The Tim Ferriss Show - #767: Tim and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck

Episode Date: September 11, 2024

Here is my brand-new conversation with Jerry Colonna, CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. Enjoy!This episode is brought to you by:The League curated dating app for busy, high-performing people: https://click.theleague.com/qmhm/timferriss; available on iOS and AndroidEight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating: https://eightsleep.com/tim (save $350 on the Pod 4 Ultra)LinkedIn Jobs recruitment platform with 1B+ users: https://linkedin.com/tim (post your job for free)*[00:00] Start [08:40] “How have I been complicit in creating the conditions I say I don’t want?” and its misinterpretations.[21:55] Recharging off the grid on sabbatical.[24:41] Is a tired dog a happy dog?[29:21] What are you hearing that’s not being said?[33:14] Closing transgenerational, transpersonal, and intergenerational wounds.[44:05] Focusing on the future when the past keeps pulling us back.[52:18] Changes in challenges Reboot’s clients have faced over the past decade.[55:34] Guilt vs. remorse and how to move from one to the other.[1:01:40] Interpretations of legacy.[1:13:17] Jerry’s parenting experience and advice.[1:19:02] My thoughts on having children and grandchildren.[1:24:54] “This Be the Verse” by Philip Larkin.[1:26:08] Book recommendations and their impact on Jerry and his children.[1:28:46] Novel truths.[1:32:40] The importance of laughter and human connection in difficult times.[1:35:45] Parting thoughts.*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello boys and girls, ladies and germs, this is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers, to interview them and such themselves, to get past sticking points, to redefine themselves, to reinvent themselves, to chart new paths forward. And my guest today, Jerry Colonna, is such a person. He is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. But prior to that, he was an operator in many different ways. Prior to being a coach, he was a partner with JPMorgan Partners, the private equity arm of JPMorgan Chase. He also led New York City-based Flatiron Partners, which he founded in 1996 with partner Fred Wilson. Flatiron went on to become one of the nation's most successful

early-stage investment programs. At age 25, he was editor-in-chief of Information Week magazine. He's written a bunch of books. We'll mention them at the end of the conversation, but one is Reboot. The other is Reunion, both highly recommended. You can find his company, Reboot, at reboot.io, and Jerry on Twitter and Instagram, at jerrycolonna, C-O-L-O-N-N-A. He has been on the podcast twice before. He is a fan favorite. People always take a ton away from our conversations. And I recap some of my favorite aspects of those in this episode. And we cover a lot of ground. There are a lot of stories I've never heard. We have a lot of laughs, almost a few cries on my side. We dig into his toolkit, the questions that he uses with himself and with clients that I have adopted as some of my favorites. There is a lot to learn and it was

a hell of an enjoyable conversation. It was a walk and talk. And I have done this before where I am out in nature today. It is a beautiful bluebird sky day in the mountains. And to sit in a dark room staring at a screen seemed like an insult to nature, complete travesty, totally unnecessary. So I have high-fidelity recording equipment. That is what I'm using right now. It is a headset. I am sitting 10 feet from a beautiful river where I'm watching the eddies swirl around rocks. So why not? get out and move?

If you can listen to this while you're moving, I encourage you to do so. Audio is a secondary activity. So if you can walk and talk or walk and listen while I'm walking and talking, all the better for you, me, everybody involved. So hopefully that all makes sense. But without further ado, please enjoy a wide ranging conversation, a very tactical, practical, and also funny conversation with Jerry Colonna. But first, a few quick words from the fine sponsors who make this show possible. I use all of their products. So this is not me just shilling. I've tried it all. I've vetted it all. And here they are. Okay, this is going to be part confessional. As some of you know, I am recently single and navigating the world of modern dating.

What a joy that is. Sometimes it's fun, but it's mostly a goddamn mess, as many of you probably know. I've tried all the dating apps, and while there are some slick options out there, the most functional that I have found is the League. Why did I end up using the League? First, most dating apps give you almost no information. It's a huge time suck. On the League, you're starting with a baseline of smart people, and you can then easily find the ones you're attracted to. It's much easier. It's like going to a conference where everyone is smart and then just looking for the people you think are cute to go up and speak with. So more than half of the league users went to top 40 colleges and you can make your filters really selective. So if that's

important to you, then go for it. It does work. And that is one of the reasons that I use it. Second, people verify using LinkedIn. So you can make sure they have a job and don't bounce around every six months. It's a simple proxy for finding people who have their shit together. It's infinitely easier than trying to figure things out on Instagram or whatever. Third, you can search by interest and in multiple locations. I haven't found any other dating app that allows you to do this. So for instance, I usually search for women who love skiing or snowboarding, have those as interests as I like to spend, say, two to three months of the year in the mountains. I'm a rivers and mountains guy. The UI is a little clunky, I'll warn you,

but it's incredibly helpful for finding good matches and not just pretty faces. So you can search by interest and specify multiple cities. So to summarize a few things that I think make it stand out, features available in the league include multi-city dating, LinkedIn verified profiles, ability to block your profile from co-workers, bosses, family, etc. That's very easy to do. You can search by interest, you can get profile stats, and there is a personal concierge in the app. So there's someone you can text with within the app as a personal concierge to get help. So what am I looking for? I am looking for a woman who is well-educated and who loves skiing or snowboarding or both. These are, and I've used this word already, proxies for like 20 other things that are important. So just I'll leave it at that for now. Someone who's default upbeat,

likes to smile, smiles often, glass half full type of person who would ideally like to have kids in the next few years. Her friends would describe her as feminine and playful, and she would love polarity in a relationship. She's athletic and has some muscle. I like strong women, not necessarily bodybuilders, but you get the idea. It could be a rock climber, dancer, whatever, but has some muscle, loves to read, and loves learning. If this sounds like you, send hashtag date Tim, so hashtag date Tim, in a message to your concierge in the app to get us paired up. So these are all reasons why I was excited when the League reached out to sponsor the podcast. They even have daily speed

dating where you can go on three three-minute dates with people who match your preferences all from the comfort of your couch. So check it out. Download the league today on iOS or Android and find people who challenge you to swing for the fences and who are in it to win it. I found it to be super fascinating. You can really get good matches instead of just looking at pretty faces and kind of rolling the dice over and over again. Much better. So download the league today on iOS or Android and check it out. Message hashtag Tim to your in-app concierge to jump to the front of the wait list and have your profile reviewed first. Check it out. The league on iOS or Android.

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I was so pleased with how much from our prior conversations has stuck with me. I just wanted to tell you that. And also to ask you, is there anything that you have repeated or shared that to you is the equivalent of a four-hour workweek in terms of being the blessing and the curse that you just can't seem to shake for better or for worse? Because I know we're going to talk about legacy but specifically i'm wondering is there a point when you get tired of hearing some of your own profound questions echoed back to you specifically can you guess which one have i

been complicit yes yes i don't get so tired of it. I will tell you that I get tired of the misinterpretation that goes along with that. Okay. Would you mind laying out the context of this question? What is the question? And then we'd love to hear you expand on misinterpretations of the question. So what is the question or what was the conditions that caused me to ask that question initially of myself? Let's do the question because we covered... Actually, you know what? Yeah. Let's rewind the clock all the way. Let's do both. And for people who are like,

what the hell are they going on about? This is a question that I revisit a lot. Maybe I'm revisiting it the wrong way. So we will find out shortly. But yes, if you could just explain the Genesis story, then the formation of the question, and then how people misinterpret it, if that order makes sense to you, that would be, I think, a great place to start. And the Genesis story, the origin story, isn't that complicated. If we go back in time to my mid-30s, when I was a prince of New York and a former VC and totally fucked up as an individual, I was knee-deep in the first decade. I'm now in my fourth decade of psychoanalysis. And I had a very tough-as-nails, nice Jewish lady psychoanalyst named Dr. Sayers.

And what she taught me repeatedly, endlessly, boxing my ears when she'd say this, is how have you been complicit in creating these conditions you complain so much about? And you have to picture it, right? I'm lying on the couch. There's this old Jewish lady who's 30 years older than me who's just basically had it with me, complaining. And so the roots of the question are really a kind of an exasperation, not just from my analyst to me, but eventually with me about me. And it was really only by taking that question, how have I been complicit in

creating the conditions I say I don't want, that there was a massive unlock for me. Now, you asked about the misinterpretation. The first level of misinterpretation that people go through is that they assume I'm saying, how have I been responsible? And I am very, very particular. I get very, very angry when people misinterpret the word complicit for responsible. And it's not because I want to let people off the hook, but quite the opposite. I want people to understand that they've been an accomplice. Here's the thing, Tim, when we get into our

mindset that says, I am responsible for all the shit in my life, we're actually walking away from doing the hard work. Could you expand on that? Yeah, sure. Because guilt is a defense mechanism. Right. Because some people might say, well, that's extreme ownership. As I say, I'm responsible for all the shit in my life.

Exactly. That's the beginning of the solution. But where do they take a wrong turn? So I like the kind of ownership. I like the word ownership. I don't like the word responsibility. And the reason for that is because, and the reason I think it can be a defense mechanism, is because it can be an old structure. So many people that I encounter, myself included, spend our childhood pendulating between grandiosity and a sense of worthlessness. I'm either shit or I am the best.

You got rid of that in your childhood? Man, good for you. Well, I got rid of it in my adulthood. This is the point. I got rid of it by actually asking the right questions of myself. If the word complicit is replaced with the words even extreme ownership, the danger is that I tip over into misunderstanding what actually has been going on, and I end up in this zone of being responsible for everything. And the truth

is, it's much more complex than that. I was just thinking that you're referring to a pendulum and that not taking any responsibility for anything is one example of sort of absolving yourself of the hard work. But I never thought of the opposite. If you're accepting that anything and everything bad that happens is your responsibility slash fault, it puts you in a similar position, it seems. Exactly. The position it puts you in is unable to actually, with discernment, diagnose what's really going on. And you know what? You don't get to transform stuff if you don't really know what's going on. And so to understand what's really happening for you, you have to understand what your role is and what it isn't. So how do you walk, say, a client through answering that

question well? How are you complicit in creating the conditions that you say you don't want or the conditions of your lives in your lives that you say you don't want? How do you walk them through their rough draft of trying to answer that? Okay, So the unlock on the question is the second half of the question, which people skip. You say you don't want. So give me an example from your own life, Tim. What do you say you don't want? Oh man, how much time do we have? I have become better at this. So I'm not dodging the question, but I would say probably some form of busyness, right? I've got this and I'm overscheduled and I've got this and that. And the other thing that is imposing on what maybe I say I want, which is more locked out

space for writing or making. Right. So you say, Mr. Four-Hour Workweek, I don't want to work more than four hours a week. Nice turn. Nice turn. I think you said that to me in the first conversation. Right. So you say you want to be so efficient and so productive that you get everything done that you want to get done so that you have time to play, take care of yourself, wear Breathe Right strips as you talk to me, right? This kind of thing. Right? Okay. Just a quick sidebar. Breathe Right, this one's on me. Next time, you got to sponsor the podcast i could recognize them because i'm a breathe right user i use them to sleep at night so oh my god and we were we were both like a lifetime supply so feel free okay so you say you don't want to be so busy, right? And you were asking, how do I walk a client through to understand the role of complicity,

right, in this regard? So how does it feel when you're not busy? I would say, and I don't want to steal your thunder here, but since I'm cheating with a cheat sheet, right, this is... It's your show. So it's your show. So it's your thunder. And action.

So segueing to a compliment or maybe a necessary component of the first question, how are you complicit in creating conditions that you don't want, which is in what ways does that complicity serve you? Okay, so to answer your question and that at the same time, I would say probably, and this is almost a certainty looking back at some of the scariest depressive episodes in my life it's when i had a lot of empty space and there is an underlying fear even though i haven't

experienced anything close to that magnitude of desperation and darkness in a very long time, there is a fear that if I create a void, that is the voice, that is the narrative that is going to come to dominate my thoughts. I would say that therefore, my complicity serves me by avoiding that. Right. And so if you really want to transform, when will you be comfortable with the void? That's a good question.

And in my defense, Your Honor, I will say that I'm about to go off the grid for a week starting this Friday. So in a few days, I'll be going completely off the grid, no phone, no nothing, for a period of time. So I have injected these periods,

but let's get into the messy stuff for a second since life is rarely as much of a randomized control trial as you would like. I've had an ongoing number of chats with friends and WhatsApp and different messaging platforms. And it's been around taking breaks, creating space, chilling out, right? So a lot of these friends of mine have passed every hurdle and objective they could have had.

And their goalposts keep moving, right? They want to make a million, and then it was 10, and then it it was 20 and then once that gets in defense one then it's a trillion once it gets indefensible then it's like what's your annual compounded growth rate and this then turns into percentages because they can't even with a straight face defend the rest of it but what they claim to want and what they believe i need is to chill out, take a break, create all this space. My experience is as social animals, or at least as a person who benefits from social interaction, I do best around other people. I just do. And there are, it's not 100%, but it's not 100 but it's not zero percent there's a risk that i do return to some of those dark places or dark narratives it's not zero so i struggle to answer the question of like when

can i allow space because i do it in small doses sometimes larger doses i took almost all of october last year off the grid so perhaps you can help me to find my way to answering the question you posed. You know, look, Tim, I feel like Uncle Jerry in that we speak every few years, and every few years, my, how you've grown. I know you don't feel that way because you're in your body. But when we first started talking, which was years and years ago, this was a big struggle for you. This was a tremendous struggle. And there was a sense that you might miss out. There was a sense of like you being falling behind in some sort of weird little race, a race to the top. And I think the speed with which you're able to go right to the fear of the void. What Blaise Pascal identified when he said that all of man's problems stem from their inability to sit alone in a room. You know,

I think you've got, like a lot of us, you've got a component of that. And I also want to say I'm watching you letting go of the need to turn that void time into productivity time, right? When I first started promoting the notion of sabbatical, which we've talked about in the past, I remember dealing with a client who would say, well, I'm going to learn Portuguese. It's like, no, you're not. You're not going to learn Portuguese in four weeks. You're going to learn to breathe without breathe right strips. You're just going to learn to enjoy yourself.

Now, what I hear you doing is learning to enjoy yourself, which is a really powerful skill. Yeah. Yeah. It's going to be a lifelong project, which is okay. A lot of things are lifelong projects. That's right. We got here because you were asking about that process and this is the process, right? This is the process so for you when you're off the grid starting friday you know what will that experience be like for you at what point might you be anxious and at what point might you start to relax because are you going to be with friends this trip too this particular example may not fit the exercise. But what I've done for the last handful of years is every year I do a past year review rather than setting, let's just say, blind, semi-uninformed, overly optimistic New Year's resolutions. I look back at the past year and figure out what the

highs and lows looked like if I were to do kind of an 80-20 analysis. Places, people, activities, the most life-giving and the most life-draining. And then I schedule time as soon as possible in blocks of one week, two weeks, depending on availability, to spend time with energy and people doing energy and things, right? And this particular week off the grid is going to be a alpine elk hunt which i do once every two years or so with bow at probably between 10 and 12 000 feet for the most of it it's going to get cold we're going to be getting a lot of shitty freeze-dried fruit hopefully a bunch of trout uh en route to finding. And I have just found that particular experience and the time dilation that it allows

to feel like a month off or two months off. It is just so regenerative for me that it's become a core piece of my annual planning. Not necessarily a hunt, but that type of shared experience with a small, very small group of people. So that's what that will look like. And I, in a sense, I don't want to say I'm disallowing myself from feeling discomfort

because there's going to be incredible discomfort physically. Sleep is probably not going to be fantastic. And we will be very, very, very active. But it's not the same as doing a silent retreat and sitting there watching your monkey brain just contort itself for 16 hours a day. It's the kind of retreat where layers of your skin are stripped away because you're so raw and rugged out in the world. And that's just going to drop you into your body and drop you more and more into the land. And that's a place of nourishment for you, for sure yeah let me ask you if i could how often do you find with your clients or your team find with their clients that the fixes in the body or in something physical versus in the mind

even though the symptoms permeate both because the cartesian separation of mind and body is ridiculous it's not saying and the reason i ask is that for me let's just say taking a trip like this it is such a restorative reminder of how what i want and need is simple and right in front of me. But that comes through, for me at least, often, not always, but physical movement, sometimes physical hardship, where, as they say in dog training, a tired dog is a happy dog. I think humans are pretty similar. Well, we're both mammals, right? Yeah. You asked how often. I would say 95% of the time. Wow. I would say you're finding your way. I'm older than you, Tim, so I get to be the wise one, but you're finding your way to that really inherent wisdom. And my take on the Cartesian Descartes notion is, instead of it

being, I think, therefore I am, I am, therefore I think, and that's where all the problems begin. You know, what you're really talking about is getting into the essence of your existence. The only cautionary note that I would sound is when we start to invade the productive thinking into that tired dog effort, meaning I'm going to do this so that I, I mean, the worst case is I'm going to do this so that I lose weight, or I'm going to do this so that I, I mean, the worst case is I'm going to do this so that I lose weight, or I'm going to do this so that I can look better, or I'm going to do this so that I can, I don't know, quiet some negative self thought. And I think you're beyond that. But I would say to those listening, what I have found is when I can let go of even those things and just get dog tired, then I'm happiest. For sure.

It was definitely possible to sort of run towards things, run away from things. movement it's not necessarily condemnation to be wanting to quiet something because you may just have too much inherent physical energy and it has nowhere to has no vehicle through which to dissipate so it just creates the yeah kind of devil on your shoulder creating all these fairy tales to drive you insane and i do think that quieting that by dissipating the energy through exercise makes a whole lot of sense but if there's a persistent problem that you are trying to avoid that requires attention then it's a different matter altogether let's just agree that bypassing is not a good strategy. I mean, it is important to take a vacation. And that wise old analyst, Dr. Sayers, used to say to me all the time, enough, Jerry, you've figured it out. Now go take a break.

But it gives you insight in what was going on in that session room. But it's really important that we let go of those things that are driving us. And that's not bypassing. When you go on this elk hunt, I mean, maybe you're avoiding the conversation that you're supposed to be having, to use one of my other questions. Maybe you're not saying the thing that you need to say. But I suspect at this point, what it's doing is it's giving you the ability to come back to the stuff that you've had to confront, but it's giving you some ground to stand on so that you can confront the things that you need to confront. That's how I feel. And it's also planned so far in advance at this point that it's not a reactive, it's

proactively basically injecting turbo boosters on my physical and mental wellbeing so that I can bring that back to everything else. And you mentioned a few things just a moment ago that I just want to reiterate for folks. And this, I believe, maybe the same therapist, could be a different one, taught you these questions to ask when in existential pain, what am I not saying that needs to be said? What am I saying that's not being heard? What's being said that I'm not hearing? Am I getting that right? That's right. Well, she taught me the first question, and it was, again, in a moment of exasperation when I had been hospitalized with a really terrible migraine

and spent a week going through neurological tests only to find out that there was nothing physiologically wrong with me. And in the first session back, she looked at me and she said, what are you not saying that you need to say? You need to talk more. So when you see those questions, please hear that voice. I'll add, by the way, that those questions have sort of bounded around the internet the way a lot of my questions do. And one woman wrote back and said, here's another one. What are you hearing that's actually not being said? That's a good one.

It's a really good one. That should be on my bathroom mirror. That's right. You hearing that's not being said. Oh, that's good. That's right. But you know, you hearing that stop being said, oh, that's good. That's really good. Because boy, oh boy, do we tell ourselves stories, eh? What we're getting at in all four of the questions and really in much of this conversation is the importance of not bullshitting yourself, the importance of not bypassing what's really going on for you. And I have found in my 61 years now that that is also a lifelong practice, that my capacity to bullshit myself

continues unabated. And no matter how progressive I think I am and evolved, I think I am, my ability to be deluded by my own mind knows no end. So I have come to see that as just a part of the human condition. Maybe when I'm as old as my friend Parker Palmer, who's 86, I'll have the wisdom of not being able to bullshit myself. Parker Palmer, also the author of one of your favorite books, I believe, Let Your Life Speak. I'm getting that right. we'll be right back to the show. This episode is brought to you by Momentous. Momentous offers high quality supplements and products across a broad spectrum of categories, including sports performance, sleep, cognitive health, hormone support, and more. I've been testing their products for months now, and I have a few that I use constantly. Personally, I've been using Momentous Mag 3-in-8 L-thean, and apigenin, all of which have helped me to improve the onset quality and duration of my sleep. Now, the Momentus Sleep Pack conveniently delivers single servings of all three of these ingredients. Momentus also partners with some

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So check it out. Visit livemomentous.com slash Tim and use code Tim at checkout for 20% off. That's livemomentous, L-I E M O M E N T O U S dot com slash Tim and code Tim for 20% off. I want to overlay a few more questions that can be used that I took note of when I was reviewing our past conversations that I really like. I don't yet have kids, so one of them won't totally apply to me, although could apply, I guess it could be hypothetical, but ways of edging into what's actually going on, right? Circumventing that bullshitting that we're all incredibly good at doing. And it may not be,

I guess it often isn't conscious bullshitting right where we know we're lying to ourselves it may just be a really compelling narrative that isn't true right we're hearing something that isn't being said so one is no really how are you doing not just how are you doing but like no really how are you doing and then the little trick of asking people if they want their kids to feel the same thing that they're feeling when they get to be the same age. And if they don't, it prompts them to start reorganizing their lives, and so on and so forth.

I'm next to a river. Such things happen. And there are more, of course, but what I was curious to ask you is, I'll segue into this by way of an anecdote. There's an amazing, fascinating sage man named Bill Richards. And Bill Richards wrote a book called Sacred Knowledge. He is a religious man. And also, I think he may be an ordained minister, something along those lines. He also has the distinction of having administered hundreds and hundreds of psychedelic-assisted therapy sessions, both before and after Prohibition.

And last time I spent time with him, he kind of looked like Santa Claus. Amazing, big white beard, kind of jolly old elf type of feeling, always smiling with a little twinkle in his eye. And I spent some time with him probably eight years ago, something like that, near Johns Hopkins, where he's done a lot of work. And I was asking him some question about doing the work, right? This is a phrase that comes up a lot in personal development circles, dealing with your shadow self and X, Y, and Z. It can take a million different forms, doing the work. And he said something to me that has stuck ever since. And it was along the lines of, well, you know, the tricky part about doing the work. And I was like, I don't, what's the tricky part? He's like, there's a very thin line between doing the work

and just picking on yourself. And he said a few things to me that day where afterwards i was like fuck i just thought it was funny but there's actually a lot to unpack there and how do you help clients or how do you think about helping people to distinguish between the two right because there can be a degree of like trauma fetishizing and past fetishizing where people are doing everything and anything to just revisit every mishap of childhood, every mistake their parents made. And the dose makes the poison, right? And it seems like Paracelsus said so long ago, not in English, obviously. And how do you think about navigating that? I think it's a brilliant question. And I think it's something I probably, as I've

slip-slided my way into elderhood, have begun to finally let go of in my own life. And so when I think about supporting other people, what comes to mind is really, I mean, think about the way Bill responded to you. Think about the way Dr. Sayers would respond to me. I think about the conversations I have with my elder friend, Parker. It's always laced with humor, and it's the humor that cuts through it. Humor, forgiveness, and not in this kind of, I don't know, self-development book, bullshit self-forgiveness thing that's out there, but genuine care and concern. I mean, I'll give you an example. I wrote a book that came out last year called Reunion.

And part of that journey was really reuniting, to use language from the book, with the parts of myself that I had disowned, but more importantly, my ancestors. And in this case, story, what I came to have a new relationship with was his own depression, his own alcoholism. And I unpacked, you know, to spoil the plot, my dad was, on his wedding day, his mother was so angry at him for marrying my mother that she screamed from the back of the church, putana, putana, putana, whore, whore, whore, because my mother was pregnant at the time. And then she screamed out, you're not my son, you were adopted. Jesus. And that's how my father, yeah, that's how my father found out he was adopted.

And I grew up, as we've discussed before, my mother was mentally ill and my father's depression and alcoholism really marked my childhood. And I would say that I spent most of my life being angry with him, and this is to the point of the forgiveness. And I think that what happened was, in writing this book, I started to really step into his body. What would it be like to be 18 months old? Because it turned out that he was given up for adoption at 18 months old, and he was given up and raised by the only parents he knew, an Italian-American couple. And the reality is his biological mother was an Irish immigrant to New York who gave birth to him when she was 20. And I ended up in Ireland at her gravesite, not only forgiving my father, but forgiving her. And I did that. I tell that story in this book. But more important, to your point, I think that that laughter came about from forgiveness where now I actually can feel myself going, he wasn't so bad. He did the best he could.

And he got a raw deal. And yeah, some of the things he did sucked but not bad was that incremental a hundred different realizations adding up over time or or were there any flash points where there were particular experiences or insights that covered the bulk of the traverse from anger to forgiveness or acceptance in the way that you just described it? It's interesting because we were talking before about the physical being, the somaticized being, and there was a moment, but it wasn't an insight, meaning it wasn't a thought. And, you know, I talk about this as well. My youngest son is named Michael, and he was a junior in college, and he did a semester abroad in Dublin. And one week for my birthday, I went to Dublin to visit with him.

And we went to visit, his girlfriend was there as well. She was also taking a semester abroad. And we went to visit the printing museum in Dublin. Printing? Printing. And we're walking through the museum, because we're freaking nerds looking at old print presses, right? And I'm explaining to him how the machine works. And he's looking at me like, oh, yeah, you're bullshitting me, Dad.

And it's like, no, no, no. My father worked in a print shop. I remember walking through the print shop and seeing molten lead flowing as they would refire lead type and that the sparks would fly as they were doing this. I remember all of this from when I was a kid. And I was explaining all of this. And I look up and they have this replica copy of the equivalent of the Irish Republican Declaration of Independence. And it was actually at that moment that I had this profound visceral experience of my father, which was not an insight, right? It was, first of all, my father would have loved

walking through the museum with his son and grandson. And all of a sudden, I realized that the folks who had put up that poster originally and declared their independence were the kinfolk of my father, which was a very different and powerful word for me. And later, about a year later, when I was in the churchyard in the gravesite and visiting my grandmother's grave, it's still weird to say this because I never knew her, and I was walking through this tiny little graveyard, I realized that I was surrounded by the bones of my kinfolk. And Tim, that was not an intellectual experience. That was not an insight.

That was a viscerally felt experience. I look up and I see the light slanting through the trees. And I swear to God, I felt like I could hear my grandmother at four years old running down the lane. What a story. To bring it all back, I feel like because of that experience, I closed a wound that was transgenerational, transpersonal, and intergenerational. This prompts me to want to ask a few different questions. And I'll first say that personally, I've found tremendous value in metabolizing a number of

things from the past. I've had some horrible things that happened to me as a small child. So it seemed important for me to, at one one point contend with that or triage it, process it in some way. Now, if I were to take not necessarily devil's advocate position, but look at, for instance, many people I've interviewed on this podcast, there are some, and I'm probably misquoting, but it's not going to be too far off. I remember chatting with Mark Andreessen, one of the most storied, famous, and successful venture capitalists of our age, also an incredible technologist in his own right, and coder slash product developer, Mosaic, being among his achievements. answered it may have been i think his billboard was raised prices his billboard so that's not it but there was some type of perhaps the question was related to if you had to live your life with one mantra what would it be and it was some version of forever forward he told this story

of a character in a detective novel who has arrows tattooed on his shoulder pointing forward to remind him always forward. And many of the most effective people, I don't know if they're the most content people, I don't have that window into them, have a philosophy along these lines, right? You can't change the past, you can change the future. Pay attention to your thoughts, behaviors, habits, those all form your destiny moving forward. There's a very forward-focused view. And it works for a lot of things. Then let's just say, on the opposite end of the spectrum,

I'm sure there are very, very successful people who also spent a lot of time metabolizing the past. I know quite a number of them. But there are also folks who get so focused on the past, and there are a lot of them in Austin, Texas, where I live, that they don't really seem to be grappling with the present or the future particularly well. And they feel like their past is this unalterable, basically shaping of a sculpture they cannot undo on some level, right? They can't seem to escape the vortex, the

gravitational pull of the narratives they have about their past. How do you help someone find the right blend of past focus versus present or future focus? I know that's a very, very long lead up to the question, but it's something I do think about a lot. I think that you are identifying a real challenge in the human existence. And I'll reframe it just slightly and take us back to the notion of bypassing. I can argue that those who are only forward-looking with no awareness of the past may be bypassing. As you know from your own experience, ignored trauma can stay in the body, can affect us forever. But the fear that many people have, and one of the reasons why we struggle to sit alone in a room is that we're afraid of our thoughts, and the thoughts are either about the future

or the past that we're afraid of. Many people fear being trapped in the past. So your question is, how do you balance those two, which is a great framing of it? And I often think of the Carl Jung quote, which is, I am not what has happened to me. I am what I choose to become. And I think that no one would ever accuse Carl Jung of ignoring the past, but seeing it as, if you will, the source material of what the future is. The reason we open the closet that is really fucking messy is so that we can straighten it up and close the closet door and

move on. Because the stuff in the closet that's ignored and messy has a way of busting through the door and messing up our lives. So I think part of your question too is how do we get somebody who's stuck in the past to move forward? Is that a fair statement? Yes. Yes. I think that the trend seems to, at least in certain places, to have swung pretty extremely from the sort of gordon gecko let's just say pure machine with just enough reflection on the past to take advantage of new opportunities but not much more all the way back to sometimes what i would say very self-indulgent past reflection and oversharing. And it's like, okay, you wrote the script, you're on your 247th read, right? Maybe it's time to stop. Yeah. I'm going to parse things a little bit.

Please. I don't feel comfortable criticizing someone for being, quote, for oversharing, having grown up with the consequences of far too much silence and secret keeping. I know the detrimental effects of that. What I really liked, though, is your word overworking. And I keep thinking of like dough, bread dough, when bread dough is overworked. I was actually thinking of clay and play dough. Yeah, yeah. But then I chose to use the writing because I know it better. Yeah, there is that tendency to overwork it.

What I have found to be helpful is a Buddhist aphorism, which I've used often, which is this being so, so what? And what's powerful about that, it's not so what, who who cares it's so what are you going to do about it which is that forward momentum whether it's mere wounds which we all have or trauma which many of us have re-traumatizing ourselves by replaying and reworking it, overworking it, doesn't release us. But acknowledging what has happened and then really empowering yourself to say, and what will you do about it, is I think that's the unlock.

I think that's the balance point that you're looking for. And I'd love to actually say something related to your pushback, which I think is valuable and valid in the sense that you mentioned being on one end of the spectrum, right? If you come from a family at a place of withholding and silence and stiff upper lip,

not communicating feelings, experiences, et cetera. Or worse, secrets. Or worse, secrets, right? It can be very therapeutic and very healthy to push yourself towards the other end of the spectrum, recognizing you're probably not going to end up at the furthest diametrically opposed point, which is something I do think is unhealthy, which is performative trauma, right? Literally, I have been at cocktail parties in Austin where I meet somebody, and this is prior to my divulging my own abuse when I was a kid. And literally the fourth sentence out of their mouth is something

about extremely graphic trauma. And I'm like, what are we doing here exactly? I don't think this is for your healing benefit. And it becomes performative in a sense. So I suppose I just feel like that is unhealthy, also not just to yourself, but to others in a way. It, I think, can diminish how severely some of these things impact other people. Just because a person happens to have gone to the point where they can casually drop graphic abuse into conversation does not mean that someone else is comfortable hearing or saying the same happy to to sit on related topics for a second but i'm very curious at reboot so reboot.io you're the ceo co-founder you have lots of clients right in the capacity of executive coaching leadership development etc when did Vboots start when was it founded July 2014

roughly so 2014 perfect so it's almost a decade ago I'm just over just over a decade you're right just over a decade ago have you seen any changes in the types of challenges people are contending with or are they mostly the same i'm just wondering as technology has changed as social dynamics have changed as the world has accelerated. Have you seen any problems crop up more and more or less and less? Or is it kind of the same old stuff that we've been talking about for thousands of years? It's about both, I would say. I think that there are unique expressions that have emerged. I think that there is a kind of global tension that exists in the world right now that, sure, there have been, call it left-right tensions, call it whatever language you want to use, those tensions have existed, but it feels heightened right now. And you couple that, I think, and this, I think, is relatively new,

the aftereffects of the pandemic. And you have this really complex mix, I think, for example, of the complexity. I know one company, for example, in November or December after the Hamas attacks on Israel on October 7th, ended up having to shut down Slack for two weeks because there was no discussion. It was all argument. And quite honestly, a lot of the argument from all sides felt performative, to use a word you were just using, and not necessarily designed to really move the conversation forward in some way or another. This being said, human nature is human nature. It's why coaching is actually a good business model. Much of what happens continues to happen. I mean, I can't name the company, but I met a new client. I rarely take on new clients, but I kind of fell in love with this kid when I first met him. Very, very hot, young company. Not quite the clusterfuck it was six months ago, but pretty close.

And as I'm sketching out on a dry erase board everything that has happened and will happen, everybody is like, well, how do you know? I was like, because I've seen this a thousand times. This is what we do. This is called dysfunctional startup and here's the path and it's going to be fine. It's going to take a year and a half to two years, you know? I hope that addressed your question. I don't know. I may have gone off on my own tangent. Well, let me hone in on one particular concept that I'd love for you to

expand upon or just riff on. And I may have it transcribed, noted down in front of me incorrectly, so you can fact check me as well. But it's around the discussion of guilt. And part of the reason I think guilt can be such a powerful driver, sort of a negative driver in a lot of cases, I think guilt and prestige, often terrible motivators to quote maria or reference maria popova but the guilt i think also7, it's hard not to feel like you are not doing enough. But this is what I've written down. Guilt is self-focused, whereas remorse is about the other person. So if you find yourself ruminating in guilt over something, that's when you bring attention to that and say,

easy boy, easy, or good man who sometimes fails to live up to your aspirations. The first part is what I want to ask you about. Could you say more about guilt being self-focused versus remorse? I just wanted to make sure I understood this clearly. I often think of my Buddhist teacher, Sharon Salzberg, whose line about that is that guilt is self-lacerating, which I find really a compelling image. And what it does is it kind of keeps us, here's an old reference, you may get it because you may have had record players, where the needle is stuck in the groove and you just like again and again and you're ruminating and you're spinning and you're like oh shit you know why did i do that

um whereas there's no opportunity for growth there's no opportunity for learning daniel pink just wrote last year i think it came Power of Regret. And as so much of what Daniel does, it's kind of a social science take on this question. I prefer the word remorse to the word regret, but I think for this instance, you can substitute them. And there's something very, very powerful that's embedded in that is the learning. And I think that that's what you're reaching for here is when we allow ourselves to internalize remorse or regret, we're opening ourselves up to other people, to knowledge, to growth, ultimately. How do you do that without slipping into guilt? Well, so if you're talking to somebody and they're like, fuck, I shouldn't have done that,

God, if it's a bad thing, terrible, I always do this. That's an exaggerated version, right? But if they're in a loop of self-lacerating guilt, how do you move them towards one of these close cousins that is perhaps more healthy? How do you do that? If you think about the setup, the setup more often than not, if I am often plagued by negative self-talk, I am going to be more subject to that ruminating guilt because I tend to see the thing about which I feel guilty as evidence of my shittiness as a person. And if that So good people do bad things all the time. Good people who do bad things who don't learn are less evolved, less mature than good people who do bad things who then learn through regret and remorse, but they remain good people who do bad things, who then learn through regret and remorse,

but they remain good people. Does that distinction help? It does. Are there any prompts or exercises that you would potentially assign, it could be something else, to a client who has developed the habit of negative narratives

around self-worth because they did A, B, and C, right? That's just a reflexive habit that they have. Is there any way that you suggest they reframe things or start training their mind to go in a different direction? Yeah, I mean, I hate to sound like a broken record again, but how does it serve you to think ill of yourself? Any patterns in responses? Are there any patterns that, any common threads that you hear in response to that? Sure. In some family of origin structures, for example, the way I can know that I belong to

my family is by turning to negative self-talk. Just like the way I could know that I belong to a family is by seeing myself as a victim, right? If I grow up with parents who see themselves as victims, that might be the way in which I interpret the world. And so by starting to unpack that and really taking a look at the way, to use my phrasing, it serves you to think ill of yourself, begins to raise the consciousness that releases you from having to repeat the pattern. So let's hop to a topic that you mentioned as we were brainstorming various directions to go in this conversation. And I have none of the fleshed out contacts, which is perfect. It's kind of boring for me to know exactly what's coming.

Me too. Legacy. Legacy seems to be something that you're thinking about and i suspect we could have a all needy conversation about this so i'll let you kick it off in whatever way you think makes sense well you know i was joking before i talked about feeling like i'm slip sliding into my elderhood you know and the title of your next book. That's right. Sliding into Albuquerque. That's right. 10 Easy Life Lessons from Uncle Jerry.

Well, but that, you know, that's kind of where I feel like I'm entering this period, you know, Tim, you know, it's like I've done two books now. I'm starting to think about, well, what do I want to do? What is next? And I've been thinking about these themes of redemption. I've been thinking about themes about legacy and what does it mean to look at, and in some ways, very similar to the conversation we've been having, to look back on the past in order to move forward in the future. And I think that, you know, someone asked me last week, well, what am I thinking about in terms of that legacy? And I don't really think about it in terms

of say, what do I want to leave behind? Which I, I don't know, maybe that is the definition of legacy. But I think about it really more in the of three different circles of impact and influence that I have. The first circle being myself. Am I proud of the man I've become? The second is my children and descendants. How do I want them to look back on me? I mean, I fucked up royally, and yet, for some unknowable reason, my 27-year-old wanted to spend five days camping with me this summer. Can you believe that?

Because I would never have wanted to spend five days trapped in a sprinter van with my father. And then the last circle is, how have I left the world? I hope, for example, all of the work that I have done made an impact on you, Tim. I don't know. Wouldn't have all these notes in front of me if it weren't the case. You know, when we were celebrating your 10th anniversary, I sent a note, I sent a video and I was telling you, like, I'm proud of what impact you've had on people. Yeah. I really appreciate the video. Thank you. You know, I don't know this to be true, but the story I tell myself is you didn't start this podcast to have an impact on some random

22 year old kid who's a little lost. As I experienced it, you started this podcast to answer questions that you had about your own life. That's right. But in doing so, you impacted a lot of people. And I think you should be proud of that. Thanks, Jerry. Yeah, it continues to this day, I think, when I'm doing it right for me to be conversations trying to answer questions I have myself. Isn't that interesting?

I want to highlight that. Isn't it interesting that when you lean into the questions that you need answered in your own life, you end up positively impacting other people. Yeah, the personal being the most universal, right? Yeah. So what if that's the definition of legacy? Meaning being so real and so honest as to make yourself a palette, if you will, or a canvas where people can work their stories out. That's pretty cool. I like that definition or that placeholder for legacy because when I've thought about leaving things behind and know a lot of fancy muckety mucks often very good people very soulful people who somehow get fixated on legacy maybe because they've just they've overshot maslow's hierarchy of needs maybe accepting taking out maybe self-actualization and transcendence but everything else certainly

they've overshot by such an absurd margin that they start thinking about legacy and i always think to myself i'm like alexander the great what was his last name again nobody knows and we are somehow going to stand the test of time like the head of the sphinx poking out of the sands in the desert come on like it's just it seems ridiculous right but maybe who knows right what i said about borrowing from bill richards like bill richards told me this thing yes or you tell me a question yes i pass that on then somebody else passes it on and like even though the attribution probably gets long lost along the way, that is some form of legacy, right? Yes.

That continues. Yes, a thousand times, yes. Listen, I know legacy as a word can sound grandiose, and I love your self-deprecating humor. Don't use it, though, to deny the thing that is true. Yeah. Okay? And because that's another form of that self-delusion and bypassing.

The fact of the matter is you have made a positive impact on the world. It may be fleeting. It may disappear. Who knows? Listen, I'll tell you a story. About five or six months after my first book came out, I received a ton of fan mail on the book. I still get mail from people saying, you know, this book really impacted my life. But I'll never forget this one day. In one day, I got two messages, one from the CEO of a Fortune 100 company and one from a man on death row. And they both wrote about the book and said in one form or another, your story is my story. I will go to my grave proud of that fact. That's amazing. Also to have it happen on the same day. On the same day. And the lesson, Tim, in that is there's really no difference between those two men. And that's what's really powerful. Can you say a little bit more about that? Because at face value, of course, you look at their CVs, very different men. But I know you mean something different. Can you say a bit more about that? Because at face value, of course, you look at their CVs, very different men. But I know you mean something different.

Can you say a bit more about that? I do. I do. And in December of 2019, well, first, in September of 2019, my first book came out in June. In September of 2019, I'm doing a book talk. You remember when we used to do things like that. And pre-pandemic. Back when we were listening to mini LPs on the record player. That's right. That's right. And I'm walking to this venue in Denver, and there's this woman who's like clearly in her 80s who comes up to me and she says, you look like our speaker.

And I said, well, that's because I am your speaker. And she laughed and she stuck out her hand and she said to me, my name is Margaret and I grew up in the Dust Bowl. And I read your book and your story is my story. And Tim, I did not grow up in the Dust Bowl during the Depression. I grew up in Brooklyn. Like, what the fuck, right? And a few months later...

That was the best follow-up too. I grew up in Brooklyn, by the way. What the fuck? I'm sorry. I shouldn't have warned you. Goodness, I did it better. Fuck is a part of our dialect. I'm sorry. No, I have to, just a brief aside aside i'm not going to mention it by name but everybody listens to this podcast would know i'm a friend of mine who grew up in new york city a lot of a lot of like brooklyn influence and his greeting to me is you fucking fuck this is like one of the most sophisticated brilliant thinkers of our time but that's how

he greets me. I don't understand. Do you have a fucking problem with that? Yeah, exactly. Because I don't have a fucking problem. Okay. Yeah, exactly. All right. Margaret. All right. So a few months later, I'm in Dublin and I'm doing a book reading and the audience is filled with, not surprisingly, white people. But there's this one black woman who's sitting in the very front row. And at the end of the talk, and this in some ways, you know, you've experienced something similar. At the end of the talk, she comes up to me and she says, I was really moved by what you were saying, especially

the part I had been talking about how when we lose a parent at an early age, it forces us into early parentification. And importantly, that that can often be a signifier of leadership. She says, that thing you're talking about, what that happened to me, my father died when I was 13. And I'm kind of dopey and exhausted, and I kind of nod my way in response. And then she says, on Robben Island. And I look at her and I say, what? And she says, yeah, Robben Island is where Nelson Mandela was held. And she says, yeah, he was a freedom fighter based in Zimbabwe and he was caught on the border of South Africa

and beaten to death in the prison. And then she says to me, your story is my story. And the thing about that, and her name, by the way, is Joy Tenday Kangari. She is going to be graduating, I think, with a PhD in law in October. She's one of the first black women in the city of Dublin to be a barrister. The thing about that experience is, to your point, our lives couldn't be more different. But there's something very, very powerful about this notion that your story is my story. Yeah, you peel back a few layers. We're all people everywhere in all times dealing with

the same things. If you go deep enough, if you go deep enough. And if you're willing to be honest, I mean, so, you know, when people come up to you and want to share their trauma, yeah, there's a performative element to it, but maybe too, they're seeing their story in your story, Tim. 100%. Just for clarity's sake, if people do it after I share publicly what happened to me, it's very different from the examples that precede that.

Where with no context, it's clear that they are showcasing their trauma within the first few minutes to anyone who will listen, which I think can get into dangerous territory. But I agree with you a hundred percent and i do i'd say probably in response to that episode more than any other but certainly there are a few where i discuss personal challenges with depression and so on which thankfully are fewer and fewer and shorter and shorter in duration but you never know and i agree with you 100 may i ask you a completely unrelated question because it's stuck in my mind and i need to scratch the itch your son and the sprinter van five days you mentioned fucking up a bunch of stuff like all parents do

even though one guy great guy i won't mention him by name, but he said, he's like, oh yeah, I'm going to send all my kids to the Hoffman process. He's like, I know I'm fucking them up. I'm just not sure how. Anyway, so you made mistakes like every parent does, but what did you get right? Why do you think if you had to try to explain it, and I know it's not a laboratory, so nothing is easy to isolate here, But what do you think you did right or what worked? Maybe it's your son out of the box. Who knows? Maybe he's just a very forgiving guy. But why did he end up wanting to spend those five days with you in the Sprinter van versus your experience with, say, your dad? The power of that question is twofold. One is, I think it's a really, really important question. And the second is, you're touching upon one of my most deep and profound fears, which was that I would have fucked it up as a parent. And so I want to be clear, I still have the capacity to fuck it up. I think the answer to your question goes back to something Dr. Sayers

used to say to me when I would lie on the couch and bemoan that I was a terrible parent and I would be wracked by guilt because of this stupid reaction that I had or this stupid thing that I said or that kind of thing. And she used to say to me all the time, two things. One, you cannot spoil children with love. You can spoil them with things, but you cannot spoil them with love. So love them. And the second thing was, she said, give them words. Give them words. And I think, I have three children. Sam is 34, Emma is 32, and Michael is 27. And Michael's the one that went camping with me, but Emma and her soon-to-be husband really enjoy the camping van as well. And the truth is I have great relationships with each of them because they're

great people. What does give them words mean? Yeah, give them the ability to talk about what's actually going on inside of them. And listen, I mean, I think that as parents, we can become so afraid of fucking it up and hurting them that we get wrapped around our own anxiety, our own narcissism, and then we lose the connection, which is the thing that our children want more than anything else. Did you give your kids words? If so, how did you do that? Two things. I do think I gave my kids words. I think I also raised the bar on what they expect from other people. They expect words from other people, which has a mixed blessing, right? Because not everybody is trained to actually talk about what's going on. Not everybody knows how to answer the question, how are you? I think I gave them, the way I did it was I modeled first and foremost.

And the second, and I think I'm good at this, I listened. Now, I also want to give a shout out to their mom, because this was not a one and done, I did it myself by any stretch of the imagination. They had two spectacular parents who each endeavored to do right by their children in different ways, in different styles, for sure. Given your experience, you have good relationships with your kids. If you had to add a third or fourth thing to your therapist's rules, let's just say, you can't spoil a kid with too much love. Number two, give them words. What might number three and or, I guess it wouldn't be or, number three, if you want to add a fourth and go for it. But what might you add to that?

I think that if I could go back in time and give myself advice the way she might have given it to me, because she tried to make me feel this. I spent far too much time feeling guilty and far too much time worried about whether or not I was being a good parent. I mean, this is another thing that she used to be exasperated with me about. It's like, all right, Jerry, they're going to be fine. But the truth is, and I'll give myself a little bit of a break, I didn't have the context. I didn't have, God rest my parents' souls, and coming to understand that they tried,

I did not have role models for good parenting. And so I had to piece it together from people like Parker or my therapists or other mentors and elders in my life as I watched how they were doing it. How were they being the elder in their life? And learn to forgive myself for the mistakes so that with regret and remorse, I can pick myself up and try again. Can you apologize to your children? Oh my God, what a powerful tool that is. Yeah, better start apologizing in advance if you don't have kids.

Build the muscle. Don't try to win the World Series as your first baseball game. Exactly, exactly. Why are you thinking about kids so much these days? Oh man, I'm so bored of this business sage on stage stuff it's just like i'm boring myself so much it's uh i'm exactly i mean look i'm being a little facetious here but beyond a certain base level of needs we're all playing games right so the trick is knowing what games you're playing and then be very hopefully conscious of the games you opt into what are the

rules what's winning what's losing what's the ranking what's quitting time what are the stakes etc right and i feel like family kids is the next big chapter, the next big adventure. I don't overly romanticize it. Almost all my friends have kids. I know it can be an enormous, enormous pain in the ass. It can involve a lot of sadness and anxiety and you name it. But then there's the other side. And joy.

And joy, of course. Then there's the other side. And laughter. And joy, of course. Then there's the other side. And laughter. Right. And a sense of completion. I mean, let's shout out, I mean, the best of all the accomplishments I've ever done,

the best has been becoming the father that I needed as a child, without a doubt. Yeah, that's a big one. A couple of years ago, before I went to Ireland, I was in Wales. I don't know if you know the Dew Lectures. It's a fabulous- I thought you were going to ask me if I knew Wales. I was like, yeah, I think I've heard of it.

But you've been to the Dew Lectures. You spoke at the Dew Lectures. I think the first or second Dew Lectures, like 2009. It was amazing. I really enjoyed it. They're fabulous. And for those who don't know, you should check it out. It's kind of like TED without all the performative shit. And with much more confusing street signs. I remember trying to drive around Wales. This is no Google Maps at the time, didn't have international data. And they're like, sure, just turn left at Widuwaka Waka. And I get to the sign and I'm like, that's 24 consonants. How do you read this?

What do you mean? It's 24 consonants in a row without a single vowel. No, that's what I mean. I'm just like, wow. Okay. Anyway, so I was at the two lectures and I was doing a reading from Reunion, the new book. And I was maybe the first three or four pages. It was just the opening chapters. But it provoked such a powerful response from the group. And as you remember, it's like you're in this old hay barn, cow barn, the cow shed, I think they call it. And my oldest son, Sam,

had come with me. And at the very end of the talk, people were sort of, you know, milling about and, you know, oh my God, you know, and telling me what I'd done wrong and telling me what I'd done right and all that stuff. You know what they do, right? Oh, that's very good. Except it was like, okay, the next time you write a book, you can talk. Okay. Anyway, I look up and Sam, who's, you know, 6'1", big guy, he's a Muay Thai fighter and trainer. He looks up and he just mouths the words, I am so proud of you, dad. That's amazing. what a moment that's the moment that's what you want you know that's what you live for that's what parenting is yeah i feel like i need to make up for lost time i've been wondering if i need to go like raise the red lantern style i have no idea

maybe just have you know survival of fittest impregnate like 40 women and see how we do. I don't want to say desperate, but I'm just like... Well, I'm a little surprised you're talking about this because are you going to now be inundated? And then you're going to call me up and say, Jerry, what do I do? And I'll say, how have you been complicit in creating these conditions? You say you don't want. You mean publishing this to millions of people? Yes, nephew Timmy. I mean, putting it on the podcast. Well, I had this, you know, I'll share this.

This I haven't really said to anybody, but I was spending time with a number of my really close friends. We do this reunion once a year. And most of them have kids. Not all of them. Most of them have kids. And one was echoing this lesson or conversation he had with someone far older than he, a grandfather. And he kept saying, you know if that's going to be a thing. I don't know if that's mathematically,

even remotely reasonable for me to entertain. And that fucked me up. I got to be honest. Not because I've really thought about grandkids much, but when he put it that way, and it happened to coincide with my birthday, which was sort of the cause for the reunion. And I was just like, wait a second here.

I'm no mathematician, but fuck me. That was a tough pill to swallow. I'm not going to lie. I was like, oh yeah, that may not be a thing. Well, not for publication on this. So I'll do it over email, but we have a mutual friend who is in exactly the same place. You guys should hang out, you know, for

sure. Just drink some whiskey and cry ourselves to sleep. Or put the red lantern out and say, I'm ready. Oh God. I'm not ready to switch teams yet. You know, never, never say never. what are you willing to do for your kids it's like i'm no biologist but yes exactly oh man well before we move off that topic let me give you a poem you're ready this is by philip larkin yeah it's called This Be the Verse. They fuck you up, your mom and dad. They may not mean to, but they do. They fill you with the faults they had and add some extra just for you. But they were fucked up in their turn by fools in old-style hats and coats who half the time were soppy stern and half at one another's throats. Man hands on misery to man.

It deepens like a coastal shelf. Get out as early as you can and don't have any kids yourself. Wow. So should I Sylvia plath myself today or tomorrow jesus jerry well he's british he's british good lord i know i'm famous for reading poems but you know usually they make people cry this one People cry. This one. It's like Dr. Suits meets A Star is Born. Good Lord.

Amazing. All right. Let me try to write the ship here. So three books. I alluded to these. I'm curious. You've mentioned a few books in our conversations before. Certainly your own, which I recommend to everybody.

Also, When Things Fall Apart by Pema Chodron. Faith by Sharon Salzberg, Let Your Life Speak by Parker Palmer. I'm wondering if any of your kids have been impacted by any of these books or if there are other books you've recommended to your kids, whether or not they've read them. Oh yeah. Sam, in particular, loved The Wisdom of Insecurity, which is a really, really powerful book. Michael is probably the one who follows most of my book recommendations, and we go back and forth from novels to nonfiction. We swap books back and forth. The novel that Michael loved the most was also really powerful in my life. It's Call It Sleep by Henry Roth.

Call It Sleep. Call It Sleep. Never even heard of it. So Henry Roth wrote Call It Sleep in the 1930s. And it tells the story of a young boy, I think he's like seven or eight years old, growing up in the Upper East Harlem when it was a Jewish neighborhood and there are Jewish immigrants. It was well-received and then lost in time. And it was, I think it was Kazan, the famous book critic who discovered a used copy in the Strand in Manhattan and then devoured the book in the 1950s and published the first review for a paperback book in the New York Review of Books. And so the book was rediscovered.

That's ballsy. I love it. And anyway, I'm going off. Henry Roth, as a novelist, was one of the most influential novelists in my life. It's a book that I remember when Michael finished it, he sent me the same passage that I had first read when I was about 17 or 18 years old and was blown away by. I was like, yeah, that's the passage. And for those who know the book, it's the passage where David is touching a trolley car's third rail with a soup ladle or milk ladle. It's really a powerful passage.

Anyway, you didn't ask about novels well i it's funny that you brought up a novel maybe i incepted you because i was going to ask you actually if there are any novels you recommend or find contain and convey a lot of truths that stick out to mine it doesn't have to be the best, but for instance, Zorba the Greek, I think is a standout for me. You remember that. Good job, yes.

So Zorba the Greek, huge standout. I've been meaning to read it again and some more of the same author's work. Do any others stand out to you? Because I've really found fiction, which is very closely related to humor, right? Let's just say Bill Richards or your therapist, parable. These are all very closely interrelated.

It's funny that you say this because I just completed volume one of a five-volume series. Do you know the Library of America series? I have either heard of it or come across it. It does ring a bell. Okay, so Library of America is a nonprofit foundation that seeks to preserve the writings of amazing American writers. And I think there are over 350 volumes that they've done. Writers like James Baldwin.

Anyway, I just finished volume one of Wendell Berry. And the thing that comes to mind, and I said this to Michael in a text message, I think this is the first set of novels and short stories I've read that have changed my thinking about writing in a profound way. And what Berry did in volume one is the material from Everything Takes Place in the Fictitious Town of Port William, Kentucky. He, of course, is from Kentucky. He still lives there. And these tell a series of stories, short stories and novellas and novels, all taking place from the end of the Civil War, in this case through World War II. And it all involves the same characters or the same extended characters, but many times the incidents that he writes about are written about from different characters' points of view.

And it's still working on me. I've been reading it. I finished it a few weeks ago and I'd been reading it for about three months because it's close to a thousand pages. Deeply, deeply moving. I'll check it out. I have more homework assignments, which of course I love.

I do love my homework. What is the basic thesis of The Wisdom of Insecurity? I know this book title and I've come across it multiple times and I've never read it. It's Alan Watts exploring what is that anxiety about? What is insecurity about? What is it that we are working with? It's a way of coming to understand the, I guess, you know, if you want to link it back to what we were talking about earlier. It's how has it been useful for us rather than something that we need to push away? Got it. How has it been useful, not in a condemning

way? That's right. How are you complicit way, but how has it actually been helpful along the lines of the gift of fear by Gavin DeBecker, right? That's right. That's right. Not something to swat away. It's not always something to swat away. How is it a gift? Right. It's a simple to understand. We're often told that the way through insecurity or anxiety is to somehow embrace what's happening in the moment. But this actually walks us through. It tells us how to do that. And of course, Alan Watts is an incredibly important Zen teacher in the Zen Buddhist tradition. Yeah, he's a one of a kind, that one. And amazing narration as well. The people who want to take it in audio format has some spectacular speeches, presentations. Jerry, we've covered a lot of ground here. Is there anything else you would

like to mention before we begin to land the plane? Is there anything else you'd like to say, ask of my audience, point people to, anything at all? actually help remind me of the importance of that. And so let me double down on that because, you know, it's kind of a fucked up world we're in right now. You know, as I've been saying recently, it's the kind of world where babies get murdered for ideology. And that's a kind of fucked up place. And not that that's material to laugh about but to understand that there's a human connection that can be gotten even in the midst of all this i think is incredibly important right now so as dr sayers would say to me you've done enough work go on off the grid go take your time go have fun and laugh your ass off good advice good advice i'm gonna work on that tonight you know something i've started doing and this is related it's a bit of a hard segue but games just tabletop games no phones yes

yeah rewind the clock these things have been with us a long time yeah amen you know what can i mention another thing that got stuck in my mind which is funny because it was your mention of a stuck record when you were asking about records and if i remembered records the one thing that popped to my mind that has been on repeat, which of course is sort of self-referential in and of itself. When I was a kid, I had this little mini, tiny, mini LP. It was the size of a tiny pancake. It was really small. And it was a song that I played a million times and drove my parents insane.

But they made the mistake of giving it to me. And it's Disco Disco Duck. I remember the song. Who wants to be a disco duck? And it's Donald Duck singing the song over and over and over and over again. Holy shit. What a wonderful song. And i actually had some speaking engagement

like uh i can't remember a year ago two years ago i don't do too many of them and they asked me what i wanted my entrance music to be i tasked them with trying to find disco disco disco duck they were not successful, but a boy can dream. A boy can dream. I mean, what's frightening is I will not, but I can sing that song. Everyone, this is my homework assignment to everyone listening.

Go find Disco Disco Duck. That's right. I'm sure it's on YouTube. It's a treasure. Jerry, where would you like people to find you? You're at Jerry Colonna on Twitter. We'll link to everything in the show notes. They can find Reboot at at Reboot HQ on Twitter. Reboot.io is the website. You're the author of Reboot, Leadership and the Art of Growing Up. And also Reunion. Exactly. leadership and the longing

to belong you got it I think tracking me down there on Instagram I'm at Jerry Colonna all sounds great to me

so I appreciate that absolutely and to everybody listening we will link to everything in the show notes including probably

some version of Disco Disco Doc at Tim Top Block and the Philip Larkin poem that's right and the Philip Larkin poem. That's right. And the Philip Larkin poem if you're too happy

and just need a moment of sadness. Tim.blog.com slash podcast. And until next time, as always, be just a little bit kinder than is necessary, not only to other people,

but also to yourselves. And thanks for listening. Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of

tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field, and then I test them, and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog.com slash Friday, type that into your browser, tim.blog.com slash Friday, drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by Eight Sleep. I have been using Eight Sleep pod cover for years now. Why? Well, by simply adding

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The League? First, most dating apps give you almost no information. It's a huge time suck. On the league, you're starting with a baseline of smart people, and you can then easily find the ones you're attracted to. It's much easier. It's like going to a conference where everyone is smart and then just looking for the people you think are cute to go up and speak with. So more than half of the league users went to top 40 colleges and you can make your filters really selective. So if that's important to you, then go for it. It does work. And that is one of the reasons that I use it. Second, people verify using LinkedIn so you can make sure they have a job and don't bounce around every six

months. It's a simple proxy for finding people who have their shit together. It's infinitely easier than trying to figure things out on Instagram or whatever. Third, you can search by interest and in multiple locations. I haven't found any other dating app that allows you to do this. So for instance, I usually search for women who love skiing or snowboarding, have those as interests as I like to spend say two to three months of the year in the mountains. I'm a rivers and mountains guy. The UI a little clunky I'll warn you but it's incredibly helpful for finding good matches and not just pretty faces so you can search by interest and specify multiple cities so to summarize a few things that I think make it stand out features available in the league include multi-city dating linked LinkedIn verified profiles, ability to block your profile from co-workers, bosses, family, etc. That's very easy to do.

You can search by interest, you can get profile stats, and there is a personal concierge in the app. So there's someone you can text with within the app as a personal concierge to get help. So what am I looking for? I am looking for a woman who is well-educated, who loves skiing or snowboarding or both. These are, and I've used this word already, proxies for like 20 other things that are important. So just I'll leave it at that for now. Someone who's default upbeat, likes to smile, smiles often, glass half full type of person who would ideally like to have kids in the next few years. Her friends would describe her as feminine and playful, and she would love polarity in a relationship. She's athletic and has some muscle. I like strong women, not necessarily bodybuilders, but you get the idea. It could be a rock climber, dancer, whatever, but has some muscle, loves to read and loves learning. If this sounds like you,

send hashtag date Tim. So hashtag date Tim in a message to your concierge in the app to get us paired up. So these are all reasons why message to your concierge in the app to get us paired up. So these are all reasons why I was excited when the league reached out to sponsor the podcast. They even have daily speed dating where you can go on three, three minute dates with people who match your preferences all from the comfort of your couch. So check it out. Download the league today on iOS or Android and find people who challenge you to swing for the fences and who are in it to win it. I found it to be super fascinating. You can really get good matches instead of just

looking at pretty faces and kind of rolling the dice over and over again. Much better. So download the league today on iOS or Android and check it out. Message hashtag Tim to your in-app concierge to jump to the front of the waitlist and have your profile reviewed first check it out the league on ios or android