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

0:00:04 Hello boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show
0:00:10 where it is my job to deconstruct world-class performers to interview them and tease out the habits, routines, favorite books,
0:00:13 and so on that you can apply to your own lives.
0:00:20 Sometimes I get not just a two-for-one, but a hundred-for-one when I interview someone who also helps
0:00:24 world-class performers, in addition to being such themselves, to get past
0:00:33 sticking points, to redefine themselves, to reinvent themselves, to chart new paths forward, and my guest today, Jared Colonna, is such a person.
0:00:40 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
0:00:46 leaders. But prior to that, he was an operator in many different ways. Prior to being a coach,
0:00:50 he was a partner with J.P. Morgan Partners, the private equity arm of J.P. Morgan Chase.
0:00:58 He also led New York City-based Flatiron Partners, which he founded in 1996 with partner Fred Wilson.
0:01:03 Flatiron went on to become one of the nation’s most successful early-stage investment programs. At age 25,
0:01:07 he was editor-in-chief of Information Week Magazine. He’s written a bunch of books.
0:01:12 We’ll mention them at the end of the conversation, but one is Reboot. The other is Reunion, both highly recommended.
0:01:19 You can find his company, Reboot, at Reboot.io and Jerry on Twitter and Instagram @JerryColonna,
0:01:24 and he has been on the podcast twice before.
0:01:29 He is a fan favorite. People always take a ton away from our conversations,
0:01:33 and I recap some of my favorite aspects of those in this episode, and
0:01:39 we cover a lot of ground. There are a lot of stories I’ve never heard. We have a lot of laughs,
0:01:42 almost a few cries on my side.
0:01:50 We dig into his toolkit. The questions that he uses with himself and with clients that I have adopted as some of my favorites.
0:01:56 There is a lot to learn, and it was a hell of an enjoyable conversation.
0:02:01 It was a walk-and-talk, and I have done this before, where I am out in nature today.
0:02:03 It is a beautiful
0:02:06 bluebird sky day in the mountains and to sit in a dark room
0:02:13 staring at a screen seemed like an insult to nature, complete travesty, totally unnecessary, so I have
0:02:17 high fidelity recording equipment. That is what I’m using right now. It is a headset.
0:02:24 I am sitting 10 feet from a beautiful river where I’m watching the eddies swirl around rocks.
0:02:29 So why not get out and move? If you can listen to this while you’re moving,
0:02:32 I encourage you to do so. Audio is a secondary activity.
0:02:38 So if you can walk and talk or walk and listen while I’m walking and talking, all the better for
0:02:40 you, me, everybody involved.
0:02:48 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
0:02:54 Jerry Colonna. But first, a few quick words from the fine sponsors
0:03:00 who make this show possible. I use all of their products, so this is not me just shilling.
0:03:04 I’ve tried it all, I’ve vetted it all, and here they are.
0:03:12 Okay, this is going to be part confessional. As some of you know, I am recently single and navigating the world of modern dating.
0:03:18 What a joy that is. Sometimes it’s fun, but it’s mostly a goddamn mess, as many of you probably know.
0:03:23 I’ve tried all the dating apps, and while there are some slick options out there, the most functional
0:03:26 that I have found is the league.
0:03:32 Why did I end up using the league? First, most dating apps give you almost no information.
0:03:37 It’s a huge time suck. On the league, you’re starting with a baseline of smart people,
0:03:41 and you can then easily find the ones you’re attracted to. It’s much easier.
0:03:43 It’s like going to a conference
0:03:48 where everyone is smart, and then just looking for the people you think are cute to go up and speak with.
0:03:54 So more than half of the league users went to top 40 colleges, and you can make your filters really selective.
0:04:00 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.
0:04:06 Second, people verify using LinkedIn, so you can make sure they have a job and don’t bounce around every six months.
0:04:09 It’s a simple proxy for finding people who have their shit together.
0:04:14 It’s infinitely easier than trying to figure things out on Instagram or whatever.
0:04:21 Third, you can search by interest and in multiple locations. I haven’t found any other dating app that allows you to do this.
0:04:27 So for instance, I usually search for women who love skiing or snowboarding, have those as interests as I like to spend
0:04:31 say two to three months of the year in the mountains. I’m a rivers and mountains guy.
0:04:36 The UI is a little clunky. I’ll warn you, but it’s incredibly helpful for finding good matches and not just
0:04:41 pretty faces. So you can search by interest and specify multiple cities.
0:04:47 So to summarize a few things that I think make it stand out, features available in the league include multi-city dating,
0:04:53 LinkedIn verified profiles, ability to block your profile from co-workers, bosses, family, etc.
0:05:00 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.
0:05:04 So there’s someone you can text with within the app as a personal concierge to get help.
0:05:09 So what am I looking for? I am looking for a woman who is well educated and who loves skiing
0:05:16 or snowboarding or both. These are and I’ve used this word already proxies for like 20 other things that are important.
0:05:21 So just I’ll leave it at that for now. Someone who’s default upbeat likes to smile,
0:05:27 smiles often, glass half full type of person who would ideally like to have kids in the next few years.
0:05:33 Her friends would describe her as feminine and playful and she would love polarity in a relationship.
0:05:37 She’s athletic and has some muscle. I like strong women, not necessarily bodybuilders,
0:05:42 but you get the idea. It could be a rock climber, dancer, whatever, but has some muscle, loves to read and loves learning.
0:05:50 If this sounds like you, send #DateTim in a message to your concierge in the app to get us paired up.
0:05:55 So these are all reasons why I was excited when the league reached out to sponsor the podcast.
0:06:00 They even have daily speed dating where you can go on three, three minute dates with people who match
0:06:05 your preferences all from the comfort of your couch. So check it out. Download the league today
0:06:10 on iOS or Android and find people who challenge you to swing for the fences and who are in it
0:06:15 to win it. I found it to be super fascinating. You can really get good matches instead of just
0:06:19 looking at pretty faces and kind of rolling the dice over and over again. Much better.
0:06:23 So download the league today on iOS or Android and check it out.
0:06:28 Message #Tim to your in-app concierge to jump to the front of the wait list and have your
0:06:33 profile reviewed first. So check it out. The league on iOS or Android.
0:06:40 This episode is brought to you by Eight Sleep. I have been using Eight Sleep pod cover for years now.
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0:08:13 Tim, to get $350 off the Pod 4 Ultra. They currently ship to the United States, Canada,
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0:08:45 I was so pleased with how much from our prior conversations,
0:08:52 has stuck with me. I just wanted to tell you that and also to ask you, is there anything that you
0:08:58 have repeated or shared that to you is the equivalent of the four-hour work week in terms of being the
0:09:03 blessing and the curse that you just can’t seem to shake for better or for worse? Because I know
0:09:11 we’re going to talk about legacy. But specifically, I’m wondering, is there a point when you get
0:09:15 tired of hearing some of your own profound questions echoed back to you? Specifically,
0:09:21 can you guess which one? How have I been complicit? Yes, yes.
0:09:28 I don’t get so tired of it. I will tell you that I get tired of the misinterpretation that goes
0:09:35 along with that. Okay. Would you mind laying out the context of this question? What is the question?
0:09:41 And then, would love to hear you expand on misinterpretations of the question.
0:09:46 So, what is the question or what was the conditions that caused me to ask that question
0:09:52 initially of myself? Let’s do the question, because we covered, actually, you know what?
0:09:58 Let’s rewind the clock all the way. Let’s do both. And for people who are like,
0:10:02 “What the hell are they going on about?” This is a question that I revisit a lot.
0:10:04 Maybe I’m revisiting it the wrong way. So, we will find out shortly.
0:10:09 But yes, if you could just explain the Genesis story, then the formation of the question,
0:10:14 and then how people misinterpret it, is that order makes sense to you?
0:10:16 That would be, I think, a great place to start.
0:10:20 And the Genesis story, the origin story, isn’t that complicated.
0:10:28 If we go back in time to my mid-30s, when I was a prince of New York and a former VC
0:10:35 and totally fucked up as an individual, I was knee-deep in the first decade.
0:10:43 I’m now my fourth decade of psychoanalysis. And I had a very tough-as-nails,
0:10:54 nice Jewish lady, psychoanalyst named Dr. Sayers. And what she taught me repeatedly, endlessly,
0:11:01 boxing my ears when she’d say this, is, “How have you been complicit in creating these conditions
0:11:08 you complain so much about?” And you have to picture it, right? I’m lying on the couch.
0:11:15 There’s this, you know, old Jewish lady who’s 30 years older than me, who’s just basically had it
0:11:23 with me complaining. And so, the roots of the question are really a kind of an exasperation,
0:11:33 not just from my analyst to me, but eventually with me about me. And it was really only by
0:11:41 taking that question, “How have I been complicit in creating the conditions I say I don’t want?”
0:11:48 That there was a massive unlock for me. Now, you asked about the misinterpretation.
0:11:54 The first level of misinterpretation that people go through is that they assume I’m saying,
0:12:03 “How have I been responsible?” And I am very, very particular. I get very, very angry when people
0:12:09 misinterpret the word complicit for responsible. And it’s not because I want to let people off the
0:12:15 hook, but quite the opposite. I want people to understand that they’ve been an accomplice.
0:12:22 Here’s the thing, Tim. When we get into our mindset that says, “I am responsible for all
0:12:27 the shit in my life,” we’re actually walking away from doing the hard work.
0:12:28 Could you expand on that?
0:12:33 Yeah, sure, because guilt is a defense mechanism.
0:12:38 Right, because some people might say, “Well, that’s extreme ownership,” as I say. “I’m responsible
0:12:39 for all the shit.” Exactly.
0:12:43 That’s the beginning of the solution, but where do they take a wrong turn?
0:12:50 So, I like the kind of ownership. I like the word “ownership.” I don’t like the word “responsibility.”
0:12:56 And the reason for that is because, and the reason I think it can be a defense mechanism,
0:13:02 is because it can be an old structure. So, many people that I encounter, myself included,
0:13:10 spend our childhood pendulating between grandiosity and a sense of worthlessness.
0:13:13 I’m either shit or I am the best.
0:13:16 You got rid of that in your childhood? Man, good for you.
0:13:19 Well, I got rid of it in my adulthood.
0:13:27 This is the point. I got rid of it by actually asking the right questions of myself.
0:13:33 If the word complicit is replaced with the words “even extreme ownership,”
0:13:41 the danger is that I tip over into misunderstanding what actually has been going on,
0:13:46 and I end up in this zone of being responsible for everything.
0:13:50 And the truth is, it’s much more complex than that.
0:13:57 I was just thinking that you’re referring to a pendulum and that not taking any responsibility
0:14:03 for anything is one example, sort of absolving yourself of the hard work.
0:14:10 But I never thought of the opposite if you’re accepting that anything and everything bad that
0:14:17 happens is your responsibility/fault. It puts you in a similar position, it seems.
0:14:23 Exactly. The position it puts you in is unable to actually, with discernment,
0:14:31 diagnose what’s really going on. And you know what? You don’t get to transform stuff
0:14:38 if you don’t really know what’s going on. And so, to understand what’s really happening for you,
0:14:42 you have to understand what your role is and what it isn’t.
0:14:49 So how do you walk, say, a client through answering that question well?
0:14:53 How are you complicit in creating the conditions that you say you don’t want?
0:14:57 Or the conditions of your lives in your lives that you say you don’t want?
0:15:01 How do you walk them through their rough draft of trying to answer that?
0:15:08 Okay, so the unlock on the question is the second half of the question which people skip.
0:15:13 You say you don’t want. So give me an example from your own life, Tim.
0:15:15 What do you say you don’t want?
0:15:17 Oh man, how much time do we have?
0:15:25 I have become better at this. So I’m not dodging the question, but I would say
0:15:33 probably some form of busyness. I’ve got this and I’m over-scheduled and I’ve got this and that
0:15:40 and the other thing that is imposing on what maybe I say I want, which is more locked out.
0:15:44 Space for writing or making.
0:15:50 Right. So you say, “Mr. Four-Hour Workweek.” I don’t want to work more than four hours a week.
0:15:53 Nice turn. Nice turn. I think you said that to me.
0:16:02 Right. So you say you want to be so efficient and so productive that you get everything done
0:16:09 that you want to get done so that you have time to play, take care of yourself,
0:16:16 wear breathe-right strips as you talk to, right? This is kind of like, right? Okay.
0:16:23 Just a quick sidebar. Breathe-right. This one’s on me. Next time you’ve got to sponsor the podcast.
0:16:30 I could recognize them because I’m a breathe-right user. I use them to sleep at night.
0:16:33 Oh my God.
0:16:41 We were both like a lifetime supply, so feel free. Okay. So you say you don’t want to be so busy,
0:16:48 right? And you were asking, how do I walk a client through to understand the role of complicity,
0:16:55 right, in this regard? So how does it feel when you’re not busy?
0:17:02 I would say, and I don’t want to steal your thunder here, but since I’m cheating with a cheat sheet,
0:17:07 right, this is- It’s your show. So it’s your thunder.
0:17:15 And action. So, segwaying to a compliment or maybe a necessary component of the first question,
0:17:19 how are you complicit in creating conditions that you don’t want, which is in what ways does that
0:17:26 complicity serve you? Okay. So to answer your question and that at the same time, I would say
0:17:33 probably, and this is almost a certainty, looking back at some of the scariest depressive episodes
0:17:40 in my life, it’s when I had a lot of empty space. And there is an underlying fear.
0:17:47 Even though I haven’t experienced anything close to that magnitude of desperation and darkness in a
0:17:56 very long time, there is a fear that if I create a void, that is the voice that is the narrative
0:18:01 that is going to come to dominate my thoughts. I would say that therefore,
0:18:09 my complicity serves me by avoiding that. Right. And so if you really want to transform,
0:18:16 when will you be comfortable with the void? That’s a good question. And in my defense,
0:18:23 your honor, I will say that I’m about to go off the grid for a week starting this Friday. So in a
0:18:30 few days, I’ll be going completely off the grid, no phone, no nothing for a period of time. So I
0:18:36 have injected these periods. But let’s get into the messy stuff for a second, since life is rarely
0:18:43 as much of a randomized control trial as you would like. I’ve had an ongoing number of chats with
0:18:51 friends and WhatsApp and different messaging platforms. And it’s been around taking breaks,
0:18:59 creating space, chilling out. Right. So a lot of these friends of mine have passed every hurdle
0:19:03 and objective they could have had. And like goalposts keep moving, right? They want to make
0:19:11 a million, and then it was 10, and then it was 20. And then once it gets indefensible, then it’s
0:19:15 like, what’s your annual compounded growth rate? And this then turns into percentages because
0:19:21 they can’t even with a straight face defend the rest of it. But what they claim to want and what
0:19:28 they believe I need is to chill out, take a break, create all this space. My experience is
0:19:35 as social animals, or at least as a person who benefits from social interaction, I do best
0:19:44 around other people. I just do. And there are, it’s not 100%, but it’s not 0%. There’s a risk
0:19:51 that I do return to some of those dark places or dark narratives. It’s not zero. So I struggle to
0:19:56 answer the question of like, when can I allow space? Because I do it in small doses, sometimes
0:20:04 large doses. I took almost all of October last year off the grid. So perhaps you can help me to
0:20:09 find my way to answering the question you posed. You know, look, Tim, I feel like Uncle Jerry and
0:20:16 that we speak every few years. And every few years, my hell you’ve grown. I know you don’t feel that
0:20:23 way because you’re in your body. But when we first started talking, which was years and years ago,
0:20:29 this was a big struggle for you. This was a tremendous struggle. And there was a sense that
0:20:35 you might miss out. There was a sense of like you being falling behind in some sort of weird little
0:20:43 race, a race to the top. And I think the speed with which you’re able to go right to the fear of
0:20:51 the void, what blaze Pascal identified when he said that all of man’s problems stand from their
0:20:58 inability to sit alone in a room. I think you’ve got, like a lot of us, you’ve got a component of
0:21:09 that. And I also want to say I’m watching you letting go of the need to turn that void time
0:21:16 into productivity time. When I first started promoting the notion of sabbatical, which we’ve
0:21:20 talked about in the past, I remember dealing with a client who would say, well, I’m going to learn
0:21:27 Portuguese. It’s like, no, you’re not going to learn Portuguese in four weeks. You’re going
0:21:36 to learn to breathe without breathe right strips. You’re just going to learn to enjoy yourself.
0:21:45 Now, what I hear you doing is learning to enjoy yourself, which is a really powerful skill.
0:21:54 Yeah. Yeah, it’s going to be a lifelong project, which is okay. A lot of things are lifelong projects.
0:21:59 That’s right. We got here because you were asking about that process, and this is the process.
0:22:09 This is the process. So for you, when you’re off the grid starting Friday, what will that
0:22:14 experience be like for you? At what point might you be anxious? And at what point might you
0:22:19 start to relax? Because are you going to be with friends this trip too?
0:22:27 This particular example may not fit the exercise, but what I’ve done for the last
0:22:33 handful of years is every year I do a past year review rather than setting, let’s just say, blind,
0:22:38 semi-uninformed, overly optimistic New Year’s resolutions. I look back at the past year and
0:22:44 figure out what the highs and lows looked like if I were to do kind of an 80/20 analysis. Places,
0:22:50 people, activities, the most life-giving and the most life-draining, and then I schedule time as soon
0:22:58 as possible in blocks of one week, two weeks, depending on availability to spend time with
0:23:05 energy and people doing energy and things. And this particular week off the grid is going to be a
0:23:13 alpine elk hunt, which I do once every two years or so, with Beau at probably between 10 and 12,000
0:23:17 feet for the most of it. It’s going to get cold. We’re going to be getting a lot of shitty
0:23:27 freeze-tried fruit, hopefully a bunch of trout on route to finding elk. And I have just found
0:23:36 that particular experience and the time dilation that it allows to feel like a month off or two
0:23:40 months off. It has just so regenerated for me that it’s become a core piece of my
0:23:47 annual planning. Not necessarily a hunt, but that type of shared experience with a small,
0:23:53 very small group of people. So that’s what that will look like. And I, in a sense, I don’t want to
0:24:00 say I’m disallowing myself from feeling discomfort because there’s going to be incredible discomfort
0:24:08 physically. Sleep is probably not going to be fantastic. And we will be very, very, very active,
0:24:15 but it’s not the same as doing a silent retreat and sitting there watching your monkey brain
0:24:25 and just contort itself for 16 hours a day. It’s the kind of retreat where layers of your
0:24:31 skin are stripped away because you’re so raw and rugged out in the world. And that’s just going to
0:24:40 drop you into your body and drop you more and more into the land. And that’s a place of nourishment
0:24:48 for you, for sure. Yeah, let me ask you, if I could, how often do you find with your clients
0:24:58 or your team find with their clients that the fixes in the body or in something physical versus
0:25:06 in the mind, even though the symptoms permeate both because the Cartesian separation of mind
0:25:14 and body is ridiculous. It’s not saying. And the reason I ask is that for me, let’s just say,
0:25:24 taking a trip like this, it is such a restorative reminder of how what I want and need is simple
0:25:32 and right in front of me. But that comes through, for me at least, often, not always, but physical
0:25:40 movement, sometimes physical hardship where, as they say in dog trading, a tired dog is a happy
0:25:46 dog. I think humans are pretty similar. Well, we’re both mammals, right? Yeah.
0:25:51 You asked how often I would say 95% of the time. Wow.
0:25:57 I would say you’re finding your way, I’m older than you, Tim, so I get to be the wise one,
0:26:05 but you’re finding your way to that really inherent wisdom. And my take on the Cartesian
0:26:13 Descartes notion is instead of it being, I think therefore I am, I am therefore I think,
0:26:19 and that’s where all the problems begin. What you’re really talking about is getting into the
0:26:28 essence of your existence. The only cautionary note that I would sound is when we start to
0:26:44 invade the productive thinking into that tired dog effort, meaning I’m going to do this so that I,
0:26:49 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
0:26:55 that I can look better, or I’m going to do this so that I can, I don’t know, quiet some negative
0:27:02 self-thought. And I think you’re beyond that. But I would say to those listening,
0:27:08 what I have found is when I can let go of even those things and just get dog-tired,
0:27:16 then I’m happiest for sure. It was definitely possible to sort of run towards things, run away
0:27:26 from things. And I think with athletics movement, it’s not necessarily condemnation to be wanting
0:27:33 to quiet something, because you may just have too much inherent physical energy, and it has nowhere
0:27:42 to, has no vehicle through which to dissipate. So it just creates the, yeah, kind of devil on your
0:27:50 shoulder, creating all these fairy tales to drive you insane. And I do think that quieting that by
0:27:55 dissipating the energy through exercise makes a whole lot of sense. But if there’s a persistent
0:28:01 problem that you’re trying to avoid that requires attention, then it’s a different matter altogether.
0:28:10 Let’s just agree that bypassing is not a good strategy. I mean, it is important to take a
0:28:15 vacation and that wise old analyst, Dr. Sayers, used to say to me all the time, “Enough, Jerry.
0:28:23 You’ve figured it out. Now go take a break.” But it gives you insight in what was going on in that
0:28:32 session room. But it’s really important that we let go of those things that are driving us.
0:28:39 And that’s not bypassing. When you go on this Elk Hunt, I mean, maybe you’re avoiding
0:28:44 the conversation that you’re supposed to be having to use one of my other questions.
0:28:50 Maybe you’re not saying the thing that you need to say. But I suspect at this point,
0:28:55 what it’s doing is it’s giving you the ability to come back to the stuff that you’ve
0:29:02 had to confront. But it’s giving you some ground to stand on so that you can confront the things
0:29:07 that you need to confront. That’s how I feel. And it’s also planned so far in advance at this
0:29:16 point that it’s not a reactive. It’s proactively, basically injecting turbo boosters on my
0:29:21 physical and mental well-being so that I can bring that back to everything else.
0:29:29 And you mentioned a few things just a moment ago that I just want to reiterate for folks.
0:29:35 And this, I believe, maybe the same therapist could be a different one,
0:29:38 taught you these questions to ask when in existential pain.
0:29:44 What am I not saying that needs to be said? What am I saying that’s not being heard?
0:29:47 What’s being said that I’m not hearing? Am I getting that right?
0:29:52 That’s right. Well, she taught me the first question. And it was, again, in a moment of
0:30:01 exasperation when I had been hospitalized with a really terrible migraine and spent a week
0:30:06 going through neurological tests only to find out that there was nothing physiologically wrong
0:30:11 with me. And in the first session back, she looked at me and she said, what are you not
0:30:19 saying that you need to say? You need to talk more. So when you see those questions, please
0:30:25 hear that voice. I’ll add, by the way, that those questions have sort of bounded around the internet
0:30:31 the way a lot of my questions do. And one woman wrote back and said, here’s another one.
0:30:34 What are you hearing that’s actually not being said?
0:30:41 That’s a good one. That’s a really good one. That should be on my master mirror. That’s right.
0:30:46 What are you hearing that’s not being said? Oh, that’s good. That’s really good.
0:30:54 Because boy, oh boy, did we tell ourselves stories. What we’re getting at in all four of
0:31:00 the questions. And really, much of this conversation is the importance of not bullshitting yourself,
0:31:09 the importance of not bypassing what’s really going on for you. And I have found in my 61 years
0:31:19 now that that is also a lifelong practice, that my capacity to bullshit myself continues unabated.
0:31:28 And no matter how progressed I think I am and evolved, I think I am. My ability to be diluted
0:31:37 by my own mind knows no end. So I have come to see that as just a part of the human condition.
0:31:43 Maybe when I’m as old as my friend Parker Palmer, who’s 86, I’ll have the wisdom of
0:31:50 not being able to bullshit myself. Parker Palmer, also the author of one of your
0:31:54 favorite books, I believe. Let Your Life Speak. I’m getting that right.
0:32:01 Just a quick thanks to one of our sponsors and we’ll be right back to the show.
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0:33:22 I want to overlay a few more questions that can be used that I took note of when I was reviewing
0:33:29 our past conversations that I really like. I don’t yet have kids, so one of them won’t
0:33:33 totally apply to me, although it could apply. I guess it could be hypothetical, but
0:33:39 ways of edging into what’s actually going on, circumventing that bullshitting that we’re all
0:33:46 incredibly good at doing, and it may not be, I guess it often isn’t, conscious bullshitting,
0:33:50 where we know we’re lying to ourselves. It may just be a really compelling narrative that
0:33:56 isn’t true. We’re hearing something that isn’t being said. So one is, no, really,
0:33:59 how are you doing? Not just how are you doing, but like, no, really, how are you doing?
0:34:05 And then the little trick of asking people if they want their kids to feel the same thing
0:34:10 that they’re feeling when they get to be the same age. And if they don’t,
0:34:15 it prompts them to start re-organizing their lives and so on, start with a whip. I’m next to a river.
0:34:21 Such things happen. Right. And there are more, of course, but what I was curious to ask you is,
0:34:28 I’ll segue into this by way of an anecdote. There’s an amazing, fascinating sage man named
0:34:35 Bill Richards. And Bill Richards wrote a book called Sacred Knowledge. He is a religious man,
0:34:40 and also, I think he may be an ordained minister, something along those lines.
0:34:44 He also has the distinction of having administered hundreds and hundreds of
0:34:50 psychedelic assisted therapy sessions, both before and after prohibition. And last time I
0:34:56 spent time with him, he kind of looked like Santa Claus. Amazing big white beard, kind of jolly old
0:35:03 elf type of feeling, always smiling with a little twinkle in his eye. And I spent some time with him
0:35:11 probably eight years ago, something like that, near Johns Hopkins, where he’s done a lot of work.
0:35:18 And I was asking him some question about doing the work. This is a phrase that comes up a lot in
0:35:24 personal development circles, dealing with your shadow self and x, y, and z. It can take a million
0:35:29 different forms, doing the work. And he said something to me that has stuck ever since,
0:35:34 and it was along the lines of, well, you know, the tricky part about doing the work. And I was like,
0:35:38 I don’t, what’s the tricky part? He’s like, there’s a very thin line between doing the work
0:35:47 and just picking on yourself. And I was like, and he said a few things to me that day where
0:35:51 afterwards I was like, fuck, I just thought it was funny, but there’s actually a lot to unpack
0:36:00 there. And how do you help clients or how do you think about helping people to distinguish between
0:36:07 the two? Right, because there can be a degree of like trauma fetishizing and past fetishizing,
0:36:13 where people are doing everything and anything to just revisit every mishap of childhood, every
0:36:20 mistake their parents made. And the dose makes the poison, right? And it seems like Paracelsus
0:36:27 said so long ago, not in English, obviously. And how do you think about navigating that?
0:36:33 I think it’s a brilliant question. And I think it’s something I probably, as I’ve slipped,
0:36:43 slide it my way into elderhood, have begun to finally let go of in my own life. And so when I
0:36:53 think about supporting other people, what comes to mind is really, I mean, think about the way
0:36:58 Bill responded to you, think about the way Dr. Sayers would respond to me. Think about,
0:37:06 you know, I think about the conversations I have with my elder friend, Parker, it’s always laced
0:37:16 with humor. And it’s the humor that cuts through it. Humor, forgiveness, and not in this kind of,
0:37:26 I don’t know, self-development, book, bullshit, self-forgiveness thing that’s out there. But
0:37:33 genuine care and concern. I mean, I’ll give you an example. I wrote a book that came out last year
0:37:43 called Reunion. And part of that journey was really reuniting to use language from the book
0:37:51 with the parts of myself that I had disowned. But more importantly, my ancestors. And in this case,
0:38:05 I went into a relationship with my father. Now, my father died 32 years ago. And in unpacking
0:38:15 his story, what I came to have a new relationship with was his own depression, his own alcoholism.
0:38:26 And I unpacked, you know, to spoil the plot, my dad was on his wedding day. His mother was so angry
0:38:33 at him for marrying my mother that she screamed from the back of the church, putana, putana,
0:38:40 putana, whore, whore, whore. Because my mother was pregnant at the time. And then she screamed out,
0:38:47 you’re not my son. You were adopted. Jesus. And that’s how my father, yeah. That’s how my father
0:38:55 found out he was adopted. And I grew up, as we’ve discussed before, my mother was mentally ill,
0:39:04 and my father’s depression and alcoholism really marked my childhood. And I would say that I spent
0:39:11 most of my life being angry with him. And this is to the point of the forgiveness.
0:39:19 And I think that what happened was, in writing this book, I started to really step into his body.
0:39:26 What would it be like to be 18 months old? Because it turned out that he was given up
0:39:33 for adoption at 18 months old. And he was given up and raised by the only parents he knew in
0:39:41 an Italian-American couple. And the reality is, his biological mother was an Irish immigrant
0:39:51 to New York, who gave birth to him when she was 20. And I ended up in Ireland at her grave site,
0:40:00 not only forgiving my father, but forgiving her. And I did that, I tell that story in this book,
0:40:09 but more important to your point. I think that that laughter came about from forgiveness,
0:40:20 where now I actually can feel myself going, he wasn’t so bad. He did the best he could.
0:40:28 And he got a raw deal. And yeah, some of the things he did sucked, but not bad.
0:40:37 Was that incremental 100 different realizations adding up over time? Or were there any flash
0:40:47 points where there were particular experiences or insights that covered the bulk of the
0:40:54 traverse from anger to forgiveness or acceptance in the way that you just described it?
0:40:59 It’s interesting, because we were talking before about the physical being,
0:41:05 the somaticized being. And there was a moment, but it wasn’t an insight,
0:41:12 meaning it wasn’t a thought. And I talk about this as well. My youngest son is named Michael,
0:41:23 and he was a junior in college. And he did a semester abroad in Dublin. And one week for
0:41:30 my birthday, I went to Dublin to visit with him. And we went to visit, his girlfriend was there
0:41:37 as well, she was also taking a semester abroad. And we went to visit the printing museum in Dublin.
0:41:44 Printing. Printing. And we’re walking through the museum because we’re freaking nerds looking at
0:41:53 old print presses. And I’m explaining to him how the machine works. And he’s looking at me
0:41:58 like, oh, yeah, you’re bullshitting me, dad. And it’s like, no, no, no. My father worked in a print
0:42:06 shop. I remember walking through the print shop and seeing molten lead flowing as they would
0:42:13 refire lead type, and that the sparks would fly as they were doing this. I remember all of this
0:42:21 from when I was a kid. And I was explaining all of this. And I look up and they have this replica
0:42:27 copy of the equivalent of the Irish Republican Declaration of Independence. And it was actually
0:42:35 at that moment that I had this profound visceral experience of my father, which was not an insight.
0:42:42 Right. It was, first of all, my father would have loved walking through the museum with his son and
0:42:50 grandson. And all of a sudden, I realized that the folks who had put up that poster originally,
0:42:57 and declared their independence, were the kinfolk of my father, which was a very
0:43:05 different and powerful word for me. And, you know, later, about a year later, when I was in the
0:43:12 churchyard in the grave site and visiting my grandmother’s grave, it’s still weird to say this,
0:43:19 because I never knew her. And I was walking through this tiny little graveyard. I realized that
0:43:27 I was surrounded by the bones of my kinfolk. And Tim, that was not an intellectual experience.
0:43:36 That was not an insight. That was a viscerally felt experience. I look up and I see the light
0:43:42 slanting through the trees. And I swear to God, I felt like I could hear my grandmother at four
0:43:55 years old running down the lane. What a story. To bring it all back, I feel like, because of that
0:44:05 experience, I closed a wound that was transgenerational, transpersonal, and intergenerational.
0:44:11 This brought me to want to ask a few different questions. And I’ll first say that personally,
0:44:18 I’ve found tremendous value in metabolizing a number of things from the past. I’ve had some
0:44:24 horrible things that happened to me as a small child. So it seemed important for me to, at one
0:44:31 point, contend with that or triage it, process it in some way. Now, if I were to take
0:44:38 not necessarily devil’s advocate position, but look at, for instance, many people I’ve
0:44:43 interviewed on this podcast, there are some, and I’m probably misquoting, but it’s not going to
0:44:48 be too far off. I remember chatting with Mark Andreessen, one of the most storied, famous,
0:44:53 and successful venture capitalists of our age, also an incredible technologist in zone right and
0:45:01 coder slash product developer Mosaic being among his achievements. He answered, it may have been,
0:45:07 I think his billboard was raised prices, his billboard answers, so that’s not it. But there was
0:45:11 some type of, perhaps the question was related to if you had to live your life with one mantra,
0:45:16 what would it be? And it was some version of forever forward. And he told this story of
0:45:23 a character in a detective novel who has arrows tattooed on his shoulder pointing forward to
0:45:31 remind him always forward. And many of the most effective people, I don’t know if they’re the
0:45:36 most content people, I don’t have that window into them, have philosophy along these lines,
0:45:41 right? You can change the past, you can change the future, pay attention to your thoughts,
0:45:46 behaviors, habits, those all form your destiny moving forward, right? There’s a very forward
0:45:51 focus to view. And it works for a lot of things. Then let’s just say, on the opposite end of the
0:45:57 spectrum, I’m sure there are very, very successful people who also spent a lot of time metabolizing
0:46:04 the past, I know quite a number of them. But there are also folks who get so focused on the past,
0:46:08 there are a lot of them in Austin, Texas, where I live, that they don’t really seem to be grappling
0:46:14 with the president of the future particularly well. And they feel like their past is this
0:46:21 unalterable, basically shaping of a sculpture they cannot undo on some level, right? They can’t
0:46:26 seem to escape the vortex, the gravitational pull of the narratives they have about their past.
0:46:37 How do you help someone find the right blend of past focus versus present or future focus?
0:46:42 I know that’s a very, very long lead up to the question, but it’s something I do think about
0:46:51 a lot. I think that you are identifying a real challenge in the human existence. And I’ll reframe
0:46:58 it just slightly and take us back to the notion of bypassing. I can argue that those who are only
0:47:09 forward looking with no awareness of the past may be bypassing. As you know from your own experience,
0:47:23 ignored trauma can stay in the body, can affect us forever. But the fear that many people have,
0:47:30 and one of the reasons why we struggle to sit alone in a room is that we’re afraid of our thoughts,
0:47:34 and the thoughts are either about the future or the past that we’re afraid of,
0:47:41 many people fear being trapped in the past. So your question is, how do you balance those two,
0:47:48 which is a great framing of it? And I often think of the Carl Jung quote, which is, “I am not what
0:47:56 has happened to me. I am what I choose to become.” And I think that no one would ever accuse Carl Jung
0:48:03 of ignoring the past, but seeing it as, if you will, the source material of what the future is.
0:48:12 The reason we open the closet that is really fucking messy is so that we can straighten it up
0:48:18 and close the closet door and move on, because the stuff in the closet that’s ignored and messy
0:48:27 has a way of busting through the door and messing up our lives. So I think part of your question,
0:48:32 too, is how do we get somebody who is stuck in the past to move forward? Is that a fair statement?
0:48:42 Yes. Yes. I think that the trend seems to, at least in certain places, to have swung pretty
0:48:51 extremely from the sort of Gordon Gekko, let’s just say, pure machine with just enough reflection
0:48:59 on the past to take advantage of new opportunities, but not much more, all the way back to sometimes
0:49:07 what I would say very self-indulgent past reflection and oversharing. And it’s like,
0:49:12 okay, you wrote the script, you’re on your 247th read, right? Maybe it’s time to stop.
0:49:18 Yeah. I’m going to parse things a little bit. Please. I don’t feel comfortable
0:49:27 criticizing someone for being, quote, “for oversharing,” having grown up with the consequences of far
0:49:34 too much silence and secret keeping. I know the detrimental effects of that.
0:49:41 What I really liked, though, is your word “overworking,” and I keep thinking of like dough,
0:49:45 bread dough, when bread dough is overworking. I was actually thinking of clay and play dough,
0:49:48 but then I chose to use the writing because I know it better.
0:49:55 Yeah, there is that tendency to overwork it. What I have found to be helpful is a Buddhist
0:50:02 aphorism, which I’ve used often, which is this being so, so what. And what’s powerful
0:50:07 about that, it’s not so what who cares, it’s so what are you going to do about it?
0:50:14 Which is that forward momentum, whether it’s mere wounds, which we all have, or trauma,
0:50:21 which many of us have. Retraumatizing ourselves by replaying and reworking it,
0:50:28 overworking it, doesn’t release us. But acknowledging what has happened,
0:50:35 and then really empowering yourself to say, “And what will you do about it?”
0:50:41 is I think that’s the unlock. I think that’s the balance point that you’re looking for.
0:50:48 And I’d love to actually say something related to your pushback, which I think is valuable and
0:50:54 valid in the sense that you mentioned being on one end of the spectrum, right? If you come from
0:51:01 a family and a place of withholding in silence and stiff upper lip, not communicating feelings,
0:51:08 experiences, etc. Or worse, secrets. Or worse, secrets, right? It can be very therapeutic
0:51:13 and very healthy to push yourself towards the other end of the spectrum. Recognizing you’re
0:51:20 probably not going to end up at the furthest diametrically opposed point, which is something I
0:51:26 do think is unhealthy, which is performative trauma, right? Literally, I have been at cocktail parties
0:51:31 in Austin where I meet somebody. And this is prior to my divulging my own abuse when I was a kid.
0:51:37 And literally, the fourth sentence out of their mouth is something about extremely graphic trauma.
0:51:45 And I’m like, what are we doing here? Exactly. I don’t think this is for your healing benefit.
0:51:53 And it becomes performative in a sense. So I suppose I just feel like that is unhealthy. Also,
0:52:00 not just to yourself, but to others in a way, it I think can diminish how severely some of these
0:52:06 things impact other people, just because a person happens to have gone to the point where they can
0:52:13 casually drop graphic abuse into conversation does not mean that someone else is comfortable hearing
0:52:18 or saying the same. I’m happy to sit on related topics for a second, but I’m very curious at
0:52:28 Reboot.io. You’re the CEO co-founder. You have lots of clients, right? In the capacity of executive
0:52:39 coaching, leadership development, etc. When did Reboot start? When was it founded? July 2014, roughly.
0:52:47 So 2014, perfect. So it’s almost a decade ago. Just over a decade. You’re right. Just over a decade
0:52:55 ago. Have you seen any changes in the types of challenges people are contending with? Or are
0:53:00 they mostly the same? I’m just wondering, as technology has changed, as social dynamics have
0:53:11 changed, as the world has accelerated, have you seen any problems crop up more and more or less
0:53:15 and less? Or is it kind of the same old stuff that we’ve been talking about for thousands of years?
0:53:22 It’s about both, I would say. I think that there are unique expressions that have emerged. I think
0:53:29 that there is a kind of global tension that exists in the world right now that, sure, there have been,
0:53:37 call it left-right tensions, call it whatever language you want to use, those tensions have existed,
0:53:46 but it feels heightened right now. And you couple that, I think, and this I think is relatively new,
0:53:56 the after-effects of the pandemic. And you have this really complex mix. I think, for example,
0:54:06 of the complexity, I know one company, for example, in November or December, after the Hamas attacks
0:54:15 on Israel on October 7th, ended up having to shut down Slack for two weeks because there was no
0:54:22 discussion. It was all argument. And quite honestly, a lot of the argument from all sides felt
0:54:32 performative to use a word you were just using and not necessarily designed to really move the
0:54:40 conversation forward in somewhere or another. This being said, human nature is human nature.
0:54:47 It’s why coaching is actually a good business model. Much of what happens continues to happen.
0:54:55 I can’t name the company, but I’m at a new client. I rarely take on new clients, but I kind of fell
0:55:01 in love with this kid when I first met him, very, very hot young company. Not quite the clusterfuck
0:55:09 it was six months ago, but pretty close. And as I’m sketching out on a driveway, sport, everything
0:55:15 that has happened and will happen, everybody is like, well, how do you know? Because I’ve seen
0:55:21 this a thousand times. This is what we do. This is called dysfunctional startup, and here’s the
0:55:30 path, and it’s going to be fine. It’s going to take a year and a half to two years. I hope that
0:55:35 addressed your question. I don’t know. I may have gone off on my own tangent. Well, let me hone in
0:55:42 on one particular concept that I’d love for you to expand upon or just riff on. And I may have it
0:55:50 transcribed, noted down in front of me incorrectly, so you can fact check me as well.
0:55:56 But it’s around the discussion of guilt. And part of the reason I think guilt can be such a
0:56:02 powerful driver, sort of a negative driver in a lot of cases. I think guilt and prestige,
0:56:11 often terrible motivators, to quote Maria, or reference Maria Popova, but the guilt, I think,
0:56:25 also seems to be having quite a moment because when you are waterboarded with disaster and crisis
0:56:33 globally 24/7, it’s hard not to feel like you are not doing enough. But this is what I’ve written
0:56:40 down. Guilt is self-focused, whereas remorse is about the other person. So if you find yourself
0:56:45 ruminating in guilt over something, that’s when you bring attention to that and say easy, boy,
0:56:49 easy, or a good man who sometimes fails to live up to your aspirations. The first part is when I
0:56:57 want to ask you about, could you say more about guilt being self-focused versus remorse? I just
0:57:02 wanted to make sure I understood this clearly. I often think of my Buddhist teacher, Sharon
0:57:12 Salzberg, whose line about that is that guilt is self-laser rating, which I find really a compelling
0:57:19 image. And what it does is it kind of keeps us, here’s an old reference, you may get it because
0:57:26 you may have had record players where the needle stuck in the groove. And you just like again and
0:57:31 again and you’re ruminating and you’re spinning and you’re like, oh, shit, why did I do that?
0:57:39 Whereas there’s no opportunity for growth, there’s no opportunity for learning. Daniel Pink
0:57:45 just wrote last year, I think it came out, the power of regret. And as so much of what
0:57:53 Daniel does, it’s kind of a social science take on this question. I prefer the word
0:57:58 remorse to the word regret, but I think for this instance, you can substitute them.
0:58:05 And there’s something very, very powerful that’s embedded in that is the learning.
0:58:13 And I think that that’s what you’re reaching for here is when we allow ourselves to internalize
0:58:24 remorse or regret, we’re opening ourselves up to other people, to knowledge, to growth ultimately.
0:58:28 How do you do that without slipping into guilt? Well, so if you’re talking to somebody and they’re
0:58:33 like, fuck, I shouldn’t have done that, God, if it’s badly and terrible, I always do this.
0:58:39 That’s an exaggerated version, right? But if they’re in a loop of self-lacerating guilt,
0:58:46 how do you move them towards one of these close cousins that is perhaps more healthy?
0:58:49 Exactly. How do you do that?
0:58:55 If you think about the setup, the setup more often than not, if I am often plagued by negative
0:59:04 self-talk, I am going to be more subject to that ruminating guilt, because I tend to see the thing
0:59:12 about which I feel guilty as evidence of my shittiness as a person. And if that’s true,
0:59:26 then the movement is towards decoupling my sense of worthiness as a person from the action. So good
0:59:39 people do bad things all the time. Good people who do bad things who don’t learn are less evolved,
0:59:46 less mature than good people who do bad things who then learn through regret and remorse,
0:59:50 but they remain good people. Does that distinction help?
0:59:57 It does. Are there any problems or exercises that you would potentially assign, it could be
1:00:08 something else, to a client who has developed the habit of negative narratives around self-worth
1:00:13 because they did A, B, and C? That’s just a reflexive habit that they have. Is there any way
1:00:18 that you suggest they reframe things or start training their mind to go in a different direction?
1:00:24 Yeah, I mean, I hate to sound like a broken record again, but how does it serve you to think ill of
1:00:31 yourself? Any patterns in responses? Are there any patterns that any common threads that you hear
1:00:38 in response to that? Sure. In some family of origin structures, for example, the way I can
1:00:46 know that I belong to my family is by turning to negative self-talk. Just like the way I could
1:00:52 know that I belong to a family is by seeing myself as a victim. If I grow up with parents who see
1:01:00 themselves as victims, that might be the way in which I interpret the world. And so by starting
1:01:11 to unpack that and really taking a look at the way to use my phrasing, it serves you to think ill
1:01:19 of yourself begins to raise the consciousness that releases you from having to repeat the pattern.
1:01:29 So let’s hop to a topic that you mentioned as we were brainstorming various directions to go
1:01:32 in this conversation. And I have none of the fleshed out
1:01:38 contacts, which is perfect because it’s kind of boring for me to know exactly what’s coming.
1:01:44 Me too. Legacy. Legacy seems to be something that you’re thinking about. And I suspect
1:01:53 we could have a all needy conversation about this. So I’ll let you kick it off in whatever way you
1:01:58 think makes sense. Well, you know, I was joking before I talked about feeling like I’m slip sliding
1:02:06 into my elderhood, you know, and title of your next book. That’s right. That’s right. Ten easy
1:02:14 life lessons from Uncle Jerry. Well, but that, you know, that’s kind of where I feel like I’m
1:02:20 entering this period. You know, Tim, you know, it’s like I’ve done two books now. I’m starting to
1:02:26 think about what do I want to do? What is next? And I’ve been thinking about these themes of
1:02:35 redemption. I’ve been thinking about themes about legacy. And what does it mean to look at? And in
1:02:41 some ways, very similar to the conversation we’ve been having, to look back on the past in order to
1:02:47 move forward in the future. And I think that, you know, someone asked me last week, well, what am I
1:02:53 thinking about in terms of that legacy? And I don’t really think about it in terms of, say,
1:03:00 what do I want to leave behind? Which I don’t know, maybe that is the definition of legacy.
1:03:08 But I think about it really more in the terms, in terms of three different circles of impact and
1:03:13 influence that I have. The first circle being myself. Am I proud of the man I’ve become?
1:03:21 The second is my children in descendants. How do I want them to look back on me? I mean,
1:03:29 I fucked up royally. And yet, for some unknowable reason, my 27-year-old wanted to spend five days
1:03:35 camping with me this summer. Can you believe that? Because I would never have wanted to spend
1:03:40 five days trapped in a sprinter van with my father. And then the last circle is,
1:03:46 how have I left the world? I hope, for example, all of the work that I have done
1:03:52 made an impact on you, Tim. Oh, no. Wouldn’t have all these notes in front of me.
1:04:00 When’s the birthday case? When we were celebrating your 10th anniversary,
1:04:08 I sent a note, I sent a video, and I was telling you, I’m proud of what impact you’ve had on people.
1:04:14 Yeah, I really appreciate the video. Thank you. I don’t know this to be true, but the story I
1:04:23 tell myself is you didn’t start this podcast to have an impact on some random 22-year-old kid
1:04:30 who’s a little lost. As I experienced it, you started this podcast to answer questions that
1:04:37 you had about your own life. That’s right. But in doing so, you impacted a lot of people.
1:04:45 And I think you should be proud of that. Yeah, it continues to this day, I think,
1:04:53 when I’m doing it right for me to be conversations trying to answer questions I have myself.
1:05:00 Isn’t that interesting? I want to highlight that. Isn’t it interesting that when you lean
1:05:07 into the questions that you need answered in your own life, you end up positively impacting
1:05:13 other people? Yeah, the personal being the most universal, right? Yeah. So what if that’s the
1:05:22 definition of legacy, meaning being so real and so honest as to make yourself a pallet, if you will,
1:05:33 or a canvas where people can work their stories out? That’s pretty cool. Yeah, I like that
1:05:39 definition or that placeholder for legacy because when I’ve thought about leaving things behind
1:05:49 and know a lot of fancy, muckety mucks, often very good people, very soulful people who somehow
1:05:56 get fixated on legacy, maybe because they’ve overshot Maslow’s hierarchy of needs, maybe accepting,
1:06:01 taking out maybe self-actualization and transcendence, but everything else certainly. They’ve
1:06:11 overshot by such an absurd margin that they start thinking about legacy. And I always think to myself,
1:06:19 I’m like, “Alexander the Great, what was his last name again?” Nobody knows. And we are somehow going
1:06:24 to stand the test of time, like the head of the sphinx poking out of the sands in the desert. Come
1:06:35 on. It seems ridiculous, but maybe who knows? What I said about borrowing from Bill Richards,
1:06:41 like Bill Richards told me this thing, or you tell me a question, I pass that on,
1:06:47 then somebody else passes it on. And even though the attribution probably gets long lost along the
1:06:57 way, that is some form of legacy. That continues. Yes, a thousand times. Yes. Listen, I know legacy
1:07:08 as a word can sound grandiose, and I love your self-deprecating humor. Don’t use it, though,
1:07:19 to deny the thing that is true. Because that’s another form of that self-delusion and bypassing.
1:07:27 The fact of the matter is, you have made a positive impact on the world. It may be fleeting.
1:07:36 It may disappear. Who knows? Listen, I’ll tell you a story. About five or six months after my first
1:07:43 book came out, I received a ton of fan mail on the book. I still get mail from people saying this
1:07:50 book really impacted my life. But I’ll never forget this one day. In one day, I got two messages,
1:07:58 one from the CEO of a Fortune 100 company and one from a man on death row. And they both wrote
1:08:05 about the book and said, “In one form or another, your story is my story. I will go to my grave
1:08:12 proud of that fact.” That’s amazing. Also, to have it happen on the same day. On the same day.
1:08:16 And the lesson, Tim, in that is there’s really no difference between those two men.
1:08:22 And that’s what’s really powerful. Can you say a little bit more about that? Because at face value,
1:08:27 of course, you look at their CVs, very different men. But I know you mean something different.
1:08:32 Can you say a bit more about that? I do. I do. And in December of 2019,
1:08:39 well, first, in September of 2019, my first book came out in June. In September of 2019,
1:08:45 I’m doing a book talk. You remember when we used to do things like that. And pre-pandemic.
1:08:48 Back when we were listening to many LPs on the record player.
1:08:54 That’s right. That’s right. And I’m walking to this venue in Denver. And there’s this woman who’s
1:08:59 like clearly in her eighties who comes up to me and she says, “You look like our speaker.”
1:09:04 And I said, “Well, that’s because I am your speaker.” And she laughed and she stuck out
1:09:10 her hand and she said to me, “My name is Margaret. And I grew up in the Dust Bowl.
1:09:18 And I read your book and your story is my story.” And Tim, I did not grow up in the Dust Bowl during
1:09:24 that depression. I grew up in Brooklyn. Like, what the fuck, right? And a few months later…
1:09:29 That was the best follow-up, too. I grew up in Brooklyn, by the way. What the fuck?
1:09:33 I’m sorry. I should have warned you. And the script did it better.
1:09:44 Fuck is a part of our dialect. I’m sorry. No, I have to just a brief aside. I’m not going to
1:09:48 mention it by name, but everybody who listens to this podcast would know. I’m a friend of mine
1:09:55 who grew up in New York City. A lot of Brooklyn influence. And his greeting to me is, “You fucking
1:10:01 fuck. The fuck are you doing?” This is like one of the most sophisticated, brilliant thinkers of our
1:10:07 time. But that’s how he greets me. I don’t understand. Do you have a fucking problem with that?
1:10:13 Yeah, exactly. Yeah, exactly. Alright, Margaret. Alright, so a few months later, I’m in Dublin
1:10:20 and I’m doing a book reading. And the audience is filled with, not surprisingly, white people.
1:10:28 But there’s this one black woman who’s sitting in the very front row. And at the end of the talk,
1:10:33 and in some ways, you’ve experienced something similar. At the end of the talk, she comes up
1:10:39 to me and she says, “I was really moved by what you were saying, especially the part I had been
1:10:46 talking about, how when we lose a parent at an early age, it forces us into early parentification,
1:10:53 and importantly, that that can often be a signifier of leadership.” She says, “That thing
1:10:57 you were talking about, what that happened to me, my father died when I was 13. And,
1:11:04 you know, I’m kind of dopey and exhausted and I kind of nod my way in response.” And then she says,
1:11:11 “On Robin Island.” And I look at her and I say, “What?” And she says, “Yeah, he was, Robin Island
1:11:18 is where Nelson Mandela was held.” And she says, “Yeah, he was a freedom fighter based in Zimbabwe,
1:11:23 and he was caught on the border of South Africa and beaten to death in the prison.”
1:11:31 And then she says to me, “Your story is my story.” And the thing about that, and her name, by the way,
1:11:40 is Joy Tende Kangari. She is going to be graduating, I think, with a PhD in law in October. She’s one
1:11:47 of the first Black women in the city of Dublin to be a barrister. The thing about that experience is,
1:11:54 to your point, our lives couldn’t be more different. But there’s something very, very powerful about
1:12:02 this notion that your story is my story. Yeah, you peel back a few layers. We’re all people
1:12:07 everywhere in all times dealing with the same things. If you go deep enough, if you go deep enough.
1:12:12 And if you’re willing to be honest, I mean, so, you know, when people come up to you and want to
1:12:20 share their trauma, yeah, there’s a performative element to it. But maybe, too, they’re seeing
1:12:28 their story in your story, Tim. 100%. Just for clarity’s sake, if people do it after I shared
1:12:34 publicly what happened to me, it’s very different from the examples that precede that, where with
1:12:38 no context, it’s clear that they are showcasing their trauma within the first few minutes to anyone
1:12:42 who will listen, which I think can get into dangerous territory. But I agree with you 100%.
1:12:51 And I do, I’d say probably in response to that episode more than any other, but certainly there
1:12:59 are few where I discuss personal challenges with depression and so on, which thankfully are fewer
1:13:07 and fewer and shorter and shorter in duration, but you never know. And I agree with you 100%.
1:13:12 May I ask you a completely unrelated question because it’s stuck in my mind and I need to
1:13:19 scratch the itch. Your son in the Sprinter van five days, you mentioned fucking up a bunch
1:13:25 of stuff like all parents do. Hey, even though one guy, great guy, I won’t mention it by name,
1:13:28 but he said, it’s like, oh, yeah, I’m going to send all my kids to the Hoffman process. He’s like,
1:13:34 I don’t fucking them up. I’m just not sure how. Anyway, so you made mistakes like every parent
1:13:39 does. But what did you get right? Why do you think if you had to try to explain it? And I know
1:13:46 it’s not a laboratory, so nothing is easy to isolate here. But what do you think you did
1:13:51 right or what worked? Maybe it’s your son out of the box. Who knows? Maybe he’s just a very
1:13:55 forgiving guy. But why did he end up wanting to spend those five days with you in the Sprinter
1:14:03 van versus your experience with, say, your dad? The power of that question is two-fold. One is,
1:14:10 I think it’s a really, really important question. And the second is you’re touching upon one of my
1:14:18 most deep and profound fears, which is that I would have fucked it up as a parent. And so,
1:14:23 I want to be clear, I still have the capacity to fuck it up. I think the answer to your question
1:14:29 goes back to something Dr. Sayers used to say to me when I would lie on the couch and bemoan
1:14:37 that I was a terrible parent and I would be wracked by guilt because of this stupid reaction
1:14:42 that I had or this stupid thing that I said or that kind of thing. And she used to say to me all
1:14:48 the time, two things. One, you cannot spoil children with love. You can spoil them with
1:14:54 things, but you cannot spoil them with love. So, love them. And the second thing was, she said,
1:15:04 give them words. Give them words. And I think, I have three children. Sam is 34, Emma is 32,
1:15:12 and Michael is 27. And Michael’s the one that went camping with me, but Emma and her soon-to-be
1:15:18 husband really enjoy the camping van as well. And the truth is, I have great relationships
1:15:23 with each of them because they’re great people. What does give them words mean?
1:15:29 Yeah, give them the ability to talk about what’s actually going on inside of them and listen.
1:15:40 I think that as parents, we can become so afraid of fucking it up and hurting them that we get wrapped
1:15:50 around our own anxiety, our own narcissism. And then we lose the connection, which is the thing
1:15:58 that our children want more than anything else. Did you give your kids words? If so, how did you
1:16:05 do that? Two things. I do think I gave my kids words. I think I also raised the bar on what
1:16:11 they expect from other people. They expect words from other people, which has a mixed
1:16:16 blessing, right? Because not everybody is trained to actually talk about what’s going on. Not
1:16:22 everybody knows how to answer the question, “How are you?” I think I gave them the way I did it,
1:16:31 was I modeled first and foremost. And the second, and I think I’m good at this, I listened.
1:16:38 Now, I also want to give a shout out to their mom because this was not a one and done. I did it
1:16:48 myself by any stretch of the imagination. They had two spectacular parents who each endeavored
1:16:59 to do right by their children in different ways and different styles, for sure. Given your experience,
1:17:05 you have good relationships with your kids. If you had to add a third or four thing to
1:17:14 your therapist’s rules, let’s just say, you can’t spoil a kid with too much love. Number two, give
1:17:21 them words. What might number three end or I guess wouldn’t be or number three if you want to add a
1:17:28 fourth and go for it? But what might you add to that? I think that if I could go back in time and
1:17:34 give myself advice the way she might have given it to me, because she tried to make me feel this.
1:17:41 I spent far too much time feeling guilty and far too much time worried about whether or
1:17:47 not I was being a good parent. I mean, this is another thing that she used to be exasperated
1:17:52 with me about. It’s like, all right, Jerry, they’re going to be fine. But the truth is,
1:18:01 and I’ll give myself a little bit of a break, I didn’t have the context. I didn’t have,
1:18:10 God rest my parents’ souls. Coming to understand that they tried, I did not have role models
1:18:22 for good parenting. I had to piece it together from people like Parker or my therapist or other
1:18:29 mentors and elders in my life as I watched how they were doing it, how were they being the elder
1:18:36 in their life, and learned to forgive myself for the mistakes so that with regret and remorse,
1:18:42 I could pick myself up and try again. Can you apologize to your children? Oh my God,
1:18:50 what a powerful tool that is. Yeah, better start apologizing in advance if you don’t have kids.
1:18:58 Build the muscle. Don’t try to win the World Series as your first baseball game.
1:19:04 Exactly. Exactly. Why are you thinking about kids so much these days?
1:19:14 Man, I’m so bored of this business sage on stage stuff. It’s just like I’m boring myself
1:19:21 so much. I mean, look, I’m being a little facetious here, but beyond a certain
1:19:27 base level of needs, we’re all playing games, right? So the trick is knowing what games you’re
1:19:32 playing and then be very hopefully conscious of the games you opt into. What are the rules,
1:19:39 what’s winning, what’s losing, what’s the ranking, what’s quitting time, what are the stakes, etc.
1:19:49 And I feel like family kids is the next big chapter, the next big adventure. I don’t overly
1:19:56 romanticize it. I have almost all my friends have kids. I know it can be an enormous, enormous
1:20:02 pain in the ass. It can involve a lot of sadness and anxiety and you name it, but then there’s
1:20:08 the other side. Enjoy. Enjoy, of course, then there’s the other side of the picture. And a
1:20:14 sense of completion. I mean, let’s shout out. I mean, the best of all the accomplishments I have
1:20:22 ever done, the best has been becoming the father that I needed as a child without a doubt. Yeah,
1:20:27 that’s a big one. A couple of years ago, before I went to Ireland, I was in Wales. I don’t know if
1:20:33 you know the due lectures. You’re going to ask me if I knew Wales. Yeah, I think I’ve heard of it.
1:20:39 But you’ve been to the due lectures. You spoke at the due lectures. I went to, I think, the first
1:20:46 or second due lectures like 2009. It was amazing. I really enjoyed it. They’re fabulous. And for
1:20:51 those who don’t know it, you should check it out. It’s kind of like Ted without all the
1:20:56 performative shit. And with much more confusing street signs. I remember trying to drive, drive
1:21:02 around Wales. This is no Google maps at the time didn’t have international data. And they’re like,
1:21:07 sure, just turn left at would you walk a walk and I get to the sign and I’m like,
1:21:13 that’s 24 consonants. How do you read this? What do you mean? It’s 24 consonants in a row
1:21:21 without a single vowel. No, that’s what I mean. I’m just like, wow, okay. Anyway, so I was at
1:21:30 the due lectures and I was doing a reading from reunion, the new book. And I was maybe the first
1:21:37 three or four pages. It was just the opening chapters. But it provoked such a powerful response
1:21:42 from the group. And as you remember, it’s like you’re in this like old hay barn, cow barn, the
1:21:50 cow shed, I think they call it. And my oldest son Sam had come with me. And at the very end of the
1:21:56 talk, people were sort of, you know, milling about and you know, oh my God, you know, and telling me
1:22:00 what I’d done wrong and telling me what I’d done right and all that stuff, you know what they do.
1:22:06 Right. Oh, that’s very good. Except it was like, okay, the next time you write a book, you can talk.
1:22:16 Okay. Anyway, I look up and Sam, who’s, you know, six one big guy, he’s a Muay Thai fighter and trainer.
1:22:21 He looks up and he just mouths the words, I am so proud of you, dad.
1:22:28 That’s amazing. What a moment. That’s the moment. That’s what you want. You know,
1:22:34 that’s what you live for. That’s what parenting is. Yeah, I feel like I need to make up for lost
1:22:38 time. I’ve been wondering if I need to go like raise the red lantern style. I have no idea.
1:22:46 Maybe just have, you know, survival of fittest, like 40 women and see how we do. I am, I don’t want
1:22:50 to say desperate, but I’m just like, well, I’m a little surprised you’re talking about this,
1:22:56 because are you going to now be inundated? And then you’re going to call me up and say, Jerry,
1:23:02 what do I do? And I’ll say, how have you been complicit in creating these conditions? You say
1:23:07 you don’t want publishing this to millions of people. Yes, nephew, Timmy, I mean, putting it on
1:23:12 the podcast. Well, I had this, you know, I’ll share this, this I haven’t really said to anybody,
1:23:18 but I was, I was spending time with a number of my really close friends. We do this reunion once a
1:23:27 year. And most of them have kids, not all of them. Most of them have kids. And one was echoing this
1:23:34 lesson or conversation he had with someone far older than he, a grandfather, and he kept saying,
1:23:39 you know, there’s nothing more precious than hugging your grandkids. And I started running
1:23:45 the math and I was like, I’m 47. I don’t know if that’s going to be a thing. I don’t know if that’s
1:23:52 mathematically even remotely reasonable for me to entertain. And that fucked me up. I got to be
1:23:57 honest, not because I’ve really thought about grandkids much, but when he put it that way,
1:24:02 and it happened to coincide with my birthday, which was sort of the cause for the reunion. And
1:24:09 I was just like, wait a second here, I’m no mathematician, but fuck me. That was, that was
1:24:14 a tough pill to swallow. I’m not going to lie. I was like, oh yeah, that may not be a thing.
1:24:21 Well, not for publication on this. So I’ll do it over email, but we have a mutual friend
1:24:27 who is in exactly the same place. You guys should hang out, you know, for sure.
1:24:33 Just drink some whiskey and cry ourselves to sleep. Or put the red lantern out and say, I’m
1:24:39 ready. Oh, God, I’m not ready to switch teams yet. That’s tight.
1:24:46 You know, never, never say never. But listen, what are you willing to do for your kids?
1:24:54 She’s like, I’m no biologist, but yes, exactly. Oh, man.
1:24:59 Well, before we move off that topic, let me give you a poem. You’re ready? This is by
1:25:09 Phillip Larkin. It’s called This Be the Verse. They fuck you up, your mom and dad. They may not
1:25:16 mean to, but they do. They fill you with the faults they had and add some extra just for you.
1:25:22 But they were fucked up in their turn by fools and old-style hats and coats,
1:25:30 who half the time were sappy stern and half at one another’s throats. Man hands on misery to man.
1:25:38 It deepens like a coastal shelf. Get out as early as you can and don’t have any kids yourself.
1:25:50 Wow. So should I Sylvia Plath myself today or tomorrow? Jesus, Jerry. Well, he’s British.
1:26:00 Good Lord. I know. I’m famous for reading poems, but usually they make people cry.
1:26:10 She’s like, Dr. Suits meets a star is born. Good Lord. Amazing. All right. Let me try to write the
1:26:17 ship here. So three books, I alluded to these. I’m curious. You’ve mentioned a few books in
1:26:22 our conversations before, certainly your own, which I recommend everybody. Also, When Things Fall
1:26:29 Apart by Pema Children, Faith by Sharon Salzburg, Let Your Life Speak by Parker Palmer. I’m wondering
1:26:36 if any of your kids have been impacted by any of these books or if there are other books you’ve
1:26:43 recommended to your kids, whether or not they’ve read them. Oh yeah. Sam in particular loved The
1:26:52 Wisdom of Insecurity, which is a really, really powerful book. Michael is probably the one who
1:27:00 follows most of my book recommendations. And we go back and forth from novels to nonfiction.
1:27:09 We swap books back and forth. The novel that Michael loved the most was also really powerful
1:27:16 in my life. It’s Call It Sleep by Henry Roth. Call It Sleep. I’ve never really heard of it.
1:27:25 So Henry Roth wrote Call It Sleep in the 1930s. And it tells the story of a young boy, I think he’s
1:27:32 like seven or eight years old, growing up in the Upper East Harlem when it was a Jewish
1:27:38 neighborhood and they’re Jewish immigrants. It was well received and then lost in time.
1:27:48 And it was, I think it was Kazan, the famous book critic who discovered a used copy in The Strand
1:27:58 in Manhattan and then devoured the book in the 1950s and published the first review for a paperback
1:28:06 book in the New York Review of Books. And so the book was rediscovered. Oh, and anyway, I’m going off.
1:28:14 Henry Roth as a novelist was one of the most influential novelists in my life.
1:28:22 It’s a book that I remember when Michael finished it. He sent me the same passage
1:28:28 that I had first read when I was about 17 or 18 years old and was blown away by,
1:28:34 I was like, yeah, that’s the passage. And for those who know the book, it’s the passage where David
1:28:42 is touching a trolley car’s third rail with a soup ladle or milk ladle. It’s really a powerful
1:28:49 passage. Anyway, you didn’t ask about novels. Well, it’s funny that you brought up a novel.
1:28:55 Maybe I incepted you because I was going to ask you actually if there are any novels you
1:29:04 recommend or find, contain and convey a lot of truths that stick out to mine. It doesn’t have
1:29:09 to be the best. But for instance, Zorba the Greek, I think is a standout for me. You remember that.
1:29:14 Good job, yes. So Zorba the Greek, huge standout. I’ve been meaning to read it again.
1:29:20 And some more of the same author’s work. Do any others stand out to you? Because I’ve really found
1:29:26 fiction, which is very closely related to humor, right? Let’s just say Bill Richards or your
1:29:31 therapist, parable. These are all very closely interrelated.
1:29:40 It’s funny that you say this because I just completed volume one of a five volume series.
1:29:45 Do you know the Library of America series? I have either heard of it or come across it. It
1:29:51 does ring a bell. Okay. So Library of America is a nonprofit foundation that seeks to preserve
1:29:58 the writings of amazing American writers. And I think there are over 350 volumes that they’ve
1:30:06 done. Writers like James Baldwin. Anyway, I just finished volume one of Wendell Berry.
1:30:11 And the thing that comes to mind, and I said this to Michael in a text message,
1:30:19 I think this is the first set of novels and short stories I’ve read that have changed my
1:30:26 thinking about writing in a profound way. And what Barry did, and volume one is the material from
1:30:33 Everything Takes Place in the Fictitious Town of Port William, Kentucky. He of course is from
1:30:40 Kentucky, still lives there. And these tell a series of stories, short stories in novellas
1:30:47 and novels, all taking place from the end of the Civil War, in this case through World War II.
1:30:54 And it all involves the same characters or the same extended characters,
1:31:01 but many times the incidents that he writes about are written about from different characters
1:31:06 points of view. And it’s still working on me. I’ve been reading it. I finished it a few weeks
1:31:12 ago, and I’ve been reading it for about three months, because it’s close to a thousand pages,
1:31:16 deeply, deeply moving. I’ll check it out. I have more homework assignments,
1:31:22 which of course I love. I do love my homework. What is the basic thesis of the wisdom of insecurity?
1:31:25 I know this book title, and I’ve come across it multiple times, and I’ve never read it.
1:31:32 It’s Alan Watts exploring, what is that anxiety about? What is insecurity about? What is it that
1:31:40 we are working with? It’s a way of coming to understand the, I guess, you know, if you want to
1:31:45 link it back to what we were talking about earlier, it’s how has it been useful for us,
1:31:48 rather than something that we need to push away?
1:31:54 Got it. How has it been useful, not in a condemning way? How are you complicit way,
1:31:59 but how has it actually been helpful along the lines of the gift of fear by Gavin DeBecca?
1:32:04 That’s right. That’s right. Not something to swat away. It’s not always something to swat away.
1:32:11 How is it a gift? Right. It’s as simple to understand. You know, we’re often told that the
1:32:17 way through insecurity or anxiety is to somehow embrace what’s happening in the moment.
1:32:24 But this actually walks us through. It tells us how to do that. And of course, Alan Watts is
1:32:27 an incredibly important Zen teacher in the Zen Buddhist tradition.
1:32:35 Yeah, he’s one of a kind, that one, and amazing narration as well, the people who want to take
1:32:40 it in, audio format, some spectacular speeches, presentations. Jerry, we’ve covered a lot of
1:32:47 ground here. Is there anything else you would like to mention before we begin to land the plane?
1:32:50 Is there anything else you’d like to say,
1:32:53 ask of my audience, point people to anything at all?
1:32:59 You know, I think I’ve really appreciated our conversation, especially the amount of laughter.
1:33:07 And you actually help remind me of the importance of that. And so let me double down on that because,
1:33:13 you know, it’s kind of a fucked up world we’re in right now. You know, as I’ve been saying
1:33:19 recently, it’s the kind of world where babies get murdered for ideology. And that’s a kind of fucked
1:33:29 up place. And not that that’s material to laugh about, but to understand that there’s a human
1:33:36 connection that can be gotten, even in the midst of all this, I think is incredibly important right
1:33:45 now. So as Dr. Sayers would say to me, you’ve done enough work, go off the grid, go take your time,
1:33:51 go have fun, and laugh your ass off. Good advice. Good advice. I’m going to work on that
1:33:57 tonight. You know something I’ve started doing, and this is related, it’s a bit of a hard segue,
1:34:05 but games, just tabletop games, no phones. Yes. Yeah. Rewind the clock. These things have been
1:34:11 with us a long time. Yeah. Amen. You know what? Can I mention another thing that got stuck in my
1:34:18 mind? What’s up? Which is funny because it was your mention of a stuck record when you were asking
1:34:22 about records. And if I remembered records, the one thing that popped to my mind that I
1:34:28 has been on repeat, which of course, is sort of self-referential in and of itself,
1:34:33 when I was a kid, I had this little, mini, tiny, mini LP. It was the size of
1:34:43 a tiny pancake. It was really small. And it was a song that I played a million times and drove
1:34:49 my parents insane. But they made the mistake of giving it to me. And it’s Disco Disco Duck.
1:34:58 I remember the song. Who wants to be a Disco Duck? And it’s Donald Duck singing the song
1:35:07 over and over and over and over again. Holy shit. What a wonderful song. Oh, and I actually
1:35:13 had some speaking engagement. Like, God, I can’t remember. A year ago, two years ago,
1:35:17 I don’t do too many of them. And they asked me what I wanted my entrance music to be.
1:35:25 I tasked them with trying to find Disco Disco Duck. They were not successful, but
1:35:33 boy can dream. Boy can dream. I mean, what’s frightening is I will not, but I can sing that song.
1:35:42 Everyone, this is my homework assignment to everyone listening. Go find Disco Disco Duck.
1:35:47 That’s right. I’m sure it’s on YouTube. It’s a treasure. Jerry, where would you like people to
1:35:51 find you? You’re @JerryColona on Twitter. We’ll link to everything in the show notes.
1:35:58 They can find a reboot at @RebootHQ on Twitter, reboot.io is the website. You’re the author of
1:36:05 Reboot Leadership in the Art of Growing Up. And also Reunion. Exactly. Leadership and the longing
1:36:10 to belong. You got it. I think tracking me down there on Instagram. I’m @JerryColona.
1:36:16 All sounds great to me. So I appreciate that. Absolutely. And to everybody listening,
1:36:21 we will link to everything in the show notes, including probably some version of Disco Disco
1:36:29 Duck. And the Philip Larkin poem. That’s right. And the Philip Larkin poem. If you’re too happy and
1:36:39 just need a moment of sadness. Tim.plug/podcast. And until next time, as always, be just a little bit
1:36:47 kinder than is necessary, not only to other people, but also to yourself. And thanks for listening.
1:36:54 Hey, guys, this is Tim again, just one more thing before you take off. And that is Five Bullet
1:36:58 Friday. Would you enjoy getting a short email from me every Friday that provides a little fun
1:37:03 before the weekend? Between one and a half and two million people subscribe to my free newsletter,
1:37:09 my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is
1:37:14 basically a half page that I send out every Friday to share the coolest things I’ve found
1:37:19 or discovered, or have started exploring over that week. It’s kind of like my diary of cool
1:37:24 things. It often includes articles I’m reading, books I’m reading, albums, perhaps gadgets,
1:37:29 gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of
1:37:37 podcast guests and these strange esoteric things end up in my field. And then I test them and then
1:37:43 I share them with you. So if that sounds fun, again, it’s very short, a little tiny bite of goodness
1:37:47 before you head off for the weekend, something to think about. If you’d like to try it out,
1:37:54 just go to tim.blog/friday, type that into your browser, tim.blog/friday, drop in your email and
1:38:00 you’ll get the very next one. Thanks for listening. This episode is brought to you by Eight Sleep.
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1:39:45 Okay, this is going to be part confessional. As some of you know, I am recently single and
1:39:50 navigating the world of modern dating. What a joy that is. Sometimes it’s fun, but it’s mostly a
1:39:56 goddamn mess, as many of you probably know. I’ve tried all the dating apps and while there’s some
1:40:03 slick options out there, the most functional that I have found is the League. Why did I end up using
1:40:08 the League? First, most dating apps give you almost no information. It’s a huge time suck.
1:40:14 On the League, you’re starting with a baseline of smart people and you can then easily find the
1:40:19 ones you’re attracted to. It’s much easier. It’s like going to a conference where everyone is smart
1:40:25 and then just looking for the people you think are cute to go up and speak with. So, more than half
1:40:29 of the League users went to top 40 colleges and you can make your filters really selective. So,
1:40:35 if that’s important to you, then go for it. It does work and that is one of the reasons that I
1:40:40 use it. Second, people verify using LinkedIn. So, you can make sure they have a job and don’t
1:40:44 bounce around every six months. It’s a simple proxy for finding people who have their shit
1:40:50 together. It’s infinitely easier than trying to figure things out on Instagram or whatever.
1:40:54 Third, you can search by interest and in multiple locations. I haven’t found any other dating app
1:41:00 that allows you to do this. For instance, I usually search for women who love skiing or snowboarding,
1:41:04 have those as interests as I like to spend, say, two to three months of the year in the mountains.
1:41:09 I’m a rivers and mountains guy. The UI is a little clunky. I’ll warn you, but it’s incredibly
1:41:15 helpful for finding good matches and not just pretty faces. So, you can search by interest and
1:41:20 specify multiple cities. So, to summarize a few things that I think make it stand out. Features
1:41:25 available on the league include multi-city dating, LinkedIn verified profiles, ability to block
1:41:31 your profile from coworkers, bosses, family, etc. That’s very easy to do. You can search by interest,
1:41:36 you can get profile stats, and there is a personal concierge in the app. So, there’s someone you can
1:41:41 text with within the app as a personal concierge to get help. So, what am I looking for? I am looking
1:41:47 for a woman who is well-educated, who loves skiing or snowboarding or both. These are, and I’ve used
1:41:52 this word already, proxies for like 20 other things that are important. So, just I’ll leave it at that
1:41:59 for now. Someone who’s default upbeat likes to smile, smiles often, glass half full type of person,
1:42:04 who would ideally like to have kids in the next few years. Her friends would describe her as feminine
1:42:09 and playful, and she would love polarity in a relationship. She’s athletic and has some muscle.
1:42:13 I like strong women, not necessarily bodybuilders, but you get the idea. It could be a rock climber,
1:42:18 dancer, whatever, but has some muscle, loves to read, and loves learning. If this sounds like you,
1:42:24 send hashtag date Tim. So, hashtag date Tim. In a message to your concierge in the app to get us
1:42:29 paired up. So, these are all reasons why I was excited when the league reached out to sponsor the
1:42:34 podcast. They even have daily speed dating where you can go on three three-minute dates with people
1:42:39 who match your preferences all from the comfort of your couch. So, check it out. Download the leak
1:42:44 today on iOS or Android and find people who challenge you to swing for the fences
1:42:49 and who are in it to win it. I found it to be super fascinating. You can really get good matches
1:42:54 instead of just looking at pretty faces and kind of rolling the dice over and over again. Much better.
1:43:00 So, download the leak today on iOS or Android and check it out. Message hashtag Tim to your
1:43:05 in-app concierge to jump to the front of the waitlist and have your profile reviewed first.
1:43:12 So, check it out. The leak on iOS or Android.
1:43:22 [BLANK_AUDIO]