How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)
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We're socialized to bullshit, not only ourselves, but everybody else, especially in the entrepreneurial community. All our companies are moving up and to the right. Every product is working. We don't really have any problems because we're crushing it. And that's just a lie.

lie the question that i often ask is how have i been complicit in creating the conditions i say i don't want the purpose of this question is actually to evoke your own agency a perfect example of that would be i say i don't want to feel busy all the time but the truth of the matter is i feel really unnerved and disconcerted if my agenda isn't jam-packed so if you want to create a high functioning team do

your work. And it starts with the person who has the most power in them.

Today, my guest is Jerry Colonna. Jerry is one of the most well-known and respected executive coaches in the world. He's co-founder and CEO of Reboot, an executive and leadership development firm grounded in the belief that better humans make better leaders. Prior to coaching, Jerry co-founded Flatiron Partners with Fred Wilson, which ended up being one of the most successful early-stage investment funds in the world. He's also a partner at JPMorgan Chase and is the author of two books, Reboot and Reunion.

As you might expect, this ended up being a very real and very open conversation about being busy and self-inquiry and the dangers of a growth mindset and the reasons that leaders and teams most often fail and it's not what you think. Also, we talk about a very simple equation that Jerry and his team use to cultivate great leaders. This is an episode that everybody should listen to and spend time with. It'll make you a better person, a better partner, and a better leader.

If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you now get a year free of linear superhuman notion perplexity and granola. Check it out at lenny'snewsletter.com and click bundle. With that, I bring you Jerry Colonna.

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Jerry, thank you so much for being here. Welcome to the podcast.

Well, thanks for having me, Lenny. It's really a delight to meet you and to be with you today. I want to start with a very classic Jerry Colonna piece of advice that I've heard you share in other places, and I just want more people to hear this advice. And this is a question that you ask people when things aren't going their way. And I'll give you a hint. The question contains the word complicit.

Right. Can you share this question and why it's so important to ask this of yourself? The question that I often ask is, how have I been complicit in creating the conditions I say I don't want? And if it's helpful, let me break down the question a little bit. Please. So I purposely chose the word complicit because complicit does not mean responsible. And that's a really important distinction.

And as I often say, to understand the word complicit, think of the word accomplice, right? As I will share, you are driving the getaway car. You're not sticking up the bank teller, okay? The second half of that question is, I say I don't want. And sometimes people hear that question and they interpret it as, how have I been responsible for the shit in my life?

And that is not the purpose of this question. The purpose of this question is actually to evoke your own agency, is to look at the ways in which you may have been deluding yourself. A perfect example of that would be, I say I don't want to feel busy all the time. But the truth of the matter is, I feel really unnerved and disconcerted

if my agenda isn't jam-packed. And the reason that this is all really important is, you know, part of my approach not only to coaching but to the process of growing up is to use what I call radical self-inquiry to really cut through our own delusions and say, "How does it serve me to feel completely busy to the point where I feel exhausted?"

And perhaps there's another more conscious way of getting that feeling than feeling like crap all the time. This is a good segue to something that I hear you. You have this equation that you and your firm use to kind of think about how to create and cultivate great leaders. And it includes one of the variables is radical self-inquiry.

Can you share this equation and just how you work with folks to kind of build this in them? Sure. I'll tell a little story about that. I remember one time I was, this is how the equation came to be. I was doing a talk, I think here in Boulder at Naropa University, where I used to be on the board of trustees. It's a Buddhist university. And as is often the case, I'm kind of winging it as I go. And I'm walking around probably without shoes on because that's what I do.

And there was a dry erase board behind me. And I was trying to explain what it was that I do, what it was that I encourage people to do. And I jumped up on the board, at the board, and I wrote practical skills. And in writing that, what I was trying to convey, what it is that people typically come to a coach for. They want to understand how to do their job. They want to understand how to live. They want to understand the how. And then I wrote plus skills.

And then I sketched out radical self-inquiry. And I said, in that moment, I said, people will come and ask me how, and I will drive them crazy because I will say something like, tell me about your father, right? Or tell me why you chose to be in the job you're in in the first place. Or tell me about your relationship to money. Or tell me about your relationship to self-worth. And then I expanded it and I put another plus sign and I said,

experiences. And then I drew an equals equation line underneath the whole thing. And I said, enhanced leadership plus greater resiliency. And so the equation is practical skills plus radical self-inquiry plus shared experiences. That is the process of actually talking about the craziness that goes on in your head equals greater leadership plus

Okay, that all makes sense. But then there was this other piece, enhanced resilience. And when I do this on a dry erase board, I will often circle that phrase and I say, that is the purpose of this whole thing. Because the truth is, if you follow my story at all, you know that in my late 30s, the depression that had really marked most of my life had gotten so bad that despite my outward success, I was suicidal.

and lost. And I will turn to the audience and I say, I get you want to be a great CEO. I get you want to be a great executive. But what I really care about is you not killing yourself in the process. So if we take a step back, the whole point of what we refer to as the equation really boils down to that point. How do we grow up and become the leaders, the adults we were born to be,

without feeling like crap. And there's this huge implication here that a lot of people think that when they reach a certain point, become successful, you know, make a certain amount of money, get a beautiful house, they'll be happy. And essentially what you're saying here is that's very often not the case. Maybe in most cases, not the case. It's not only not the case, it's the big lie that we're socialized with since childhood.

I remember one time I was on the road doing a talk for, I was promoting my first book, Reboot. And I was at, I think it's called the Fitzer Club in Philadelphia. I was doing a fireside chat. And after talking with my conversation partner, a guy named Chris Freilich, who was one of the co-founders of First Round, really, really good guy. We turned to the audience and there was a Q&A, as there often is.

And this young guy shoots his hand up and he introduces himself and he says, I'm 19. And he looks over to his right and his mother is sitting there and he says, and my mother brought me here, which I laughed. And he said, so what you're telling me is you don't have to be an asshole to be successful. And I could not think of a better summation of everything that I'm about than for a 19-year-old kid

to look up and say, you don't have to be an asshole to be successful. And of course, the corollary to that is you don't have to feel miserable just because you're trying to create a career.

As people start to think about this and think, okay, I feel like I've been heading in this direction of I just need to keep climbing the ladder, making more money. As they hear you talk, what's kind of the pivot that folks should make in their mind around where they should actually be heading? Like what is a direction where they'll end up not wanting to kill themselves in spite of being successful? To be clear, not everyone ends up in that level of depression. But the hack, if you will,

is consciousness. So what do I mean by that? Part of what makes radical self-inquiry radical is we are socialized not to ask certain kinds of questions. So for example, someone says, I feel really, it's really important for me to be ambitious and achieve a particular goal. What's radical, a radical question to ask is, and what will that do for you?

What is it that you believe being quote-unquote successful will do for you? How do you define success? Where does that come from? You know, in Reboot, my first book, I tell the story of what I refer to as my pursuit of lemon drops. And briefly, when I was a boy, there was a lot... I grew up with an enormous amount of chaos and...

insecurity, financial and otherwise, and a big source of stability in my life were my mother's parents, my grandfather and grandmother. And Grandpa Guido, who was an ice man and emigrated from southern Italy in the early 20th century, always seemed to have, well, he had this endless supply of lemon drops,

And they were always kept in this green pantry outside of the kitchen. And for me, the stability and what I considered wealth seemed to match to this notion of this endless supply of lemon drops. And when I got to my 30s and I was outwardly successful and I was a hotshot VC, I had lemon drops, but I didn't feel safe.

which was kind of a mind throb. And so I told that story in Reboot as part of my exploration into the core question of how did my relationship to money shape my career choices, shape my school choices, shape my own sense of safety and self-worth. So long-winded response to your question,

What I encourage people to do is to ask themselves these kinds of questions so that they can raise their level of consciousness so that they can be in the driver's seat of their lives and not some learned behavior that they developed as a child to answer perhaps their parents' or grandparents' anxieties. I feel like a lot of people hearing this are afraid to ask these sorts of questions. The reason they don't ask these questions and...

is because they worry that this is going to be like, okay, I got to quit my job, move to the woods, give up all these luxuries I have. I don't even want to think about that. I got a whole family to support. I got to succeed. Advice for getting over that hump of just like, okay. Okay, so let's just pause, Lenny. Yeah. Okay, so what you're doing in this moment is empathetically imagining what may be going on for your listener. Okay, but the empathy is actually based on your own question.

Because, you know, you invited me on the show. You knew I was going to get to this point. So I'm imagining that as you take this in, that thought stream shows up for you. Jerry, says Lenny, if I open up that closet, all the shit's going to fall out. And what am I going to do with it?

Does that resonate at all? This is why I was nervous to have you on this podcast. So answer my question. I don't think it's that strong for me to be afraid of that because I've kind of taken a different path already and gotten off the career ladder climbing treadmill. On the other hand, back to your original question, we talked about being busy. I'm very guilty of that. I'm constantly trying to do less.

but constantly doing more and my life is just very busy. Thank you for giving me more of that answer. And trust me, your listeners are going to appreciate you being fully there and just the way you were. Right. So let's take a step back. The fear is, if I can reflect back to your original question, the fear is if, if, if I go there, I don't know what's going to happen next.

as a consequence of that, right? If I pause and ask myself, is this relationship working out for me? I might end up leaving this relationship. If I pause and ask myself, if this career isn't working for me, I might leave my career. And the good news, bad news is that's true. That is absolutely true. And if we look at some of the other observations we were making before, like

anxiety and depression. We have this belief system that if I pay no attention to the thing that I'm afraid of, it's somehow going to magically go away. If we pay no attention to the source of discomfort, it's somehow going to go away. And that's not actually how life works. More often than not, what we do is we respond to the source of challenge, whether it's a

discomfort in our relationship, whether it's a discomfort in the way my life has unfolded. We respond to it by kind of blasting over Band-Aids. And sometimes they're relatively healthy. We become obsessed with working out. Or sometimes they're unhealthy. We become obsessed with

work or substance abuse or that kind of thing. Or sometimes, and this is super popular right now, we lean into what I would call as a kind of spiritual bypassing, where we go to Peru and we go do ayahuasca or we, you know, spend the weekend doing mushrooms with friends. And what we're really not doing, Lenny, is confronting the parts of ourselves that need some tending to because we're afraid of the consequences.

But I'll tell you a quick quote. One of my favorite books is Bruce Springsteen's autobiography. And about in the middle of the book, he has this passage where he talks about having spent 25 years in psychoanalysis. So let me just let that statement land. Bruce fucking Springsteen, 25 years in psychoanalysis. Okay?

And he has this passage where he talks about the unsorted baggage of our childhood. And what he rightly asserts is that we all have unsorted baggage. And at some point, we're going to pay the price of not sorting that baggage. And the price, more often than not, is in tears. Now, this is Bruce Springsteen talking about this.

Okay, this is not some airy-fairy, transpersonal, Jerry Colonna coach, right? And the reason I draw that out is we, as children, are socialized not to develop these consciousness skills. We are socialized to develop what I would call bypassing skills. And as he correctly points out, if you continue to bypass sorting out your baggage, there's going to come a day

where you're going to have to pay that price. It could be in your own depression. It could be in, I've seen this a thousand times, Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success, so let me blow it up. We put this all under the rubric of midlife, but I don't know, when does midlife begin? 35? When does it end? 70?

What I do know is it's the bulk of our adulthood. Okay. I think you've done an excellent job convincing me and others to spend time on this now.

And I think there's an assumption of it gets harder. The tears get more intense as you wait longer, right? There's kind of this ticking time bomb that better some amount of tears now than 10 times more tears later. Is that right? Well said. Okay. Okay. Okay. So coming back to this equation, I think I want to give people some things to do now that there may be likely convinced, okay, I should really rethink what I'm doing. So back to the equation, practical skills plus radical self-inquiry plus shared experiences equals enhanced leadership and greater resilience. Okay.

So the three things you can work on there are practical skills, radical self-inquiry, shared experiences, skills I think people get. So radical self-inquiry, these are essentially questions to dig into what drives you, what makes you happy. What are some questions, again, that people should be asking there as they're listening or maybe after they finish listening? In the time since I've been a coach, which is now going on 27 years, the popularity of journaling has gone up, which is awesome.

And part of what happens is people journal, but they don't know what they should be journaling on or how they should. So let me give some questions. And this is a way to approach it. Let's imagine that what we're trying to do, whether we're sitting in meditation, whether we're journaling, whether we're taking time away, we're just pausing and starting to ask ourselves questions. So my famous questions include things like, what am I not saying that I need to say?

So let's imagine ourselves in a relationship that's not working. Talk about something that could be terrifying. What am I not saying in that relationship that I need to say? By the way, this is a good question to ask if one is responsible for leading people to. Corollary questions to that would be, what am I saying that's not being heard? And then, of course, what's being said that I'm not hearing?

You know, so if we just pause and look at those four questions, how have I been complicit in creating the conditions I say I don't want? What am I not saying that I need to say? What am I saying that's not being heard? And what's being said that I'm not hearing? Can you feel the power of all of that? Yeah. Just in those questions? Scary questions. They are scary questions. Okay. You know you're in the radical self-inquiry zone when the questions take your breath away.

And by the way, you don't have to share the answers to these questions with anybody but yourself. Now, there could be some power in sharing them in a group of friends and sharing them with a group of colleagues, sharing them with a coach, sharing them with a therapist. But the most important person with whom you should share the answers is oneself. This is a little bit of Buddhism here. Self-delusion along with attachment

are the biggest contributors to our own suffering. Self-delusion. Everything's great. How you doing? Everything's great. Bullshit. Can we just not bullshit each other? So let me just pause. Those are just four questions. My first book, Reboot, has a set of questions after every single chapter. We also have a journal that we put out that has questions and questions. But the more important thing to take away from this is

Questions that startle us, questions that may cause us to be a little afraid of the answer, that's where the gold is. And we'll point people to the book for many more of these questions and the worksheets. For the third part of the equation, shared experiences, can you explain what that is? We were talking about socialization, for example. Prior to launching Reboot the Company, my co-founder, Ali Schultz, and I

The roots of Reboot the Company began with me designing or Allie and I designing these boot camps. And the original iteration of the boot camp we used to call CEO boot camp because it was originally we would get first-time CEOs together. And we would kind of do a bait and switch. We would pretend to sell them practical skills. And then I would start asking really tough questions like, who would you be without the story of who you are? It's like, what?

Okay, the notion of shared experience as an important component grew out of that. Because what would happen is, imagine sitting in a circle of people who just have your back, who really care about you as a person. And imagine then discussing some of the answers to those questions. Who would you be without the story of who you are? What is it that you wish the people in your life knew about you?

but you're too afraid to tell them. And imagine sitting in a group of people who can just hold that space without fixing you, without telling you what you're doing right or wrong. We, too often than not, especially in what I would say the entrepreneurial community, we're socialized to bullshit, not only ourselves, but everybody else, right? All our companies are moving up and to the right.

Every product is working. We don't really have any problems because we're crushing it. And that's just a lie. Imagine having the capacity to be in relationship with people where you can just tell the truth. That's what shared experiences are. My wife does a women's circle where they gather and just share what's really going on within their lives. That's it. Yeah. And it's very confidential. There's a ritual to it. And it feels like...

That's a really good avenue for things like that. What circle do you sit in? No circles. This is my circle. But there is something powerful here. I think in the last 15 years, the rise of podcasts, good podcasts, what I think what happens is, let's hope this is happening for your audience right now, good quality, intimate conversation between people who are authentic and real,

creates space for someone to be authentic and real, even if it's just with themselves. So you're doing a mitzvah. You're doing a good deed by creating this space. Thanks, Jerry.

Let's go back to the busyness point and I'll talk about myself a bit to kind of get it real again. And because I think it's also something a lot of people struggle with. I listen to this or just like I am so busy every time someone asks me how I'm doing. Busy, so busy, like swirly eyes emoji, swirly eyes emoji. Yeah.

With a little head shake. And the melting face emoji. And that's very much me. And it's funny because I started this journey of the newsletter of just like, I call the project Avoid Getting a Real Job. And it was just like, cool, I'll just do this newsletter thing, not have a job. It'll be chill, write an email once a week. But I just find myself taking on endlessly more and more. And for me, I feel like the drive is, it's just like fun to see it grow and for it to keep growing.

building and doing well. This reminds me, there's a quote that Will Smith shared once that I think you'll like. Someone asked him what it's like to be famous. And he's like, really awesome as you're going up to fame. Pretty okay as a famous person. Really bad when you lose that fame. And that's how it feels with the growth of this thing. It's just like, you know, growth is up. Oh, life's good. And then it starts to stall. I'm like, oh no, it's all going to fall apart. So I think that's where a lot of that comes from. For me, it's just like, oh, what's next? I gotta see what else I can do here.

Well, how do you feel about yourself when you're on that growth trajectory? I feel great. Say more. I feel like I'm achieving and heading in a... Part of it is just fun. It's like fun to win. So it's just like, yeah, we're doing it. It's working. And when you're not growing, how do you feel about yourself? About myself? Yeah.

Like there's this sense that it's all over. Like, oh, maybe it's all going to fall apart and maybe I'm not as good at this as I thought. Okay, so stay in that spot for a moment. So imagine, and I don't know that this is true, but I can imagine that there's a little whispery voice in your head that's always there that says, Lenny, you're not as good as you think you are. In fact, Lenny, they might even find out

Yep. Yeah, imposter syndrome.

to your sense of self-esteem if you succeed or fail. What if what drove you was not quieting that voice, but what drove you was, "Oh, this is just fun." Seth Godin, who's a dear, dear friend of mine, talks about art projects. Also former podcast guest. Yeah. So what if you just approached the project as if it was an art project?

I think it's going to show up this way. What if it turns out it's wrong? What if it's this? What if it's that? And your sense of self-esteem is not attached to the outcome. What's interesting is that's how I started this whole thing. I had no intention of it being a career and way I make a living. It was just, this is cool. People seem to like it. I enjoy it. Let's just see where it goes. No expectations. And then what happened? And then it worked. It became successful. That's right. It worked out. Right. It became successful.

Meaning you developed an audience. Yeah. Meaning you developed a following. And an income. That's a big part of it. And then you developed an income. Yep. And then the stakes went up. Yeah. And then all of a sudden, my heart, the anxiety. Like not quite that strongly. At times it is, but yeah. But there's a bit of just, oh, wow, I can't, like I'm relying on this now. I can't just let it fall apart. Because my life would fall apart if I let it fall apart.

Yeah, like life would change in a big way, you know, if this whole thing ends. Right, right. So what you're talking about, what we're talking about right now, remember before I said in Buddhism we talk about self-delusion and attachment? Mm-hmm. Now we're talking about attachment. Mm-hmm. Okay, when we become attached to the outcome, we inadvertently fuel our own suffering.

When we become attached, and in this case, okay, I get it. There's a financial reality. This is important because it helps pay the bills if it doesn't entirely pay the bills. Great, got it. Fabulous. But really, the deeper attachment is, see, I'm not nothing. See, I'm not a nobody. I'm a somebody. And that's...

that's the source of the suffering. That is so true. That is very much a part of what has driven me. I was always a very shy kid growing up, and I don't think people expected a lot of me, except my mom and dad, I guess. And so I always had the sense, like, I'll show them. I'll show them what I can do. And that's always this kind of chip on the shoulder thing that I know drives a lot of people. How old are you, Lenny? 43. Okay. So maybe now, at 43...

you can take in the fact that you are a somebody regardless of what you do. What's your wife's name? Michelle. Is she going to love you even if the podcast fails? Absolutely. What, is she an idiot? No, she's a smart person. The people who actually know you and care about you may be proud of your efforts, but their love for you is not dependent upon its success. And that is

That's like a rewiring. Do you have children? Yeah, we got a 22-month-old now. Oh, mazel tov. That's wonderful. My children are 34, 32, and 28. So I'll speak like the old man that I am. When we take that test, that spelling test, and we stick it with magnets on the refrigerator, it's out of pride. The challenging message is,

that we inadvertently can send to our children is that we only love them because they got an A on the spelling test. And so it's really critically important that we as parents do our own internal work to convey that unconditional love that is our birthright as human beings. And

We hold on to the goal because the goal is cool, because solving a puzzle is fun, because doing hard work and experiencing the reward from that is affirming. But your value as a human being is unshakable. Now, as a father, isn't that the feeling you want your child to have? Absolutely. And there's a lot of parenting advice these days that helps you.

Learn to do that. Like there's all these TikToks now where you don't say good job, just say good choice or great and hard work. Great job working hard on that. Right, right, right. I don't know how I feel about getting parenting advice from TikTok, but okay.

I'm excited to have Andrew Luo joining us today. Andrew is CEO of One Schema, one of our longtime podcast sponsors. Welcome, Andrew. Thanks for having me, Lenny. Great to be here. So what is new with One Schema? I know that you work with some of my favorite companies like Ramp and Vanta and Watershed. I heard you guys launched a new data intake product that automates the hours of manual work that teams spend importing and mapping and integrating CSV and Excel files. Yes. So we just launched the 2.0 of One Schema file feeds.

We've rebuilt it from the ground up with AI. We saw so many customers coming to us with teams of data engineers that struggled with the manual work required to clean messy spreadsheets.

FileFeeds 2.0 allows non-technical teams to automate the process of transforming CSV and Excel files with just a simple prompt. We support all of the trickiest file integrations, SFTP, S3, and even email. I can tell you that if my team had to build integrations like this, how nice would it be to take this off our roadmap and instead use something like one schema?

Absolutely, Lenny. We've heard so many horror stories of outages from even just a single bad record in transactions, employee files, purchase orders, you name it. Debugging these issues is often like finding a needle in a haystack. One schema stops any bad data from entering your system and automatically validates your files, generating error reports with the exact issues in all bad files.

I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Andrew, thank you so much for joining me. If you want to learn more, head on over to oneschema.co. That's oneschema.co.

Just to kind of close the loop on this, I think as people hear this, you know, they can, like, I feel like, okay, cool. Everything falls apart. Sure, my parents will love me. My wife will love me. They won't think less of me. However, it's nice to get that really nice couch and that nice hotel and income. You know, the comfort that comes with income at a certain level is hard to give up. What do you, how do you help people get past that? That might go away and feel comfortable. Well, the good news is, and again, this is a Buddhist reference. The good news is there was a,

There's a wisdom tradition that teaches all about this. Okay, so very briefly, the Buddhist story is, you know, in his mid-30s, he wakes up to the truth of birth, old age, sickness, and death. Birth, old age, sickness, and death. And he wanders into the forest, and he becomes a wandering mendicant, and he becomes a holy man, and he's still not satisfied.

And as I like to tell the story, one day he decides, fuck it. I'm just going to sit under the Bodhi tree and I'm not going to move until I figure this shit out. And so he sits and sits and sits. And the story is he sat for 40 days living on a single grain of rice every day because always, right? Crazy stuff. And when he woke up, he woke up to the four noble truths. And the four noble truths are life is filled with suffering. That which we do to push away suffering increases suffering.

The third noble truth is that there's an end to suffering. That's a really important one. And the fourth noble truth is what's known as the Eightfold Path to the End of Suffering. So let's focus on the second noble truth, because that's really what you're talking about. When we acquire that nice couch, when we buy that nice house that stretches our income to its maximum,

If we're doing it to enjoy the couch or the house, then A-OK. But if we're doing it because we're trying to push away the suffering of, am I good enough to be loved, to feel safe, and that I belong? That which we do to push away suffering will increase suffering. And in this case, oh my God, what if they take my house away from me? Oh my God, what if I fall backwards down that staircase of life?

Oh, my God, what if all of those people who have signed up to my substack suddenly disappear? Yeah. Okay? You see how the attachment becomes that source of suffering? You see how the thing that we do to make ourselves feel better, in fact, fuels the tenuous hold that we have on our okayness? I'm okay, just as I am. I'm okay. Mm-hmm.

It all comes down to why we're doing what we're doing. Now, to be clear, this is hard for me. I think it's hard for everybody. When my first book came out, Dan Harris, who's a really good friend and client, I'm 10% happy, said to me, don't read the Amazon reviews. And the truth is, I've read two reviews.

I read it in the first hour after it was released, and I've never read a review since. Because there's no way I can experience those reviews without becoming attached to how people feel. So thank you. I'll put it over here, and I'll just stay focused on the experience that I get from writing. And yes, do I want to sell thousands of books? Do I want people to feel moved by my writing? I do.

But you know who gets the most out of my writing? Me. Because when I sit down, this is a file folders for whatever I might do for our next book. What I'm trying to do is answer questions that I have. For example, Captain Chaos is running the country right now. What is it that the world is going to need two or three years from now? And what's my contribution to that world? Now, just as I say that, how does that feel to you?

It's kind of settling. Yeah, yeah. Right? So I know that in order for me to feel good about my existence on this planet, I have to ask myself these questions and I have to attempt to answer these questions. Whether it turns into a book that people buy or not is secondary. I have to do this work regardless.

That super connects with exactly, again, the way I started this whole thing is I started writing just to crystallize my own thinking. And it ends up being useful to other people. Yes. So I think there's like people hear this and they're like, why would I want to give up this great couch and house and car and all these things? Like that's really hard. And risking that by just doing something that feels good versus it will make income. But it actually works. That's what I found. If you focus on

a thing that is useful to yourself and interesting.

and not come at it from how do I make the most amount of money and turn this into a whole thing, but more just, this is really interesting. I'm going to see where this goes. It will work for me. Lenny, you implicitly asked a how question a few minutes ago. How do I do this? How do I, this radical self-inquiry? And I responded by offering a few questions. Let's build upon that for a moment. Because what you're articulating right now

is in the process of asking those questions, you can go back to what Simon Sinek would say is your why. You could go back to your core principle. You could go back to the sort of centerpiece within you, which is what do I believe to be true about the world? And how do I want to be in that world? You know what animates me right now is a question?

With my children being fully-fledged adults, I am really focused on what kind of ancestor to my descendants would I like to be? 20 years from now, 30 years from now, 40 years from now, I'll be gone. But would I like those who follow after me to believe to be true about me? And you just paused. I can tell from the Adam's apple jumping up and down that that question landed for you.

It's a question of legacy. It's a question of meaning and purpose. At the end of my days, this is a question in Reboot, at the end of my days, what would I like the people who come after me to say about me? And what I want people to say about me is that he gave a shit about the world, he cared, and he tried, and he was kind. Those are the things that matter to me.

I'm always reminded of that frame of reference when I go to a funeral and people reading, you know, the eulogy and the old advice of what do you want your eulogy to say and making that your mission. But kind of on the flip side, there's this viral video of Mike Tyson. Someone was coming up to him, I think, before his big match recently and asked him about his legacy. And he's like, I don't give a shit about my legacy. It's just a made up thing that doesn't matter. So let me just ask you this, why...

Why is it important to think about legacy? Does legacy even matter? Like, you know, we're dead. What's the difference? Far be it for me to criticize Mike. And don't hit me, Mike. Because even as an old guy, I wouldn't want to be hit by Mike Tyson. I don't know what's behind his response, but I can tell you what's true for me. Okay? I made oblique reference to Captain Chaos and the world as it is right now. The world's a tough place right now.

We live in a world where it's almost normalized that a teenager will shoot other teenagers in school. It's almost normalized that people are dragged off to jail. Something is happening. Something is really disturbing. Now, to be clear, we've always had disturbing times. I mean, I was reminded recently, I'm reading a book called Soldiers and Kings, which I highly recommend, which is about human smuggling.

from Central America into the United States. And it's an extraordinary book. And in reading that, I was reminded of policies that the U.S. government has used over the years, whether it's supporting dictators in Central America or other sorts of things, things that I oppose, that feel immoral, if not directly immoral. Why does this come up for me? I can't shake the feeling that someone down the line in my lineage

is going to ask of me, and what did you do, Grandpa? And what did you do, Great Grandpa? I know what I want that answer to be, which is I tried. Lenny, God gave me the ability to put two sentences together in a way that people listen. I feel a moral responsibility to use that God-given gift to help create the world that I would like to see.

a world of kindness and empathy, a world where poverty is diminished, a world where people feel safe, however the fuck they identify. I don't give a damn. So is that my legacy? Yeah. And maybe there's some ego implicit in that. But can I go on for just a bit on this? Absolutely. At the end of Reboot, I write about this moment where,

And in this moment, I'm in Marin County. My wife, Allie, and I are together. And I'm once again torturing myself with this question. Have I been a good man? I drive myself crazy with that question. Have I been a good father? Have I been a good partner? Have I been a good man? And she says in a very frustrated way, all right already, enough. You're a good man. Stop. Stop.

And so I go for a walk, and as I'm walking, I encounter this toppled over oak tree. And the roots are all torn up, and you've seen trees like this. And clearly the tree died, and clearly a wind came, and clearly knocked the whole thing down. And I look at the tree, and I say to myself, here lies a good man. And I liken myself to this toppled over oak tree. And I imagine that that tree had lived its life

with its limbs gnarled and twisted by actions that it should have taken and actions that it shouldn't have taken, by good choices and bad choices. But that for the majority of its 75, 80 years, it lived into its purpose of providing shelter and shade for those that may have come from beneath it. And I make this point that at the end of my days, I want to be like this tree.

just slowly dissolving into the earth, having done the best job I could of being purposeful. I feel better. My suffering is eased when I can lean into that, which then makes me able to be present for the other person, whether it's a coaching client, whether it's a podcast conversation, whether it's just going for a walk with one of my children. I just feel better.

And I think I am a better person when I think about things like that. So far be it for me to disagree with Mike Tyson, but I think he's wrong. Good callback. It sounds like the giving treat to me. Oh, yes. Yes. Shel Silverstein.

To give people something to do with this area of legacy, how did you approach coming up with kind of figuring out what you wanted your legacy to be? Were there some questions you asked? Is there something you recommend folks do to help them think through this for themselves? Well, it's delightful that we've ended up here because I think that I'm still working through those questions. You know, as I said before, as we both connected with,

I use my writing to find my way to answers to questions. So part of what I'm dealing with right now is, you know, look, I'll turn 62 this year. That feels old. But it also feels settled. And, you know, part of what I'm trying to figure out is, what do I want my elderhood to be like? And I'll be honest, you know, I'm enjoying this time of my life where I'm finding myself

Being a voice of comfort, being a voice of maybe even sanity in a time where that feels really insane and challenging. So maybe that's what my legacy will be. I'm not 100% sure. Is this maybe hinted the new book you're working on? Is this the topic you're thinking about or is this not? Yeah, it and other things. That's right. That's right.

Speaking of the world being very crazy right now, you talked about your kids. AI is very top of mind for a lot of people in particular. It's stressing a lot of people out in a lot of ways. It's quite unsettling in future careers, in skills. It is unsettling, isn't it? Quite unsettling. But, you know, there's a world where we don't need humans in the future, potentially. Yeah.

Just what advice do you share with clients to help them work through this period of worry with the future, with AI being the core of it? Well, if we go back to the equation for a moment, I think it's really important that we actually talk about these things. I would say a year ago, I likened it to the experience that I had. I'm old enough to remember when not everything had an IP address. Now our refrigerators have IP addresses, right? I mean, it's fucking crazy.

I'm old enough to remember when you had to install an IP stack into your personal computer in order to connect to the web. That's how old I am. Did you have the phone modem where you had to put the phone? Absolutely. Absolutely. It was a big, big deal to go from $1,200 to $2,400 to $56K. Oh, my God. It was like a rocket ship.

A year ago, I thought we were going through a similar kind of transition. We're clearly not. This is different. And in the coaching therapeutic world, everybody's like, oh my God, GPT is going to replace me. And I don't know, maybe. What I am finding is, like I wear glasses. So for those of you who are only listening to the audio, you may find that news.

What I am finding is in my own life, it's like I have put on a pair of glasses that are really, really sharp and helpful. And it is disturbing and unsettling because I think it does challenge this question of what is our role as human beings? Now, what I come back to, and I could be wrong, but what I come back to is, you know, we're talking through...

a medium, a mediated experience. You know, my signal is bouncing up into the sky, onto a satellite. I won't name the company. It's coming back down. I don't know what your access is. We're using this platform, Riverside, to record this. But somehow we're still finding the capacity to be present for one another in a heart-to-heart way. And so when I look at this phenomena, what I lift up

is that what I am hopeful about is that that which does not matter in the experience of being human kind of gets burned away and is taken care of, call it by AI, but that that which matters, which is presence and connection, human-to-human contact, strategic thinking, formulation. You want to talk about it in terms of engineering,

the conceptualization, that that gets elevated and our skills get better at doing that. And in the most optimistic point of view, what ends up happening is we spend more time on that which matters and less time on that which doesn't matter. And I could be completely wrong and we could all be out of work and making sure that the robots are well-oiled and that becomes our purpose. Yeah.

There's a along these lines of glasses and even coaching the world of coaching. There's a really interesting use case I saw today that Dan Schipper shared that I think you'd love, which is now that ChatGPT has memory and remembers everything you've said and you can think back, you can ask it, what are what are blind spots in the way I see the world that I'm not seeing? You could also upload all your chat transcripts from your meetings and ask it like, what do you what do you what could you do better in meetings?

I mean, look, one of my colleagues in the coaching company, he has uploaded, he kept all of his journal entries, I think over 10 years, journal entries from Evernote. And he uploaded that. I think he uses Claude.

And he's asked Claude to highlight things. What am I not saying that I need to say? What am I saying that's not being heard? He's asked it to reflect back. And I think it's been incredibly helpful for him. I think the result is that he is a better coach, which is kind of interesting, right? Because the feeling is, well, does this replace it? I am finding, I'm using ChatGPT

really as a writing and thinking partner in a way that I did not have before. And I'm still using my live real human writing buddies, which are really important to me. Where does this all end up? I have no idea. It is unsettling, it's uncanny, and it's also enlivening and exciting. Well put.

I love that you can ask these hard questions of Claude slash JGPT, these questions that make you really scared. You could ask it, what are the answers and not even, you know, not have to do the hard work, but, and maybe get a better answer. I doubt that that's, we'll give you the best answers. Well, what it might do, which I think would be wonderful is it might give you more questions to ask yourself. I'm a huge fan of powerful questions.

And the answer I give to a question like, what am I not saying that I need to say? That question, you can ask yourself that question every single day. The question of how have I been complicit in creating the conditions I say I don't want? You can ask yourself that question every single day. You know, to take a step back, the subtitle of my first book is Leadership in the Art of Growing Up. The art of growing up is a practice. It's not a scientific practice.

moment where one day you wake up and you're done. It's an ongoing practice of not continuous improvement, but continuous inquiry that can feel exhausting when you contemplate it, but enlivening when you live it. All this, some people may think of as this whole idea of growth mindset. I know that you're not a big fan of this term.

that it's used in a harmful way a lot of times? Can you just talk about that, why you find that growth mindset as a concept isn't necessarily useful? - Here's what I have a problem with. First of all, having a growth mindset is a very, very helpful thing. What I have a problem is in having and how we can turn a notion like a growth mindset into a fixed mindset, okay?

which is it's this funny little trick the ego does, and the ego says, okay, well, this is a growth mindset. Oh, this is not a growth mindset. Okay, then this is good. This is not good. This is bad. What Buddhism has taught is that everything's falling apart all the time, even our growth mindset. When we get too fixed on the proper way to do things,

We're setting ourselves up for attachment and therefore suffering. So if you can hold something like a mindset loosely with that attachment, go for it. Have a blast. Enjoy it. But the minute you start to nail it down to the floor and say, this is the way it ought to be, I ought to always have a growth mindset, you've become fixed. And that's what the ego does.

To be more explicit about it from a business context, for example, the great business writer Peter Senge says, "It is virtually impossible to challenge the assumptions that made you rich in the first place." So think about it in our experience of starting a business. We have what the Zen Buddhists would say is beginner's mind. All things are possible. And then we experience, you were talking about it a little before, a little bit of success.

And the ego, which is so terrified of not having success, starts to say, aha, this is the way to do it. And then we start to deviate from that because life happens. And then the anxiety starts. So the question is, how do you hold a growth mindset? Loosely. Knowing that you ought to stay present to the world as it is, respond to the changing dynamics, figure out what's next, because that's the growth. So...

Put succinctly, stay attached to the growth and hold mindset a little loosely. I love that. It reminds me of advice. I did a meditation retreat once. And there's always a sense with Buddhism. And it's interesting how often Buddhism and advice from Buddhist teachings comes up on this podcast, by the way. When the student is ready, the teacher will appear. You're inviting it in. But keep going. That makes sense as you say that.

Interesting. Okay, so there's like this fear I think people have with Buddhist teachings that you will not be as ambitious and you will not achieve as much if you're not like, you know, attaching. If you're not anxiously chasing something. Yeah, exactly. If you're just like, why do I need that? I don't need to be the CEO or the VP because like, oh, I won't attach to that. And then, you know, so people fear that downside. So I asked this question at this retreat.

And the advice they shared there was don't attach to this idea, but just kind of point your cart in that direction and head there. Yeah, I like that. Look, the fear you're talking about is the fear of complacency. Yeah. And if we look at the structures of the mind and we look at our socialization, the way we were socialized to ward off complacency is anxiety.

Right. And so if we go back to some of the things we were saying before, if I grow up believing that the way I'm going to make my parents love me is by achieving, then if I become complacent, then what's at risk is their love for me. So just like we made the connection before where unconditional love exists, unconditional positive regard for self, otherwise known as self-compassion,

can be a powerful motivator, especially when you get to the point where you say, I am enjoying, as painful as it is for me to write, I enjoy writing. I enjoy working out. I enjoy pushing myself. I don't necessarily enjoy it in the moment, but I certainly, when I look at two books on my desk,

And I say, you know what? That feels good. That makes me happy. To me, the ability to hold the seeming contradiction of those things is a hallmark of my adulthood. It's to get satisfaction out of hard work, for me, is a much greater motivator than fear of complacency. As I've sort of slip-slided my way into that place,

I have found myself, I work seven days a week. I don't have to, but I enjoy it. There's another, maybe a last area I want to spend some time on, which is around teams and what often causes trouble for teams, what breaks teams, what breaks companies. You have this point you make that it's rarely lack of talent on the team, lack of strategy, lack of execution, that it's something else.

What is that something else would often define as the source of the problem for teams that aren't working? Well, it's the unresolved, I'll be dramatic with the language, demons from their childhood. It's the unsorted baggage. Okay, here's what happens. Teams are groups and there are group dynamics that always happen. There is the scapegoat. There is the truth teller who has to say, let me tell you what's really wrong with everything that's going on.

Without the individual's radical self-inquiry skills, groups tend to be condemned to repeating patterns, oftentimes of their family of origin. I'll tell you a quick story. There's a very famous software blogger, blogger-owned software that I coached for many years, and we were doing an executive team meeting. And...

Something happened in the group as we were talking that I observed once, twice, and three times. And finally, I said, okay, guys, I'm seeing something happening. Every time we get close to talking about something that's really painful, somebody makes a joke. And all the energy disappears. And everybody laughs. And everybody's nice. And as soon as I said it, my client who was CEO at the time said, Jesus Christ, that's just like my family. I was like, yes, absolutely.

That's just like your family. Carl Jung once said, "Until you make the unconscious conscious, it will direct your life and you will call it fate." Let's apply it here. Until you make conscious the unconscious patterns operating in the group, the group will continue to repeat those patterns and you will blame somebody in the group. Romantic relationships, from a Buddhist perspective,

Part of what we do in romantic relationships is we find the perfect foil for us to work out our unconscious phenomena. When we join a group, when we form up in teams and organizations, we are unconsciously finding the perfect foils for us to work out our own shit. So if you want to create a high-functioning team, do your work. And it starts with the person who has the most power in the group.

If that person refuses to do their work, the entire group will become a manifestation of early dysfunction in the individual's lives. Does that make any sense? 100%. And this comes up a number of times on this podcast just now.

Yeah, the impact the leader's issues have on the rest of the team. And also just this idea that the conditions they're trying to avoid are the conditions they invite in because they're avoiding it. That's it. That's it. One of my favorite teachers and dear friends is Parker Palmer. And he builds on this. I think it was Socrates who said, the unexamined life is not worth living. And he builds on that and makes a joke. And he says...

But if you choose to live an unexamined life, please don't take a job that involves other people. And that's it. You have a responsibility to examine your own shit. So say you're on this team. So there's kind of two sides to this. You're on a team. The leaders clearly got some stuff that they need to work through, but they're not. Is there something you can do there other than just, hey, please, this is hurting us? And then from the leader's perspective, listening to this, what should they do? Is it like get a coach? What can you do?

So for the one who has less power, one of the things to ask oneself is, what draws me to this position in the first place? How have I been complicit, not responsible in creating the conditions I say I don't want? How have I benefited from the dysfunction that exists in this organization? And benefit is a funny word. It doesn't necessarily mean I'm making more money. It means...

For example, a benefit might be, "Boy, this feels familiar. I always find myself working on teams that are dysfunctional in this way. What is there in that experience for me to learn?" So that's one. You asked about the person who has power. You were using the word leader. I will talk about power. And you threw out, "Well, should they get a coach?"

let's put it into larger context. Should you examine your life with radical self-inquiry? Yes. I would argue that the more power you have, the more moral responsibility you have to actually pause and figure out what it is that you're doing to be complicit in creating the conditions you say you don't want. To be a very quick example when I'm talking about

A couple of years ago, I was doing a talk at a venture firm's CEO portfolio summit, the portfolio company's CEO summit. And we're sitting in a room and of course I'm walking around again with shoes off and whatever, and people are firing questions at me. And one woman says, well, I'm the CEO of this 15 person company and I have a question for you.

why is it that nobody on my team can make a decision without me? And I said, who hired them? And she, well, I said, okay, how does it make you feel when they make a decision that you disagree with? She said, I'm furious. Well, how can you hire people whom you expect to make decisions without running them through you if you can't tolerate them making a decision that you disagree with?

You want to build a scaled leadership team, you have to be willing to have them make boneheaded decisions. And that's really, really hard, especially if we're, quote, in founder mode, driving all the decisions. So that's your growth edge. We were talking before about growth mindset. That's your growth edge. How can I be...

With the people in my life making boneheaded decisions about something that I care so much about and what is the best way for me to be in relationship about that. So much of this comes back to that question we started this with of just how are you complicit in creating the conditions you don't want.

A big takeaway for me here, and it just keeps coming up again and again, is if you're struggling as a leader, if your company's not working as well as you want it to, if you're having a hard time with your team, it's less going back to that equation. It's not about building more skills like public speaking skills or email skills or, I don't know, financial skills. It's self-awareness, radical self-inquiry, understanding what drives you, what makes you happy. Is that generally correct? Yeah.

Lenny, I was just going to say, you just made me so happy, you saying what you just said. Yes. I've been coaching now, as I said, for a couple of decades. Before that, I was a VC for 15, 17 years. What you just said is the wisdom of my 40 years as an adult. That's it. This is why radical self-inquiry is so damned important.

Because it leads to a little bit less suffering and a lot more resilience. For folks that want to actually do that, well, they can rewind back to kind of the middle of the episode where we actually ask the questions that are associated with radical self-inquiry. And then obviously, if they want to dig deeper, they can buy your book. Or 10 copies of the book. Or 100 copies for everyone at the company. Yeah.

We'll link to Amazon. Jerry, is there anything else that we haven't touched on that you think is really important for people to hear maybe as a last piece of wisdom? No, one of the hopes that I have, you asked me at the start, like, what would be my hope? And instead, we ended up being closer and friends. And I feel that. Let me extend that out to everybody. What I always hope from all of these intimate conversations that I try to do in podcasts is that people walk away going, geez, I'm not alone.

We've made different references to the fact that it's a hard time. The truth is it's always a hard time. And what makes it hardest is to feel like I'm the only one who's going through this. So what I appreciate about what you do, Lenny, is that under the guise of talking about product, you're really talking about the process of being human. And that is a mitzvah. That's a good deed.

And so I hope in the process of listening to this, people walk away going, okay, I feel a little bit better today. I really appreciate that. The way I think about these sorts of conversations and episodes, I call them Trojan horse episodes, where people come for the other stuff, tactical, practical stuff, and then they get stuff they really need to hear. And so I appreciate you. Jerry, thank you so much for being here. Thank you for having me. It was a delight. Same for me. Bye, everyone. Bye.

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