#767: Jerry Colonna — Tim and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck

0:00 Hello, boys and girls, ladies and gyms. This is Tim Ferris. Welcome to another episode of the Tim Ferris Show, where it is my job to deconstruct world class performers, to interview them and tease out the habits, routines, favorite books. And so on that you can apply to your own lives. Sometimes I get Not just a two for one, but a hundred for one. When I interview someone Who also helps world class performers in addition to being such themselves.

0:25 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.

0:46 Prior to being a coach, he was a partner with JP Morgan Partners, the private equity arm of JP Morgan Chase. He also led New York City based Flatiron Partners, which he founded in nineteen ninety six. with partner Fred Wilson, Flatiron went on to become one of the nation's most successful early stage investment programs. At age twenty five, 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 JerryCalona C O L O N N A. And 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.

1:33 And uh 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

2:01 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

2:13 High fidelity recording equipment. That is what I'm using right now. It is a headset. I am sitting Ten feet from a beautiful river where I'm watching the eddies swirl around rocks. So

2:25 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. Four. You, me, everybody involved.

2:41 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.

3:01 I've tried it all. I've vetted it all. And Here they are. Okay, this is gonna 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 m, as many of you probably know. I've tried all the dating apps and while there's some slick options out there, the most functional That I have found is the league.

3:27 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 forty 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.

4:32 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 on the league include multi city dating. LinkedIn verified profiles, ability to block your profile from co-workers, bosses, family, et cetera. That's very easy to do. You can search by interest.

4:56 You can get profile stats and there is a personal concierge in the app. So you 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 twenty other things that are important. So just I'll leave it at that for now. Someone who's default upbeat. Likes to smile.

5:21 Smiles often. class 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. I 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 dateTim 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.

6:10 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 leak 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 review. First. Check it out. The league. On iOS or Android.

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8:17 At this altitude, I can run flat out for a half mile before my hands start shaking. So nothing else do you post my question? No, we're just seeing that. I'm a cybernetic organism, living tissue over metal endoskeleton. Me So I was so pleased.

8:43 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 the four hour work week in terms of being the blessing and the curse that you just can't seem to shake? For better or for worse.

9:03 I know we're gonna 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 How have I been complicit? Yes. Yes.

9:21 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?

9:32 laying out the context of this question. What is the question? And then would 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 c we covered Actually, you know what? Yeah. Let's rewind the clock all the way.

9:55 Let's do both. Uh. 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

10:11 Misinterpreted, 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. You know, if we go back in time to my mid thirties when I was A prince of New York and a former VC

10:29 And totally fucked up as an individual. I was knee deep in The first decade I'm now my fourth decade of psychoаліз. And I had a very Tough as nails.

10:44 Nice Jewish lady psychoanalyst named Dr. Sayers. And What she taught me. Repeatedly. Endlessly boxing my ears when she'd say this, and

10:57 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 You know, old Jewish lady who's thirty years older than me, who's just basically had it with me. Complaining.

11:17 And so the roots of that question are really a kind of an exasperation, not just from my analyst to me, but eventually with me About me. Mm-hmm.

11:31 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 uh a massive unlock for me. Now you asked about the misinterpretation.

11:49 The first level misinterpretation that people go through. is that they assume I'm saying how have I been responsible. Mm-hmm. And I am very, very particular. I get very very angry when people misinterpret The word complicit for responsible.

12:07 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.

12:24 We're actually walking away from doing the hard work. Can you expand on that? Yeah, sure. Because guilt Is a defense mechanism. Right, because some people might say, Well that's extreme

12:36 Ownership, as I say, I'm responsible for all the shit. 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

12:59 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.

13:14 You got rid of that in your childhood? Man, good for you. Well I got rid of it in my adulthood. This is the pointing. I got rid of it. By actually asking the right questions of myself. If the word complicit Is replaced with the words

13:32 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.

13:45 For everything. And the truth is It's much more complex than that. I was just thinking. That

13:52 Your 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

14:08 Anything and everything bad that happens. is your responsibility slash fault. It puts you in A similar position. It seems. Exactly.

14:18 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

14:29 Yeah. To transform stuff. If you don't really know what's going on. And so To understand what's really happening for you.

14:39 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.

14:53 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

15:07 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?

15:16 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. Uh I've got

15:31 This and I'm over scheduled 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. Right. space for writing or making.

15:44 Right. So you say Mr. Four Hour Work Week. I don't want to work more than four hours a week. Nice turn. Nice turn. I think you're to me. Right. 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, f wear, breathe, right strips as you talk to right, you know this kind of thing. Right. Okay.

16:17 Just a quick sidebar. Breathe right, this one's on me. Next time you gotta 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 would we would 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?

16:49 Right, in this regard. So How does it feel when you're not busy? I would say And I don't wanna

16:58 Since I'm Cheating with a cheat sheet. Right, this is It's your show. So it's your thunder. And accent. So segueing to a compliment or maybe a necessary component of first question.

17:15 Are you complicit in creating conditions that you say 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's an underlying fear.

17:41 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

18:00 Therefore. My complicity serves me by Avoiding that. Right. And so if you really want to transform

18:10 When will you be comfortable with the void? Yeah, that's a good question. And uh in my In my defense, your honor, I will say that Yeah, I'm about to go off the grid for a week. Starting

18:23 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 as rarely as uh

18:37 much of a randomized control trial as we would like. I've had an ongoing number of Chats with friends and what's up and different messaging. platforms and It's been around

18:50 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 the goalposts keep moving, right?

19:03 They wanted to make a million and then it was ten and then it was twenty and then Once it that gets trillion defense trillion. Once it gets indefensible, then it's like what's your annual compounded growth rate and this then turns into percentages'cause 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

19:24 to Chill out, take a break, create all this space. My experiences as social animals or at least as a person who benefits from social interaction, I do best Around other people.

19:38 I just do. And there are It's not a hundred percent, but it's not zero percent. There's a risk. That I do. return to some of those

19:47 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.

20:00 Yeah. Off the grid. So perhaps you can help me to Find my way to answering. The question you posed.

20:07 You know, look, Tim, we I feel like Uncle Jerry and 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.

20:25 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 play is Pascal?

20:47 identify 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 you've got Like a lot of us, you've got component of that.

20:59 And I also Wanna say I'm I'm watching you letting go of the need to turn that void time into productivity time. Mm-hmm. Right. When I first started promoting the notion of sabbatical, which we've talked about in the past.

21:18 I remember dealing with a client who would say, Well, I'm gonna learn Portuguese. It's like, no, you're not. You're not gonna learn Portuguese in four weeks, you know. You're going to learn to breathe. Without breathe right strips, you're going to You know, you're just going to learn. To enjoy yourself. Now what I hear you doing is

21:38 is learning to enjoy yourself. Mm-hmm. Which is a really powerful skill. Yeah.

21:48 Yeah, it's gonna be uh Lifelong project. Which is okay. Lot of things are lifelong projects. That's right. We got here because you were asking about that process, and this is the process.

22:01 Right. This is the process. So For you when you're Off the grid starting Friday. You know

22:08 What will that experience be like for you? At what point might you be anxious and at what point might you Start to relax.'Cause are you gonna be with friends? This trip too? This particular example may not

22:22 But 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 eighty twenty analysis. Places, people, activities. the most life giving and the most life draining and then I

22:48 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. This particular week off the grid is going to be a

23:05 Alpine Elk Hunt, which I do once every two years or so. With Bo. At probably between ten and twelve thousand feet for the Most of it. It's gonna get cold.

23:18 Freeze dried fruit. Hopefully a bunch of trout. Oh. En route to finding elk. And I have just found that

23:27 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 it's become a core piece of my Annual planning. Not necessarily a hunt, but that type of shared experience with a small

23:47 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.

23:56 feeling discomfort because there's going to be incredible discomfort physically. Sleep is probably not gonna be fantastic. And we will be very, very, very active. But it's not the same as doing

24:11 A silent retreat and sitting there. Watching your monkey. Brahm. Contort itself for Sixteen hours a day.

24:21 It's the kind of retreat where like layers of your skin are stripped away because you're so raw and rugged out in the world. And that's just gonna drop you into your body. And drop you more and more into the land. And that's a a place of nourishment for you. For sure.

24:42 Yeah, let me ask you if I could. How often Do You find with your clients or your team find with their clients that

24:54 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 it's And the reason I ask is that

25:12 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.

25:27 Through For me at least, often, not always, but physical. Movement. Sometimes physical hardship. Where

25:38 As they say in dog training, a 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 Ninety five percent 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.

26:00 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.

26:13 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.

26:26 is when we start to Invade the productive Thinking into that Tired dog.

26:39 Effort. Meaning I'm going to do this so that I I mean the worst case is I'm gonna do this so that I lose weight, or I'm gonna do this so that I can look better, or I'm gonna do this so that I can I don't know, quiet some negative self. Thought.

26:57 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 of those things and just get dog tired. Then I'm happiest. For sure.

27:12 It was definitely possible too. sort of run towards things, run away from things. And I think with Athletics movement. It's Not necessarily condemnation.

27:25 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

27:38 The Yeah. And have devil on your shoulder. Okay. creating all these fairy tales to drive you insane.

27:47 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.

28:02 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

28:20 It gives you insight in what was going on in that session room. It's really important. That we let go. Of

28:29 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, you know, to use one of my other questions, maybe you're not saying the thing that you need to say.

28:48 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, but it's not a reactive

29:10 It's proactively Basically injecting turbo booster on my physical and mental well being so that I can bring that back to everything else. And you mentioned a few things. Just

29:25 I'm about to go. That's I just want to reiterate for folks. And This I believe maybe the same therapist?

29:34 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?

29:47 That's right. Well, she taught me the first question and it was again in an 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. Um So when you 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.

30:26 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. That should be on my bathroom mirror. That's right. But you know what you earn that's not 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 much of this conversation is

30:57 The importance of not Bullshitting yourself. The importance of not bypassing what's really going on for you. And I have found in my sixty one years now.

31:10 that that is also a lifelong practice. That my capacity To bullshelf? continues unabated.

31:20 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 eighty six?

31:41 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.

31:53 I'm getting that right. I Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by Mementis. Mementus 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 Mementus Mag3N8, Ltonine, and Apigenin, all of which have helped me to improve the onset quality and duration of my sleep. Now, the Mementus Sleep Pack conveniently delivers single servings of all three of these ingredients. Mementus also partners with some of the best minds in human performance to bring world class products to market.

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33:15 Overlay few More questions that can be used. that I uh took note of when I was reviewing our past conversations that I I really Like I don't yet have kids, so one of them won't. Totally applied me, although

33:31 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. uh doing and it may not be

33:43 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.

34:06 That Their feeling when they get to be The same age. And if they don't, it prompts them to start reorganizing their lives. And so I'll start with a whip. I'm next to a river. Such things happen. Right. And there are more, of course, but what I was curious to ask you is

34:21 I'll segue into this by way of an anecdote. There's uh Amazing. Fascinating. Sage man named. Bill Richards and Bill Richards wrote a book called Sacred Knowledge.

34:34 She 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 kinda looked like Santa Claus.

34:53 Amazing Big white beard. kind of jolly old elf type of feeling. Always Smiling. With a little twinkle in his eye.

35:01 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.

35:11 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.

35:21 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 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 I was like And he said a few things to me that day where afterwards I was like

35:49 I just thought it was funny, but there's actually a lot to unpack there. And How would you help you? 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

36:11 Every mishap of childhood, every mistake their parents made. And The dose makes the poison, right? It it seems like Paracelsus said so long ago. Not in English, obviously. And

36:25 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.

36:42 And so When I think about Supporting other people. What comes to mind is Really? I mean

36:52 Think about the way Bill responded to you. Think about the way doctor Sayers would respond to me. Think about Yeah, I think about the conversations I have with my elder friend. Parker. Eight.

37:05 Always laced. With humor. And it's the humor that cuts through it. Humor

37:12 Forgiveness. And not in this kind of I don't know self development. Yeah.

37:22 Bullshit. Self forgiveness. thing that's out there. But genuine Care and concern. I mean I'll give you an example.

37:32 I wrote a book that came out last year called Reunion. And part of that journey was really reuniting She's Language from the book.

37:43 with the parts of myself that I had disowned. But more importantly, my ancestors, and in this case. I went into a relationship with my father. Now my father had died. Thirty two years ago.

38:02 And In Unpacking his story. What I came to have a new relationship.

38:11 with was his own depression. His own alcoholism. And I unpack, you know, to spoil the plot. My dad was On his wedding day.

38:23 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 'Cause my mother was pregnant at the time. And then she screamed out

38:40 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

38:50 I grew up As we Discussed before, my mother was mentally ill, my father's depression and alcoholism really marked my childhood. Yeah. And

39:02 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

39:16 I started to really Step into his body. What would it be like? To be eighteen months old. 'Cause it turned out that He was given up for adoption at 18 months old.

39:29 And he was given up. And raised by the only Parents he knew an Italian American couple. And The reality is his biological mother

39:40 was an Irish immigrant. To New York. Who gave birth to him? When he w she was twenty. And I ended up

39:49 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,

40:03 I think that that laughter Came about. From forgiveness. We're now I actually can feel myself

40:16 Going He wasn't so bad. He did the best he could. And he got a raw deal. And yes, some of the things he did sucked.

40:27 But not bad. Was that Incremental a hundred different realizations adding up over time, or or were there any flashpoin There were particular

40:42 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'cause we were talking before about a f

40:57 The physical being The semanticized being and You know, 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.

41:12 And he was a junior in college. Yeah. And He did a semester abroad in Dublin. And one week.

41:23 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.

41:39 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 You know, he's looking at me like oh yeah, you're bullshitting me, Dad. And it's like no, no, no. My father

41:57 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.

42:18 And I look up and they have this replica copy of the equivalent of the Irish Republican Declaration of Independent. 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

42:38 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

42:51 and declare their independents. were the kinfolk of my father. Which was a very Different and powerful word for me. And

43:02 You know, later, about a year later, when I was in the church in 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

43:17 Graveyard. I realized that I was surrounded By them. Bones of my kinfolk.

43:24 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

43:38 I swear to God, I felt like I could hear my grandmother at four years old running down the lane. You know. What a story. Mm.

43:48 You know, to bring it all back. I feel like because of that experience. I closed a wound? That was m

44:01 Transgenerational. Transpersonal and intergenerational. This prompts me to want to ask a a few different questions. And I'll first say that personally I've found

44:12 Tremendous value and metabolizing number of things from the past. I've had some horrible things that happened to me as a small child, so Seemed important for me to at one point contend with that.

44:26 Or Triage it. Process it in some way. Now If I were to take

44:33 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 gonna be too far off. I remember chatting with Mark Andrewson, one of the most storied, famous, and successful venture capitalists of our age, also an incredible technologist in his own right. And Coder slash.

44:55 product developer mosaic being among His cheatments He answered it may have been I think his billboard was raise prices, his billboard answered, so that's not it. But There was some type of

45:08 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 the story of A character in a detective novel. Who has arrows. tattooed on his shoulder pointing forward.

45:23 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.

45:41 behaviors, habits, those all form your destiny moving forward, right? 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

46:02 Focused on the past. 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.

46:21 Why 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? Uh Past focus versus present or future focus. I know that's very

46:39 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.

46:56 I can argue that those who are only forward looking With no awareness of the past. Maybe bypassing? As you know from your own experience. Ignored

47:12 Trauma. Can stay in the body. Can affect us. Forever. But

47:20 The fear that мені people have. And one of the reasons why we struggle to s 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.

47:38 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

47:53 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.

48:10 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.

48:25 So I think part of your question too is how do we get somebody who is stuck in the past to move forward? Is that a fair statement? Yes. Yes. The Trend seems to, at least in certain places.

48:40 To have swan 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.

48:56 All the way back to Sometimes what I would say. Very Self indulgence. Past reflection and oversharing and

49:06 It's like okay, you wrote the script. You're on your Two hundred and forty seven three, right? Maybe it's time to stop that. Yeah. Yeah.

49:14 I'm gonna parse things a little bit. Please. I don't feel comfortable Criticizing someone for being quote For oversharing.

49:24 Having grown up with The consequences of far too much silence and secret keeping? I know With the Detrimental effects of that.

49:34 What I really liked, though Is your word overworking? And I keep thinking of like Dough, bread dough, when bread dough is overwhelming.'Cause I know it better. Yeah, there is that tendency to overwork it. What I have found to be helpful

49:54 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 cares? It's so what are you gonna do about it. Which is that forward momentum. Whether it's mere wounds.

50:12 which we all have, or trauma which many of us have. re-traumatizing ourselves. By replaying an Reworking it? Over it.

50:22 Working it. Doesn't release us. But Acknowledging what has happened. And then

50:30 really empowering yourself to say, and what will you do about it? Is I 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

50:45 pushback, which I think is Valuable, valid. Night in The sense that You mentioned being on one end of the spectrum.

50:53 I think you come from a family and 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.

51:08 and very healthy to push yourself. towards the other end of the spectrum. Recognizing you're probably not gonna end up. At the furthest diametrically opposed point, which is

51:20 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

51:32 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.

51:46 And it becomes performative in a sense. So I 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

52:03 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. Um related topics for a second, but I'm very curious.

52:18 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, et cetera.

52:31 When did Reboot start. When was it founded? July Twenty fourteen. Roughly.

52:39 So twenty fourteen, 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

52:51 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

53:08 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? Uh it's about both, I would say. I think that there are unique expressions that have emerged. I think that there is a 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

53:33 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.

53:47 the after effects 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.

54:04 After the Hamas attacks on Israel on Octob seventh. Ended up having to shut down Slack. For two weeks. Because the there was no discussion, it was all argument. And

54:19 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.

54:35 This being said Human nature is human nature. It's why coaching's actually a good business model. Much of what happens continues to happen, you know, I mean I I can't name the company, but I'm at a uh New client. I rarely take on new clients, but I kinda fell in love with this kid.

54:56 When I first met him. Very, very hot young company. Not quite the clusterfuck it was six months ago, but pretty close. And You know, as I'm sketching out on a dry race board.

55:09 Everything that has happened and will happen. Everybody's like, Well how do you know? It's 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 gonna be fine. It's gonna take a year and a half to two years, you know. Yeah.

55:27 I hope that addressed your question. I don't know. I I may have gone off on my own tangent. Well, let me let me hone in on one. concept that I'd love for you to expand upon or just riff on. And I may have it

55:44 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 f I think guilt can be such a powerful driver Sort of a negative.

55:59 Driver in a lot of cases, I think. Guilt and prestige. Often terrible. Motivators? to quote Maria or reference Maria Popova, but the

56:10 Guilt I think also Seems to be having quite a moment because When you are Waterboarded.

56:22 with disaster. and crisis globally twenty four seven It's hard not to feel like you are not doing enough. But this is what I have written down.

56:34 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 one I want to ask you about. Could you say more about Guilt being self focused versus

56:55 Remorse. I just wanted to make sure I understood this clearly. I often think of my Buddhist teacher Sharon Salzburg. Whose

57:04 line about that is that guilt is self lacerating. Which I find really A compelling image. And What it does is it kinda keeps us

57:16 Here's an old reference. You may get it. 'Cause you may have had record players. Where the needle's stuck in the groove. And you're 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.

57:38 Daniel Pink just wrote last year, I think it came out, the 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

57:56 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

58:07 What you're reaching for here is When we allow ourselves to internalize remorse Or regret. We're opening ourselves up. Two

58:19 Other people. 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 badly I'm terrible. Da da da da da. I always do this.

58:33 That's an exaggerated version, right? But if they're In a loop of self Lacerating Guilt. How do you move them? Towards.

58:42 Close cousins that is perhaps More healthy. Exactly. How do you do that? If you think about the setup.

58:51 The setup more often than not, if 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.

59:07 as evidence of my shittiness as a person. And if that's true. Then the movement is towards decoupling.

59:19 My sense of worthiness as a person. from the action. So good people do bad things. Mm. Ah.

59:29 Time. Good people who do bad things who don't learn. Uh Less. Evolve plus mature.

59:40 than good people who do bad things. Who then learn. True. Regret and remorse. But they remain good people.

59:49 Does that distinction help? It does. prompts or exercises that You display. Potentially a sign.

59:59 To a client. True. has developed the habit. Oh negative narratives around

1:00:07 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 refrain or start training their mind to go In a different direction. Yeah, I mean it hate to sound like a broken record again.

1:00:22 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.

1:00:31 Into that. 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

1:00:46 can 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.

1:01:02 And really Taking a look at the way to use my phrasing. It serves you. To think ill of yourself.

1:01:13 begins to raise the consciousness that releases you. From having to repeat the pattern. So let's Hop.

1:01:22 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.

1:01:34 Contacts, which is perfect. 'Cause it's kinda boring for me to know exactly what's coming. Me too. Legacy.

1:01:41 Legacy seems to be something that you're thinking about. We could have a Midy. conversation about this. So I'll let you

1:01:52 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. Yeah, and That's right. Sliding it down. That's right. Ten easy life lessons from Uncle Jerry.

1:02:10 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 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. Two

1:02:33 look at and 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?

1:02:57 Which I I don't know, maybe that is the definition of legacy. But I think about it. Really more in the terms in terms of three different circles of impact and influence that I have.

1:03:09 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

1:03:21 I fucked up royally. And yet For some unknowable reason my twenty seven year old wanted to spend five days camping with me this summer. Can you believe that? 'Cause I would never have wanted to spend

1:03:35 Five days trapped in a sprinter van with my father? And then the last circle is what how have I left the world? I hope for example All of the work that I have done is Made an impact on you, Tim.

1:03:49 Yeah. Wouldn't have all these notes in front of me, yes. With the case. You know When we were celebrating your tenth anniversary.

1:04:01 I sent a note, I sent a video and I was Telling you. Like I'm proud. Avoid. impact you've had.

1:04:08 And people. Yeah, 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.

1:04:19 to have an impact on some random twenty-two 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.

1:04:32 That's right. But in doing so You impact it. A lot of people. And I think you should be proud of that.

1:04:39 Thanks, Jerry. Yeah, it's uh continues to this day, I think, when I'm doing it. right for me to be conversations trying to answer questions I have myself.

1:04:53 Isn't that interesting? I wanna highlight that. Isn't it interesting? that when you lean into the questions that you need answered in your own life

1:05:05 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?

1:05:14 Meaning being so real. And so honest. As to make yourself a palate. If you will. Or a canvas.

1:05:26 Where people can work their stories out. That's pretty cool. Yeah. I like that.

1:05:34 Definition. Or that's the placeholder for legacy because when I've thought about leaving things behind and No a lot of Fancy muckety mucks. Often very good people.

1:05:46 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

1:06:08 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

1:06:31 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

1:06:45 probably gets long lost along the way. That Is some form of legacy. Right. Yes, uh a thousand times, yes. Listen, I know m legacy as a word can sound grandiose and And I love your self deprecating humor.

1:07:05 Don't Use it though to deny the thing That is true. Yeah. Okay.

1:07:15 And'cause 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.

1:07:30 Who knows? Listen, I'll I'll tell you a story. About five or six months after my first book came out. I've received a ton of fan mail on the book. I still get mail from people saying, you know, this book really inf you know 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 One Hundred company. And one from a man.

1:07:55 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.

1:08:11 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 C V is very different, man. But I know you mean something different. Can you say a bit more about that?

1:08:29 I do, I do. And in December of twenty nineteen. Well first In September of twenty nineteen, my first book came out in June. In September twenty nineteen, I'm doing a book talk. You remember when we used to do things like that. And and pre-pandemic, beer back. When we were listening to Mini L P is on the record player. That's right. That's right. And I'm I'm walking to this venue in Denver, and there's this woman who's like clearly in her eighties, who comes up to me and she says, You look like our speaker.

1:09:00 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 ball.

1:09:12 And I read your book. And your story is my story. Now, 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. But what the fuck.

1:09:30 Fuck is A part of our dialect. I'm sorry. No, I have to just just a brief aside, I'm not gonna mention it by name, but Everybody who listens to this podcast would know a friend of mine who grew up in New York City. Lot of lot of like Brooklyn influence. And his greeting to me is

1:09:54 You fucking fuck. What are you doing? This is like one of the most sophisticated, brilliant thinkers of our time. But that's how it's He agreed me.

1:10:04 I don't understand. Do you have a fucking problem with that? Okay. Yeah. Anyway. 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.

1:10:20 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, y you 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 I had been talking about how when We lose a parent at an early age, it forces us into early parentification and

1:10:46 Importantly, that that can often be a signifier of leadership. Yeah. She says, That thing you're talking about, but that happened to me, my father died when I was thirteen. And you know, I'm kind of dopey and exhausted, and I kinda nod my way. In response. And then she says, on Robin Island. And I look at her and I say, What? And she's yeah, he was

1:11:10 Robin Island is where Nelson Mandela. 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.

1:11:24 And then she says to me Your story is my story. And the thing about that And her name, by the way, is Joy Tende Kangari. She is going to be graduating, I think, with a PhD in law.

1:11:38 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.

1:11:54 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.

1:12:07 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 to They're seeing their story and your story, Tim. One hundred percent. Just for clarity's sake. If people do it.

1:12:26 After I shared 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

1:12:45 I do I'd say probably in response to That episode more than any other, but certainly there are few Where I discuss personal challenges with depression. And so on, which thankfully are

1:12:58 Fewer and fewer. And shorter and shorter. in duration, but you never know. And I agree with you a hundred percent. 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 you mentioned

1:13:18 Fucking up a bunch of stuff like all parents do. Hey. Even know one guy, great guy. I won't mention it by name, but he said. It's like, oh yeah, I'm gonna 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.

1:13:32 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?

1:13:46 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.

1:14:00 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.

1:14:17 And so I wanna 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 racked 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,

1:14:43 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.

1:14:57 Them. Words. And I think I have three children. Sam is thirty four, Emma is thirty two. And Michael is twenty seven. And Michael's the one that went camping with me, but

1:15:10 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?

1:15:24 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?

1:15:37 And hurting them? That we get wrapped around our own Anxiety our own narcissism? And then we lose The connection.

1:15:49 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.

1:16:02 I think I also raise the bar on what they expect from other people. They expect words. From other people. Which, you know, 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

1:16:21 The way I did it. Was I modelled. First and foremost. And the second And I think I'm good at this.

1:16:30 I listened. Now I also want to give a shout out to their mom. 'Cause this was not a one and done, I did it myself by any stretch of the imagination. They had Two

1:16:44 Spectacular parents. Who each endeavored To do Right. by their children.

1:16:53 In different ways, in different styles. For sure. Given your experience You have good relationships. With your kids.

1:17:02 If you had to add a third or fourth thing. to Your therapists. Rules, let's just say. You can't spoil the kid with too much love. Number two, give them words. What might number three?

1:17:18 And or I guess it wouldn't be or number three. If you want to add a fourth. And go for it. What may you add to that? I think that

1:17:26 If I could go back in time and give myself advice the way she might have given it to me, Cause 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.

1:17:50 They're gonna be fine. But the truth is, you know. And I'll give myself a little bit of a break. I didn't have The context. I didn't have

1:18:02 God rest my parents' souls. And Coming to understand that they tried. I did not have role models. For good parenting.

1:18:12 And so I had uh Piece it together. From people like Parker. Or my therapists.

1:18:21 Or other mentors and elders in my life as I watched the how they were doing it. How were they being the elder? in their life. And learn to forgive myself for the mistake so that with regret and remorse I can pick myself up and try again. Can you apologize to your children?

1:18:42 Oh my god. What a powerful tool that is. Yeah. Better start apologizing in advance. If you don't have kids, build the muscle. Mm-hmm. Don't try to win the World Series as your first baseball game.

1:18:58 Exactly. Exactly. Why are you thinking about kids so much these days? Oh man, I'm so f I'm so Business.

1:19:09 Sage on stage stuff. It's just like I'm boring myself so much. It's uh I'm exact 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

1:19:29 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, et cetera. Right. And I feel like

1:19:43 Family kids. Is The next big chapter, the next big adventure. I don't overly romanticize it. I have uh almost all my friends have kids. I know it can be an enormous enormous pain in the ass. It can involve a lot of

1:19:59 Sadness and anxiety and you name it. But then there's the other show. Joy. Enjoy, of course. Then there's the other side of the chair. And A and a sense of completion. I mean let's shout out

1:20:12 I mean the best Of all the accomplishments I have ever done, the best has been becoming the father that I needed as a child. Without a doubt. Yeah, it'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 Do lectures. You're gonna ask me if I knew Wales. I don't think I've heard of it.

1:20:34 But you you you've been to the do lectures. You you spoke to the do lectures. I think the first or second do lectures like two thousand nine. It was amazing. I really enjoyed it. D fabulous. And for those who don't know it, 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 drive around Wales. This was no no Google Maps of the time didn't have international. data and they're like, sure, just turn left at Would you Waka Waka? And I get to the sign and I'm like That's twenty four continents. How do you read this?

1:21:10 What you guys it's 24 consonants in a row without a single vowel. That's what I mean. I'm just like, wow. Okay. Anyway, so I was at the do the do 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 w provoked such a powerful response from the group. And you and as you remember, it's like you're in this like old hay barn, cow barn, the cow shed, I think they call it. And My oldest son, Sam.

1:21:47 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 done wrong and telling me what I done right and all that stuff. You know what they do. Right. Oh, that's very good. Except it's like okay. The next time you write a book, you can talk.

1:22:06 Okay. Anyway, I look up and Sam, who's, you know, six one. 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. Uh-huh. That's amazing. What a moment. That's the moment.

1:22:26 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

1:22:40 Mm pff, you know. survival of fittest impregnate like forty women and see how we do. I I I am 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 gonna now be inundated? And then you're gonna call me up and say, Jerry, uh, what do I do? And I'll say, How have you been complicit in creating these conditions? You say you don't want to be. You mean publishing this to millions of people? Yes, nephew Timmy. I mean putting it on the podcast.

1:23:09 Well, I had this you know, I'll share this. This I haven't s really said to anybody, but I was I was spending time with a number of my really close friends. We do this reunion once a year. And The most of them have kids. Not all of them. Most of them have kids. And one was

1:23:25 Echoing this lesson or conversation he had with someone far older than he, a grandfather. And he kept saying, You know, there's nothing more precious than Hugging your grandkids. And I started running the math and I was like, I'm forty seven. I don't know if that's gonna be a thing.

1:23:44 I don't know if that's mathematically, even remotely. reasonable for me to entertain and that fucked me up. I gotta 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

1:24:06 Fuck me. That was that was a tough pull to swallow, not gonna lie. It 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.

1:24:24 You guys should hang out. You know, for sure. Yeah. Drink some whiskey and Cry ourselves to sleep. Or put the red lantern out and say, I'm ready. Oh God. Not ready to switch teams yet. You know? Never never say never.

1:24:45 What are you willing to do for your kids? Like I'm no biologist, but Yes, exactly. Oh man. Well, before we move off that topic, let me give you a poem. You ready? This is by Philip Larkin. Yeah, it's called. This be the verse. Mm-hmm.

1:25:06 They fuck you up. Your mom and dad. They may not mean to. But they do. They fill you with the faults they had.

1:25:14 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 Sopy Stern.

1:25:25 and half at one another throats. Man hands on misery to man. It deepens like a coastal shelf. Get out as early as you can.

1:25:36 And don't have any kids yourself. Yeah. Wow. So should I Sylvia plasma myself today or tomorrow?

1:25:47 Jesus, Jerry. Well he's British. I'm famous for reading poems, but you know usually they make people cry. This one's like It's like Doctor Suits meets a star is born. Good Lord. Amazing. Alright, so let me try to write the ship here.

1:26:11 Okay. So three books I alluded to these, I'm curious. You you've mentioned a few books in our conversations. Or Certainly your own, which I recommend everybody.

1:26:21 Also when things fall apart. By Pemetrod. Faith by Sharon Salzburg, 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.

1:26:37 To your kids. Whether or not they read them. Oh yeah, Sam I in particular loved the wisdom of insecurity. Which is a really, really powerful book. Michael

1:26:49 is probably the one who follow most of my book recommendations and 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 uh call it sleep.

1:27:12 I had called sleep. Call it sleep. Never even heard of it. So Henry Roth wrote Call It Sleep in the nineteen thirties 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 east Harlem. when it was a Jewish neighborhood and they're Jewish immigrants, it was well received and then lost in time.

1:27:38 And It was I think it was Kazan. The famous

1:27:44 book critic who discovered a used copy in the strand. In Manhattan. And then devoured the book in the nineteen fifties and published the first Review.

1:27:57 For a paperback. Look. In the New York Review of Books. And so the book I love it. And anyway, I'm going off.

1:28:07 Henry Rothbard. As a novelist. was one of the most influential novelists in my life. It's a book that I remember when Michael finished it.

1:28:19 He sent me the same passage. That I had first read when I was about seventeen or eighteen years old and was blown away by It's like yeah. That's the passage. And for those who know the book, it's the passage where David is.

1:28:35 Touching. A trolley car's third rail with a soupletle. Yeah, our milk ladle. It's really a powerful passage. Anyway, you didn't ask about novels.

1:28:46 Well, I it's funny. That you brought up a novel. Maybe I accepted you because I was going to ask you. Actually if there are any novels you

1:28:56 recommend or find Container. and convey a lot of truths that stick out to mind. 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 it was a really great huge standout.

1:29:13 I've been meaning to read it again. And uh some more of the same author's work. Do any others stand out to you? Because I've I've really found fiction, which is very closely related to humor, right? Let's just say Bill Richards or your Therapist.

1:29:29 Parrible. 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, come across it, it does ring a bell.

1:29:46 Okay, so Library of America is a nonprofit foundation that seeks to preserve the writings of amazing Americans. And I think there are over three hundred and fifty volumes that they've done. Writers like James Baldwin. Uh anyway, I just finished volume one. Uh Wendell Barry. And

1:30:07 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 Barry did in the volume one is the material from

1:30:27 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.

1:30:42 all taking place from the end of the civil war In this case through World War Two. 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.

1:31:02 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. 'Cause 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.

1:31:19 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're talking about earlier, it

1:31:43 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? Not in a how are you complicit way, but how has it actually been? That's the thing. Along the lines of The Gift of Fear by Gavin DeBecker.

1:31:59 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. You know, we're often told that the way through insecurity or anxiety is to somehow embrace what's happening.

1:32:17 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 he's a one of a kind. That one. And uh amazing. Narration.

1:32:33 As well. People who want to. Take it in audio format. Has some spectacular speeches. Presentations.

1:32:40 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. Or anything else you'd like to do? Say ask of my audience, point people to anything at all. You know, I think I've really appreciated our conversation, especially the amount of laughter.

1:32:59 And you actually helped 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.

1:33:18 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

1:33:34 Incredibly important right now. So As Doctor Sayers would say to me, You've done enough work Going off the grid. Go take your time.

1:33:45 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.

1:33:55 Segue. Games. Just table top games. No phones. Yes. Yeah. Rewind the clock. These things have been with us a long time.

1:34:07 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.

1:34:17 When you were asking about records and if I remembered records. The one thing that popped to my mind that I Which of course. Is sort of self referential. In and of itself.

1:34:28 When I was a kid I had this little mini tiny mini L P is the size of Tiny pancake. It was really small. And it was

1:34:39 A son. 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.

1:34:50 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.

1:35:05 Oh And I actually Had some speaking engagement. Like uh I can't remember.

1:35:12 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 disc. They were not successful, but Boy can dream. A boy can dream. I mean what's frightening is I I I I will not, but I can sing that song.

1:35:34 Everyone this is this is yeah, one of this this is my my homework assignment to everyone listening. Go find Disco Disco Doc. 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 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.

1:35:57 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.

1:36:12 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 the Philip Larkin poem. That's right. And the Philip Larkin poem if you're if you're if you're too happy and just need a moment of sadness. Tim.blog 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 yourself. And

1:36:46 Thanks for listening. Hey guys, this is Tim again, just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? 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 kinda 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.

1:37:30 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 slash Friday. Type that into your browser. Tim.blog slash. Friday, drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by 8Sleep. I have been using 8Sleep podcover for years now. Why?

1:38:04 Well by simply adding it to your existing mattress on top like a fitted sheet, you can automatically cool down or warm up each side of your bed. 8 Sleep recently launched their newest generation of the Pod, and I'm excited to test it out, Pod 4 Ultra. It cools, it heats, And now it elevates automatically. More on that in a second. First, Pod4 Ultra can cool down each side of the bed as much as 20 degrees below room temperature, keeping you and your partner cool, even in a heat wave. Or you can switch it up depending on which of you is heat sensitive. I am always more heat sensitive, pulling the sheets off, closing the windows, trying to crank the AC down. This solves all of that. Pod 4 Ultra also introduces an adjustable base that fits between your mattress and your bed frame and adds reading and sleeping positions for the best unwinding experience. And for those snore heavy nights, the pod can detect your snoring and automatically lift your head by a few degrees to improve airflow and stop you or your partner from snoring. Plus with the Pod 4 Ultra, you can leave your wearables on the nightstand. You won't need them because these types of metrics are integrated into the Pod 4 Ultra itself. They have imperceptible sensors which track your sleep time, sleep phases, and HRV.

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1:40:02 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.

1:40:56 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 on 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 you 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.

1:41:45 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.

1:41:58 class 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 dateim. Hashtag DTM 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.

1:42:54 Much better. So download Blake today on iOS or Android and check it out. Message hashtag Tim to your ENF concierge to jump to the front of the wait list and have your profile reviewed. first. So check it out, the leak. On iOS or

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