#1 Habit Expert: Here's how you become dramatically better

All right, Charles, I want to show you something. So in 2014, I wrote about how I lost weight, but previously I used your book a year before because I had a little bit of a drinking issue and it was frankly was kind of ruining my life. And I read your book, and the idea of the habit loop changed my life. And that's why I'm so excited to talk to you. I'm putting my laud Let's travel.

Your book changed my life probably more than any book I've ever read. And I have read probably thousands of books. So I'll tell you the story. So basically, uh yeah, I had like an issue with with alcohol. And I read your book and y you can correct me if I'm wrong, but the way that I distinctly remember it is that a habit doesn't go away. You just have to change part of the routine and replace it. That's exactly right.

one of the ways that people continue being stuck on this treadmill, and this sounds very oversimplified, but it's true in my case. Like you start like craving carbohydrates the day after you drink. Like you still crave because I was drinking like twenty beers a day and I still craved like the sugar. And so I actually just made a small habit. Every time I wanted to uh drink alcohol, a beer.

I ate a pack of M and M's and that like sugar replacement actually helped me like kick booze. Then I replaced that with non alcoholic beer and I got fat along the way. But I was like, I'll get fat and then I'll I'll I'll kick that habit later. I love this. I look because you're exactly right. So so for folks who aren't familiar with it, the the habit loops is what research tells us is that every habit in our life, and about forty to forty-five percent of what we do every day is a habit.

Every habit has these three components. There's a Q, which is like a trigger for the automatic behavior. And then the routine, right? Picking up the beer and drinking it or you going for a run if you're if you have an exercise habit. And when we do that, it delivers a reward to us. Every habit in your life delivers a reward, whether you're aware of it or not.

And over time, our brain begins to associate this cue, this routine, and this reward into a little package that happens almost automatically inside our brain. And at the core of it, you're exactly right is this craving. And there's a woman named Dr. Ann Grabiale at the at MIT who's done research on habits. And what she's found is that if you create a habit in, say, a rat's brain for running a maze, and then you remove it from the maze for literally years.

And then bring it back and drop it in the maze again, it that habit re-emerges instantaneously. And it's because this Q routine and reward, the neural pathways associated with those three things are have gotten thicker and thicker and thicker. And so when you start trying extinguish a habit, when you just say, I'm gonna stop drinking, just you know, I'm gonna, I'm gonna white knuckle it and give up cigarettes.

Because that neural pathway still exists, you still have that craving. You still have that urge. So you're exactly right. The key is. Don't try and extinguish the habit, rather try and change it. Find a new behavior like eating MMs that corresponds to the old cue and that delivers something similar to the old reward. And in doing so, you're kind of overriding that neural pathway inside your brain. Right. And I did this with uh the help of a doctor. And I was like, look

the doctor was like, just get fat for a little while. We'll we'll figure that out later. So I got fat. And then uh that's when I wrote this blog post of how I lost weight. And the way that I lost weight, it was very simple. You had this idea called a Keystone Habit. Which I don't know if you invented that term, but that's crazy because like it's like a term that everyone uses now. But basically my keystone habit was that I would put my running shoes

next to my bed and then I would sleep in my workout gear that morning. So when I woke up, I was in my running gear or in my, you know, what uh workout gear and then I had I when I said when my feet touched the floor, they went into the shoes. Yeah. That's a really smart, a really smart cue. And yeah, I actually did come up with a phrase Keystone Habit. It's um. Oh really? That's awesome. Well my my wife is a biologist and there's this concept of keystone species.

And so I was talking through this idea, which exists in the scientific literature, but had never been kind of called this. And and we were like, that's kind of like a keystone habit. But what I love about what you just said is that so there's like there's a writer named David Epstein who um he's written a bunch of books. He will also sleep in his workout clothes. And it's because

That cue, when you wake up and you throw your feet out of bed and you're already in your clothes, that cue, it just makes it so easy to like take the next step and like go out the door, right? Like you probably at this point when you are running, you're not even thinking about running and as you start. You're just kind of on autopilot. You're doing what feels natural. And this is the power of habits, is that we can choose these behaviors that we want to encourage.

And we can make them not a product of willpower or of, you know, sort of white knuckling it, but rather something that happens automatically because there's this part of our brain, the basal ganglia that exists just to make habit. And that's what ultimately makes us successful is choosing the habits that we want, figuring out how to design them by paying attention to the cues and rewards around them.

And then making those behaviors so automatic that you don't have to decide to go for a run in the morning. You don't have to decide to skip that that beer. You don't have to decide to sit down and, you know, pound out all those emails you've been thinking about. It just happens automatically and as a result, it feels much easier.

I uh my my last company, I think we had thirty ish employees when I sold. And then my current company now, we are at around that. And both of those stages are when systems and processes start to really matter.

Yeah. And there's this like phrase in the CEO world something like you don't rise to like your willpower, you fall to your system. Or something like that, where it's like the system is what like dictates whether you're gonna be successful or not, not like, you know, willpower or not like how you feel. And the point being at a company, you have to have systems because that's what you fall that's what's which is what you default to.

That's and that's what you rely on. Yeah. And can I ask you, okay, so when you've thought about the systems you've created now that you guys are at 30 people and the systems really matter, what's a system that you've developed that you're really proud of? Like an institutional organizational habit?

I'll give you one really simple example, but I will say like people like me, entrepr like entrepreneurial people, we are the the skill set that re that is required to start stuff is the exact opposite typically of a process creating skill set. Oh interesting. I work my ass off at creating and sticking to processes, but it does not come natural. But I'll tell you one that has made a huge difference. Every day at 3 PM, the company stops for 10 minutes.

And we clean. We clean the office because I cannot stand clutter at our office. And the the what I'm trying to convince my staff, and it's actually working, they're doing this at their homes and everything, which is we're just trying to like uh sweat the small stuff and do the small things really nicely. And it starts with like cleaning your bed or making your bed. Yeah. Uh and so I'm really proud of that.

It's and I'm sure you're giving everyone this sense of accomplishment, right? Like cleaning up the clutter is not that big an accomplishment, but to come together and have someone say, like, this is who we are. This is how we prove to ourselves what what we stand for, that's enormously rewarding. Yeah. And it and it actually gets to this other thing that really interesting about psychology, which is what's known as revealed versus stated preference. That oftentimes when you ask people

Do you do you want to exercise every day? They'll say, yes, I want to exercise every day. It's really important to me. But when we look at their behavior, they exercise like twice a week, right? So the revealed preference is actually different from the stated preference. And our brain pays attention to that.

Our brain actually is kind of skeptical of our stated preferences, but it pays attention to how we behave to figure out who we really are. And so this act of cleaning up every day at three o'clock. And I'm sure, look, you could go a day without cleaning at three and it the company's not going to fall apart, right?

But it's not about organizing the clutter, it's about revealing to ourselves, proving to ourselves that we are the kinds of people who do this. We are the kinds of people who we we say we are. That's really powerful. All right, so this episode is all about excellence. A while back I shared my personal framework for building excellence in my own life, and the team at HubSpot turned it into a thirty day operating system that you can check out right now.

It breaks down the systems that took me ten years to figure out and shows how exactly I use them day to day. These are systems that genuinely changed my life. So if you want to build a good life, scan the QR code or click the link in the description. Now let's get back to the show. How many copies did the Power of Habit sell? Gosh, uh worldwide it's sold over ten million now. So it's Crazy.

It's been great. Yeah. And the best part is just getting emails from folks like like with stories like yours that say, you know, I struggled with drinking for years and then I finally figured out how to how to think about the cues and rewards to make this easier to overcome. That's what's really meaningful. That's crazy, man. That's a lot of copies. Did you uh and where were you before? You were a reporter?

Yeah, so I I was a reporter of the New York Times. I was uh and in fact I I continued being a reporter for the New York Times for a number of years after the book came out. Weirdly, I actually The same year that The Power of Habit came out, I won a Pulitzer Prize for um for a series I had done at the New York Times. And so 2013 was like kind of a crazy year. Was that the apple?

That was the Apple series. Yeah, yeah, exactly. The Apple series. And one of the things I learned, I I was talking to Jim Collins, the guy who wrote Good to Great last night on on stage because he has a new book out, and he talked about the the bewildering fog of success.

And that year 2013 was exactly that for me. It like on paper, it was the best year of my life. I had a best selling book. I won a Pulitzer Prize. In reality, it was like the hardest year of my life because And and you know this, when when success comes, it can kind of catch you off guard with all of its demands and

and emotions. And so that was that was like a big year, but also in retrospect, a tough year. And and since then, I've written a couple more books, including Super Communicators, which which you'd mentioned. And now I write for the for the New Yorker magazine.

I remember I felt uh defensive of you when Atomic Habits came out because you were my guy and I'm friends with James. Um and I I'm sure you are too. But when I saw Atomic Habits come out, I was like, but I already read the original. This is Like I don't know. Nice to you. R the truth is as whatever it takes to get it into people's hands, like

It feels so good to be able to be the master of your own habits. It feels so good to be the person you want to be. And so, whatever it takes to like to get that, to get that empowerment into people's lives, I am all for that. So like a lot of our listeners are like uh type A go getters who are probably a little neurotic at times and maybe they're like me where I like I'm pretty like emotional and react re I I react to things fast, which is kind of silly.

Is there a way that you have seen a lot of these like type A people use the power of habit at work or in their career to be more productive?

Yeah, absol you know, what I hear a lot from from executives is Is is them saying, Look, I was in this bad pattern that I didn't even recognize was a pattern, which is I knew I had to write an email, right? It was a tough email. I didn't I didn't want to like I didn't want to deal with a question that the email was asking. I knew I might disappoint someone.

And and so I would put it off. I would basically, you know, it'd be in my inbox. I would say, I'm gonna deal with this later. And hours would go by, days would go by. And what's happening during that period is that there is a cognitive load, a cognitive burden associated with that email going unanswered. Right. There's some part of your brain that says, like, look, you've got this task you need to get done.

And it's an unpleasant task. You don't like thinking about it. You like shying away from it. But the more you shy away from it, the more it becomes like this monster in your head. And sometimes it's the smallest thing. Totally. And what we know is that if you build this habit that your immediate response is to hit reply and just deal with it right away, the benefits of that are huge.

Right. Now you might not write the most polished email on the face of the planet. Right. You might not have all the time to think it through. So you have to you have to question, is this something I can respond to right away? But when we get it off our plate, what we're doing is we're freeing up our brain to think about other things. Our brain is constantly keeping track.

of the thousands of things that might be threats or might be opportunities or might be crises. And the more that we clear our brain and give it space to think about the good stuff, the opportunities, the ways to move forward, the new ideas. the more we're empowering ourselves to actually get things done. So I have as we speak, I have three hundred and forty nine unread text messages. Okay. And I have a shitload of voicemails.

tons of Twitter and Instagram DMs. The amount of inbound and notifications and partially because I'm on a podcast as a lot of listeners, but even if you're not that, the amount of inbound notifications that people get, it's unsustainable. So it so just because you get an email, like like that we have this instinct to hit reply, does not mean you have to reply, right? Because another habit that's equally important is just to ignore.

Like the fact that somebody sends me an email, that does not create an obligation on my to-do list to respond to them. What it does is it gives me the option to kind of choose, do I want to respond? And so one of the things that I do, because very similarly, there's just an overwhelming amount of stuff that comes in. I try and be really disciplined. And my my first habit, my first instinct is just to hit delete.

Like when something, and oftentimes someone will send me a really interesting article or there'll be something I'm like, oh man, I should really go back and read that. That's really I want to save that for later. And instead what I do is I hit delete because I know I'm never gonna go back and read it, right?

And I don't think that we have to get to inbox zero. I don't think we have to interact with every single thing that's sent to us. I think what we should have is a habit to graze over it and to forgive ourselves for hitting delete because ultimately.

The most important choice that we make is where to spend our attention. And if we're making that choice based on the whims of other people because they send us an email or a DM, then we're not actually making a choice. We're abdicating that responsibility. It's sort of like um I think we had uh Tim Ferris on and people make fun of Tim Ferris because he they're like, dude, you're working more than four hours a week.

You know what I mean? And so he sort of like kind of created his own little trap. When you have bad habits in your life, I have to imagine that people like your buddies mess with you. They're like

Oh no my wife is is merciless. What bad habits do you have still that you have been unable to break? So he here's the thing about habits is In our brain, there's no such thing as a bad habit or a good habit, right? The basal ganglia is this part of our brain that creates habits and it actually evolved just to do that. And every animal on earth actually has a basal ganglia. If we couldn't form habits, we would not evolve because

it we would have to spend too much time thinking about whether we pick up the rock or the apple and take a bite out of it. So habits are really, really important. But to our brain Our brain just says, look, if there's a pattern of a cue, a routine, and a reward, I'm going to make that easier and easier to do. It doesn't say this is a good habit or this is a bad habit. It's up to us to decide which habits are good and which are bad, which ones we want to encourage and discourage.

And so I would say I have lots of bad habits, right? Things that But they're bad habits that I choose. Like I like to have Once or twice a week, I like to have a cocktail when I come home from work, right? And that in some people's eyes could be a bad habit. But for me, it's just a nice way of signaling to myself that I can relax. Some people might see that as a bad habit, but for me, it speaks to like how I like what I like about life.

So I would say the thing that's happened to me as a a as a product of my research is that I've recognized that you get to choose your habits. And just because other people think they're good or bad, that does not mean that they have to be good or bad for you. The key is to have agency, to have control over your life. And the way we do that is by not just focusing on the behavior, but by looking for these cues and these rewards, looking for these leverage points that we can use.

News. to change and become the person we want to be. And frankly, it's challenging. It's challenging to decide which is the thing. Yeah. I think that I I could I call myself like a high functioning person. Like I I think I have a a lot of horsepower. And uh the strength of that is that I can run through a wall and the weakness of that is that I can run through a wall because I have this thing called a five year diary.

where every year on the same day or uh every day on a on a page I write how I feel that day and then yeah the the next year I see the same page. So I can like see how I'm feeling a year prior. I I was joking with Sean but I w my uh co host on this podcast. I was like, dude, I've been com I wrote about this thing in my journal this day last year and I complained about the same problem. I'm like if I'm supposed to be this high functioning person that like

changes or adapts and grows, I'm sure not doing it. What the hell? Who why can't I change? And so it is sort of interesting that you become like a prisoner of habits. And what you said was cool because You do want to become this person who can change their life. But the fact is, my opinion is most people don't change. And I think it's really because I think it's like almost impossible to change.

Well, and what what I hear in that that diary that you've you mentioned is what's known as a cognitive routine. So what's what are you really doing when you write that one line? Because writing one line is not like, It's not like life changing, right? To like sit down and write like a one liner about how you feel about your day.

But what you are doing is you're creating a mental habit for yourself. And the most important habits tend to be mental habits. In psychology, they're known as cognitive routines. And their job is to allow us to think more deeply when thinking deeply is hardest. Right. When we're feeling stressed out or when we're feeling overwhelmed or when we don't have that much time. We only have time to write one line in a little diary.

What that cognitive routine does, that mental habit, is it causes you to pause and look at the previous year. And the fact that you say to yourself, okay, look, I'm stuck in the same rut that I was a year ago. And actually I didn't even really recognize that. Or if I did recognize it, it's just I wasn't paying attention to it. But this is something that's forcing me to think about this rut, to ask myself like.

Why am I in this rut? How do I get out of this rut? Do I really care about this rut that much? Those cognitive routines, these mental habits that we build for ourselves are really, really powerful because they allow us to do the thing that you just mentioned, which is make decisions without being exhausted. And one of the most powerful is.

When I come home from work, I describe my day in like excruciating detail to my wife. And she does not really care about my day. Like she doesn't want to know like all the specifics of the meeting I was sitting through. But I'm not really doing it for her. I'm doing it for me. This is my cognitive routine to help me review my day and figure out what I did well and what I did poorly.

And building those cognitive routines, those mental habits, that is how we end up becoming successful. Because it's, it's those small little habits that determine if we're using our attention wisely or not. You know that feeling when strategy is done, the brief is written, and everyone is aligned? And you realize someone still has to sit down and actually create the content. That someone is you and it's due tomorrow. Bree's assistant can help.

It works right inside of HubSpot. Drafting, campaign copy, blog posts, emails, all in your brand voice. All grounded in your actual customer data. So you don't just create content, you create content that converts. hubspot.com, the agentic customer platform for growing businesses. You have this book called Super Communicators. I haven't read it yet, but I read uh a great article on it. And When I was younger I read this book called How to Win Friends and Influence People. Yeah. Dale Carnegie.

Yeah, it changed my life. I'm not naturally like a very good conversationalist or a good people person. I uh my my family calls me a little neurospicy. You know, I had a Yeah.

I I kinda had to learn a little bit. Like I had to like read a few playbooks on how to like have like normal interactions. And so Dale Carnegie kinda changed my life and there was a handful of takeaways from that book. And one of the books was basically if you have a conversation with someone If you let them do most of all the talking and you ask them all about their lives and their themselves, uh, they're gonna think that it's the greatest conversation they've ever had.

Yeah. And your job, uh your book, Super Communicators, it did a good j I believe the premise of the book is like if you ask Not only if you but you you took a step further. If you ask more questions, but also ask these I don't know, you give some questions, but y you give like a framework. If you ask different types of questions that fall under a bucket that I w I want you to tell me, you will get people to open up more, is that right? Yeah.

Yeah, that's exactly right. So so one of the things that we know is is First of all, we are all super communicators at one time or another, right? We we all know like the right thing to say to our friends to make them feel better. Or or sometimes you walk into a meeting and you just like you know exactly what to say to get everyone on your side. But there are some people who are consistent super communicators, people who can seem to connect with anyone anytime.

And the difference between them and everyone else is not this inborn like capacity. It's not that they like are born with the gift of gab. It's that they think about communication a little bit more and they recognize that communication is just a set of very simple skills. That if you practice them, they become habits. And when you start practicing them and using them, you can kind of treat everyone like your best friend and they all they'll all respond the same way.

And one of those skills is asking questions. Consistent super communicators ask 10 to 20 times as many questions as the average person. And some of those questions are like just invitations, like, oh, what'd you think about that? Or like, did you see that movie? Like it's invitations into the conversation. But some of them are what are known within psychology as deep questions.

And a deep question is something that asks me about my values or my beliefs or my experiences. And that can sound a little bit intimidating, but it's as simple as like if you meet someone who's a doctor, instead of saying, oh, what hospital do you work at, asking them, oh, what made you decide to go to medical school?

Right, that second question. That second question is something that invites them to tell you who they really are. They gotta tell you about like their dad getting sick and seeing seeing the doctors help him or that they they wanna be a healer. They wanna help their community. Deep questions are the things that allow us to really connect with other people.

Because they invite others to tell us who they are. And then the best part is it's very natural to answer our own deep question ourselves to say, Oh yeah, you became a doctor because you saw your uncle get sick. That's really interesting. I became a lawyer because I had a brother-in-law who got who got arrested when I was a kid. And I thought that that was really like really wrong. Now we're having a conversation about who we are. We're connecting with each other.

And that means that we're going to trust each other more, we're going to like each other more, and more importantly, we're going to be able to hear each other much more accurately. This sounds like a such a dumb question. But why do I care? Like, why do I want someone to think that I'm a super connector? Like, why do I want them to? open up to me. Yeah, absolutely. So okay, so there's a couple of ways. And first of all, you don't have to

communicate with everyone, right? Sometimes you're gonna get in the Uber and you just want to check your phone in the back of the Uber. You don't want to have a conversation with the driver. That's okay. You don't you don't have to have any conversation you don't want to have. But there are times that we do want to connect with other people. And the reasons why is because we are a pro-social species.

The way that our brains have evolved is to push us to connect with other people because connecting with other people over time has been the most successful strategy in building things, building communities, building families, building products. And when we connect with someone else, when we communicate with them, even if we disagree with them about some pretty fundamental things, there is this.

Almost this almost subconscious thing that happens within our brain that we're powerless against, which is if I feel connected to you, if I feel like you're listening to me and I'm listening to you. And that we're actually connected somehow. And within neuroscience, this is known as neural entrainment. In that moment, we trust each other more. And if you think about it, trust is at the core of pro-sociality. I can't.

I can't police you all the time to see if you're if you're a threat or if you're being genuine. All I can do is try and figure out whether I can trust you enough to let you live in the in the hut next to me without without fear that you're gonna come in and kill me. And the way I figure out whether I should trust you or not and like you and want to work with you is by connecting with you. Cause if that connection feels genuine.

Then it doesn't mean I'm gonna give you my life savings, but it means that for the time being I've said, this person is at least trustworthy enough that I know who they are, they know who I am, I have a hard time seeing them betraying me. And so as a result, we can live side by side peacefully.

And if you think about it in business, trust is everything, right? The reason you're successful in business, the reason you're successful in life, the reason you're successful in romantic relationships is because you figure out ways to connect with other people that are not just transactional, but are real. That's that's fascinating. So I can ask questions that get like v th I think you said value based. What else can I do?

Okay, so so the first thing is ask more questions, right? Ask these deep questions. The second thing is that you need to be having the same kind of conversation as the person you're talking to. And explain this also to give you an example.

So when I started writing super communicators, one of the reasons why was because I had fallen into this bad pattern where I'd come home from work and I'd start complaining about my day and tell my wife, you know, like my coworkers don't appreciate me and my boss doesn't realize what a genius I am. And she would give me some good advice. She would say something like, Why don't you take your boss out to lunch and you guys can get to know each other a little bit better?

But instead of being able to hear her advice, I would get even more upset. And I would start like saying, you know, you should be outraged on my behalf. You should be like, you should be on my side.

And I couldn't figure out why there was this tension between us. And so I went to these researchers and they said, well, the the main thing that's happening here is when you're having a discussion, you think you know what that discussion is about, right? You're talking about your day or next year's budget. But actually, if we look inside your brain, what we see is there's a bunch of different kinds of conversations all happening at the same time.

And in general, these conversations tend to fall into one of three buckets. There's these practical conversations where we're making plans together or we're solving problems. But then there's emotional conversations where I tell you what I'm feeling. And I don't want you to solve my feelings. I want you to empathize.

And then there's social conversations, which is about how we relate to each other and how we relate to other people, the identities that are important to us. And they said, What we've discovered is. All three of these conversations are equally important. And all three of them will probably happen during a discussion. But if you and the person you are talking to are not having the same kind of conversation at the same moment.

You cannot fully hear each other. You definitely won't feel connected to each other. Your trust in each other will not go up. So the key is, this is the second big skill in addition to asking more questions that super communicators, consistent super communicators have is

Pay attention to what kind of conversation is happening. Does this feel practical? Does it feel emotional? Does it feel social? What kind of words is the other person using? And then match them. What's known within psychology is the matching principle.

If you're talking about next year's budget and you say something like, look, I'm really anxious that we get this right because I don't want to lay people off. As a super communicator, in my head, I should be hearing, oh, you're actually having an emotional conversation right now. Well, we're not talking about the budget. We're talking about how you feel.

And I need to empathize with that before we can start talking about practical things. I need to say to you, I understand exactly what you're feeling. I feel exactly the same way. I want you to know my number one goal here is that we don't have any layoffs.

that we get to protect our people. So with that in mind, can we talk about the budget, like how to how to how to actually get that done? In other words, with your permission, can we move from an emotional to a practical conversation together?

When I do that, what I'm doing is I'm signaling to you that I'm listening to you. I understand your mindset, and we are getting aligned. We are getting gnarly and trained. We are getting in sync, which means that we're going to hear each other much, much better and we're going to trust each other more. I'm obsessed with like I I love uh history and I've read um biographies on a huge uh a lot of the presidents.

And three presidents that are very, very different and are very effective communicators are George Washington, Bill Clinton, and Donald Trump. They they communicate drastically differently, but I would argue they're all very effective. I I absolutely agree. George Washington was significantly more stoic and mysterious and spoke seldom. And when he did spoke, you listened no matter what. And he had this like regal status.

Bill Clinton was very charming. And then Donald Trump, his shtick is more like uh way more crude, like riffin' with you, like we're it we're boys. Absolutely. In fact, a as a reporter I've been to a lot of Trump rallies and and whether you you like Donald Trump or whether you d intensely dislike Donald Trump.

Going to a rally is well worth the time because what you see is he is a super communicator. And he uses the this exact same thing, thing that I just talked about. He leans, he proves he's listening to the crowd by leaning into the type of conversation they want to have. So on a stage, Donald Trump will say something. And and if the crowd starts applauding and over and and reacting to it.

He'll say it again and then he'll just start riffing on that. That's why, that's why from a stage he often says like things that in retrospect look a little crazy is because he's kind of feeding off the crowd. The crowd is telling him if he gets up on stage and he says, you know, something emotional like, I worry about the future of the nation because we're being overrun by immigrants and the crowd just kind of goes nuts.

He'll lean into that and he recognizes this is an emotional conversation, right? This is this is not about the practicalities of immigration reform. This is people feeling like they're lost at home, like they're losing ground. And he'll lean into that. Now I've also met with Donald Trump one on one in in like, you know, settings where he's meeting with reporters. The dude asks questions constantly.

Right. And a lot of the questions are like about him. He's like, what do you think? Why do you think these people hate me so much? Or what do you think about this thing that I did? But the fact is the fact of the matter is, instead of giving little speeches, he's asking questions. He's drawing you into the conversation. We are all really good at communication, right? Our because we're a pro social species, our brain has evolved to be really good at communication.

And the people who are best at communication, it is not because they were born that way. It's because they think about communication. Right. Bill Clinton's a great example. If you ask Bill Clinton, were you always a good communicator? He says no.

He says that when he was a kid, he actually had trouble making friends with other kids. He didn't know how to talk to them. But he said that in high school, he really studied how kids talked to each other. Like he felt like this is something, and that because his parents got divorced, he had to be the peacemaker between them. He trained himself to think just a little bit more about communication. And that's what makes him a great communicator. And all of us can do that.

I'm not a Donald Trump supporter. Um, but I am intoxicated. But like I think he's hilarious. Like if I I have to remove the fact that like I don't agree with what he just said, but I can also acknowledge I'm like, that's so funny. Like, were you intoxicated when you met him? No, I was not I was not intoxicated when I when I met him. And I I would also say I'm not a Donald Trump fan. I I like I I as a particularly as a reporter, I try and not be a fan of anyone.

Um, but this running for office, because you have to be skeptical. But I I will say this about Trump is that he comes off as being very authentic. And this is another thing that super communicators do really well, right? You believe that you're seeing the real version of them. And the way that we actually create a sense of authenticity, this has been studied a lot, is that we'll often do something that's a little bit vulnerable.

Yeah. And we tend to misunderstand what this word vulnerability means. We think it's like crying on each other's shoulders or something like that. Actually, vulnerability is a very specific thing that happens inside a brand. Vulnerability is a neural cascade that occurs when I say something to you that you could judge. And if in that moment you withhold judgment, and more importantly, if you share something about yourself that I could judge in return.

then we will feel closer to each other. So think about when Donald Trump's on that stage, you know that like weird dance he does, right? Yeah. That like it's not, it's not an attractive dance, right? He's not a, he's not a graceful man on his two feet.

And yet it's incredibly endearing because it's vulnerable. Now it's not vulnerable in a way that like makes him open to attack. It's vulnerable in that he's sharing something that you could judge. You could say, that's the dumbest dance I've ever seen in my entire life.

But when you withhold that judgment, you actually feel closer to him. And so one of the things that he does that all great leaders do. Is that they reveal things about themselves. They they allow these moments of vulnerability when I'm gonna say something that I know you could judge, I'm gonna make it available to you for your judgment. Because in that moment, You will believe I am authentic. You will believe you're seeing the real me. And that's really, really powerful.

I think that word I hate I hate the word authenticity. I hate that word. Yes. Um and I'll explain why. I um I think it's bullshit. I actually don't think you should be authentic because the fact is is that we're all performing. And I want to convince you.

this girl to go on a date with me. I want to convince this employee to work at my company. I want to convince someone to do everything. Saying to be authentic, that's like saying someone just be yourself and they'll like you. No, don't be yourself. Change yourself so you are a better person and that people then will like you. So I'm gonna push back a little bit because I actually think I think what you just said is authenticity. I don't think authenticity means It's all an act.

Well I I think but I think authenticity is choosing Not necessarily which act, choosing which part of myself I want to expose right now. Right. Like the truth of the matter is I could look in this conversation, you could have spent this conversation just telling me how impressive you are, like all of your successes. But instead, you the the act that you choose, the aspect of yourself you choose to to share with me.

is like a really curious guy who like doesn't have all the answers and and recognizes that luck is part of it and the hard work is part of it and wants to understand how to get better. I don't think that's an inauthentic display of who you are. I think it's you authentically choosing which part of yourself to share with the world. And I think that I I I understand the skepticism towards authenticity. The word has become like such a bugaboo of meaning like.

meaning so many different things. But what I think for me it means is genuinely wanting to connect with another person and wanting to connect with them on both their terms and my terms. And saying, like, look, like, this is who I am. I I want you to know who I am, the real me, at least to some degree. And I might, that doesn't mean I'm gonna necessarily tell you all about my childhood trauma or my drinking problems.

But I want you to be able to know who I am on some level, the real me. And I want to know the real you. And it's that act of actually saying I want to be authentic or I want to be vulnerable that creates the connection. It's not the authenticity itself. It's the act of saying, I'm willing to be vulnerable with you because I want, I want to connect with you. That is the first and most important step for us actually feeling connected to each other.

Who's a super communicator that's a famous person that I should go and study? Ooh gosh, that's a really good question. I mean, there's so many of them. I mean, honestly, one of them is Steve Jobs. And we don't think of Steve Jobs as a super communicator, right? Everything about Steve Steve Jobs is like he was such a jerk to his employees and he would create this reality distortion field.

But if you go and you watch interviews with C jobs, what you see is you see him constantly authentically sharing who he is and then asking questions and proving to the other person that he's listening to them. Right. So there's there's a number of speeches he gave at like graduate uh Stanford Graduate School of Business.

Where the clips that get put on social media are the clips of Steve Jobs talking about like doing LSD or like his vision. But if you watch the entire time that he was in that classroom, what you see is that he, Steve Jobs, one of the most famous guys on earth. He spends like about a third of the time asking the students questions. Like, what do you think about that? Why did you make that decision? What was your experience when you picked up this device?

He is a guy who genuinely not only wants you to understand him, he wants to understand you. And you get that feeling, right? That's the Bill Clinton thing. Like I've I've met Bill Clinton also. And like the truth of the matter is. Bill Clinton genuinely wants to charm and know the people he is talking to. What did he say to you that uh was an example of charming?

Yeah, I had written this article and and it's clear that like s one of his aides had briefed him that I'd written the article. But he comes up and he goes, Man, that article you wrote, it was just great. It was just great. And I'm wondering. What was the thing you carried away from it? Because you must know so much about this. It must have been so powerful for you.

What did you carry away? And of course, the former president of the United States is asking me about my work. I'm like, I'm like, oh, Mr. President, let me tell you. Like, I'm so glad you read that. Right. I was bowled over by it. But like what he did is he asked me a question and he seemed genuinely curious in in the response. And to be honest, and maybe I'm just a sucker.

I believed him. I believed that he actually wanted to know because he's a curious guy. He wanted to know what I had learned. And I felt wonderful as a result. This is for the folks out there who have a business that does at least three million dollars a year in revenue. Because around this point, that's when you're able to look up after being heads down for years building your company and you realize two things.

One, you've done something great, but you're still a long way from your final destination. And two, you look around and you realize I am all alone. I've outrun my peers, which means you're now making$10 million decisions alone by yourself. And that is when mediocrity can creep in. My company Hampton, we solved this problem by giving a room of vetted peers, of other entrepreneurs.

who are gonna hold you accountable, call you out on your nonsense and help show you the way. Because the fact is is that there's only a tiny number of people in your town who know what you're going through and who have been there. And they're hard to find. And if you can find them, it's hard to have this explicit time, this explicit place where you sit down, where the rules are clear that we are here to help each other and to be one another's board of directors.

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What's a good famous example of a speech or a moment in time that you point to or you or multiple examples where that you point to where you're like, that's a textbook example of super communicating. Oh, so um so one of the my favorites is Ronald Reagan. So if you remember it it was a long time ago. So you w you might have been too young and I was actually too young myself, but

When Ronald Reagan was running for this second term, there were all these questions about his mental acuity, right? Like people, there were all these articles about the fact that his memory was failing. And and he gets up on this on stage on the stage to to debate Walter Mondale. This is the second debate.

Well Mondale was younger than him and Mondale was like seen as like like his reputation, he had never lost an election before. And he was seen as this like wonder kind, right? Like the the like his brain was so smart. And Ronald Reagan gets up on the stage, and one of the first things he says is he makes a joke, he says, I want you to know that during this debate, I will at no time make fun of my opponent's youth and inexperience.

Yeah. Right. And everyone kinda laughs because they all realize what he's talking about. There's he's saying, like, look, like I I'm not gonna I I'm not gonna make fun of the fact that like he's younger than me because he's gonna say I'm too old and that my memory's going. And what it did is it first of all is kind of vulnerable, right? Like it's him admitting that there's this criticism of him that he's aware of. It's exposing something that other people could judge.

But then by making a joke of it, he completely disarms the issue. Like in that moment, it stopped his mental acuity stopped being an issue. Now, if you'll remember, actually later in his second administration. This becomes an issue because it turns out that he's suffering from from what people think are early early signs of uh of Alzheimer's dementia.

So it was totally a legitimate issue to bring up during the election, but he just did this jujitsu by being a little bit vulnerable about it about it and making a joke of it, that all of a sudden it became an attack that didn't have any teeth. That's an example of super communication. And he just connected with people in that moment in a way that that surprised everyone. So asking um value based questions, getting tactical vulnerability, um what what else?

So figuring out what kind of mindset, what kind of conversation is happening. Are you in an emotional mindset? Are you in a practical mindset? And then the last one is. Super communicators succeed because they not only listen, but they prove that they're listening. So there's this kind of like myth that like the key to listening is like close your mouth and open your ear. And that's the first step to listening, but it turns out study after study shows that is not enough on its own.

The key to listening is to make listening an active process. It's to prove to you that I am paying attention to what you're saying. And you actually just did this really well. You repeated what I said, right? You were like, okay, here's the three things I've heard from you. You're proving that you're paying attention to it.

So if I'm in a conversation with someone, particularly if I'm in a conflict conversation where we're disagreeing about something, what I should do is I should use this technique called looping for understanding. Which is step one is I'm going to ask you a question, preferably a deep question. Tell me why this issue is important to you. Tell me what you really think about this question, like why it's why, why this matter.

I'm going to listen to your answer. And then step two is I'm going to repeat back in my own words what I heard you say. And the key here is not mimicry. If I just mimic you, it doesn't work. The key here is to prove to you that I've actually been thinking about what you've been saying. I've been paying attention. So what I heard you say is I heard you say that like, you know, you wake, you wear your your workout clothes. And I think that what I'm really hearing you say is.

Working out is a keystone habit for you. It's a way that you tell yourself who you are. You prove your discipline in the morning. That's step two is I'm repeating back what I'm hearing, I'm adding something to it. And most people kind of do this intuitively, step one and step two as they get older. Step three is the one that I always forget.

Is that when I say that, I ask you if I got it right. Did I hear you? Am I am I understanding the role that exercise plays in your your life correctly? Did did I get it? Because what I'm doing in that moment is I'm asking you for permission to acknowledge that I was listening. And if you acknowledge that I'm listening to you,

you become something like ten times more likely to listen to me in response. It's this inborn instinct known as social reciprocity. Yeah. That that when we think someone's listening to us, we want to listen to them. And so super communicators prove they are listening. They don't just sit there, you know, that they don't do the Dale Carnegie thing. They don't just ask question after question after question. They layer on top of that.

proving that they're paying attention by saying things like, oh, it's so interesting you mentioned that, because something similar happened to me. Or I want to ask you about this thing that you said before, because it reminds me of this question I've been thinking about. They prove that they're paying attention. And in doing so, we believe that they are listening to us because in fact they are listening to us.

Dude, this is so interesting and it becomes like meta because as you're like telling me things, I'm like, All right, I have to make sure that I do a loop when he's su like No, but then the nice thing is first of all, you do a lot of this stuff intuitively because you are a good community. It's not intuitive. I'm telling you, I had to learn all this. I was a really uncomfortable 14 year old.

And do you know what changed my life? And what's up? I don't I don't mind admitting this because I'm happily married, but reading books and how to meet women. When I was fourteen and fifteen, I looked like Napoleon Dynamite. I was really goofy looking. I was uncomfortable. I didn't have a lot of guy friends. Like people didn't particularly like me. And I read all of these books on how to pick up girls.

Uh it wasn't like a matter of like hooking up, although that would have been awesome, which it didn't happen. But it was like I just wanna like be accepted. And so I read pretty much every book you could ever find about how to Pick up a girl. And what you learn is that those like it's it starts like where you just learn the tactics of how to have a conversation. But then you realize that like the secret in all of this.

Is to becoming a good person who's worthy of love and who's worthy of other people's attention. And that is like the true secret. And that is a good one. Okay. So I'm gonna point something out that I think is really interesting. You as an authenticity skeptic.

What you just told me was really authentic, right? Like you told me that you read books about picking up girls, which is something that like in in your head, you know I could judge. I could be like, oh, this guy's a dirt bag. You're the kind of guy who like reads books on picking up girls.

But by sharing that with me, by saying something that you know I could judge, by being a little bit vulnerable, it actually brings us closer together. You're exactly right. Authenticity is not having a trick in my back pocket that I can use.

'Cause if it's not genuine, it's not real. And people are gonna feel that. Authenticity is actually Sharing with you who I really am with full knowledge that you could hold it against me, but trusting that you're not going to because we're gonna, because we're gonna learn things about each other that make us feel closer. You're not like I wouldn't say that you're the most prolific author. Like you well, in terms of books, like it seems like you find a topic and you like go super deep.

So so I I have this basic this basic desire with everything I write, which is to write something that I genuinely believe twenty years from now someone can pick it up and just love it. And and actually I do this myself. I buy old copies of magazines. I just bought In Cold Blood by Truman Capote, right? Which kind of created the true crime genre. One of my favorites. Yeah, it's wonderful. I found a copy of the original New Yorker magazine that it was printed in. And I bought it online from eBay.

And so as a result, if that's your goal is to write something really big, it does take time. In part it takes time because you don't know what the big idea is when you start the process. Speaking of old magazines, I collect old magazines. Here, here's Wow. You have the first issue of George. That's like going for like$10,000 online right now.

I've had this for three years, my friend. Really? I'm a Kennedy uh historian. Um and I and I I owned a publishing company, so I had these. I still get my Thrasher magazines by scaling these. Oh, it's amazing. I read that you um cold call d I think I read this, that you cold call nine hundred people to get a source for a book. Is that is that right? Yeah. Yeah, yeah, yeah. It was actually, so it was the Apple series.

So the series is about like looking at the global economy through the lens of Apple and getting people inside Apple is to talk is really, really hard. It's a very secretive company. And so what I did is I was like, the only way I can do this is through like mass pitches.

And so I'd go on LinkedIn and look for people who were former Apple employees and I would email them and say, look, my name is Charles Duhig, I'm a reporter. This is what I'm working on. Can you please talk to me? And the yield was really low. The yield was like, three or four percent of people even bothering to respond. All you need is two or three great sources to introduce you to other sources.

And so this has always been my reporting technique is if you want to write something great, if you want to create anything that's great, you just have to waste a lot of time. Because you don't know what's going to pay off. You don't know which person you're going to email and they're going to say, yeah, I have all these files. I can share them with you.

And so I think a big part of making important big things is being okay with spending an entire week and saying, nothing productive happened during this week. I tried again and again and again and none of it paid off. Because that is the process of finding something amazing. And so it's interesting to say that like a lot of your productive time feels unproductive.

Well, and I think that that's a key. So so the idea, that book is called Smarter, Faster, Better. And the idea behind it is sort of what I mentioned before, that throughout history, the killer productivity app has been thinking more deeply, particularly when thinking deeply is harder. So tell me about your routine then. So let's say you had a deadline for an article or you had a deadline for a book. What is your daily routine in order to think deeply?

So oftentimes oftentimes I won't have a deadline. Like I'll try and basically not have a deadline. So I have all the time I need. But my my my process for thinking deeply is that. I do to-do lists in a very specific way. My to-do list at no time has more than three things on it, and hopefully it only has one. For the day.

For the day. Right. So so I have a memory list. All the things I want to get done go on my memory list. And that's very long. But the night before, every night, I look at the memory list and I choose what is the number one thing on my to-do list for the next day. And I'll write that down. And this is actually a routine, the cognitive routine that forces me to think about priorities, right? And what I what I'll do is periodically during the day, I force myself to take a break.

And to just take a step back and ask myself like The way I spent the last hour, is it getting me closer to that one thing on my to-do list? Or is it actually me distracting myself? So you only do one like you would consider a successful day just doing one thing?

Yeah, I mean it it's gonna be a big thing, right? Like like m my my to-do list, for instance, for tomorrow, because it's Saturday, but I'm gonna be I'm gonna I I have a to-do list for tomorrow. My to-do list for tomorrow is to come up with the outline of my next book. Now I'm not gonna be able to do that in a day, right? And that's a huge task.

But I intend to sit down at nine o'clock in the morning with a pad of paper and I'm just gonna start outlining. And those outlines are gonna be terrible. And then I'm gonna get up at 10:30 or 11 and go get a snack and I'm gonna ask myself, Am I writing stuff down just to write stuff down? Or is this actually getting me closer and closer and closer to understanding what the outline is? There is so much in life that can distract us from what's important.

And the people who are most successful are the ones who empower themselves to be masters of their time and their attention. I think you if I had to guess you read a lot and you've written like three or four different books on like drastically different topics. Yeah. And so you're like an onion. You got layers of like interesting knowledge. What have you read in the last year, whether it's a book or an article or a podcast or a YouTube video that you'd suggest that I consume?

So okay, so there's a couple of them. Um, there's this book named Void Star. It's actually a novel. And it it came out like seven or eight years ago. And it's written by a computer scientist. It's about AI. And first of all, it's just a great novel. It's like it's just fun to read, particularly because we're living through this age of AI AI. He is the first writer I've encountered who tries to actually get inside an AI's head, right? And sort of say like,

If if people actually were interacting with AI, what would that look like? Because an AI isn't going to be like a human. It's going to be some something significantly different. So I found that book to be really, really profound. And then in addition, let me think what else. So David Epstein, as I mentioned, he has a new book coming out called Inside the Box, which is about how constraints actually make us better. That like when we have constraints around us, when we have

fewer resources than we need when we create artificial limits for ourselves, it actually pushes us to be more creative, to be more productive. And I think that's been really, really important because we live in an age of surplus and excess, right? If you're starting an AI company, the first thing you do is you raise billions and billions of dollars.

But what David's saying is actually avail yourself of those surplus of resources if you can get them. But when you're thinking about how to make decisions, give yourself constraints because it's the constraint.

that show you the right path forward. Dude, you're really fascinating to talk to. Did you um you make me want to become an author. Um You should be an author. You're fascinating to talk to too. You you have you have the natural disposition for it, the curiosity.

I don't know if I've got the grip for it. It seems really hard. Did you for any of their your best works? So like the power of habit as well as some of your articles, did you at any point were you like, something's here something's here. This is gonna hit. Yeah. So I think what happens is very similarly, uh I'll of I'll say that oftentimes the chapters that get the most attention are the chapters where I was like, Oh, that wasn't my best chapter. Like I I could have I should have done better.

And I cannot reread my stuff. If I reread my stuff, it's like, oh, this is so painful. Like it's it's so bad. There's so I could have done so much better. But I will say that there is usually a point where I'm like, You know, I would actually read this. Like there's something going on in this that if I encountered it in the wild.

I would read it. And that doesn't mean it's poetic. That doesn't mean it's perfect. But there's just something there that I find personally captivating. The trust I'm having, the bet I'm making is that if I find it captivating, There's gonna be at least some other people like me who also find it captivating. So I wrote this um this article for the New Yorker about a guy named Shamath Palhaptia. Yeah, the SPAC thing. Yeah. I it was I like that stuff.

Yeah, like I it was about Chamath and about and about um Spax. And it was kind of like it Chamath is kind of like a I con artist, that's not fair, but Chamath is an operator, right? He's a guy who like sells a dream pretty actively. And so I wrote an article about him selling the dream and why actually sometimes in in economic cycles, like the salesman, the, the, the, the bullshit artist is actually the most important figure because he helps everyone else believe in what the economy can be.

And it was an article. It didn't do that well. Like not that many people read it. But I I loved it because I would have read the hell out of that thing. If I had come across that article in the magazine, I would have just read it like two or three times. That's ultimately what I'm trying to do. I'm trying to write something that like so amuses and delights me that I would read it. And so hopefully other people will too.

What um yeah, man, I I'm leaving this conversation v invigorated. What seems like Me too. What age did you become successful financially? Ooh, actually extra power of habit. So I would s let's see, so I was probably Late thirties? Were you like broke? No, I wasn't broke. I wasn't broke. I was right working in the New York Times, but one of the reasons I wrote The Power of Habit was because I was really happy being a reporter and my wife was pregnant with our first kid.

And I I and we were living in New York and I was like, I don't know that we can afford to live in New York with kids on my salary, right? I'm a reporter. I I don't earn that much money. The only way that I can make this work is to go write books. Like I I need a secondary line of income.

To be able to continue living in New York, to continue our the lifestyle that we have. And so and it and and I will say, I'm curious if this is true of you as well. Like once I started making money, the the scarcity mindset was with me for a long time and actually is still kind it's still there. It's still there. So if you grow up with scarcity It doesn't go away. It's traumatic. And it also teaches you that like money does not solve your problems.

I think it I think it removes so many problems. It removes so many problems. And like I've talked about this on the podcast and this is a very douchey thing to say, but I say it all the time. The people who say it doesn't make you happier, I think, are doing it wrong. It definitely makes you happier because it rose removes so much uncertainty. But we have quite similar tendencies. I've noticed this about you, is that you're quite paranoid.

Uh, like we've agreed that you're one of the best selling authors of all time. And yet you say you're a horrible author. And like there's this like I think there's this commonality, not with all successful people. I know a lot of successful people that were like, I felt like I was great and I knew I was gonna be great and and I was confident the whole time. But then there's whole other subset of people, which I think I fall into and it sounds like you fall into.

Which is I'm shit. I have to prove myself. I suck. I suck so much. I have to do this. It's all gonna go away. And frankly, it's exhausting, but I do find it very useful. I totally agree. And I think of it as a cultivated anxiety. And I think you're right. I think it's actually a blend of those. Cause if you asked me objectively, am I a good writer, I'd I'd say, look, I've been writing for 20 years, man. Like I spent all my time thinking about how to

How to write in ways that make people desperate to finish the chapter they're writing. So, like ob objectively, I am a good writer. But it's also this cultivated anxiety of like, well, my previous books were okay, but I want to try something new for my next book. And that could fall on its face. I need to work really hard to make sure it doesn't. I think both of us probably do that, right? Like. Success is a combination of

Feeding the insecurities that push you to be better. And then also taking comfort in the securities that you you can be better. You know what you're doing if you push yourself hard enough. The thing that I love about capitalism and business, and it's like I'm not even into business that much. I just think that capitalism, there there's some of the more practical ways to kind of bend the earth to your will.

And so, like what I loved about my journey of going from fat to skinny is like, check this out. I manipulated myself. Like, isn't that awesome? I I changed.

my tiny world, that just being my body. I set a goal and I f did it. Yeah. And I I that's what I like about entrepreneurship is um even if it's just a small business, it doesn't matter if it's what it is, it's just a really cool it's just a very practical way to to to kick your dent into the world and say, This is my world that I've created, even if it's just my my bedroom.

Absolutely. And that is that mastery, right? Mastery is envisioning something in the world and then making it real. And it is so satisfying. Well thanks for doing this. I uh Thank you. Thanks for having me on. This is super fun. I hope you realise how much of an impact you've had on me. Thank you. I really appreciate you saying that. And I love the show. I like I I love listening to the show. And by the way, when you come out to California, let me know. We'll we'll go out I do you surf? Poorly.

I surf poorly every single day. So we we go we'll go surfing together in Santa Cruz. It'd be fun. Alright, let's do it. Alright, that's it, that's the pod. I put my all in it like this Let's travel, never looking back.

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