How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

30:19So you're doing a mitzvah. You're doing a good beat 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. They're just like, I am so busy. Every time someone asks me how I'm doing busy. So busy. Like, Swerley, size emoji, Swerley, I say mochi.

30:44With a little head shake. And the melting, 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, well, just do this newsletter thing. Not have the 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 just like fun to see a grow and for it to keep building and doing well. So when this reminds me, there's a quote that will, we'll smith shared ones that I think you'll like.

31:21Someone asked them 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. Like, oh, no, it's all going to fall apart. So I think that's where a lot of that comes from for me is just like, Oh, what's next? I get it. Let's 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 and heading in that it's like part of it is just fun.

32:01You know, it's like fun to win. It's just like, yeah, we're doing it. It's working. But and and when you're not growing, how do you feel about yourself? About myself. Like, there's this sense that it's all over. Like, oh, maybe it's all going to fall apart and maybe you're not as good at this as I thought. Okay, so stay in that spot for a moment. Okay. 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.

32:51I'm positive. Yep. No shit. So by being busy and by being on that growth trajectory, that voice maybe sounds a little less persistent. Yeah. Maybe a little less loud. Now, I want to offer a different potential. What if you could enjoy the puzzle of trying to create something new, trying to create magic, something out of nothing?

33:27But it doesn't matter to your sense of self esteem if you succeed or fail. Now, what if what drove you was not quieting that voice, but what drove you was, oh, this is just fun. Seth Goen who is a dear, dear friend of mine, Hux Bat Art Projects. Hmm. 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.

34:22It 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 became successful. That's right. It worked out. Right. It became successful. Meaning you developed an audience. Yeah. Meaning you developed a following. And then income as 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, yeah, my heart, the anxiety. Like not quite that strongly at times it is. But yeah, but there's a bit of just, oh, well, I can't like I'm relying on this now. I can't just let it fall apart.

35:03Because my life would fall apart if I let it fall apart. Yeah. 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. Now we're talking about attachment. Okay. When we become attached to the outcome, we inadvertently fuel our own suffering.

35:36When 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 as I always, always a very shy kid. Early grown up and I don't think people expected a lot of me except my mom. I'm dead. I guess. And so I always have a sense like I'll show them. I'll show them what I could do.

36:24And that's always this kind of, this chip on the shoulder thing that I know drives a lot of people. How old are you, Lenny? Forty three. 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 needed? 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, that's like a rewiring. That, that, you know, do you have children?

37:27Yeah, we got a 22 month old now. Oh, mausole tough. 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 at a pride. The challenging message that we inadvertently can send to our children is that we only love them because they got an hand in 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 onto the goal because the goal is cool because solving a puzzle is fun, because doing hard work and experiencing a reward from that is affirming.

38:37But 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 always tech talks now, or you don't say good job. Just say good choice or great and hard work. They have a 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 OneSkima, one of our longtime podcast sponsors, Welcome Andrew. Thanks for having me Lenny.

39:20Great to be here. So what is new with OneSkima? 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 spent importing and mapping and integrating CSV and Excel files. Yes, so we just launched the 2 .0 of OneSkima 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. File feeds 2 .0 allows non -technical teams to automate the process of transforming CSV and Excel files with just a simple prompt.

39:58We support all 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 OneSkima? 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. OneSkima stops any bad data from entering your system and automatically validates your files, generating error reports with the exact issues in all bad files.

40:32I 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 oncekima .co. That's oncekima .co. Just a kind of closed loop on this. I think as people hear this, they can... I feel like, 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 in that nice hotel and income. The comfort that comes with income at a certain level is hard to give up. How do you help people get past that?

41:06That might go away and feel comfortable. Well, the good news is, and again, this is a bit of reference. The good news is 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 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 Buddha tree and I'm not going to move until I figure this shit out.

41:55And so he sits and sits and sits in the story as 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. Okay. So let's focus on the second noble truth. Because that's really what you're talking about.

42:40When 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've signed up to my substay suddenly disappear? No. Okay.

43:40You 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 okayness. I'm okay, just as I am. I'm okay.

44:03It 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, 10 % happy, he 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 that 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.

45:04And 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.

45:20Because when I sit down, 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 going to need two or three years for now? And what's my contribution to that world? Now, just as I say that, how does that feel to you? Kind of settling. 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.

46:18I have to do this work regardless. That 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's a beautiful to other people. Yes. So I think there's like people here 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?

46:55But more just, this is really interesting. I'm going to see where this goes. You know, for me, Lenny, you implicitly asked a how question a few minutes ago. How do I do this? How do I does 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 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.

47:47I 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. What 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.

48:46He cared and he tried. And he was kind.

48:56Those 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 mattress, and he 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 is it important to think about legacy? Does legacy matter? Like, you know, we're dead.

49:31What'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.

50:14It'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 in 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 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 amoral, if not directly amoral.

51:14Why 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?

51:40I know what I want that answer to be, which is I tried.

51:48Let me, 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.

52:39So is that my legacy? Yeah. And maybe there's some ego implicit in that.

52:50But can I go on for just a bit on this? Absolutely. At the end of reboot, I write about this moment. And in this moment, I'm in Marin County, my wife, Ali 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, ready enough. You're a good man. 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.

53:47And it's 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. But 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.

54:43Just slowly dissolving into the earth, having done the best job I could of being purposeful.

54:55I 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 call back. It sounds like the giving tree to me. Oh, yes. Yes. Shell Silvesty. To give people something to do with this area of legacy, how did you approach coming up with to figure out what you wanted your legacy to be?

55:52What are there some questions you asked? There's something you recommend folks do to help 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. As I said before, as we both connected with, I use my writing to find my way to answer this to questions. So part of what I'm dealing with right now is, look, I'll turn 62 this year. That feels old. But it also feels settled. And part of what I'm trying to figure out is, what do I want my elderhood to be like? And I'll be honest, 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.

56:57So 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? 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, people. It is unsettling, isn't it? Quite unsettling. But there's a world where we don't need humans in the future potentially. Any, 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?

57:45Well, 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 freaking 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 motor? Absolutely. Absolutely. It was a big, big deal to go from 24 hundred, 1200 ,000 to 24 hundred, 400 ,000 to 56 K.

58:34Oh 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.

58:46And in the coaching therapeutic world, everybody's like, oh my God, GPD is going to replace me. I don't know, maybe.

59:00What 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.

59:29And 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, immediate 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 or a side 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 which matters, which is presence and connection, human to human contact, strategic thinking, formulation.

1:01:07You 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 at a work and making sure that the robots are well oiled and that becomes our purpose. 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 chat Gbt has memory, you members, everything you said and you can think back.

1:02:00You can ask it, what are what are blank 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 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 Quad and he's asked Quad 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.

1:02:46I 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 ChatGbt 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 in liveening and exciting. Well, put, I love that you can ask these hard questions of Claude slash ChatGbt, these questions that make you really scared, 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.

1:03:44I 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.

1:04:30It's not a scientific 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 in live -ning when you live it. All this, some people may think of as there's 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 harmful way a lot of times. Can you just talk about that while 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.

1:05:26What I have a problem is in having, in how we can turn a notion like a growth mindset into a fixed mindset, which is it's this funny little trick that 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 Buddha has taught me. Is it 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, without attachment, go for it.

1:06:28Have 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 Sange 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 Buddhist would say, beginner's mind, all things are possible. And then we experience, you were talking about it a little before, a little bit of success.

1:07:20And the ego, which is so terrified of not having success, start 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 the podcast, by the way.

1:08:18When the student is ready, the teacher will appear. You're inviting it in, but keep going. That makes sense. 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 the, I don't need to be the the CEO of the VP because like, I won't attach to that. And then, you know, so people fear that downside. So I asked this question at this retreat.

1:08:55And they'd 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, like I, as painful as it is for me to write, I enjoy writing.

1:10:18I enjoy working out. I enjoy 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. I mean, it's to get satisfaction out of hard work. For me, as a much greater motivator than fear of complacency.

1:11:13As 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? What often define as the source of the problem for teams that aren't working? It's the unresolved might be dramatic with the language demons from their childhood.

1:12:04It'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 and the doll, no. Without the individual 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 on software that I coached for many years, and we were doing an executive team meeting. Something happened in the group as we were talking that I observed once, twice, and three times.

1:13:02Finally, 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 was CEO at the time, said, Jesus Christ, it's just like my family. I was like, yes, that's just like your family.

1:13:35Carl 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 a 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.

1:14:26So 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%. This comes up with a number of times on this podcast. The impact the leaders 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 what that's it. That's it. One of my favorite teachers and dear friends is Parker Palmer, and he builds on, I think it was Socrates who said, the unexamined life is not worth living.

1:15:28And 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 to involve so the people. And that's it. You have a responsibility to examine your own shit. So say you're on this team. So there's going to two sides of 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 leaders' 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?

1:16:12How 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 experienced for me to learn. So that's one. You asked about the person who has power. You were using a 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?

1:17:11Yes. 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 see you don't want. To be a very quick example when I'm talking about it. A couple of years ago, I was doing a talk at Adventure Firm's CEO, Portfolio Summit. The Portfolio companies CEO Summit. And we're sitting in a room and of course I'm walking around again when she was 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.

1:18:01Why is it that nobody on my team can make a decision without me? And I said, who hired them? And she, wow, 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 who you expect to make decisions without running them through you if you can't tolerate making 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.

1:18:57So 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? 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 and again and again is if you're struggling as a leader, if your company's not working as well as you wanted to, if you're having a hard time with your team, it's it's the less going back to that equation.

1:19:36It'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? Lenny, I was just going to say you just made me so happy. You're 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.

1:20:28For folks that want to actually do that, they can rewind back to kind of the middle episode where we actually ask the questions that are associated with the radical self -inquiry and then obviously if they want to dig deeper they can buy your book or or 10 copies of the book or 100 copies for everyone at the company. We'll link to Amazon. Jerry, is there anything else that we haven't touched on? I think is really important for people to hear. Maybe it's the 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 that we ended up being closer in friends and I feel that.

1:21:06Let 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.

1:21:22We've made different references to the fact that it's a hard time. The truth is, it's always hard time. What makes it hardest is to feel like I'm the only one who's going through this. 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. That is a mitzvah. That's a good deed. I hope in the process of listening to those 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.

1:22:14And 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. 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 a leaving review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcasts .com. See you in the next episode.