Lenny's PodcastJerry Colonna: How leaders create the conditions they hate
Through the complicit reframe and Colonna's leadership equation; busyness, attachment to success, and the getaway-car analogy expose what CEOs avoid.
EVERY SPOKEN WORD
120 min read · 23,948 words- 0:00 – 4:12
Introduction to Jerry Colonna
- JCJerry Colonna
... or socialize the bullshit, not only ourselves but everybody else, especially in the entrepreneurial community. All our companies are moving up into the right. Every product is working. We don't really have any problems 'cause we're crushing it. And that's just 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.
- LRLenny Rachitsky
(instrumental music) 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 lennysnewsletter.com and click Bundle. With that, I bring you Jerry Colonna. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by ContentSquare, the analytics platform that helps companies build better digital experiences. Ever wonder why customers drop off before converting or why some pages perform better than others? ContentSquare takes the guesswork out of digital experiences, giving you real-time insights into how users interact with your site or app. With AI-powered analytics, automatic frustration detection, and clear visualizations, you'll know exactly what's working and what's holding your customers back. Whether you're optimizing an e-commerce checkout, refining a B2B lead flow, or improving a mobile app experience, ContentSquare pinpoints exactly what needs fixing and why. ContentSquare powers better customer journeys across 1.3 million websites and apps. Discover the insights you've been missing at contentsquare.com/lenny.
- 4:12 – 6:55
Jerry’s key question
- LRLenny Rachitsky
Jerry, thank you so much for being here and welcome to the podcast.
- JCJerry Colonna
Well, thanks for having me, Lenny. It's, it's really a delight to meet you and to be with you today.
- LRLenny Rachitsky
I want to start with a, 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. Uh, and I'll give you a hint, the question contains the word complicit.
- JCJerry Colonna
(laughs) Right.
- LRLenny Rachitsky
Can you share this question and why it's so important to ask this of yourself?
- JCJerry Colonna
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.
- LRLenny Rachitsky
Please.
- JCJerry Colonna
So I purposely chose the word complicit, 'cause complicit does not mean responsible. And that's a really important distinction. And as I often say, to understand the- the word complicit, think of the word accomplice, right? As I, 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- A- 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, you know, 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
- 6:55 – 9:37
The equation for great leadership
- JCJerry Colonna
all the time.
- LRLenny Rachitsky
This is a, a good segue to something that I hear you, uh, 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, and just how you work with folks to kind of build this in them?
- JCJerry Colonna
Sure. I'll, 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 'cause 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 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." (laughs) 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, "shared experiences." And then I drew an equals equation line underneath the whole thing and I said, uh, "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. 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."
- 9:37 – 12:12
The big lie of success and happiness
- JCJerry Colonna
'Cause the truth is, if you followed 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 would, 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?
- LRLenny Rachitsky
And there's this, uh, huge implication here that a lot of people think that when they reach a certain point and 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, not the case. Maybe in most cases not the case.
- JCJerry Colonna
It's not only not the case, it's the big s- lie that we're socialized with since childhood. I remember one time I was on the road doing a, uh, talk for, uh, I was promoting my first book, Reboot. And I was at, uh, I think it's called the Pfitzer Club in Philadelphia, I was doing a fireside chat. And after talking with my conversation partner, a guy named Chris Freylik who was at, uh, was one of the co-founders at 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, he's... And he, 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.
- 12:12 – 15:56
The consciousness hack
- LRLenny Rachitsky
As people start to, think about this and think, "Okay, uh, I feel like I've been heading in this direction of, I just need to keep cr- climbing the ladder, making more money." As they hear you s- talk, what would be, 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?
- JCJerry Colonna
To be clear, not everyone ends up in that level of depression. But the hack, if you will, is consciousness. S- 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, 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, I, I, in, in Reboot, in Reboot, my first book, I tell the story of what I refer to as, uh, 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, uh, a big source of stability in my life were my mother's parents, my grandfather and grandmother. And Grandpa Gido, uh, who was an ice man and emigrated from Southern Italy in early 19, early 8 and 20th century, always seemed to have ... Well, he ha- 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, the stability and what I considered wealth, seemed to match to this, 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 fuck. And so I, 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 pri- perhaps their parents' or grandparents' anxieties.
- 15:56 – 20:23
Getting over the fear of consequences
- JCJerry Colonna
- LRLenny Rachitsky
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 they're, this is gonna be like, "Okay, I gotta quit my job, move to the woods, give up all these luxuries I have. Like, I don't even wanna think about that. I got a whole family to support. I gotta, I gotta succeed." Uh, advice for getting over that hump of just like, "Okay, should I-"
- JCJerry Colonna
Okay, so let's just pause, Lenny.
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
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. 'Cause you know, you invited me on the show, you knew I was gonna 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 gonna fall out and what am I gonna do with it?" Does that resonate at all?
- LRLenny Rachitsky
This is why I was nervous to have you on this podcast, I knew- (laughs)
- JCJerry Colonna
(laughs) Uh-huh. So answer my question. (laughs)
- LRLenny Rachitsky
I don't think it's that strong for me to be afraid of that, 'cause I've kind of taken a different path already and, and gotten off the, you know, career ladder climbing treadmill. Uh, on the other hand, back to your original ques- question, we talked about being busy. I'm very guilty of that. I am constantly (laughs) trying to do less, but constantly doing more. And my life is just very busy.
- JCJerry Colonna
Thank you for giving me more of that answer. And trust me, your listeners are gonna appreciate you being fully there in just the way you are. 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 gonna happen 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 gonna magically go away. If we, if we pay no attention to the source of discomfort, it's somehow gonna 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 a relationship, whether it's a discomfort in the way my life is unfolded. We respond to it by kind of plastining over Band-Aids, and sometimes they're, they're relatively healthy. We become obsessed with, you know, 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 is 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 da-da-da-da-da. 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.
- 20:23 – 23:22
The problem with bypassing our childhood baggage
- JCJerry Colonna
One of my favorite books is, uh, uh, 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, all right? And the reason I, I draw that out is, we as children are socialized not develop, not to, 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 gonna 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, wh- when does midlife begin? 35?
- LRLenny Rachitsky
Mm-hmm.
- JCJerry Colonna
When does it end? 70? What I do know is, it's the adult, it's the bulk of our adulthood.
- LRLenny Rachitsky
Okay. I think we've done, I think you've done an excellent job convincing me and others to spend time on this now, uh, and I think there's an assumption of it gets harder, it, the tears get more intense as you wait longer, right? There's kind of this ticking time bomb that better th- some amount of tears now than 10 times more tears later. Is that right?
- JCJerry Colonna
Well said.
- LRLenny Rachitsky
Okay. (laughs) Okay.
- JCJerry Colonna
Mm-hmm.
- LRLenny Rachitsky
Okay. So going back to this equation, and I think, I want to give people some things to do now that they're 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.
- 23:22 – 27:05
Radical self-inquiry: asking the tough questions
- LRLenny Rachitsky
So the three things you can work on there, 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 their, as they're listening or maybe after they finish listening?
- JCJerry Colonna
In the time since I, 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, 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, uh, responsible for leading people too. Corollary questions for that would be, uh, what am I saying that's not being heard? And then of course, uh, 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-
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
... just in those questions?
- LRLenny Rachitsky
(laughs) Scary questions.
- JCJerry Colonna
They are scary questions. Okay. You know you're in the radical self-inquiry zone when the questions take your breath away. When the questions, 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're 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, it has a set of questions after every (laughs) 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.
- LRLenny Rachitsky
And we'll point people to the book for many more of these questions and,
- 27:05 – 30:25
Shared experiences: the power of community
- LRLenny Rachitsky
and the worksheets. For the third part of the equation, shared experiences, can you explain what that is?
- JCJerry Colonna
You, we were talking about socialization, for example. Prior to launching Reboot The Company, um, my co-founder Ali Schulz and I, the roots of Reboot The Company began with me designing, or Ali 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, 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?" (laughs) It's like, "What?" Okay. The notion of shared experience as a, 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, 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 that 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, are 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 'cause 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 about.
- LRLenny Rachitsky
My, uh, my wife does a, a, a s- a women's circle where they gather and just share what's really going on with their, in their lives. And it's-
- JCJerry Colonna
That's it.
- LRLenny Rachitsky
Yeah. And it's very confidential, you know?
- JCJerry Colonna
Mm-hmm.
- LRLenny Rachitsky
S- there's a ritual to it and it feels like that's a really good avenue for things like that.
- JCJerry Colonna
What circle do you sit in?
- LRLenny Rachitsky
No circles. This is my circle.
- JCJerry Colonna
(laughs) But, but, but, there is something powerful here.
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
I think in the last, you know, 15 years, the rise of podcasts, good podcasts, what I think what's 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.
- LRLenny Rachitsky
Mm-hmm.
- JCJerry Colonna
So you're doing a mitzvah. You're doing a good deed by creating this space.
- LRLenny Rachitsky
Thanks,
- 30:25 – 40:45
The trap of busyness and attachment
- LRLenny Rachitsky
Jerry.Let's go back to the, the busyness point and I'll talk about myself a bit to kinda get it real again and... 'Cause I think it's also something a lot of people struggle with that listen to this are just like, "I am so busy. Every time someone asks me how I'm doing, busy, so busy." Like swirly-
- JCJerry Colonna
So busy.
- LRLenny Rachitsky
... eyes emoji. Swirly eyes emoji.
- JCJerry Colonna
(laughs)
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
With a li- with a little head shake. (laughs)
- LRLenny Rachitsky
That's right. And a melting, melting face emoji.
- JCJerry Colonna
(laughs)
- LRLenny Rachitsky
And that's, that's very much me. And it's funny 'cause I started this journey of the newsletter of just like, I call the project Avoid Getting A Real Job.
- JCJerry Colonna
(laughs)
- LRLenny Rachitsky
And is... And it was just like, "Oh, I'll just do this newsletter thing and 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 it's... I feel like the drive is that j- it's just like fun to see it grow and for it to keep building and doing well. Someone... This reminds me, there's a quote that Will, uh, Will Smith shared once, uh, 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 is just like, you know, growth is up, "Oh, life's good," and then it starts to stall and like, "Oh no, it's all gonna fall apart." So I think that's where a lot of it comes from. For me, it's just like, "Oh, what's next? I gotta... Let's see what else I can do here."
- JCJerry Colonna
Well, how do you feel about yourself when you're on that growth trajectory?
- LRLenny Rachitsky
I feel great.
- JCJerry Colonna
Say more.
- LRLenny Rachitsky
Uh, I feel like I'm achieving and, uh, uh, and heading in a... It's... Like part of it is just fun, you know, it's like fun to win.
- JCJerry Colonna
Mm-hmm.
- LRLenny Rachitsky
So it's just like, "Yeah, it's... We're doing it. It's working." But yeah.
- JCJerry Colonna
And, and, um, when you're not growing, how do you feel about yourself?
- LRLenny Rachitsky
About myself? Uh, like there's this sense that it's all over. Like, "Oh, maybe it's all gonna fall apart and maybe I'm not as, uh, not as good at this as I thought." And maybe it's just-
- JCJerry Colonna
Okay, so stay r- stay in that spot for a moment.
- LRLenny Rachitsky
Okay.
- JCJerry Colonna
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."
- LRLenny Rachitsky
Yep. Yeah, imposter syndrome.
- JCJerry Colonna
Yep. "Oh, shit."
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
So by being busy and by being on that growth trajectory, that voice maybe sounds a little less persistent.
- LRLenny Rachitsky
Yep, yep.
- JCJerry Colonna
Maybe a little less loud. Now, I wanna offer a different potential. What if you could enjoy the puzzle of trying to create something new, trying to create magic, something outta nothing, but it doesn't matter 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.
- LRLenny Rachitsky
Mm-hmm. Oh, also former podcast guest.
- JCJerry Colonna
Yeah. So what if you just approached the project as if it was an art project? I think it's gonna 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.
- 40:45 – 46:58
Understanding our own intentions
- LRLenny Rachitsky
Just to kind of close loop on this, th- I think as people hear this, you know, they can, uh, like, I feel like, okay, cool, I, 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- 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 might, that might go away and feel comfortable?
- JCJerry Colonna
Well, the good news is, and again, this is a Buddhist reference, the good news is there was, uh, 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 gonna sit under the Bodhi Tree and I'm not gonna 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, 'cause always, right? Crazy stuff.
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
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. Okay? So let's focus on the no- the second noble truth, 'cause 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-okay. 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?"
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
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 hole that we have on our okay-ness? "I'm okay just as I am. I'm okay."
- LRLenny Rachitsky
Mm-hmm. Mm-hmm. Yeah.
- JCJerry Colonna
It all comes down to why we're doing what we're doing. Now, t- to be clear, this is hard for me. I think it's hard for everybody. When- when my first book came out, Dan Harris, who's a really good friend and client from 10% Happier said to me, uh, "Don't read the Amazon reviews." And, uh, the truth is, I've read two reviews. I read it in the first hour that, uh, 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- 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 i- this is my 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 gonna 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.
- LRLenny Rachitsky
Yeah, yeah.
- JCJerry Colonna
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.
- LRLenny Rachitsky
That, uh, super connects with exactly again the way I started this whole thing is I was started writing just to crystallize my own thinking and it ends up being useful to other people.
- JCJerry Colonna
Yes.
- LRLenny Rachitsky
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, 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 gonna see where this goes,"
- 46:58 – 55:43
Legacy and purpose
- LRLenny Rachitsky
it-
- JCJerry Colonna
You know-
- LRLenny Rachitsky
... works for me.
- JCJerry Colonna
Lenny, you- you- you implicitly asked a how question a few minutes ago. "How do I do this? How do I do this radical self-inquiry?" And you know, I ask, I- I responded by ans- by offering a few questions. Let's build upon that for a moment because what you're- 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 as 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 what I like those who follow after me to believe to be true about me. And- 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.
- LRLenny Rachitsky
I'm always reminded of that, uh, 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, your mission. But kind of on the flip side, there, there's this, uh, 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, 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 does, why does, like, why is, why is it important to think about legacy? Does legacy even matter? Like, you know, we're dead. What's the difference?
- JCJerry Colonna
Far be it from me to criticize Mike.
- LRLenny Rachitsky
Indeed.
- JCJerry Colonna
And don't hit me, Mike, um, 'cause even as an old guy, I wouldn't want to be hit by Mike Tyson.
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
I don't know what's behind his response, but I can tell you what's, what's true for me, okay? I made oblique reference to Captain Chaos in 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, uh, reminded recently of 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 US 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 ab- that God-given gift to help create the world that I would like to see, a world of kindness and empathy, a world where, um, poverty is diminished, a world where people feel safe, however the fuck they identify.
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
I don't give a damn. So is that my legacy? Yeah, and maybe there's some ego imli- implicit in that. But can I go on for just a bit on this?
- LRLenny Rachitsky
Absolutely.
- JCJerry Colonna
At the end of Reboot, I write about this, uh, this moment, and in this moment, I, I'm, I'm in Marin County. My wife, Ali, and, and I are together, and, 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." And so I go for a walk, and as I'm walking, I, 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've 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.
- LRLenny Rachitsky
(laughs) Good, good, uh, callback. Uh, sounds like The Giving Tree to me. Um-
- JCJerry Colonna
Oh, yes, yes. Shel Silverstein.
- 55:43 – 57:12
Writing for self-discovery
- JCJerry Colonna
- LRLenny Rachitsky
To, to give people something to do with this, uh, this area of legacy, is there ... How, 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?
- JCJerry Colonna
Well, it's, it's, uh, 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, 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? Uh, and, and I'll be honest, you know, I'm enjoying this time of my life, where I'm, I'm finding myself ... being a voice of comfort, being a voice of maybe even sanity, in, in a time where that feels really insane and challenging. So maybe that's what my legacy will be. I'm not 100% sure.
- LRLenny Rachitsky
Is this, uh, maybe a hint at the new book you're working on? Is this the topic you're thinking about or is this not?
- JCJerry Colonna
Y- y- yeah, it and other
- 57:12 – 1:04:56
The impact of AI on humanity
- JCJerry Colonna
things. That's right. That's right.
- LRLenny Rachitsky
Speaking of the world being very crazy right now, you talked about your kids. Uh, 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, people-
- JCJerry Colonna
It is unsettling, isn't it?
- LRLenny Rachitsky
Quite unsettling.
- JCJerry Colonna
Yeah.
- LRLenny Rachitsky
But, you know, there's a world where we don't need humans in the future potentially. Uh, any ... Just what advice do you share with clients to help them work through this period of worry with the future, with, you know, AI being the, the core of it?
- JCJerry Colonna
Well, if we go back to the equation for a moment, uh, I think it's really important that we actually talk about these things.
- LRLenny Rachitsky
Hm.
- JCJerry Colonna
I would say a year ago, I likened it to the experience that I had ... Remember, I'm old enough to remember when not everything had an IP address.
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
(laughs) 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.
- LRLenny Rachitsky
Mm-hmm.
- JCJerry Colonna
That's how old I am.
- LRLenny Rachitsky
Did you have the phone modem where you had to put the, the phone in?
- JCJerry Colonna
Absolutely, absolutely. It was a big, big deal to go from 24- 1200 baud to 24- 400 baud 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, uh, you know, in the coaching, therapeutic world, everybody's like, "Oh my God, ChatGPT is gonna replace me." And ... I don't know, maybe. What I am finding is, uh ... 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, 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, into 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 fan- 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 kinda gets burned away and is taken care of, uh, call it by AI. But that that which matters ...... which is presence and connection, human to human contact, strategic thinking, formulation. You wanna talk about it in terms of engineering, the, 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, uh, 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, um, making sure that the robots are h- are well-oiled-
- LRLenny Rachitsky
That's right.
- JCJerry Colonna
... and that becomes our purpose.
- LRLenny Rachitsky
(laughs) . There's a, as, along these lines of Glasses and, and even coaching, the world of coaching, there's a really interesting use case I saw today, uh, that Dan Shipper shared that I think you'd love, which is, now that ChatGPT has memory, it remembers everything you said and you can think back, you can ask it, "What are, what are blank spots in-"
- JCJerry Colonna
Yeah.
- LRLenny Rachitsky
"... the way I see the world that I'm not seeing?"
- JCJerry Colonna
Yeah.
- LRLenny Rachitsky
You could also upload all your chat transcripts from your meetings and ask it like, "What do you, what do you-"
- JCJerry Colonna
Yeah.
- LRLenny Rachitsky
"... what could you do better in meetings?"
- JCJerry Colonna
I mean, look, look, uh, one of my colleagues, uh, in the coaching company, he, uh, has uploaded, he kept all of his journal entries, I think over 10 years of journal entries from Evernote.
- LRLenny Rachitsky
Mm-hmm.
- JCJerry Colonna
And he uploaded that, I think he uses Claude, and he's asked Claude to highlight things, you know, "What am I not saying that I need to say? What am I saying that's not being heard," right? 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? 'Cause the, the, the feeling is, well, does this replace it? I am finding... I, 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. You know? It is unsettling. It's uncanny. And it's also enlivening and exciting.
- LRLenny Rachitsky
Well put. I love that you can ask these hard questions (laughs) of Claude/ChatGPT, 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, will give you the best answers
- NANarrator
That's
- JCJerry Colonna
Well, and what it might do, which I think would be wonderful is, it might give you more questions to ask yourself.
- 1:04:56 – 1:11:28
Turning a growth mindset into a fixed mindset
- JCJerry Colonna
- LRLenny Rachitsky
All this, uh, some people may think of as a, as, as this whole idea of growth mindset. I know that you're not a big fan of this term. That there's kind of, that it's used in a, in a, 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, uh, useful?
- JCJerry Colonna
Here, here's what I have a problem with. I, I, first of all, having a growth mindset is a very, very helpful thing. Uh, what I have a problem is in having, in how we can turn a notion like a growth mindset into a fixed mindset. Okay? Which is, it's the, 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. This is..." What Buddhism has taught me 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 are setting ourselves up for attachment, and therefore suffering. So if you can hold something like a mindset loosely, without 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. Uh, to be more explicit about it from a business context, for, for example, the great, uh, business writer Peter Senge says, "It is, uh, 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, 'cause that's the growth. So put succinctly, stay attached to the growth and hold mindset a little loosely.
- LRLenny Rachitsky
I love that. There's a, it reminds me of advice, I- I did a meditation retreat once, and there's always a sense (clears throat) with Buddhism, and it's interesting how often Buddhism and advice from Buddhist teachings comes up on this podcast, by the way.
- JCJerry Colonna
When the student is ready, the teacher will appear. You're inviting it in, but keep going.
- LRLenny Rachitsky
That (laughs) that makes sense as you say that (laughs) . Interesting. Okay, so there's a l- there's like this, uh, 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 to-
- JCJerry Colonna
If you're not anxiously chasing something.
- LRLenny Rachitsky
Yeah, exactly. If you're just like, "Why do I need that? I don't need the, I don't need to be the- the CEO or the VP," 'cause like, "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.
- JCJerry Colonna
Yeah. (laughs) I like that. Look, I, the fear you're talking about is the fear of complacency.
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
And if we look at the structures of the mind and we look at our socialization, the way we've, we're socialized to ward off complacency is anxiety, right?
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
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," look, I, as- as painful as it is for me to write, I enjoy writing. I enjoy working out. I enjoy, uh, pushing myself. I don't necessarily enjoy it in the moment, okay? 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. Right? It's, um, 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, Lenny. I- I don't have to, but I enjoy it.
- 1:11:28 – 1:19:24
The role of radical self-inquiry in leadership
- JCJerry Colonna
- LRLenny Rachitsky
There's another, uh, maybe a last area I wanna spend some time on, which is around teams and what often causes trouble for teams, what breaks teams, what breaks companies. You have this, uh, 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?
- JCJerry Colonna
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, grr." 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, uh, software blogger, blogger on software that, uh, I- I coached for many years, and we were, 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 happen here. 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." And it's like, yes, 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 replete 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 in 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, uh, a manifestation of early dysfunction in the individual's lives. Does that make any sense?
- LRLenny Rachitsky
100%. And this, this comes up a number of times on this podcast, just, yeah, the, the, the impact of the leader's issues have on the rest of the team, and al- also just this idea that the conditions they're trying to avoid are the conditions they invite in because they're avoiding.
- JCJerry Colonna
That's it. That's it.
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
My, my, one of my favorite teachers and dear friends is Parker Palmer, and he builds on, uh, this, the, 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."
- LRLenny Rachitsky
(laughs)
- JCJerry Colonna
(laughs) And that's it. You have a responsibility to examine your own shit.
- LRLenny Rachitsky
So say you're on this team. So there's kind of two sides to this. You're on a team and the leader's clearly got some stuff that they need to work through, but they're not ... Is, is there something you can do there other than just say, "Please, this is hurting us"? And then from the leader's perspective listening to this, what, what should they do? Is it like get a coach? What can you do?
- JCJerry Colonna
So for the, for the one who has less power-
- LRLenny Rachitsky
Yeah.
- JCJerry Colonna
... one of the things to ask oneself is, what draws me to this position in the first place? How have I been complicit, 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, um, uh, 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 thing. You asked about the person who has power, and you were using the word leader. I will talk about power. And you threw out, "Well, should they get a coach?" Uh, l- 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 give you a very quick example of what I'm talking about. A couple years ago, I was doing a talk at a venture firm's CEO portfolio summit, um, uh, the portfolio s- company's CEO summit. And we're sitting in a room and I've, 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 making th- them making a decision that you disagree with?" Okay. 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. You were talking about, 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?
- LRLenny Rachitsky
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?
- 1:19:24 – 1:22:49
Final thoughts and reflections
- LRLenny Rachitsky
A big takeaway for me, here, and it just keeps coming up, and 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, it's less, going back to that equation, it's not about building more skills, like public speaking skills, or email skills, or, 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?
- JCJerry Colonna
Lenny, I was just gonna say, you just made me so happy-
- LRLenny Rachitsky
Mm-hmm.
- JCJerry Colonna
... you saying what you just said. Yes. I've, 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. (laughs) That's it. This is why radical self-inquiry is so damned important, 'cause it leads to a little bit less suffering and a lot more resilience.
- LRLenny Rachitsky
For folks that wanna actually do that, well, they can rewind back to kind of the middle of the episode where we actually ask the questions that, uh, are associat- associated with radical self-inquiry, and then obviously if they want to dig deeper, they can buy your book.
- JCJerry Colonna
Or, or 10 copies of the book. No. (laughs)
- LRLenny Rachitsky
Or 100 copies for everyone at the company. We'll link to Amazon. (laughs) 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?
- JCJerry Colonna
No, one of the hopes that I have, you asked me at the start, like, what would be my hope, and said 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." It, you know, 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."
- LRLenny Rachitsky
I, I really appreciate that. The way I think about these sorts of conversations and episodes, I call 'em Trojan horse episodes, where people come for the other stuff, tactical, practical stuff, and then they get the stuff they really need to hear. And so I appreciate you. Jerry, thank you so much for being here.
- JCJerry Colonna
Thank you for having me. It was a delight.
- LRLenny Rachitsky
Same for me. Bye, everyone. (instrumental music) Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
Episode duration: 1:22:49
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