No Comments

 

 

Todd Henry shares how to build the courage to chase after opportunities amidst uncertainty.

You’ll Learn:

  1. How to muster courage in the moment 
  2. The biggest myth that holds us back 
  3. Five steps to feel braver every day 

About Todd

Todd Henry teaches leaders and organizations how to establish practices that lead to everyday brilliance. He is the author of seven books: The Accidental Creative, Die Empty, Louder Than Words, Herding Tigers, The Motivation Code, Daily Creative, The Brave Habit, which have been translated into more than a dozen languages, and he speaks and consults across dozens of industries on creativity, leadership, and passion for work.

With more than fifteen million downloads, his podcast offers weekly tips for how to stay prolific, brilliant, and healthy.

Resources Mentioned

Todd Henry Interview Transcript

Pete Mockaitis

Todd, welcome back.

Todd Henry

Pete, it is so good to be back on the show. Thanks for the kind invitation.

Pete Mockaitis

Oh, thank you. You’ve got a fresh book, and you’ve said a lot of interesting things, and written a lot of cool books. I’m curious, why bravery as the topic now?

Todd Henry

10 years ago, I wrote a book called Die Empty. It released, and did really well, but there was something that I overlooked in that book, and it always plagued me. There was one topic that I didn’t write about. And it was kind of one of those forehead-slap moments when I realized, “Oh, there’s kind of an important thing I overlooked here,” and that topic was bravery.

Because I talked about all the ways that we can overcome these hurdles we encounter, these pitfalls, when doing difficult creative work, and some strategies for doing that, but the one key element that I found in people and in teams who were willing and able to do that was that they exhibited bravery. And so, I kind of committed to looking into, to investigating that topic of bravery.

And my ingoing assumption was that, “Well, some people are just wired for it. They’re just more risk-tolerant and some people aren’t.” But the more I researched the topic, I realized, actually, bravery is exhibited in all different kinds of places by all different kinds of people, and people who historically had not exhibited bravery suddenly started exhibiting bravery, and vice versa.

What I realized was that bravery is not a baked-in personality trait, that bravery is actually a habit, it’s a discipline that we can train ourselves to exhibit. And so, that was kind of the initial source of the book.

And so, for the last six years, it’s been a passion project. I’ve been working on this book, and it took me six years to kind of pull it all together, and now it’s finally here. So, it’s called The Brave Habit, and it’s about how to develop the habit of bravery as you approach creative work, leadership, relationships, and everything that you have to do in life.

Pete Mockaitis

All right. Well, tell us, what impact does having upgraded bravery deliver for us?

Todd Henry

So, I think that we often conflate two things. We conflate bravery with boldness. And we also conflate cowardice with wisdom. And what I mean by that is we all have moments in our life where we recognize an opportunity, where we see that there’s something possible for us if we were willing to act, but there’s a little voice inside of us that says, “Well, maybe it would be better if…” or, “Maybe someone else is better equipped to…” or, “You really don’t have the skills to…” or things of that nature. And that’s really cowardice whispering in our ear, but we often conflate it with wisdom. We think this is wisdom speaking to us.

And what I discovered was that there really are two things that comprise bravery in those moments. There are two core attributes, two core traits, that people who consistently ignore the voice of cowardice that comes disguised as wisdom, and, instead, choose to engage in brave action. There are two core attributes and they tend to exhibit in those moments. The first is they have an optimistic vision of the future, meaning that they have a vision of a better possible future that they could be navigating toward. And the second attribute that they tend to exhibit is a sense of perceived agency to bring that better possible future about.

So, think about a team. When I look at the teams who are consistently doing what I would consider to be brave work, they are teams who have a vision that they’re navigating toward, they have a very clear North Pole that they believe in and that they’re willing, if necessary, to sacrifice on behalf of because they believe deeply in that vision.

Versus people who have kind of a pessimistic vision of the future, “Well, I really don’t know what the future holds. And who can really tell anyway, right?” And so, that’s sort of the opposite of what I’m talking about. And they tend to have a sense of agency, meaning, “We believe that we have the platform, the proficiency, that we have people around us who can help us accomplish that vision.”

So, when you have those attributes, you’ve created a fertile field within which bravery is likely to occur. Now, it doesn’t mean it will occur but you’re creating a fertile field within which bravery is likely to occur. So, how does that play out for us as individuals in the workplace?

Well, we all have to confront uncertainty, we have big projects we’re working on, ideas maybe that are noodling around the back of our mind, and we’re thinking about bringing them into the world, but that little voice of cowardice is whispering in our ear, “Well, maybe somebody else would be better suited to do that,” “Well, maybe you should wait and let somebody else step up,” “Well, maybe you’re not the right person to lead this,” or, “Well, maybe you need to do a power grab because you need to prove that you’re the right person.” Well, that’s not necessarily bravery. That’s just boldness.

So, we have these little voices whispering in the back of our ear. In those moments where we’re tempted with cowardice, we can ask ourselves, “Okay, am I afraid to act because I don’t have a clear vision of where I’m going, or I don’t have a vision of a better possible future? Or, am I afraid to act because I don’t trust that I have agency to be able to create meaningful change in the direction of my vision?”

And simply by asking ourselves those questions consistently, by putting some qualifiers on what we feel, inherently, that self-protection instinct that we have, we can, a) develop a better narrative to help ourselves get through those moments, and, b) identify any areas where maybe we are lacking. We tend to think bravery is, “Well, just do it. Just leap. Just jump from the cliff, right? Just say the thing. Just have the conversation.”

That’s not necessarily always bravery. Sometimes it’s boldness. Boldness and bravery are not necessarily the same thing. Sometimes bravery means waiting until the right time. So, when you ask yourself those questions, “Do I have a clear vision of where I’m going? And do I trust that I have the agency to be able to bring it about?”

If the answer to either of those is no, maybe the bravest thing you can do is wait as your vision is clarified, or wait until you develop the skill necessary to bring it about. That doesn’t mean you’re being a coward. That means you’re being strategic. And so, when you ask, “How does bravery benefit us?” It benefits us by giving us a sense of the places in our life where we can act in a meaningful way to develop our capacity to do work that is surprising, valuable, and, ultimately, contributive to the body of work that we want to build.

Pete Mockaitis

Now, I think there’s a lot of interesting tidbits here in terms of the voice of cowardice can be sneaky, and we may not even recognize that that’s what that is. I remember we had Kwame Christian say once early on the show that fear masquerades in many forms. And I thought that was really clever in terms of it’s procrastination, or, “You know what, maybe this isn’t the right time,” like, any number of voices. And it’s good to just say, “Oh, no, what’s really happening is I’m scared. What’s really missing here is bravery.”

And you’ve done a cool segmentation, so, “Is it a matter of vision or is it a matter of agency?” And help me out, when I’m feeling un-brave, I think what’s going on is I think, “There’s a substantial chance that this is going to go badly for me.” And so, do we categorize that as a vision matter, or an agency matter, or where does that fall into your schema?

Todd Henry

Well, that’s a really great example. Can I tell you a story of how that’s playing out actually for me right now? I think I mentioned to you, so before we started recording, I’ve been doing The Accidental Creative podcast since 2005.

As I was writing this book, I began challenging people, in the book, to ask some really brave questions and very dangerous questions, maybe. And among those questions that I began asking myself was, “If I were starting over again, would I be doing things the way that I’m doing them right now?” And the uncomfortable answer that I came to, Pete, was, “No. No, I wouldn’t.” Like, it’s fine, it’s working, people seem to enjoy it, it’s great, but would I be doing it this way? No.

Why? Because I have a vision of a way that things could be better, and I was feeling a little bit of discontentment around the way I was doing things. Well, there’s a lot of costs involved in changing something that has a substantial audience, and that has been successful, and that’s financially contributive to the bottom line of my business. There’s a substantial risk involved. And, to your point, you asked the question, “Well, what if this goes badly for me?” Yeah, there’s a lot of risk involved in doing something like that.

What compelled me to make the change that we made, which was basically completely rebranding the show, redoing the format, and eliminating thousands of back episodes of the podcast, and starting over with Episode 1 on January 1st, what compelled me to do it was that vision. I knew I had the agency to bring it about because I have created a podcast, I know how to do this, I know how to do creative work and make audio shows, but the vision was what compelled me. I had a very clear vision of what this could be.

And so, the question I asked myself was, “If I fail, will it be worth it if it’s in pursuit of a vision that I care about?” And the answer was, “Yes.” And like Seth Godin likes to say, “This might not work,” and it might not work. It still might not work. But the vision superseded my fear of failure in this case. And so, what my response was, “If it fails, I want to go down doing the thing that I believed to be the right thing. I want to pursue the vision for the work that I think is the best possible manifestation of this kind of work that I’m trying to do right now.”

And so, I think the answer to your question, that you have to be able to say, “It’s worth failing in the pursuit of this vision. It’s worth sacrificing something in the pursuit of this vision if I believe it’s the right direction.” And that doesn’t mean it’s always the case for everyone. In my case, it was, but the problem is we often don’t stop to ask the question because we just assume that the goal of life is to protect, to be comfortable.

Khalil Gibran said, “Verily the lust for comfort murders the passion of the soul, and then walks grinning the funeral.” So, when we succumb to the love of comfort, the lust for comfort, we murder our own soul. And so, the challenge I would have for listeners is, “Where are you falling prey to the love of comfort?” Not comfort itself. There’s nothing wrong with comfort, but when you fall in love with comfort, you’re inherently going to compromise what’s possible because nothing great is ever done from a position of comfort.

Pete Mockaitis

Okay. So, then it sounds like the fear I have that things are going to go badly, in your categorization system, that’s a matter of the vision may not be clear or strong enough to overpower, in the internal tug of war, the reluctance or internal fear.

Todd Henry

Yeah, that’s right. Or, in some cases, like in organizations, it could be that that vision just hasn’t been communicated clearly enough, or people don’t understand how they play into that vision. There are a lot of organizations with people who are more than willing to be brave, and to do brave work, and to have brave conversations, and to confront uncertainty, but they don’t really understand how their efforts would matter because the leader hasn’t given a compelling vision for where the organization is going.

And so, the result is you have all these people who are at the ready, they want to do something, but they don’t really know what to do. Or, you have organizations where the leader is casting vision constantly but they’re not reinforcing the agency. They try to be overcontrolling in their organization. They step in and do the work for people instead of equipping people and giving them agency to do their own work, to come up with their own ideas. And the net result of that is people just feel powerless, they just succumb, and they say, “Okay, fine. Just tell me what to do.”

Well, are they going to do brave work? No, of course not because they’ve been robbed of a sense of agency. And so, as leaders of organizations, the biggest gift that we can give to people is to position them in places where bravery is likely to occur, which means being very clear about our vision but also speaking agency into them, speaking encouragement into them, giving them the ability to try things, to experiment, even to fail in small ways that aren’t fatal to the organization so that they have that sense of agency to act bravely in the face of uncertainty.

Pete Mockaitis

All right. Well, let’s maybe zoom way in. Let’s say we have an individual, and they want to say something that’s maybe uncomfortable, unpopular, because they are going against the status quo, they’re challenging someone so they might get offended, outraged, create some political rifts, etc. Help us out, Todd. What are the key steps to follow in order to speak up when bravery is required?

Todd Henry

So, you have to be absolutely certain that your action is in the service of a vision, of a better possible future. It’s not self-serving, it’s not bold, because boldness is mostly self-serving. Bravery is always empathetic. So, how is speaking up going to be in service of a greater vision, whether that’s creating a better environment on the team, communicating something to the leader that maybe they’re not aware of, and they need to be aware of because this is impacting everyone else around us?

So, if the answer to that is yes, and the second question you have to ask is, “Am I the right person to have this conversation?” Because if a random person at a low level of an organization decides to ambush the CEO in the lobby of the building one day and say something, well, you have no agency, you have no platform. You’re doing something but that’s just boldness. That’s not necessarily bravery because what impact is that going to have? Probably very little impact. And, in fact, it could be detrimental to the overall cause.

And so, those are the two questions you have to ask, “Am I doing this in the service of a better vision, a greater vision? Or, am I just doing this to be self-serving for my own political purposes?” And the second question you have to ask is, “Am I the right person to be able to do this? So, do I have the agency? Do I have the platform to be able to do this?”

And if the answer to that second question is no, “Well, then who does have the platform? Who am I connected to who I might be able to, then, have this conversation with and we can go together to the leader, we can go together to whoever this person is and have a conversation together because the other person has platform, they have relationship, they have credibility that maybe I don’t have?”

So, again, this framework helps you in those moments where you have to make a brave decision, it helps you sort of gauge and diagnose places where, “Well, why do I feel hesitant to do this? Oh, it’s because I don’t really have the agency to do this. I could just go ambush this person with a conversation but they’re not going to listen to me because I don’t have the right platform, but I do know someone who does, so I’m going to go to them. We’re going to have a conversation, and we’re going to go together to them, and then we’re going to have a higher probability chance of creating the change we’re trying to create.”

So, two questions, again, “Is this in service of a greater vision or in service of me?” That’s the empathy question. And then the second one is, “Do I have the credibility, the platform, the proficiency to be able to have this conversation? If not, then how can I gain that agency in order to create this meaningful change toward the vision that I’m pursuing?”

Pete Mockaitis

Okay. Well, could you maybe share some stories in which we’ve got a professional who is finding they would like an upgrade to their bravery, and then they walked these paths of upgrading the vision, or upgrading the agency to make it happen?

Todd Henry

Yeah, so this example I shared in the book of a guy named Scott. Scott was a commercial real estate agent, and it was the very fortuitous time of the late 2000s, so right around 2008, and you can kind of imagine where this story is going because we experienced a tremendous collapse in the real estate industry, and, thus, the entire economy in 2008, and so Scott was really in danger of just being without livelihood.

And so, he was talking with his wife, and they were expecting their first child, and it was obviously a really kind of nerve-racking time for them. And he was considering the possibility of making a transition into doing residential real estate but he didn’t really have a tremendous amount of experience doing residential real estate, so he had a job offer to go sell office furniture, and he was thinking about just going to sell office furniture because, “This is something that can pay the bills with our first child on the way.”

And as he was talking about this with his wife, his wife said, “Hey, listen, you have all of this experience in the real estate industry, you have some connections in the real estate industry, albeit not in the residential real estate industry, and you have a very clear vision of how you could do this differently, how you could be a different kind of real estate agent that could be more attractive to people, that could actually be kind of a partner with people rather than just sort of being the go-between in these transactions.”

And she said, “Let’s do this. Let’s establish some time, a timeframe, let’s call it six months, and why don’t you try this, let’s see what happens. And if we see some momentum, then we’ll keep moving forward. And if we don’t, then you can always go take the office furniture job, and we’ll just say, ‘Okay, now you’re an office furniture salesman,’ or whatever.”

And so, he did. So, he decided to launch his real estate practice, and it did not go well for the first handful of months, and it was a really difficult time in the market. But just in the nick of time, he did make his first sale, and that was enough to generate some cashflow and kind of keep the business moving forward. And the way that he did it was because he was following his vision, his vision of a better possible future, the way that things could be different in the real estate industry.

And the reason I share that story is because his instinct in the moment was, “Well, I just need to retreat to the easiest thing I can do, which is go take a salaried job to pay the bills.” Someone else came along, someone who had a very vested interest in his success came along and spoke agency into him, said, “Hey, you could do that. That’s fine. But that’s not what you’re capable of.”

“You don’t even know what you’re capable of yet. We haven’t even tried yet. You have agency you haven’t even tapped into. So, why don’t you go try this? I see what you’re capable of. I know what you’re capable of. You have a vision. Go try this.” He had someone, his wife, who spoke courage into him. And so, Scott did because she put him in that very fertile field where brave action is likely to occur, that place of agency and vision.

Now, 10 years later, his real estate practice is one of the top real estate practices in the country within his company, which is remarkable. But even if it hadn’t worked out that way, would he have made the brave choice? Even if it hadn’t worked out for him, would he have made the brave choice?

The answer, I believe, is yes, absolutely, because bravery has nothing to do with outcomes. You can make a good decision, Pete, that has a bad outcome, and you can make a bad decision that has a good outcome. That’s why it’s so difficult often to analyze our decisions because we tend to associate our outcomes with our decisions. But the reality is we make decisions with the best information we have at the time, and we can’t always control where those decisions are going to lead.

And so, even if Scott had failed, he still made a brave choice, and it still was probably a good decision for him to try it to see if he could make it work. And that’s part of the thing that I think leads us to succumb to cowardice, is that we are constantly analyzing our past decisions through our present understanding, and the net result is that we think that things were bad decisions, when, actually, they may have been good decisions, they just had bad outcomes. We made the best decision we could at the time.

So, I think that story of Scott is one that kind of illustrates what it looks like to have someone speaking agency and optimism into you in those moments of uncertainty.

Pete Mockaitis

That’s lovely. Thank you. And we had Annie Duke, a professional poker player, say a similar point in terms of you may have made the best decision though the outcome didn’t work out, and that doesn’t mean it wasn’t the best decision. So, that’s good to consider. I’d love to hear the counterpoint to that in terms of we may be more likely to regret what we didn’t do. How do we judiciously, astutely, wisely, prudently determine, “Ah, this harebrained scheme of mine, I should kill right now rather than pursue it to my detriment”?

Todd Henry

Yeah. So, interestingly, we’re doing an episode of our podcast that kind of deals with that, how sometimes we get frozen in these moments. And as part of the interview, we revisited the conversation with Seth Godin about his book The Dip. And I don’t know if you’re familiar with the book but in the book, he talks about…

Pete Mockaitis

Oh, yeah, it’s short. I read it. It’s fun.

Todd Henry

Yeah, the fantastic. The two ways that we get stuck. The first way is what he calls a cul-de-sac, which is basically a dead end where we’re just going round and round and round and round the cul-de-sac, and it feels like we’re making progress but, really, we’re just stuck, we don’t really have a vision. And the best thing to do in the cul-de-sac is just to quit because you’re never going to get anywhere if you’re in a cul-de-sac.

And then he said the second thing, the second kind of place where we get stuck is in what he calls the dip. And the dip is that inevitable difficult moment after we’ve started a creative project, and we have all this energy at the beginning because it’s new, and it’s fresh, and we have a vision, and then it gets really hard, and so a lot of people give up. Scott Belsky calls this the project plateau. It’s the moment where it starts getting really hard but we don’t have the same excitement about the work, and so we tend to want to quit. But you don’t quit in the dip.

If you have a vision, of the way things could be, and you can see a path to get there, you don’t quit in the dip. You keep pushing. You keep going because there are rewards on the other side. So, when we talk about a vision of a better possible future, and the agency to bring it about, that’s really kind of where I’m playing as well, is when you get into those moments where you’re in the dip, and it’s uncertain, you don’t know what to do, and you don’t know if you really feel like pushing forward, if you have a vision, you need to push forward.

If you believe that you have the agency, the will, the capability to bring that about, you need to push forward. Not only do you need it, we need you to push forward because that’s how the world moves forward. So, if you’re in a cul-de-sac, quit. If you have no vision, quit. If you don’t believe you have the agency, just quit. Or, develop it, develop the vision, develop the agency, but if you’re in the dip, the brave thing to do is to keep moving forward.

Pete Mockaitis

Alrighty. Okay. Well, Todd, I would love to get your perspective. Do you have any top do’s or don’ts for folks looking to be awesome at their job as they are contemplating this bravery stuff?

Todd Henry

Yeah, the main thing, and this is why the book called The Brave Habit, is that bravery is a habit, which means that we can build practices into our life to prepare us for moments where we need to be brave. So, the main do I would say is have some time that you block off in your life, and I walk people through this in the book, where you basically follow B-R-A-V-E. Which is basically block time once a week to look at your calendar, look at your commitments, look at everything coming up in your life that week, conversations in your life, projects you’re accountable for. So, block the time, and the reason I say that first is because it seems like an obvious thing but we don’t do it, we don’t plan time for the things that are most important.

The second part is review. Review upcoming conversations that maybe you’re a little nervous about. Review client projects, conversations, that you’re going to be having, and review them for points of uncertainty, for tensions that you know are inevitably going to be there. The third is claim agency, meaning assess what agency you have in those moments. What are you bringing to those moments that you uniquely are able to contribute? Why are you right person to have that conversation? Why are you the right person to do that project? So, re-root yourself in your sense of agency.

The fourth is vision. So, what is your vision for each of those relationships, for each of those projects, for your work as a whole, your vision for your life, your vision for your relationships? What is your vision? Re-root yourself. And then, finally, express your intent, E, that’s the E part. Express your intent, meaning, “Here is the outcome that I am committed to for each of these areas.” By doing this, what you’re doing is getting ahead of those moments.

We’re often surprised by these moments where we have to be brave. We come into a conversation, and we’re completely ill-prepared because we haven’t done the pre-work to set ourselves up for bravery, for exhibiting bravery in the moment. But, again, as we get ahead of it, and as we build practices to prepare us for those moments, then, in the moment itself, we’re not reacting. We’re simply enacting the plan that we’ve already put in place, that we know that we’re going to enact. And then as we do that consistently over time, it becomes more of a habit for us.

Pete Mockaitis

Okay. Lovely. And any don’ts?

Todd Henry

The biggest don’t, and this is, by the way, true of anything that we do as creative professionals, people have to solve problems, is don’t wing it. Talent gets you in the game but your practices keep you in the game. Talent is the price of entry. People think that they can wing their entire career based on talent alone. You cannot. You will, eventually, fail. You’ll eventually succumb to the negative drag forces of the marketplace.

You have to have practices in your life to prepare you for those moments and to help you be successful. And so, that would be the biggest thing, is don’t wing it. Have practices in your life to prepare you for critical moments.

Pete Mockaitis

All right. Well, Todd, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Todd Henry

I think the biggest thing that I would encourage people to consider is, listen, your life is comprised of moments, and how you approach those moments is going to define your life. We tend to think of life as a passage of days, and years, and months, and whatever, and that’s true but the reality is some of those moments are weighted far more significantly than others.

And how you respond in critical moments in your life is going to determine the arch of your life, and, ultimately, the body of work that you build, the relationships you have, and the degree to which you have deep regret later in your life. So, your moment is coming, make sure that you’re prepared for that moment when it arrives.

Pete Mockaitis

All right. Now, could you share a favorite quote, something you find inspiring?

Todd Henry

Thomas Merton is one of my favorite thinkers, one of my favorite writers.

And he once wrote, “There can be an intense egoism in following everyone else. People are in a hurry to magnify themselves by imitating what is popular, and too lazy to think of anything better. Hurry ruins saints as well as artists. They want quick success, and they are in such a hurry to get it, they cannot take time to be true to themselves. And when the madness is upon them, they justify their very haste as a species of integrity.”

Pete Mockaitis

Okay. And a favorite study or experiment or bit of research?

Todd Henry

So, one thing that is really interesting to me in researching this book, I came across the work of a couple of key people. One was Martin Seligman, who’s kind of known as the father of positive psychology, and the other one was Albert Bandura, who did significant research into agency, and how agency affects us.

And one of the key tidbits that came out of the research was that people who live with an optimistic mindset versus a pessimistic mindset tend to outlive people who have a pessimistic mindset in their life, to the extent that people who live with a generally pessimistic mindset exhibit health effects that are similar to smoking packs of cigarettes a day in their life. Those are the kinds of health effects that they experience. Pessimism has such a negative drag on your physical health that is the equivalent of smoking packs of cigarettes a day. So, I thought that was pretty fascinating, actually.

Pete Mockaitis

All right. And a favorite book?

Todd Henry

I was watching a video of a guy who was talking about the five-foot shelf of books, which is the complete Harvard Classics which were assembled like in the early 1900s by the president of Harvard. And he said, “If you read these books, this five-foot shelf of books, you will have all that you need in terms of, like, a Western liberal education.”

And so, I decided to commit myself to reading the complete Harvard Classics.

Pete Mockaitis

Okay. Can you share with us a couple titles that we’d recognize in that and a couple titles that we wouldn’t?

Todd Henry

Absolutely. So, right now, I’m in the midst of The Autobiography of Benjamin Franklin, which is the very first part.

Pete Mockaitis
Oh, it’s so good. All right. And a favorite tool, something you use to help you be awesome at your job?

Todd Henry

The tool that I use more than any other tool right now, as a podcaster, as a content creator, is Descript. It has radically changed my world, and I don’t say that very often. I’m not, like, a big jump-on-the-bandwagon-of-a-tool kind of guy but Descript has completely changed my world. If you do any audio or video creating, you 100% need to be using Descript.

Pete Mockaitis

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

Todd Henry

The one that I see circulating the most, because it got picked up by some of the, like, habit apps and things, is, “Don’t let your rituals become ruts,” and so, I think, every so often, or I know, every so often, it’s important to do a review of your rituals and make sure that they’re still serving you, and they’re not just there for you to serve them.

Pete Mockaitis

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

Todd Henry

So, ToddHenry.com is my personal website. You can find all my books. Our podcast is called Daily Creative with Todd Henry. We just started over with episode one. So, you could listen to the podcast where you get podcasts. My books are at ToddHenry.com or wherever you buy your books. The Brave Habit is available now.

Pete Mockaitis

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

Todd Henry

It’s really important that we understand that your time is finite, and this is almost something we say so often, it becomes cliché, but it’s cliché for a reason, it’s because it’s true. And so, treat today, treat this moment, treat your next conversation, treat the project you’re working on not as if it’s going to be your last, but as if it’s going to be your legacy.

We often hear this advice, “Live every day as if it’s your last,” and I think that’s terrible advice because if it was my last day, I’m going to eat donuts and do whatever I want to do because I don’t have to worry about my health. Instead, I like to think, “What if today was my legacy? What if this was the only day? What if a biographer was going to follow me around today and look at everything I do, and then was going to write the story of my life based on this day? How might I approach this day differently? How might I approach that next conversation or that conflict differently? How much effort might I put into this project I’m working on?”

Pete Mockaitis

Beautiful. Well, Todd, thank you. I wish you much fun and bravery.

Todd Henry

Well, thank you. And thanks so much for having me on the show, and thanks for the great work that you do.