Please enjoy this transcript of my interview with Jerry Colonna, CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong.
Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!
Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.
DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:
Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.
WHAT YOU’RE WELCOME TO DO: You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the tim.blog/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.
WHAT IS NOT ALLOWED: No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on tim.blog or (obviously) license photos of Tim Ferriss from Getty Images, etc.
Tim Ferriss: It’s nice to see you.
Jerry Colonna: Good to see you.
Tim Ferriss: I was so pleased with how much from our prior conversations has stuck with me. I just wanted to tell you that and also to ask you, is there anything that you have repeated or shared that to you is the equivalent of The 4-Hour Workweek in terms of being the blessing and the curse that you just can’t seem to shake, for better or for worse? Because I know we’re going to talk about legacy, but specifically I’m wondering is there a point when you get tired of hearing some of your own profound questions echoed back to you? Specifically, can you guess which one?
Jerry Colonna: How have I been complicit?
Tim Ferriss: Yes. Yes.
Jerry Colonna: I don’t get so tired of it. I will tell you that I get tired of the misinterpretation that goes along with that.
Tim Ferriss: Okay. Would you mind laying out the context of this question? What is the question? And then would love to hear you expand on misinterpretations of the question.
Jerry Colonna: So what is the question? Or what [were] the conditions that caused me to ask that question, initially, of myself?
Tim Ferriss: Let’s do the question because we covered — actually, you know what? Let’s rewind the clock all the way. Let’s do both. And for people who are like, “What the hell are they going on about?” This is a question that I revisit a lot. Maybe I’m revisiting it the wrong way. So we will find out shortly. But yes, if you could just explain the genesis story, then the formation of the question, and then how people misinterpret it? If that order makes sense to you, that would be I think a great place to start.
Jerry Colonna: Sure. And the genesis story, the origin story, isn’t that complicated. If we go back in time to my mid-30s when I was a prince of New York and a former VC and totally fucked up as an individual, I was knee-deep in the first decade. I’m now in my fourth decade of psychoanalysis. And I had a very tough-as-nails nice Jewish lady psychoanalyst named Dr. Sayres. And what she taught me repeatedly, endlessly, boxing my ears when she’d say this is, “How have you been complicit in creating these conditions you complain so much about?” And you have to picture it. I’m lying on the couch. There’s this old Jewish lady who’s 30 years older than me, who’s just basically had it with me complaining.
And so the roots of the question are really a kind of an exasperation, not just from my analyst to me, but eventually with me about me. And it was really only by taking that question, “How have I been complicit in creating the conditions I say I don’t want?” that there was a massive unlock for me. Now you asked about the misinterpretation. The first level of misinterpretation that people go through is that they assume I’m saying “How have I been responsible,” and I am very, very particular. I get very, very angry when people misinterpret the word “complicit” for “responsible.” And it’s not because I want to let people off the hook, but quite the opposite. I want people to understand that they’ve been an accomplice. See, here’s the thing, Tim, when we get into our mindset that says, “I am responsible for all the shit in my life,” we’re actually walking away from doing the hard work.
Tim Ferriss: Could you expand on that?
Jerry Colonna: Yeah. Sure. Because guilt is a defense mechanism.
Tim Ferriss: Right. Because some people might say, “Well, that’s extreme ownership if I say I’m responsible for all the shit in my life.”
Jerry Colonna: Exactly.
Tim Ferriss: That’s the beginning of the solution, but where do they take a wrong turn?
Jerry Colonna: Right. So I like the kind of ownership — I like the word “ownership.” I don’t like the word “responsibility.” And the reason for that is because — and the reason I think it can be a defense mechanism is because it can be an old structure. So many people that I encounter, myself included, spend our childhood pendulating between grandiosity and a sense of worthlessness. “I’m either shit or I am the best.”
Tim Ferriss: You got rid of that in your childhood? Man, good for you.
Jerry Colonna: Well, I got rid of it in my adulthood. But this is the point.
Tim Ferriss: I’m just joking.
Jerry Colonna: I got rid of it by actually asking the right questions of myself. See, if the word “complicit” is replaced with the words — even “extreme ownership,” the danger is that I tip over into misunderstanding what actually has been going on and I end up in this zone of being responsible for everything. And the truth is it’s much more complex than that.
Tim Ferriss: I was just thinking that you’re referring to a pendulum and that not taking any responsibility for anything is one example of absolving yourself of the hard work. But I never thought of the opposite. If you’re accepting that anything and everything bad that happens is your responsibility/fault, it puts you in a similar position, it seems.
Jerry Colonna: Exactly. And the position it puts you in is unable to actually, with discernment, diagnose what’s really going on. And you know what? You don’t get to transform stuff if you don’t really know what’s going on. And so to understand what’s really happening for you, you have to understand what your role is and what it isn’t.
Tim Ferriss: So how do you walk, say, a client through answering that question well? “How are you complicit in creating the conditions that you say you don’t want,” or “the conditions of your lives and your lives that you say you don’t want?” How do you walk them through their rough draft of trying to answer that?
Jerry Colonna: Okay. So the unlock on the question is the second half of the question, which people skip, “You say you don’t want.” So give me an example from your own life, Tim, what do you say you don’t want?
Tim Ferriss: Oh, man. How much time do we have? I have become better at this, so not dodging the question, but I would say probably some form of busyness, like, “Ah, I’ve got 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 blocked out space for writing or making.
Jerry Colonna: Right. So you say, Mr. 4-Hour Workweek, “I don’t want to work more than four hours a week.”
Tim Ferriss: Nice turn. Nice turn. I think you said that to me in our first conversation.
Jerry Colonna: 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, wear Breathe Right strips as you talk to — right. This kind of thing. Right? Okay. Now —
Tim Ferriss: Just a quick sidebar. Breathe Right, this one’s on me. Next time you’ve got to sponsor the podcast.
Jerry Colonna: I could recognize them because I’m a Breathe Right user. I use them to sleep at night. So —
Tim Ferriss: Oh, my God.
Jerry Colonna: And we would both like a lifetime supply. So feel free. Okay. So you say you don’t want to be so busy. And you were asking, “How do I walk a client through to understand the role of complicity in this regard?” So how does it feel when you’re not busy?
Tim Ferriss: Right. I would say, and I don’t want to go and steal your thunder here, but since I’m cheating with a cheat sheet. This is —
Jerry Colonna: It’s your show. So it’s your thunder.
Tim Ferriss: And action. So segueing to a complement or maybe a necessary component of the first question, “How are you complicit in creating visions 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. Even though I haven’t experienced anything close to that magnitude of desperation and darkness in a very long time, there is a fear that if I create a void, that is the voice, that is the narrative that is going to come to dominate my thoughts. I would say that therefore my complicity serves me by avoiding that.
Jerry Colonna: Right. And so if you really want to transform, when will you be comfortable with the void?
Tim Ferriss: That’s a good question. And in my defense, Your Honor, I will say that I’m about to go off the grid for a week starting this Friday. So in a few days, I’ll be going completely off the grid, no phone, no nothing for a period of time. So I have injected these periods. But let’s get into the messy stuff for a second since life is rarely as much of a randomized controlled trial as we would like. I’ve had an ongoing number of chats with friends on WhatsApp and different messaging platforms. And it’s been around taking breaks, creating space, chilling out. So a lot of these friends of mine have passed every hurdle and objective they could have had. And the goalposts keep moving. They wanted to make a million and then it was 10 and then it was 20 and then — once that gets —
Jerry Colonna: A trillion.
Tim Ferriss: Then it’s a trillion. Once it gets indefensible, then it’s like, “What’s your annual compounded growth rate,” and this, that? Turns into percentages because they can’t even with a straight face defend the rest of it. But what they claim to want and what they believe I need is to chill out, take a break, create all this space. My experiences as [a social animal], or at least as a person who benefits from social interaction, I do best around other people. I just do. And there are — it’s not a hundred percent, but it’s not zero percent. There’s a risk that I do return to some of those dark places or dark narratives. It’s not zero. So I struggle to answer the question of when can I allow space, because I do it in small doses, sometimes larger doses. I took almost all of October last year off the grid. So perhaps you can help me to find my way to answering the question you posed.
Jerry Colonna: Look, Tim, I feel like Uncle Jerry in that we speak every few years and every few years, my, how you’ve grown.
Tim Ferriss: Oh, thanks.
Jerry Colonna: I know you don’t feel that way because you’re in your body, but when we first started talking, which was years and years ago, this was a big struggle for you. This was a tremendous struggle. And there was a sense that you might miss out. There was a sense of you being falling behind in some sort of weird little race, a race to the top. And I think the speed with which you’re able to go right to the fear of the void, what Blaise Pascal identified when he said that all of man’s problems stem from their inability to sit alone in a room, I think you’ve got — like a lot of us, you’ve got a component of that. And I also want to say I’m watching you letting go of the need to turn that void time into productivity time.
When I first started promoting the notion of sabbatical, which we’ve talked about in the past, I remember dealing with a client who would say, “Well, I’m going to learn Portuguese.” It’s like, “No, you’re not. You’re not going to learn Portuguese in four weeks. You’re going to learn to breathe without Breathe Right strips. You’re just going to learn to enjoy yourself.” Now, what I hear you doing is learning to enjoy yourself, which is a really powerful skill.
Tim Ferriss: Yeah. Yeah. It’s going to be a lifelong project, which is okay. A lot of things are lifelong projects.
Jerry Colonna: That’s right.
Jerry Colonna: We got here because you were asking about that process, and this is the process. This is the process. So for you, when you’re off the grid starting Friday, what will that experience be like for you? At what point might you be anxious? And at what point might you start to relax? Are you going to be with friends this trip too?
Tim Ferriss: Yes. This particular example may not fit the exercise, but what I’ve done for the last handful of years is every year I do a past year review. Rather than setting, let’s just say, blind, semi uninformed, overly optimistic New Year’s resolutions, I look back at the past year and figure out what the highs and lows looked like if I were to do an 80/20 analysis. Places, people, activities, the most life-giving and the most life draining. And then I schedule time as soon as possible in blocks of one week, two weeks, depending on availability to spend time with energy and people doing energy and things.
And this particular week off the grid is going to be an alpine elk hunt, which I do once every two years or so, with bow, at probably between 10 and 12,000 feet for most of it. It’s going to get cold. We’re going to be eating a lot of shitty freeze-dried fruit, hopefully a bunch of trout en route to finding elk. And I have just found that particular experience and the time dilation that it allows to feel like a month off or two months off. It is just so regenerative for me that it’s become a core piece of my annual planning, not necessarily a hunt, but that type of shared experience with a small, very small, group of people. So that’s what that will look like. And in a sense, I don’t want to say I’m disallowing myself from feeling discomfort because there’s going to be incredible discomfort physically. Sleep is probably not going to be fantastic. And we’ll be very, very, very active. But it’s not the same as doing a silent retreat and sitting there watching your monkey brain just contort itself for 16 hours a day.
Jerry Colonna: It’s the kind of retreat where layers of your skin are stripped away because you’re so raw and rugged out in the world. And that’s just going to drop you into your body and drop you more and more into the land. And that’s a place of nourishment for you, for sure.
Tim Ferriss: Yeah. Let me ask you if I could, how often do you find with your clients, or your team find with their clients, that the fix is 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 a thing. And the reason I ask is that for me, let’s just say taking a trip like this, it is such a restorative reminder of how what I want and need is simple and right in front of me. But that comes through for me at least often, not always, but physical movement, sometimes physical hardship where — as they say in dog training, a tired dog is a happy dog. I think humans are pretty similar.
Jerry Colonna: Well, we’re both mammals, right?
Tim Ferriss: Yeah.
Jerry Colonna: You asked how often. I would say 95 percent of the time.
Tim Ferriss: Wow.
Jerry Colonna: I would say you’re finding your way. I’m older than you, Tim, so I get to be the wise one. But you’re finding your way to that really inherent wisdom. And my take on the Cartesian, Descartes notion is instead of it being “I think, therefore I am, I am, therefore I think,” and that’s where all the problems begin. What you’re really talking about is getting into the essence of your existence. The only cautionary note that I would sound is when we start to invade the productive thinking into that tired dog effort, meaning, “I’m going to do this so that I…” I mean, the worst case is, “I’m going to do this so that I lose weight,” or, “I’m going to do this so that I can look better,” or, “I’m going to do this so that I can,” I don’t know, “Quiet some negative self thought.” And I think you’re beyond that. But I would say to those listening what I have found is when I can let go of even those things and just get dog tired, then I’m happiest for sure.
Tim Ferriss: Yeah. It was definitely possible to run towards things, run away from things. And I think with athletics, movement, it’s not necessarily a condemnation to be wanting to quiet something because you may just have too much inherent physical energy and it has no vehicle through which to dissipate. So it just creates the —
Jerry Colonna: Yeah.
Tim Ferriss: — kind of devil on your shoulder, creating all these fairy tales to drive you insane. And I do think that quieting that by dissipating the energy through exercise makes a whole lot of sense. But if there’s a persistent problem that you’re trying to avoid that requires attention, then it’s a different matter altogether.
Jerry Colonna: 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. Sayres, used to say to me all the time, “Enough, Jerry. You figured it out. Now go take a break.” But it gives you insight in what was going on in that session room. But it’s really important that we let go of those things that are driving us. And that’s not bypassing. When you go on this elk hunt, I mean, maybe you’re avoiding a conversation that you’re supposed to be having. To use one of my other questions, maybe you’re not saying the thing that you need to say. But I suspect at this point what it’s doing is it’s giving you the ability to come back to the stuff that you 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.
Tim Ferriss: That’s how I feel. And it’s also planned so far in advance at this point that it’s not a reactive — it’s proactively, basically, injecting turbo boosters on my physical and mental well-being so that I can bring that back to everything else. And you mentioned a few things just a moment ago, that I just want to reiterate for folks. And this, I believe may be the same therapist, could be a different one, taught you these questions to ask when in existential pain. What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing? Am I getting that right?
Jerry Colonna: That’s right. Well, she taught me the first question, and it was again, a moment of exasperation, when I had been hospitalized with a really terrible migraine and spent a week going through neurological tests only to find out that there was nothing physiologically wrong with me. And in the first session back, she looked at me and she said, “What are you not saying that you need to say? You need to talk more.” So when you see those questions, please hear that voice. And I’ll add, by the way, that those questions have sort of bounded around the internet the way a lot of my questions do. And one woman wrote back and said, “Here’s another one. ‘What are you hearing that’s actually not being said?’” Which —
Tim Ferriss: That’s a good one. That’s a good one.
Jerry Colonna: That’s a really good one.
Tim Ferriss: That should be on my bathroom mirror.
Jerry Colonna: It’s a really good one. That’s right.
Tim Ferriss: What are you hearing that’s not being said? Oh, that’s good. That’s really good.
Jerry Colonna: Because boy, oh, boy, do we tell ourselves stories, eh? What we’re getting at in all four of the questions, and really in much of this conversation, is the importance of not bullshitting yourself. The importance of not bypassing what’s really going on for you. And I have found, in my 61 years now, that that is also a lifelong practice. That my capacity to bullshit myself continues unabated. And no matter how progressive I think I am, and evolved I think I am, my ability to be deluded by my own mind knows no end. So I have come to see that as just a part of the human condition. Maybe when I’m as old as my friend, Parker Palmer, who’s 86, I’ll have the wisdom of not being able to bullshit myself.
Tim Ferriss: Parker Palmer, also the author of one of your favorite books, I believe. Let Your Life Speak?
Tim Ferriss: I want to overlay a few more questions that can be used that I took note of when I was reviewing our past conversations that I really like. I don’t yet have kids, so one of them won’t totally apply to me, although it could apply, I guess it could be hypothetical, but ways of edging into what’s actually going on, right? Circumventing that bullshitting that we’re all incredibly good at doing. And it may not be, I guess it often isn’t, conscious bullshitting, right? Where we know we’re lying to ourselves.
Jerry Colonna: Right.
Tim Ferriss: It may just be a really compelling narrative that isn’t true. 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 “No, really, how are you doing?” And then the little trick of asking people if they want their kids to feel the same thing that they’re feeling when they get to be the same age. And if they don’t, it prompts them to start reorganizing their lives and — sorry for the wind, I’m next to a river. Such things happen.
Jerry Colonna: Right.
Tim Ferriss: And there are more, of course, but what I was curious to ask you is, and I’ll segue into this by way of an anecdote, there’s an amazing, fascinating sage man named Bill Richards. And Bill Richards wrote a book called Sacred Knowledge. He is a religious man and also I think he may be an ordained minister, something along those lines. He also has the distinction of having administered hundreds and hundreds of psychedelic-assisted therapy sessions, both before and after prohibition.
And last time I spent time with him, he kind of looked like Santa Claus, amazing, big white beard, kind of jolly old elf type of feeling, always smiling with a little twinkle in his eye. And I spent some time with him probably eight years ago, something like that, near Johns Hopkins, where he’s done a lot of work and I was asking him some question about doing the work. This is a phrase that comes up a lot in personal development circles: dealing with your shadow self and X, Y and Z. It can take a million different forms. Doing the work. And he said something to me that has stuck ever since. And it was along the lines of, “Well, you know the tricky part about doing the work?” And I was like, “I don’t, what’s the tricky part?” And he’s like, “There’s a very thin line between doing the work and just picking on yourself.”
And he said a few things to me that day where afterwards I was like, “Fuck.” I just thought it was funny, but there’s actually a lot to unpack there. And how do you help clients or how do you think about helping people to distinguish between the two, right? Because there can be a degree of trauma fetishizing and past fetishizing where people are doing everything and anything to just revisit every mishap of childhood, every mistake their parents made. And the dose makes the poison, it seems like Paracelsus said so long ago, not in English, obviously. And how do you think about navigating that?
Jerry Colonna: I think it’s a brilliant question, and I think it’s something I probably, as I’ve slip-slided my way into elderhood, have begun to finally let go of in my own life. And so when I think about supporting other people, what comes to mind is really — I mean, think about the way Bill responded to you. Think about the way Dr. Sayres would respond to me. I think about the conversations I have with my elder friend, Parker. It’s always laced with humor.
And it’s the humor that cuts through it. It’s humor, forgiveness, and not in this kind of, I don’t know, self-development book bullshit self-forgiveness thing that’s out there, but genuine care and concern. I mean, I’ll give you an example.
Tim Ferriss: Yeah, please.
Jerry Colonna: I wrote a book that came out last year called Reunion, and part of that journey was really reuniting, to use language from the book, with the parts of myself that I had disowned. But more importantly, my ancestors. And in this case, I went into a relationship with my father. Now, my father had died 32 years ago. And in unpacking his story, what I came to have a new relationship with was his own depression, his own alcoholism. And I unpack — to spoil the plot, my dad was — on his wedding day, his mother was so angry at him for marrying my mother, that she screamed from the back of the church, “Putana! Putana! Putana!” “Whore! Whore! Whore!” And because my mother was pregnant at the time. And then she screamed out, “You are not my son. You were adopted.”
Tim Ferriss: Jesus. That’s so hardcore.
Jerry Colonna: Yeah, that’s how my father found out he was adopted. And I grew up — as we’ve discussed before, my mother was mentally ill and my father’s depression and alcoholism really marked my childhood. And I would say that I spent most of my life being angry with him. And this is to the point of the forgiveness. And I think that what happened was in writing this book, I started to really step into his body. What would it be like to be 18 months old? Because it turned out that he was given up for adoption at 18 months old, and he was given up and raised by the only parents he knew, an Italian-American couple. And the reality is his biological mother was an Irish immigrant to New York, who gave birth to him when she was 20.
And I ended up in Ireland at her grave site, not only forgiving my father, but forgiving her. And I did that. I tell that story in this book, but more important to your point, I think that that laughter came about from forgiveness. I actually can feel myself going, “He wasn’t so bad. He did the best he could and he got a raw deal. And some of the things he did sucked, but not bad.”
Tim Ferriss: Was that incremental a hundred different realizations adding up over time, or were there any flashpoints where there were particular experiences or insights that covered the bulk of the traverse from anger to forgiveness or acceptance in the way that you just described it?
Jerry Colonna: It’s interesting, because we were talking before about the physical being, the somaticized being. And there was a moment, but it wasn’t an insight, meaning it wasn’t a thought. And I talk about this as well. My youngest son is named Michael, and he was a junior in college and he did a semester abroad in Dublin. And one week for my birthday, I went to Dublin to visit with him, and we went to visit — his girlfriend was there as well. She was also taking a semester abroad. And we went to visit the printing museum in Dublin.
Tim Ferriss: Printing?
Jerry Colonna: Printing. And we’re walking through the museum because we’re freaking nerds looking at old print presses. And I’m explaining to him how the machine works. And he’s looking at me like, “You’re bullshitting me, Dad.” And it’s like, “No, no, no. My father worked in a print shop. I remember walking through the print shop and seeing molten lead flowing as they would refire the lead type, and that the sparks would fly as they were doing this.”
I remember all of this from when I was a kid. And I was explaining all of this, and I look up and they have this replica copy of the equivalent of the Irish Republican Declaration of Independence. And it was actually at that moment that I had this profound visceral experience of my father. Which was not an insight. First of all, my father would’ve loved walking through the museum with his son and grandson. And all of a sudden, I realized that the folks who had put up that poster originally and declared their independence were the kinfolk of my father, which was a very different and powerful word for me.
And about a year later when I was at the churchyard and grave site and visiting my grandmother’s grave, it’s still weird to say this, because I never knew her, and I was walking through this tiny little graveyard, I realized that I was surrounded by the bones of my kinfolk. And Tim, that was not an intellectual experience, that was not an insight, that was a viscerally felt experience. I look up and I see the light slanting through the trees, and I swear to God, I felt like I could hear my grandmother at four years old running down the lane.
Tim Ferriss: What a story.
Jerry Colonna: To bring it all back, I feel like because of that experience, I closed a wound that was transgenerational, transpersonal, and intergenerational.
Tim Ferriss: This prompts me to want to ask a few different questions. And I’ll first say that personally, I’ve found tremendous value in metabolizing a number of things from the past. I’ve had some horrible things that happened to me as a small child, so it seems seemed important for me to at one point contend with that or triage it, process it in some way. Now, if I were to take, not necessarily devil’s advocate position, but look at, for instance, many people I’ve interviewed on this podcast, there are some, and I’m probably misquoting, but it’s not going to be too far off. I remember chatting with Marc Andreessen, one of the most storied, famous and successful venture capitalists of our age, also an incredible technologist in his own right and coder/product developer, Mosaic being among his achievements.
He answered, it may have been — I think his billboard was “Raise prices” as billboard answers. So that’s not it. But there was some type of — perhaps the question was related to “If you had to live your life with one mantra, what would it be?” And it was some version of “Forever forward.” And he told this story of a character in a detective novel who has arrows tattooed on his shoulder pointing forward to remind him “Always forward.”
And many of the most effective people, I don’t know if they’re the most content people, I don’t have that window into them, have a philosophy along these lines. You can’t change the past. You can change the future. Pay attention to your thoughts, behaviors, habits, those all form your destiny moving forward. There’s a very forward-focused view. And it works for a lot of things. Then let’s just say on the opposite end of the spectrum, I’m sure there are very, very successful people who also spent a lot of time metabolizing the past. I know quite a number of them. But there are also folks who get so focused on the past, 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 past is this unalterable, basically shaping of a sculpture they cannot undo on some level. They can’t seem to escape the vortex, the gravitational pull of the narratives they have about their past. How do you help someone find the right blend of past focus versus present or future focus? I know that’s a very, very long lead up to the question, but it’s something I do think about a lot.
Jerry Colonna: I think that you are identifying a real challenge in the human existence, and I’ll reframe it just slightly and take us back to the notion of bypassing. I can argue that those who are only forward-looking with no awareness of the past, maybe bypassing, as you know from your own experience, ignored trauma, can stay in the body, can affect us forever.
But the fear that many people have, and one of the reasons why we struggle to sit alone in a room is that we’re afraid of our thoughts. And the thoughts are either about the future or the past that we’re afraid of. Many people fear being trapped in the past. So your question is how do you balance those two? Which is a great framing of it. I often think of the Carl Jung quote, which is, “I am not what has happened to me. I am what I choose to become.”
And I think that no one would ever accuse Carl Jung of ignoring the past, but seeing it as, if you will, the source material of what the future is. The reason we open the closet that is really fucking messy is so that we can straighten it up and close the closet door and move on. Because the stuff in the closet that’s ignored and messy has a way of busting through the door and messing up our lives.
So I think part of your question too is how do we get somebody who’s stuck in the past to move forward? Is that a fair statement?
Tim Ferriss: Yes. Yes. I think that the trend seems, at least in certain places, to have swung pretty extremely from the sort of Gordon Gekko, let’s just say, pure machine with just enough reflection on the past to take advantage of new opportunities, but not much more, all the way back to sometimes what I would say very self-indulgent past reflection and oversharing. It’s like, “Okay, you wrote the script. You’re on your 247th rewrite, maybe it’s time to stop writing.”
Jerry Colonna: Yeah, yeah. I’m going to parse things a little bit.
Tim Ferriss: Please.
Jerry Colonna: I don’t feel comfortable criticizing someone for “oversharing.” Having grown up with the consequences of far too much silence and secret keeping, I know the detrimental effects of that. What I really liked though, is your word, overworking, and I keep thinking of dough. Bread dough. When bread dough is overworked.
Tim Ferriss: Yeah, I was actually thinking of clay and Play-Doh, but then I chose to use the writing, because I know it better.
Jerry Colonna: Yeah, there is that tendency to overwork it. What I have found to be helpful is a Buddhist aphorism, which I’ve used often, which is “This being so, so what?” And what’s powerful about that, it’s not “So what, who cares?” It’s “So what are you going to do about it?” Which is that forward momentum. Whether it’s mere wounds which we all have, or trauma, which many of us have, re-traumatizing ourselves by replaying and overworking it doesn’t release us. But acknowledging what has happened and then really empowering yourself to say, “And what will you do about it?” I think that’s the unlock. I think that’s the balance point that you’re looking for.
Tim Ferriss: And I’d love to actually say something related to your push-back, which I think is valuable and valid in the sense that you mentioned being on one end of the spectrum. If you come from a family and a place of withholding and silence and stiff upper lip, not communicating feelings, experiences, etc.
Jerry Colonna: Or worse, secrets.
Tim Ferriss: Or worse, secrets, right. It can be very therapeutic and very healthy to push yourself towards the other end of the spectrum, recognizing you’re probably not going to end up at the furthest diametrically opposed point, which is something I do think is unhealthy, which is performative trauma. Literally, I have been at cocktail parties in Austin, where I meet somebody, and this is prior to my divulging my own abuse when I was a kid, and literally the fourth sentence out of their mouth is something about extremely graphic trauma. And I’m like, what are we doing here exactly? I don’t think this is for your healing benefit. And it becomes performative in a sense.
So I suppose I just feel like that is unhealthy, also not just to yourself, but to others in a way. It, I think can diminish how severely some of these things impact other people. Just because a person happens to have gotten 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.
But happy to sit on related topics for a second, but I’m very curious, at Reboot, so Reboot.io, you’re the CEO, co-founder, you have lots of clients. The capacity of executive coaching, leadership development, et cetera. When did Reboot start? When was it founded?
Jerry Colonna: July 2014. Roughly.
Tim Ferriss: So 2014. Perfect. So it’s almost a decade ago.
Jerry Colonna: Oh. Just over.
Tim Ferriss: Just over a decade. You’re right. Just over a decade ago. Have you seen any changes in the types of challenges people are contending with, or are they mostly the same? I’m just wondering, as technology has changed, as social dynamics have changed, as the world has accelerated, have you seen any problems crop up more and more, or less and less? Or is it the same old stuff that we’ve been talking about for thousands of years?
Jerry Colonna: It’s about both, I would say. I think that there are unique expressions that have emerged. I think that there is a global tension that exists in the world right now, that, sure, there have been called left-right tensions, whatever language you want to use, those tensions have existed. But it feels heightened right now.
And you couple that, and this, I think, is relatively new, 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, after the Hamas attacks on Israel on October 7th, ended up having to shut down Slack for two weeks, because there was no discussion, it was all argument. And, quite honestly, a lot of the argument from all sides felt performative, to use a word you were just using.
And, not necessarily designed to really move the conversation forward in some way or another. This being said, human nature is human nature. And, it’s why coaching is actually a good business model. Much of what happens continues to happen. I mean, I can’t name the company, but I met a new client. I rarely take on new clients. But I fell in love with this kid when I first met him, very, very hot young company. Not quite the clusterfuck it was six months ago, but pretty close. And, as I’m sketching out on a dry erase board, everything that has happened and will happen, everybody was like, “Well, how do you know?” I was like, “Because I’ve seen this a thousand times. This is what we do. This is called dysfunctional startup, and here’s the path, and it’s going to be fine. It’s going to take a year and a half to two years.” I hope that addressed your question. I don’t know. I may have gone off on my own tangent.
Tim Ferriss: Well, let me home in on one particular concept that I’d love for you to expand upon or just riff on. And I may have it transcribed, noted down in front of me incorrectly so you can fact check me as well.
But it’s around the discussion of guilt. And part of the reason, I think, guilt can be such a powerful driver, a negative driver, in a lot of cases. I think, guilt and prestige, often terrible motivators, to quote Maria, or reference Maria Popova, but the guilt I think also seems to be having quite a moment, because when you are waterboarded with disaster and crisis globally, 24/7, it’s hard not to feel like you are not doing enough. But this is what I have written down: guilt is self-focused, whereas remorse is about the other person. So if you find yourself ruminating in guilt over something, that’s when you bring attention to that and say “Easy boy, easy. You’re a good man who sometimes fails to live up to your aspirations.” The first part is what I wanted to ask you about. Could you say more about guilt being self-focused, versus remorse? I just wanted to make sure I understood this clearly.
Jerry Colonna: I often think of my Buddhist teacher, Sharon Salzberg, whose line about that is: “Guilt is self-lacerating.” Which I find really a compelling image.
And what it does is it keeps us — here’s an old reference. You may get it, because you may have had record players, where the needle is stuck in the groove. And, just again, and again, and you’re ruminating, and you’re spinning, and you’re like, “Oh, shit. Why did I do that?” Whereas there’s no opportunity for growth. There’s no opportunity for learning. 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 a social science take on this question. I prefer the word “remorse” to the word “regret,” But I think, for this instance, you can substitute them. And there’s something very, very powerful that’s embedded in that is the learning. And I think that that’s what you’re reaching for here is when we allow ourselves to internalize remorse or regret, we’re opening ourselves up to other people, to knowledge, to growth ultimately.
Tim Ferriss: How do you do that without slipping into guilt? So if you’re talking to somebody and they’re like, “Fuck. I shouldn’t have done that. God, I feel so badly and terrible. Dah, dah, dah, dah. I always do this.” That’s an exaggerated version. But if they’re in a loop of self-lacerating guilt, how do you move them towards one of these close cousins that is perhaps —
Jerry Colonna: More healthy.
Tim Ferriss: Exactly. How do you do that?
Jerry Colonna: If you think about the setup, the setup more often than not, if I am often plagued by negative self-talk, I am going to be more subject to that ruminating guilt, because I tend to see the thing about which I feel guilty as evidence of my shittiness as a person. And if that’s true, then the movement is towards decoupling my sense of worthiness as a person from the action. So good people do bad things all the time. Good people who do bad things who don’t learn are less evolved, less mature, than good people who do bad things who then learn through regret and remorse, but they remain good people. Does that distinction help?
Tim Ferriss: It does. Are there any prompts or exercises that you would potentially assign, could be something else, to a client who has developed the habit of negative narratives around self-worth, because they did A, B, and C? That’s just a reflexive habit that they have. Is there any way that you suggest they reframe things or start training their mind to go in a different direction?
Jerry Colonna: Yeah, I mean, I hate to sound like a broken record again. But, how does it serve you to think ill of yourself?
Tim Ferriss: Any patterns in responses? Are there any common threads that you hear in response?
Jerry Colonna: Sure. Sure. In some family of origin structures, for example, the way I can know that I belong to my family is by turning to negative self-talk. Just like the way I could know that I belong to a family is by seeing myself as a victim, right? If I grow up with parents who see themselves as victims, that might be the way in which I interpret the world. And so, by starting to unpack that and really taking a look at the way, to use my phrasing, it serves you to think ill of yourself, it begins to raise the consciousness that releases you from having to repeat the pattern.
Tim Ferriss: So let’s hop to a topic that you mentioned as we were brainstorming various directions to go in this conversation. And I have none of the fleshed out context, which is perfect. It’s boring for me to know exactly what’s coming.
Jerry Colonna: Me too.
Tim Ferriss: Legacy. Legacy seems to be something that you’re thinking about. And I suspect we could have a meaty conversation about this. So I’ll let you kick it off in whatever way you think makes sense.
Jerry Colonna: Well, I was joking before I talked about feeling like I’m slip-sliding into my elderhood.
Tim Ferriss: Could be the title of your next book.
Jerry Colonna: That’s right.
Tim Ferriss: Slip-Sliding Into Elderhood.
Jerry Colonna: That’s right.
Tim Ferriss: 10 Easy Life Lessons from Uncle Jerry.
Jerry Colonna: Well, but that’s where I feel like I’m entering this period, Tim. I’ve done two books now, I’m starting to think about what do I want to do, what is next? And, I’ve been thinking about these themes of redemption. I’ve been thinking about themes about legacy, and what does it mean to look at — and in some ways, very similar to the conversation we’ve been having, to look back on the past in order to move forward in the future. And, I think that — 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?”
Jerry Colonna: Which, I don’t know, maybe that is the definition of legacy. But I think about it really more in terms of three different circles of impact and influence that I have, the first circle being myself. Am I proud of the man I’ve become? The second is, my children and descendants. How do I want them to look back on me? I mean, I fucked up royally. And yet, for some unknowable reason, my 27-year-old wanted to spend five days camping with me this summer. Can you believe that? Because I would never have wanted to spend five days trapped in a Sprinter van with my father.
And then the last circle is, how have I left the world? I hope, for example, all of the work that I have done made an impact on you, Tim.
Tim Ferriss: I wouldn’t have all these notes in front of me if that weren’t the case.
Jerry Colonna: When we were celebrating your 10th anniversary, I sent a note, I sent a video, and I was telling you, I’m proud of what impact you’ve had on people.
Tim Ferriss: Yeah, I really appreciate the video. Thank you.
Jerry Colonna: I don’t know this to be true, but the story I tell myself is, you didn’t start this podcast to have an impact on some random 22-year-old kid who’s a little lost.
As I experienced it, you started this podcast to answer questions that you had about your own life.
Tim Ferriss: That’s right.
Jerry Colonna: But in doing so, you impacted a lot of people, and I think you should be proud of that.
Tim Ferriss: Thanks, Jerry. Yeah, it continues to this day, I think, when I’m doing it right for me to be — conversations trying to answer questions I have myself.
Jerry Colonna: Isn’t that interesting? I want to highlight that. Isn’t it interesting that when you lean into the questions that you need answered in your own life, you end up positively impacting other people?
Tim Ferriss: The personal being the most universal, right, in a sense.
Jerry Colonna: So what if that’s the definition of legacy?
Meaning being so real and so honest as to make yourself a palette, if you will, or a canvas, where people can work their stories out. That’s pretty cool.
Tim Ferriss: Yeah. I like that definition, or that placeholder for legacy, because when I’ve thought about leaving things behind and a lot of fancy-muckety-mucks, often very good people, very soulful people who somehow get fixated on legacy, maybe because they’ve overshot Maslow’s hierarchy of needs, maybe taking out maybe self-actualization and transcendence, but everything else certainly, they’ve overshot by such an absurd margin that they start thinking about legacy. And, I always think to myself, I’m like, “Alexander the Great. What was his last name again?” Nobody knows. And, we are somehow going to stand the test of time, the head of the Sphinx, poking out of the sands in the desert. Come on. It seems ridiculous.
Jerry Colonna: Right.
Tim Ferriss: But maybe, who knows? Right? What I said about borrowing from Bill Richards, like Bill Richards told me this thing.
Jerry Colonna: Yes.
Tim Ferriss: Or you tell me a question.
Jerry Colonna: Yes.
Tim Ferriss: I pass that on.
Jerry Colonna: Yes.
Tim Ferriss: Then somebody else passes it on. And, even though the attribution probably gets long-lost along the way, that is some form of legacy, right?
Jerry Colonna: Yes.
Tim Ferriss: That continues.
Jerry Colonna: Yes. A thousand times, yes. Listen, I know “legacy” as a word could sound grandiose. And I love your self-deprecating humor. Don’t use it, though, to deny the thing that is true.
Tim Ferriss: Yeah, good point.
Jerry Colonna: Okay? Because that’s another form of that self-delusion and bypassing. The fact of the matter is, you have made a positive impact on the world. It may be fleeting, it may disappear. Who knows? Listen, I’ll tell you a story. About five or six months after my first book came out, I received a ton of fan mail on the book. I still get mail from people saying, “This book really impacted my life.” But I’ll never forget this one day. In one day, I got two messages, one from the CEO of a Fortune 100 company and one from a man on death row. And they both wrote about the book and said, in one form or another, “Your story is my story.” I will go to my grave proud of that fact.
Tim Ferriss: That’s amazing. Also, to have it happen on the same day. What a gift.
Jerry Colonna: On the same day. And the lesson, Tim, in that, is there’s really no difference between those two men. And that’s what’s really powerful.
Tim Ferriss: Can you say a little bit more about that? Because at face value, of course, if you look at their CVs, very different men. But, I know you mean something different. Could you say a bit more about that?
Jerry Colonna: I do. I do. In December of 2019 — well first, in September of 2019, my first book came out in June. In September of 2019, I’m doing a book talk. You remember when we used to do things like that. And, it was pre-pandemic —
Tim Ferriss: Back when we were listening to mini LPs on the record player.
Jerry Colonna: That’s right. That’s right. And, I’m walking to this venue in Denver, and there’s this woman who’s clearly in her 80s, who comes up to me and she says, “You look like our speaker.” And I said, “Well, that’s because I am your speaker.” And she laughed, and she stuck out her hand. And she said to me, “My name is Margaret. And I grew up in the Dust Bowl. And I read your book, and your story is my story.” 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 —
Tim Ferriss: That was the best follow up too. “I grew up in Brooklyn, by the way. What the fuck?” Perfect.
Jerry Colonna: I’m sorry. I should have warned you.
Tim Ferriss: Couldn’t have scripted it better.
Jerry Colonna: Fuck is a part of our dialect. I’m sorry.
Tim Ferriss: No, just a brief aside, I’m not going to 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 Brooklyn influence. And his greeting to me is, “You fucking fuck. What the fuck are you doing?” This is one of the most sophisticated, brilliant thinkers of our time. But that’s how he greets me.
Jerry Colonna: I don’t understand. Do you have a fucking problem with that?
Tim Ferriss: Yeah, exactly.
Jerry Colonna: I don’t have a fucking — anyway.
Tim Ferriss: All right, Margaret.
Jerry Colonna: All right. So, a few months later I’m in Dublin, and I’m doing a book reading, and the audience is filled with, not surprisingly, white people. But there’s this one black woman who’s sitting in the very front row. And, in some ways, you’ve experienced something similar, at the end of the talk, she comes up to me and she says, “I was really moved by what you were saying, especially the part…”
I had been talking about how when we lose a parent at an early age, it forces us into early parentification. And importantly, that that can often be a signifier of leadership. And, she says, “That thing you were talking about. Well, that happened to me. My father died when I was 13.” And I’m dopey and exhausted, and I nod my way in response. And then she says, “On Robben Island.” And I look at her and I say, “What?” And yeah, Robben Island is where Nelson Mandela was held. And she says, “Yeah, he was a freedom fighter based in Zimbabwe. And he was caught on the border of South Africa and beaten to death in the prison.”
And then she says to me, “Your story is my story.” And the thing about that — and her name by the way is Joy-Tendai Kangere. She is going to be graduating, I think, with a PhD in law in October. She’s one of the first black women in the City of Dublin to be a barrister. The thing about that experience is, to your point, our lives couldn’t be more different. But there’s something very, very powerful about this notion that, “Your story is my story.”
Tim Ferriss: 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.
Jerry Colonna: And if you’re willing to be honest. So, when people come up to you and want to share their trauma, yeah, there’s a performative element to it. But maybe too, they’re seeing their story in your story, Tim.
Tim Ferriss: 100 percent. Just for clarity’s sake, if people do it after I share it 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.
Jerry Colonna: Right, right.
Which I think can get into dangerous territory. But, I agree with you a hundred percent. And I do, I’d say, probably in response to that episode more than any other, but certainly, there are a few where I discuss personal challenges with depression and so on, which thankfully, are fewer and fewer, and shorter and shorter in duration. But, you never know. And I agree with you 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 mentioned fucking up a bunch of stuff, like all parents do.
I even know one guy, great guy, I won’t mention him by name, but he’s like, “Oh, yeah, I’m going to send all my kids to the Hoffman Process.” He’s like, “I know I’m fucking them up. I’m just not sure how.” Anyway. So you made mistakes, like every parent does, but what did you get right? Why do you think, if you had to try to explain it, and I know it’s not a laboratory, so nothing is easy to isolate here, but what do you think you did right or what worked? Maybe it’s your son out of the box, who knows? Maybe he’s just a very forgiving guy. But why did he end up wanting to spend those five days with you in the Sprinter van, versus your experience with, say, your dad?
Jerry Colonna: The power of that question is twofold. One is, I think it’s a really, really important question. And the second is, you’re touching upon one of my most deep and profound fears, which was that I would have fucked it up as a parent.
And so, I want to be clear, I still have the capacity to fuck it up.
I think the answer to your question goes back to something Dr. Sayres used to say to me when I would lie on the couch and bemoan that I was a terrible parent and I would be wracked by guilt because of this stupid reaction that I had, or this stupid thing that I said, or that kind of thing. And she used to say to me all the time, two things. One, “You cannot spoil children with love. You can spoil them with things, but you cannot spoil them with love. So love them.” And the second thing was, she said, “Give them words. Give them words.” And I think, I have three children, Sam is 34, Emma is 32, and Michael is 27. And Michael’s the one that went camping with me, but Emma and her soon-to-be husband really enjoy the camping van as well. And the truth is, I have great relationships with each of them because they’re great people.
Tim Ferriss: What does “Give them words” mean?
Jerry Colonna: Yeah, give them the ability to talk about what’s actually going on inside of them and listen. I mean, I think that as parents, we can become so afraid of fucking it up and hurting them, that we get wrapped around our own anxiety, our own narcissism. And then we lose the connection, which is the thing that our children want more than anything else.
Tim Ferriss: Did you give your kids words? If so, how did you do that?
Jerry Colonna: Two things. I do think I gave my kids words. I think I also raised the bar on what they expect from other people. They expect words from other people, which has a mixed blessing because not everybody is trained to actually talk about what’s going on. Not everybody knows how to answer the question, “How are you?” I think I gave them — the way I did it was I modeled first and foremost. And the second, and I think I’m good at this, I listened. Now I also want to give a shout out to their mom because this was not a one and done, I did it myself by any stretch of the imagination. They had two spectacular parents who each endeavored to do right by their children in different ways in different styles, for sure.
Tim Ferriss: Given your experience, you have good relationships with your kids. If you had to add a third or fourth thing to your therapist’s rules, let’s just say, that you can’t spoil a kid with too much love. Number two, give them words. What might number three and/or, well, I guess it wouldn’t be or. Number three, if you want to add a fourth and go for it, what might you add to that?
Jerry Colonna: I think that if I could go back in time and give myself advice the way she might’ve given it to me, because she tried to make me feel this. I spent far too much time feeling guilty and far too much time worried about whether or not I was being a good parent. I mean, this is another thing that she used to be exasperated with me about. It’s like, “All right, Jerry, they’re going to be fine.” But the truth is, and I’ll give myself a little bit of a break, I didn’t have the context. I didn’t have, God rest my parents’ souls and coming to understand that they tried, I did not have role models for good parenting.
And so I had to piece it together from people like Parker or my therapist or other mentors and elders in my life as I watched how they were doing it. How were they being the elder in their life? And learn to forgive myself for the mistakes so that with regret and remorse, I can pick myself up and try again. Can you apologize to your children? Oh, my God, what a powerful tool that is.
Tim Ferriss: Yeah, better start apologizing in advance if you don’t have kids. Build the muscle. Don’t try to win the World Series as your first baseball game.
Jerry Colonna: Exactly. Why are you thinking about kids so much these days?
Tim Ferriss: Oh man, I’m so bored of this business, sage-on-stage stuff. It’s just like I’m boring myself so much. I mean, look, I’m being a little facetious here, but we’re all beyond a certain base level of needs. We’re all playing games. So the trick is knowing what games you’re playing and then be very hopefully conscious of the games you opt into. What are the rules? What’s winning? What’s losing? What’s the ranking? What’s quitting time? What are the stakes, et cetera?
And I feel like family, kids is the next big chapter, the next big adventure. I don’t overly romanticize it. Almost all my friends have kids. I know it can be an enormous, enormous pain in the ass. It can involve a lot of sadness and anxiety and you name it. But then there’s the other side —
Jerry Colonna: And joy.
Tim Ferriss: — and joy, of course. Then there’s the other side of nature.
Jerry Colonna: And laughter and a sense of completion. I mean, let’s shout out. The best of all the accomplishments I’ve ever done — the best — has been becoming the father that I needed as a child, without a doubt.
Tim Ferriss: Yeah, that’s a big one.
Jerry Colonna: A couple of years ago before I went to Ireland, I was in Wales. I don’t know if you know the DO Lectures. It’s a fabulous —
Tim Ferriss: I thought you were going to ask me if I knew Wales. Yeah, I think I’ve heard of it.
Jerry Colonna: — but you’ve been to the DO Lectures. You spoke at the DO Lectures.
Tim Ferriss: I went to, I think the first or second DO Lectures, in like 2009. It was amazing. I really enjoyed it.
Jerry Colonna: They’re 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.
Tim Ferriss: And with much more confusing street signs. I remember trying to drive around Wales. We had no Google Maps and so I didn’t have international data. And they’re like, “Sure, just turn left at Wyydyywkyywyyky,” and I get to a sign and I’m like, “That’s 24 consonants. How do you read this?” Anyway, but yes.
Jerry Colonna: What do you mean it’s 24 consonants in a row without a single vowel?
Tim Ferriss: That’s what I mean. I’m just like, wow. Okay.
Jerry Colonna: Anyway, so I was at the DO lectures and I was doing a reading from Reunion, the new book, and it was maybe the first three or four pages. It was just the opening chapters. But it provoked such a powerful response from the group. And as you remember, it’s like you’re in this old hay barn, cow barn, the cow shed I think they call it. But my oldest son, Sam, had come with me and at the very end of the talk, people were sort of milling about and oh, my God, and telling me what I’d done wrong and telling me what I’d done and all that stuff. You know what they do. Oh, that’s very good, except. It was like, “Okay, the next time you write a book, you can talk.” Anyway, I look up and Sam, who’s 6’1″, big guy, he’s a Muay Thai fighter and trainer. He looks up and he just mouths the words, “I am so proud of you, Dad.”
Tim Ferriss: That’s amazing. What a moment.
Jerry Colonna: That’s the moment. That’s what you want. You know. That’s what you live for. That’s what parenting is.
Tim Ferriss: Yeah. I feel like I need to make up for lost time. I’ve been wondering if I need to go raise the red lantern style. I have no idea. Maybe just have survival of fittest. Impregnate 40 women and see how we do. I don’t want to say desperate, but I’m just like —
Jerry Colonna: I’m a little surprised you’re talking about this because are you going to now be inundated? And then you’re going to call me up and say, “Jerry, what do I do?” And I’ll say, “How have you been complicit in creating these conditions you say you don’t want?”
Tim Ferriss: “Do you mean publishing this to millions of people?” “Yes, nephew Timmy.” I mean, putting it on the podcast. I’ll share this, this I haven’t really said to anybody, but I was spending time with a number of my really close friends. We do this reunion once a year. And most of them have kids, not all of them. Most of them have kids. And one was echoing this lesson or conversation he had with someone far older than he, a grandfather. And he kept saying, “There’s nothing more precious than hugging your grandkids.”
And I started running 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 mathematically even remotely reasonable for me to entertain. And that fucked me up. I’ve got to be honest. Not because I’ve really thought about grandkids much, but when he put it that way, and it happened to coincide with my birthday, which was the cause for the reunion. And I was just like, wait a second here. I’m no mathematician, but fuck me. That was a tough pill to swallow. Not going to lie. That was like, oh, yeah, that may not be a thing.
Jerry Colonna: 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. And you guys should hang out for sure.
Tim Ferriss: Drink some whiskey and cry ourselves to sleep.
Jerry Colonna: Or put the red lantern out and say, “I’m ready.”
Tim Ferriss: Oh, God, not ready to switch teams yet. Last I — never say never. But —
Jerry Colonna: Listen, what are you willing to do for your kids?
Tim Ferriss: He’s like, “I’m no biologist, but…” Yes, exactly. Oh, man.
Jerry Colonna: Before we move off that topic, let me give you a poem. You ready? This is by Philip Larkin.
Tim Ferriss: Yes, I’m ready.
Jerry Colonna: It’s called “This Be the Verse.”
They fuck you up, your mum and dad.
They may not mean to, but they do.
They fill you with the faults they had
And add some extra, just for you.
But they were fucked up in their turn
By fools in old-style hats and coats,
Who half the time were soppy-stern
And half at one another’s throats.
Man hands on misery to man.
It deepens like a coastal shelf.
Get out as early as you can,
And don’t have any kids yourself.
Tim Ferriss: Wow. So should I Sylvia Plath myself today or tomorrow? Jesus, Jerry.
Jerry Colonna: Well, he’s British.
Tim Ferriss: Good Lord.
Jerry Colonna: I know.
Tim Ferriss: I’ve got to write that —
Jerry Colonna: I’m famous for reading poems, but usually they make people cry.
Tim Ferriss: I was like, this is like Dr. Seuss meets A Star Is Born. Good Lord. Amazing. Let me try to right the ship here. So three books. I alluded to these. I’m curious, you’ve mentioned a few books in our conversations before. Certainly your own, which I recommend to everybody. Also, When Things Fall Apart by Pema Chodron, Faith by Sharon Salzberg, Let Your Life Speak by Parker Palmer. I’m wondering if any of your kids have been impacted by any of these books or if there are other books you’ve recommended to your kids, whether or not they’ve read them.
Jerry Colonna: Oh, yeah. Sam in particular loved The Wisdom of Insecurity, which is a really, really powerful book. Michael is probably the one who follows most of my book recommendations. And we go back and forth from novels to nonfiction and we swap books back and forth. The novel that Michael loved the most was also really powerful in my life. It’s Call It Sleep by Henry Roth.
Tim Ferriss: Call it Sleep. I’ve never even heard of that.
Jerry Colonna: So Henry Roth wrote Call It Sleep in the 1930s. And it tells a story of a young boy, I think he’s like seven or eight years old, growing up in upper East Harlem when it was a Jewish neighborhood. And they’re Jewish immigrants. It was well received and then lost in time. And I think it was Kazin, the famous book critic, who discovered a used copy in the Strand in Manhattan. And then devoured the book in the 1950s and published the first review for a paperback book in The New York Review of Books.
Tim Ferriss: That’s ballsy.
Jerry Colonna: And so the book was rediscovered.
Tim Ferriss: I love it.
Jerry Colonna: Anyway, I’m going off. Henry Roth, as a novelist, was one of the most influential novelists in my life. And it’s a book that — I remember when Michael finished it, he sent me the same passage that I had first read when I was about 17 or 18 years old and was blown away by it. And was like, yeah, that’s the passage. And for those who know the book, it’s the passage where David is touching a trolley car’s third rail with a soup ladle or milk ladle. It’s really a powerful passage. Anyway, you didn’t ask about novels.
Tim Ferriss: Well, it’s funny that you brought up a novel. Maybe I incepted you because I was going to ask you actually if there are any novels you recommend or find, contain, and convey a lot of truths. That stick out to mind. It doesn’t have to be the best. But for instance, Zorba the Greek, I think, is a standout for me.
Jerry Colonna: You remember that. Good job. Yes.
Tim Ferriss: Yeah. So Zorba the Greek, huge standout. I’ve been meaning to read it again. And some more of the same authors work. Do any others stand out to you? Because I’ve really found fiction, which is very closely related to humor, right? Let’s just say Bill Richards or your therapist parable. These are all very closely interrelated.
Jerry Colonna: Well, 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?
Tim Ferriss: I have either heard of it or come across it. It does ring a bell.
Jerry Colonna: Okay. So Library of America is a nonprofit foundation that seeks to preserve the writings of amazing American writers. And I think there are over 350 volumes that they’ve done. Writers like James Baldwin. Anyway, I just finished volume one of Wendell Berry. And the thing that comes to mind, and I said this to Michael in a text message, I think this is the first set of novels and short stories I’ve read that have changed my thinking about writing in a profound way.
And what Berry did in volume one is the material from — everything takes place in the fictitious town of Port William, Kentucky. He, of course, is from Kentucky. He still lives there. And these tell a series of stories, short stories in novellas and novels all taking place from the end of the Civil War, in this case, through World War II. And it all involves the same characters or the same extended characters, but many times the incidents that he writes about are written about from different characters’ points of view. And it’s still working on me. I’ve been reading it. I finished it a few weeks ago and I’d been reading it for about three months because it’s close to a thousand pages. Deeply, deeply moving.
Tim Ferriss: I’ll check it out. I have more homework assignments, which of course I love. I do love my homework. What is the basic thesis of The Wisdom of Insecurity? I know this book title and I’ve come across it multiple times and I’ve never read it.
Jerry Colonna: Well, 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, if you want to link it back to what we were talking about earlier, it’s how has it been useful for us rather than something that we need to push away?
Tim Ferriss: Got it. How has it been useful not in a condemning way?
Jerry Colonna: That’s right.
Tim Ferriss: Not in the “How are you complicit?” way, but “How has it actually been helpful?”
Jerry Colonna: That’s right.
Tim Ferriss: Along the lines of The Gift of Fear by Gavin de Becker, right?
Jerry Colonna: That’s right.
Tim Ferriss: It’s not always something to swat away.
Jerry Colonna: That’s right.
Tim Ferriss: How is it a gift?
Jerry Colonna: Right. It’s simple to understand. We’re often told that the way through insecurity or anxiety is to somehow embrace what’s happening in the moment. But this actually walks us through. It tells us how to do that. And of course, Alan Watts is an incredibly important Zen teacher in the Zen Buddhist tradition.
Tim Ferriss: Yeah, he’s one of a kind, that one. And an amazing narration as well for people who want to take it in audio format, it has some spectacular speeches and presentations. Jerry, we’ve covered a lot of ground here. Is there anything else you would like to mention before we begin to land the plane? Is there anything else you’d like to say, ask of my audience, point people to? Anything at all?
Jerry Colonna: I think I’ve really appreciated our conversation, especially the amount of laughter. And you actually help remind me of the importance of that. And so let me double down on that because it’s kind of a fucked up world we’re in right now. As I’ve been saying recently, it’s the kind of world where babies get murdered for ideology. And that’s a kind of fucked up place. And not that that’s material to laugh about, but to understand that there’s a human connection that can be gotten even in the midst of all this, I think, is incredibly important right now. So as Dr. Sayres would say to me, “You’ve done enough work, go off the grid. Go take your time. Go have fun and laugh your ass off.”
Tim Ferriss: Good advice. I’m going to work on that tonight. Do you know something I’ve started doing? And this is related, it’s a bit of a hard segue, but games. Just tabletop games. No phones. No stress.
Jerry Colonna: Yes.
Tim Ferriss: Rewind the clock, these things have been with us a long time.
Jerry Colonna: Amen.
Tim Ferriss: Can I mention another thing that got stuck in my mind? Which is funny because it was your mention of a stuck record when you were asking about records and if I remembered records. The one thing that popped to my mind that has been on repeat, which of course is sort of self-referential in and of itself. When I was a kid, I had this little tiny mini LP. It was the size of a tiny pancake. It was really small. And it was a song that I played a million times and drove my parents insane. But they had made the mistake of giving it to me. And it’s “Disco, Disco Duck.”
Jerry Colonna: I remember the song.
Tim Ferriss: “Who wants to be a disco duck?” And it’s Donald Duck singing the song over and over and over and over again. Holy shit. What a wonderful song. And I actually had some speaking engagement like — God, I can’t remember. A year ago, two years ago? I don’t do too many of them. And they asked me what I wanted my entrance music to be. I tasked them with trying to find “Disco, Disco Duck.” They were not successful. But a boy can dream.
Jerry Colonna: What’s frightening is I will not, but I can sing that song.
Tim Ferriss: Everyone, this is my homework assignment to everyone listening, go find “Disco, Disco Duck.”
Jerry Colonna: That’s right. I’m sure it’s on YouTube.
Tim Ferriss: It’s a treasure. Jerry, where would you like people to find you? You’re @jerrycolonna on Twitter. We’ll link to everything in the show notes. They can find Reboot at @reboothq on Twitter. Reboot.io is the website. You’re the author of Reboot: Leadership and The Art of Growing Up, and also —
Jerry Colonna: Reunion.
Tim Ferriss: Exactly. Leadership and the Longing to Belong.
Jerry Colonna: You got it. Yeah. I think tracking me down there or on Instagram, I’m @jerry.colonna, all sounds great to me. So I appreciate that.
Tim Ferriss: Absolutely. And to everybody listening, we will link to everything in the show notes, including probably some version of “Disco, Disco Duck” at tim.blog.
Jerry Colonna: And the Philip Larkin poem.
Tim Ferriss: That’s right, and the Philip Larkin poem. If you’re too happy and just need a moment of sadness, tim.blog/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.
Jerry Colonna: Amen.
Tim Ferriss: And thanks for listening. All right, well that was super fun.
Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)