Good Life Project - The Art of Growing Wise | Jerry Colonna

Episode Date: July 16, 2019

In the late 1990s, Jerry Colonna co-founded the iconic Flatiron Partners with Fred Wilson. Flatiron became one of the world’s most successful, early-stage investment funds. Five years later, Jerry's work and life fell off a cliff and he found himself questioning whether he wanted to stay alive. Sage advice from a therapist sent him on a journey that would eventually lead him away from the industry, into Buddhism and his own personal reclamation. Stepping back into the light, he decided to devote his life to profound service and compassion, becoming one of the most sought-after coaches and advisors to founders of many of the fastest growing ventures in the world. He is now the CEO, and co-founder, of Reboot.io (http://www.reboot.io/book), a leadership development collective dedicated to the notion that better humans make better leaders. He's also the author of an incredible new book, Reboot (http://www.reboot.io/book), that not only takes you deep into his personal journey, but also redefines what it means to be a grown-up in a position of leadership in business and life.-------------Have you discovered your Sparketype yet? Take the Sparketype Assessment™ now. IT’S FREE (https://sparketype.com/) and takes about 7-minutes to complete. At a minimum, it’ll open your eyes in a big way. It also just might change your life.If you enjoyed the show, please share it with a friend. Thank you to our super cool brand partners. If you like the show, please support them - they help make the podcast possible. Hosted on Acast. See acast.com/privacy for more information.

My guest today, Jerry Colonna, grew up in Brooklyn in the 60s and 70s, a time when there was a lot of turmoil in New York and his immediate family was no smaller representation of that same inner turmoil with a lot of strife happening within the household. That set the stage for the way that he would perceive himself, the way he would perceive his own life, his value, his contribution, the way he would and would not act. And in no small part, the way that he then went out into the world, built his living. He ended up going to college, moving into the world of publishing, succeeding at a very high level very quickly, then into the world of venture capital in the tech world,

and at a very young age, being sort of one of the high-flying pairs who did stunning things. Then at the age of 38, everything came crashing down and led him to a major breaking point in his life. And he had to make some decisions about how he wanted to move forward. That led to a profound shift in career and to the world of Buddhism, the world of being in support of others. And he now is one of the most sought after coaches, if not the most sought after coach, especially in Silicon Valley for founders who are going through the fierce cauldron of starting and building something big with massive stakes. A lot of his journey and his philosophy is shared in a beautiful new book that he's written called Reboot. And we dive into this journey today. I would strongly recommend

you pick up and read the book, but we really deep dive into some super important ideas and principles and his own personal narrative in this conversation. So excited to share it with you. I'm Jonathan Fields, and this is Good Life Project. The Apple Watch Series X is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping.

And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman.

I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him. We need him. Y'all need a pilot.

So good to be hanging out with you again. You too. It's been years. I think we were just figuring probably late 2012, 2013, back in the day when GLP started and we were actually shooting video on location, hanging out in your office, which I guess you still have, but now you kind of go back and forth. I do. And it's exactly the same way because it provides a sense of consistency to clients. So

just like when I would go to my therapist's office for 30 years and stare at the same freaking wallpaper, it's like changed nothing. You'll freaking wallpaper. It's like, change nothing. Right. It's like, you'll induce panic. It's like, is your chair like two inches to your left today? It's really freaking me out. You got it. It's amazing what creatures of habit we are, right?

It's like the older we get, I think the more we're locked into that. No. This is the way it's supposed to be. Right. Well, it's like, but it's like there are places in our lives where we know, like, that's the place where we're supposed to be on that. And there are other places where we just really want to lock them down and know it's always going to be the same. Well, I think I, you know, we're joking about it and I made the association with the therapist's office, but I think the, the issue is that, issue is that when we drop into that vulnerable space,

so much of that early childhood person in us comes out. And to make that feel safe is really important. And sometimes you need the peas and the carrots lined up exactly right. And daddy, don't let them touch. You know. Yeah, I think we all know. We all have our own version of whatever the peas and carrots are. Yeah, amen. Which kind of gives us a nice entry also if we're talking about childhood. You know, you have this beautiful new book out now.

And I want to touch down on some moments. But let's cover some sort of like fairly more straightforward, which is you, so you grew up in Brooklyn. We're similar ages. I think I'm 53 or a couple of years old. I'm 55. Don't you forget it. Okay. I'm the older brother. Yes, sir. And you grew up in a time where Brooklyn was a very profoundly different neighborhood than it is now, especially the part of Brooklyn that you were in. Tell me more about it. Because I think a lot of people think of Brooklyn now,

like, oh, hipster, safe. Oh, geez. Different time. Yeah. So the Brooklyn of my youth, and by the way, everybody from Brooklyn has a Brooklyn of my youth because Brooklyn is always changing.

What did Thomas Wolfe write? Only the dead know Brooklyn, true and true. What was it like? So I grew up in Flatbush, East 26th Street and Avenue D, 377 East 26th Street between D and Clarendon Road, just to be specific. In the 1960s, it was a tough time of, I think, massive economic dislocation foisted upon a lower middle class, middle class that didn't know what had hit it. And racial tensions were exacerbated. And remember this term? Redlining. And for those youngsters listening on the podcast, you can go Wikipedia that.

And it was an awful expression of oppression and racism and bias. And Brooklyn was subjected to these kind of economic forces that exacerbated tensions between folks and folks who otherwise would naturally be together. And so that created this stew of tension going on. And then you sort of go broadly. New York City was going through its own upheavals. You're old enough to remember perhaps you were four. Bobby Kennedy being shot, Martin Luther King being shot. I remember watching on television the fall of saigon i remember being in the back of a station wagon that my father had rented to take the whole family

up to fordham in the bronx to go to my sister's wedding her first wedding on the campus fordham university and listening to richard nixon resign the office of Fordham University and listening to Richard Nixon resign the office of the presidency. Yeah, it's so bizarre because we're on a similar age. Sitting here today, for some odd reason, I remember exactly where I was and what the TV looked like because all the adults were gathered around it.

Yeah, everyone's gathered around it when Nixon resigned, which is a bizarre thing that I would actually remember that sitting here today. Right, right, yeah. Everyone was gathered around it when Nixon resigned. Right. Which is a bizarre thing that I would actually remember that sitting here today. Right, right, right. And it's even embedded in that phrase, I hereby resign the office of the presidency of the United States of America. New York City also, I mean, was essentially bankrupt in the late 60s and 70s. It was a horrible economic time in the city. Yeah, remember the daily news headline, Ford to New York dropped dead? Right. So hopefully some of you are out there scrambling back to Wikipedia to know what the heck we're talking about. But I think to loop it back to your question, I think what's going on is you asked me what was it like in that time period. And it was, I mean, I'm naming some of the things that made it a difficult time period.

It made it feel unsafe in many ways. It made it feel like, I felt like, I mean, do you remember Ford almost assassinated? I remember Reagan being shot when I was in high school. And so for me, I think I grew up, I was born a month after JFK was killed. And yes, there were some amazing achievements. We think we made progress in civil rights, for example, during that period. I don't know so much about that anymore. We did land somebody on the moon, a few people on the moon, which was pretty fucking awesome, if you think about it. And we were in the midst of a war in which, you know, my brother's friends would come home or not.

I mean, this was the 60s and 70s. And then you go into the 70s and, yeah, the economic crisis in New York City. And that's the backdrop, I guess. And that's, I guess, what you were getting to is that's the backdrop against which I grew up. Yeah, I mean, because that's the macro backdrop of unsafety. And then when you zoom the lens in even further and just you and your family, it seems like that was just amplified. Yeah. Hard to say if it was amplified because I don't know other than sense of being safe, that I was safe on a continuous basis, that I could look back and recall what it felt like to not feel safe all the time.

It was the absence of threat that made me see that I lived under a threat all that time. Yeah, because when you're in it and you know nothing else, it just seems like you're normal. It's just life. It's just life. It's just life to know that you could be quote unquote stopped. That was the term. Walking home from school, Catholic school uniform. Hey, you got a quarter? Stopped, right? Mugged, whatever that means. Yeah, David Foster Wallace's water. There you go. And part of that also was, I mean, your parents had a pretty contentious relationship,

but also your mom struggled mightily. Tell me more about your experience of that. Well, it was complex. Here again, they created a sense of well this is water right this is normal um the water in which i swam in was um a mother who would i might come home from school and find out and find her talking to somebody who wasn't in the room. Bobby Kennedy, standing in the corner, except he wasn't. And that's weird. Hours later, my dad might come back from going to John's grocery store

with two six-packs of Pabst Blue Ribbon, although my brother Vito says it was Schlitz. I disagree, Vito. Memory's imperfect. And him sitting there with a folding TV table to his right with an open can. Back in the day, we had can owners, didn't even have pop tops and mom's in the kitchen talking to somebody and i'm sitting to the left of my father and he's staring at the black and white tv on wheels and he's not doing anything and mom's talking And the tension is rising. And I guess in some ways it does mirror some of the issues in the community in that it was ever-present. And then in a moment's notice, she might tip over and start saying or doing things that were really scary.

And that oftentimes would then escalate into a fight that was loud. But can I say something? You said your parents had a contentious relationship, and my first impulse was, no, they didn't. This is water. It's like, oh, right. Isn't this just what everybody does you know you know standing outside on the street corner trying to make sure that none of your friends can hear your parents arguing about whether or not your father had had an affair yeah and with your mom also it wasn't

this wasn't just contention it wasn't't just her, you know, like having conversations with people who she, you know, like felt like having conversations with. It was, was it actually diagnosed mental illness then? Oh, yeah, yeah, yeah. She had multiple trips to the hospital when we were young, very young. This is before my sister Mary would put a stop to it because she's the oldest well she's the second oldest but she was a mom shout out to mary um they would parse us out they the family would parse us out to aunts and uncles and one of the things about growing up in brooklyn was we also had this massive extended family and um my brother john and I, we'd go to my grandparents' house. Various siblings

would go to various aunts and uncles' houses. And then when mom was better, we would come back and not talk about it, which was really bizarre. Yeah. It seems like so much of your childhood was about doing whatever or not doing whatever was on offer in the name of trying to keep things as peaceful as humanly possible. Yeah, yeah. That's the sense of don't upset your mother, which is a line that my father would use, God rest his soul,

but they're both past, by the way. But this notion that you are walking on eggshells, not upsetting the apple cart. And by the way, he might say it about her, but the truth is we could feel it about him as well. And so one of the ways I think he coped was to make it about him as well, right? And so one of the ways I think he coped was to make it about my mother. And, you know, dad's alcoholism and the bifurcated personality that it resulted in,

where there was good dad and there was bad dad, created a similar sense of lack of safety. You had to be sure that you were nice and quiet as the hours in the evening ticked on and the number of beers that disappeared increased. Yeah. So as you're living in this every day, what's happening internally with you? How is this affecting you? That's a great question. I think that it exacerbated the hypervigilance that I often speak about. This notion that I can feel and sense things. Years later, I honed that into superpower. It was a great skill as a reporter. I could sort of sense when something was off.

It's a great skill as a coach. But the price that I paid was probably mostly somatic in that I grew up with consistent, persistent migraines. I grew up with the sense of my body being kind of disconnected from me. And all of that was means of keeping me safe. I see that clearly now. Yeah, it's like turn off all the switches of anything that could be perceived as messing with whatever calm lasted for as short a window as it might have lasted. That's right.

I know this all culminated also in a level of depression that led you to consider the worst option, I guess, when you're around 18 years old. Yeah, I think, again, everything is in hindsight right now. And so in hindsight, all the pieces fit nicely into place. But I think that, you know, the persona that I adopted as a child was compliant, happy, you know, a pleasing personality to go out into the world and, you know, make people happy, do things, take care of people. And inside, it kind of masked a rage that would periodically show up. And, like, I tell a story about how this neighbor kid tried to throw rocks at my younger brother, John. And I ran downstairs after seeing this and pulled him over the fence and just pummeled him to the point where I was scared.

I had no idea where that anger was coming from. And it periodically would spike up like that in these odd ways. So I say all that because I think now with hindsight and with adult eyes, I think that I was battling aspects of depression going back to childhood. And then what you're referring to is that, you know, in senior year high school, I began, the house of cards began to fall apart. And I stopped, I started missing classes. I started cutting school. I started just acting in ways that were just not consistent with the compliance straight A kit that I was. Culminating, I guess, in not just

a suicide attempt, but in trying to, and not applying to colleges effectively and efficiently and avoiding talking to my father about needing money to apply for colleges, because that's kind of a crazy scenario, right? We actually charge children money to apply to school to change their economic conditions. Don't get me started. Ultimately, to freshman year in college, at the end of freshman year, between first and second semester, cutting my wrists and ending up in a hospital for several months.

And then, fortunately, using that time period, prompted in large part by a good therapist I was working with at the time, to have the entire family come into a family therapy session and say, this is bullshit. This is not working. Something's got to change. And you know what? From that moment, my father stopped drinking i give him a hell of a

lot of credit for that he lived for another 12 years never drank again because we basically said to him either you stop or you or you're losing all of us. Because, you know, as difficult as my mother's mental illness was and her official diagnosis was bipolar schizoid affective disorder, and as much as alcoholism is a disorder and a disease, we felt he had more agency and power then. And he did.

I did not realize at the time that he could actually stop like then. And he did. I did not realize at the time that he could actually stop like that, but he did. And I admire him for that. It gave us our life back. Did you ever, between the time that he stopped and later in your life,

or when he passed, did you ever have an opportunity to sit down with him and reflect with him at all about that moment and what was actually happening in his head? Now you're going to make me cry. No. No.

But I think I'll talk to him tonight. He passed when I was 30, and we repaired a lot of our relationship between 18 and 30 for me. And to be clear, he was a good man. And I loved him. But he, yeah, we did not get to talk fully. A side note to this, a few months ago,

the anniversary of his passing is December 21st, and I was in Italy, in Cortina with my daughter skiing. It was a gift I had given her. And we were there that day and I had dinner with her and I was thinking about and reflecting on my dad and thinking about the book coming out and realizing that he would be so fucking proud. And she looked at me and she said, he is. I have wise kids. Well, the apple doesn't fall far from the tree there. Oh. The Apple Watch Series X is here. It has the biggest display ever.

It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary.

Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die.

Don't shoot him, we need him. Y'all need a pilot. Flight Risk. So things kind of repair to a point where you can step back into some semblance of your life. Back at that moment in time. You end up coming out of school and finding yourself in the world of publishing. It seems like it was kind of through an unusual mechanism. Yeah.

Yeah. An asteroid struck me. Yeah. Yeah, I got, so, like, how do you unwind it all back? So I almost had to drop out of Queens College, even though Queens College tuition at the time was $750 a semester. And I had this brilliant advisor, Robert Green, Green Greenberg, I forget his name. I have it right in the book. But anyway, he made sure that I won a scholarship, which would pay my tuition for the next four semesters.

And with that came an internship at a small publishing company on Long Island, which I thought at the time meant a poetry publishing company. Turned out to be a technology magazine company, which I knew nothing about. I was an English major hoping to write poetry for a living. And I ended up with a summer job on the copy desk, which turned into a job as a reporter, which turned into a part-time job as a reporter, which turned into a full-time job as the news editor, which became the editor, and the rest of my life happened.

Poetry. What drew you to that? I wanna jump back into the timing frame, but I'm curious about this, because it seems like a lot of your life is lived in almost like a poetic philosophy now. I'm curious what all the way back then drew you to poetry. Well, what comes to mind is my oldest assistant, Mary, whom I mentioned before, gave me a book when I was probably five or six years old called Robert Louis Stevenson's Treasury of Children's Poetry.

And these must have been like awful romantic poems, but I loved that book. It was big and colorful, and I can still see it in my mind's eye right now. And I memorized a bunch of the poems. I can't remember them, so don't even ask, because it'll embarrass me. And I remember, I make reference a few times to my siblings reading children's books to me. My brother Vito would read Winnie the Pooh, Christopher Robin stories to us, which have a poetic quality to them. me reading with me a bar the elephant series and madeline um and being able to memorize the poems the the i still think of them as poems so so my relationship to words and poetry um goes back to the earliest memories that i have and i think that i always took comfort in words.

Words matter. Yeah. When you go from there and having a deep interest in that and studying that in college and then into this world of publishing, which quickly reveals itself to be something profoundly different. Yes, it's about words, but it's kind of funny too,

because C&P, which is the company that you sort of like started at. So I'm a Long Island boy. I grew up in Washington. So this was a place where a lot of kids would have summer internships and stuff like that, because it was just down the block, basically. So I kind of know that business well. And you rise up eventually to run this one particular publication there. Did it feel Week. Did it feel right? Did it feel good along the way? I did feel a little bit of a fish out of water. But there's this other experience that I would have,

which is I was successful, whatever that means. Right. Because you're in your early to mid-20s now running. Yeah. I mean, I became editor of Information Week at 24, 25 years old. And we were, so now I'm going to get all publishing in my lingo. We were number five in a four-book market. Right. That's a joke. Right. We were number five in a four book market, right? That's a joke,

right? We were not doing well, so might as well give it to the kid. And within two years, we were number one. And because I shifted the focus of the magazine from an emphasis on those who were building technology and the vendors, as we call them, of technology, to those who were using technology, which I found much more interesting. When I look back, I can see that I was much more interested in the human side of the equation than I was interested in which processor was going to be faster than the next processor,

which is what all of the other publications we were competing with were focused on, which features and functions were coming out that were so super exciting, thinking that they were in the service business when I was much more interested in, how do we use technology? This is my naivete. How do we use technology? This is my naivete.

How do we use technology to improve how businesses function? So you go from there, you rise up really quickly. You're running this publication, but you also take, it's interesting because it seems like there are sort of like these series of hard stops and abrupt left turns. You're thinking about when I left, see? Yeah. Yeah. So, you know, one of the things that I always trace that back. So, yes.

So, I guess it was an abrupt hard turn. I was approaching my 10th anniversary, and I always get nervous at the 10th anniversary. It's like, something's got to shift. I've been here too long. I need to replant myself. I need to find, you know, new potted soil or something like that. And that goes back to childhood and worrying about my father in some ways.

But I'll leave that for a different story. So what happened for me at that point was I had reached a certain amount of success. I had launched a internet-based set of services called TechWeb early, early on in 94. So if you don't like advertising on the internet, I'm one of the people you should blame because we kind of invented that shit. And I left to do something completely and radically different, which was venture capital. And I didn't know anything about that business. But I was interested in what was happening

in that intersection between human beings and technology. And I was fascinated by the ways in which we would quote, go online and live online. And what was that happening? And so I sort of came into the venture capital business more as a use case expert than actually as a finance person. So you end up partnering up fairly soon with Fred Wilson to start Flatiron Partners. Right, 96. Okay. So 96 in the context of what was happening there, this was, everything was golden. Everything was growing fast. Like there was, there wasn't talk about a bubble at that point, right? It was just like, let's get in faster now. And you guys got in fast and you got

in and you, you built a pretty stunning track record and a lot of big wins. Tell me about you and Fred, tell me about your relationship. And I'm just curious about the dynamic between you two back then. Well, I'll tell you a little bit about it by telling you about how, I mean, we met at a company called Freeloader, which had been founded by Mark Pincus and Sunil Paul, went on probably most well-known for Zynga, and they were selling advertising on screensavers. There was more to it than that, but we met. I was looking at funding the deal because I knew Sunil. He knew Mark. He went ahead and funded the deal through Euclid Partners. I was at CMG Adventures, my first venture firm. We ended up not doing the deal.

He did the deal, but we stayed close. And later on, Mark suggested that we might want to partner up and be in business together. We made arrangements to have lunch. And this was the moment where that really stands out for me. He canceled the lunch at the last minute because he wanted to have, he wanted to attend his daughter's kindergarten graduation, Jessica's graduation. And that meant a lot to me. It said to me he had actually had his priorities straight. And so I liked him from that moment. So he had me at hello. Or goodbye. Or goodbye. Or like next week. Yeah. I love that. It's such a powerful sort of reflection on the value set. Yeah, and those who know him know how important his children are to him.

I mean, that is incredibly, an incredibly strong part of his personality. Were you a dad at this point? I was, I am, and I was, but we both had three children. Okay. I was, I am, and I was, but we both had three children. Okay. And his Josh and my Michael were not yet born when we met.

My Michael was born in 97. I think Josh was born in 96, so right around that same time. Right. So you're growing a family. You end up in this new endeavor with him. You guys experienced some pretty extraordinary success in your building over a period of years. That eventually comes to an end as well. What happens? Well, first of all, all things end. Yeah. All things. So we just acknowledge impermanence. Fuck. Right. So what happened there? What happened there was the internet crashed. And I don't mean a denial of service attack. Right. The music stopped.

There weren't enough chairs for everybody to sit down. And a bunch of people sat down on the floor. A lot of things started crashing. And it really began in March of 2000. year and a half while everything that it used to be that everything we touched turned to gold everything we touched turned to brown shit you know and all of a sudden even great companies were struggling and um so that was sort of the macroeconomic uh things going on in hindsight i also turned 37 in hindsight i realized i was staring down the gun barrel of 40, looking at big midlife questions, saying, what the heck is happening to me? And all of the systems that I had put in place to keep that kid at bay, the kid that we talked about before, started to crash. And so my depression came back probably in the fall of 99 began it's hard to pinpoint straight on through to 2002 2003 2004 2005 and then in the middle of this not insignificantly we have 2001 september yeah september 11th boy knocked me on my ass. As it did with everybody who was in the city then.

Yeah, yeah. I mean, for me, I knew that I was not well when I was staying up late at night in the weeks afterwards researching bomb shelters and, you know, emergency go bags and, you know, where could we leave? Where could we escape if we needed to? You know, I was in an extreme anxiety place. Yeah. There's a moment that brings you to your knees and effectively to a point of reckoning and decision-making. Yeah.

Was that true for you? You know, it's interesting. I've done a lot of thinking lately on the idea of the hero's journey. And I've asked the question of so many people that I know have been brought to that place where their ego and a large part of their identity has been annihilated, you know, supposedly in the name of making space for something else to step in and emerge and the elixir to be given. I'm always curious whether that level of gutting is mandatory to get to a place where life is good and you can stand in your true essential nature. I'm not convinced that it has to be done, but I also have seen very few cases of people who have avoided it

and landed in that same place. Well, that reminds me of the way I think about that question, because a lot of people ask, you know, is suffering necessary to some sort of path-based growth or, you know, to use my own term, adulthood. And the way I often say is the problem with the question is that it implies agency that you don't have. You don't have the agency to choose whether or not you're going to suffer you don't have the agency to choose whether or not you're going to be wiped out and annihilated so you can ask the question donathan whether or not it's necessary be my guest it's not going to prevent it from happening if you conclude that it's not necessary? And karma says,

guess what? And so what is helpful, I think, is to say, what will be my response should this happen? Because the first noble truth, of course, is that life is filled with suffering. Right? And it's

not that life needs suffering, it just is. Right? And you can unpack why that is so, but it doesn't change the fact that life is filled with suffering. So what are you going to do about it? Yeah. For you, this moment arrives when essentially you have to choose. You're back in a very dark place again. This time you're 38, 39 years old. This time also, you've got people looking to you. You've got kids. So it's not just your life that you're making a decision about, which makes things harder and easier simultaneously. And you come to the same point of reckoning.

Like, am I staying here or am I out? Do I die or do I live? Yeah. And it seems like there was one moment with the therapist that effectively set you on a different course. Yeah, Dr. Sayers. Who you also dedicate the book to in part. Yeah, Dr. Sayers was my psychoanalyst from age 30 to age 55.

She, you know, I'll reveal the end of the plot. She passed in uh 2018 we stopped working together in the summer of 2017 because she was so sick at 93 and uh in march of 2018 she passed from that life form into a different form anyway um yeah february 2nd 2002 i was standing outside the pile of 911 the pile of the world trade center which i like to point out contained human remains it wasn't't just a building rubble. It's a very sacred spot. And I wanted again to kill myself.

And I wisely called her and she yelled at me as she was, as was her want and told me to get your ass out to Long Island and come see me. And I did that. And I remember saying to her, stick a fork in me, I'm done. Put me in the hospital. I cannot do it anymore. And she said, what do you want to go to a hospital for? The food sucks. She made me laugh. She said, you should go to Canyon Ranch. You'll get a massage every day. That's what you need. And so I went to Canyon Ranch instead. And choosing to do that

and the lightness with which she responded to what was arguably a very, very difficult moment gave me a sense of hope. You know, it's easy when you're in that really really dark place to think you're never going to get out of that really really dark place and so you end up staying in that really really dark place i mean that's sort of the the fundamental source like when you're in depression you know it's part of it is the darkness but part of it is the belief that it'll never end. That's it. And that you're all alone in there and no one understands. And there you are, you know,

the hoodie drawn over your head and you're just, fuck. And, you know, someone asked me recently, what would I want as an epitaph? And that just occurs to me again here. You're not alone. Even in that dark, dark, dark, dark spot, elders have come before you and have walked through that path and have walked through that fire. And our life is proof that you can get through that period. And I want you to know that I know it sucks.

And no amount of positive psychology is going to make it go away. And no amount of just walk outside and get some sunshine helps. But if I could reach out, reach this microphone microphone and tap you on the shoulder and just say i know you're not alone and you can choose something other than that it's like the agency that you were talking about before. You may not have agency over the circumstance that will or will not bring you to your knees. But at some point, you do have agency over the choices you make when you're there.

I guess the challenge is realizing that. I just want to pause and recognize how brilliant it was that what you just said and how you said it. That's exactly right. Right down to the challenges, not realizing that you have that agency. And I think that is the place the community lives, to remind us that we have agency in our lives. Not the agency that we would want. I can't magically make you realize that you can magically make bitcoins fall from the sky

as if such things existed, right? But you have more agency than you can feel you have, even if you have the agency to take a shower. Yeah. I mean, it's interesting because to me it seems like, and I wonder if this is a common experience, the thing that allows you to start to acknowledge that, or at least in your case, maybe it sounds like, again, from the outside looking in, was you had cultivated a relationship and a sense of trust in somebody over time so that when you were in that place and that person told you, no, you have a choice here, you might not have felt it,

you might not have fully believed it, but you believed it just enough to take that person's advice and start to go from a place of reactivity to intentionality and let your actions start to prove the truth of what you said. You know, here again, Jonathan, I think you're saying something really important and brilliant. And you're helping me see something that I didn't see before. Yes, you're right about everything that you said. And I would add to it that I believed, I may not have believed that I had agency,

but I believed in Dr. Sayers. And if Dr. Sayers said I could go to Canyon Ranch, then I could go to Canyon Ranch. It was like I outsourced my agency to my therapist because I could trust her. Because if all else failed, she hadn't yet proved me wrong or proved me right. She hadn't yet failed me. That didn't mean she didn't piss me off at times, but it meant that if she said I could go to Canyon Ranch, I could go to Canyon Ranch. I could never have come up with that idea

on my own. No. So thank you for helping me see that. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg.

You know what the difference between me and you is? You're going to die. Don't shoot him, we need him. Y'all need a pilot. Flight Risk. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever,

making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series 10. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. So, and it was during that trip that you not only started to, you know, like take certain actions and make decisions for yourself that would pull you out of this place, but also become exposed to a couple of different people.

Parker Palmer being one of them and his lens on meaningful living and his raw transparency about his own struggles in a very beautiful and open way, Pema Chodron, and her beautifully real-world lens on Buddhism and what it really is and how it operates in the world. And it seems like also such an important part of who, at least I understand her to be in the world. And what you took from her was rewiring your lens on impermanence. So, yes. And the other person I would add to that trifecta was Sharon Salzberg and her book, Faith. Because I took three books with me on that trip.

Faith by Sharon Salzberg, When Things Fall Apart by Ani Pema, and then Parker Palmer's Let Your Life Speak. And I'll just say it out loud. I have the great good fortune of counting each one of those folks as friends, which I must have done something right in a previous life. Because holy crap. Frequent humans. And I hit the trifecta there. Yeah, so the lessons began before I actually met any of them for sure. And the lesson of impermanence became visceral a year after that.

But over the next several years, there was our reinforcement of things. From Parker, I came to understand, for example, the power in presence, in being with someone in suffering, and not needing to fix or set straight or make it better, but to just be present. And the power of understanding, he has a chapter in Let Your Life Speak called Leading from Within, which really, really moves me. But with Sharon, I found, and in particular with her book Faith, which is one of the lesser known books that she's had, what I found was her willingness to confront her own issues in a way that was deeply powerful and kind of a model for what I was trying to do, which is, oh, I actually have to look in the mirror.

I don't like looking in the mirror, but that's actually where I have to look. Yeah, radical self-inquiry. Radical self-inquiry, thank you. My term for looking at yourself and stripping away the delusions and the bullshit and the personas and the stories you tell yourself, but doing so with compassion and kindness to yourself. Yeah. I think that last part is so important too, right?

Because I think a lot of us start to say, okay, I'm all in. I'm going to strip myself down to the bone so I can rebuild. But we don't do it necessarily with that lens of just, okay, here's another thing I get to judge. Right. Let me just keep adding to this list of how badly I suck and how much I screwed up. It's like, it's like, rather than compassionate, it's just like, wow, I am an awful human being who shouldn't even. Right. Right. You said it well. It's like, I wonder sometimes whether, people shy away from that process of radical self-inquiry because they're afraid that they may end up just with that massive laundry list of all the ways

that they have gone bad in the world, rather than saying, okay, so let me just strip things down to my essence so I can understand. I can just examine my life and who I am, the choices that I've made so that I can, and who I actually am and what I care about. That's right. That's right. And, you know, we've evoked her so much. I'll evoke her again. Dr. Sayers used to say to me many, many things, but one of the things she used to say to me, which used to make me laugh,

was when I'd be in that process of really trying to understand what had happened to me and the conditions in which I grew, she would say, well, not bad considering. It's like a New York, like cartoon,

the classic New York therapist, right? It's like, well, not so bad. It's all right. It's not terrible. I was like, He's like, man, that's so bad. It's all right. It's not terrible. I was like, all right, Jerry. That's so bad, you know? And it's like, what? You're on a stand.

Get the humility out of you. That's great. So you start to sort of come out of it. You start to step more into not just your own inner light, but you start to really understand a lot more about who you are, like processing your past, the things that have created you and the shields that you have put up in order to avoid actually seeing what happened in your past, which I think so many of us can share in that experience and how that has formed the decisions that you say, yes, I know too, and the way you behave in the

world and the people you run to and the people that you run from. Stepping into Buddhism was a meaningful part of that for you as well. Absolutely. Absolutely. In fact, where my in a moment, and now I understand why, was thinking about what I believe to be true about the fundamental nature of people. That's a big statement. Okay, it boils down to this. I believe human beings are fundamentally good. And I believe, like a lot of my Tibetan friends have taught me, that we just forgot that we're fundamentally good. And I believe, like a lot of my Tibetan friends have taught me, that we just

forgot that we're fundamentally good. And so the process of growing up is just remembering, hey, not bad considering. You're fundamentally good. And I really think the entire world can split into two groups of people. People who think human beings are fundamentally good and just forgot and need a little encouragement. And people who think human beings are fundamentally bad and need to be discouraged and beaten up and beaten into submission and compliance and all those things. And that choice affects every decision you make and affects your leadership and affects everything. Now, back to Buddhism. The most profound sutra, teaching of the Buddha,

that really changed my life was the belief that I was born whole, basically good, perfect, in need of nothing, and therefore in no need of saving or fixing or changing or anything, but occasionally reminding that I forget that I'm fundamentally good. And with that belief in mind, if I do radical self-inquiry and I look in the dark places and I look in the mirror and I do not like what I see because of shame, take a breath, reset my'm shameful, remember that the things that I have done that are cringeworthy, that there are lessons implicit in those cringeworthy moments. And to be gentle so that I may learn.

So that I don't do those things again. So that I can be happy. It's relatively simplistic and it's super hard. Yeah. I mean, because it requires you to separate behavior from identity. Amen, brother. That's not an easy thing for most of us. Well, the whole system is rigged so that you don't separate identity from activity. And since there's, I'm blanking and with apologies on the psychologist who first brought this to my attention. when we see others, you know, to making, behaving in a way that we view as bad,

as labeling them at an identity level as bad. But if we do the exact same thing, we say, well, we're a good person. We just screwed up. So it's interesting because I think on one hand, we have trouble separating these two things in ourselves. But I think we even have more trouble. With the other.

With others, yeah. Yeah, yeah. Which then exacerbates the disconnect from each other. And it exacerbates the disconnect from our own fundamental nature. And so then we live in this world of isolation, worried like hell that someone's gonna figure out, you know, we're awful

and that sort of thing. And so then we put the shields up and we put the guards up and we put the personas up and then, you know, and then the violence continues and continues and suffering continues and continues. Yeah. You, along the way, process your own stuff and continue to this day to process your own stuff, as do we all. We get to a point where you also have to really reconsider, what is my contribution from this point forward? How do I want to step back into a role of being of service, of earning a living, of making meaning. And for you, the most recent incarnation for a number of years now is in the

form of taking your own experience, really digesting it, exploring it, and then bringing what you've learned in a coaching capacity, most often to founders. Very often, most often to founders of fast growth startup businesses, which is about the fiercest cauldron on the planet, the fiercest self-imposed cauldron on the planet to push every button to either destroy you or build you up. It's the fire that either burns you or forges you, depending on how you move through it. One of the questions that I know has become central as you sit with the people that you now work with is built around the idea of being complicit.

Tell me more about this. So one of the core radical self-inquiry questions that I encourage people to look at is, how have I been complicit in creating the conditions I say I don't want? And the phrasing in that sentence, in that question is really important, so I'll repeat it. How have I been complicit?

Complicit, not responsible, not solely responsible, not the guilt bearing party, evil person, but how have I helped it along in creating the conditions I say I don't want is really important because implicit in that is the recognition that we can say we don't want to live a harried, frenetic, frantic life. And yet we persist in behavior that leads to a harried, frenetic, frantic life. And so the curious coach-like question to ask is, huh, what's up? Because how does living a life on the edge of that time vortex serve you? Because in my experience, behaviors persist when they serve us. Then we get really curious. Do we need to be served like that anymore? Are there other ways in which that need can be serviced? So for example, I might need to feel really self-important.

And one of the ways I feel super important is by staying busy. And so if a coach walks in and magically cleans up your schedule, within two weeks, you will magically fill it up again. Because you need to feel important. Okay, so feeling important is really important. So how do we get you to feel that feeling without the behavior that's so hurtful? And that's why that question is so important.

Yeah, I think it really, it turns, my sense is, I know you've asked this to so many people, and not people, you know, people who the outside world looks at and perceives as astonishingly successful when very often when they come and sit down with you, you know, to this day, I remember asking you, I don't remember whether we caught this on camera or not, like, what do people come to you for? And your answer to me was something like they need a place to cry. You know, but to the outside world, they're massively successful,

but there's something inside of them, which knows that this is not the way that they wanna be living. And that question, I think, is one that really just starts to unlock so much about our role in creating those circumstances, which I don't think we like to step into. No, no.

So much easier to just blame like the world, this is what's demanded of me at this moment in time. I mean, I was working with two clients this morning and they kept saying things like, well, we didn't have any choice. We were talking about the fact that they hate their employees. And I said, well, who know, we didn't have any choice. You know, we were talking about the fact that they hate their employees. And I said, well, who hired them?

And they said, well, we hired them. I said, well, why didn't you fire them? And they said, well, because we didn't have any choice. And I said, well, why didn't you have any choice? And they said, well, we didn't have a choice because, you know, we would be sued if we fired them. And I looked at them and I said, what are you talking about?

Can't you potentially be sued at any moment in time? And what it came down to was that they needed to have a sense of superiority over those employees. So they consistently and persistently hired people who were less capable. Now, that's their complicitness in it. Part of the structure is they were a fast-growing startup. And who's most likely to step into that but people who lack experience and maturity? So you're taking a risk. So guess what? You're going to hire people who are

not the best in their job because they're looking for experience. They're trading their lack of experience for your poor salaries. So you're going to have to continuously change people. The complicitness part of it was it helped them feel superior to always hire people who are just marginally not so good. The hating is an interesting thing because hating kind of implies something's going on on a projection basis,

but we don't have to go there right now. Yeah, it's almost like we bring people into our orbits to serve as proxies for the ways that we don't want to personally be in the world, yet still have to in some way be expressed for us to feel like we're okay. Yeah. The phrase I often use is that you've outsourced that particular negative feeling to someone else.

Oh, you're perfect. Will you carry my greed for me? Right, right. Because I don't really want to acknowledge that I have some greed and ambition. But somebody's got to. But somebody's got to have greed. So who's got greed? For me to be okay, right?

That's right. So we think we're filling roles in an organization chart. We're actually filling holes in our psychological psyche, you know, in our psyche. That's big right there. One of the things that becomes pretty clear to me through the work that you're doing in the world is, yes, you've got tools. Yes, you've now steeped in a lot of philosophy and a lot of Buddhism, a lot of different skill sets, a lot of different modalities to really work with people and help them navigate these things. But fundamentally, what it seems like, one of the roles that you provide for so many people who are moving through these windows

that are feeling the heat of the fire and they don't know which way is up and what to do, goes back to when you have gone through those moments in your own life and somebody sat there with you and didn't say, it's gonna be okay, but they were just with you. Yeah. And I wonder if you feel like a big part of what you do, part of it is yes, about the process of inquiry

and all the stuff and the skills that you bring to it. But if a big part of it is also the quality of inquiry and all the stuff and the skills that you bring to it. But like, if a big part of it is also the quality of attention and presence, regardless of what you ever said or did or didn't do, and just letting somebody know that there is a person who is offering that quality and that presence in this moment in time. Yeah, I mean, absolutely.

And that's actually something you don't need a coach for. That's actually something we can do for each other. It's like we can sit in a nonjudgmental stance, shoulder to shoulder, sit on a park bench on Broadway and just look at the sky and go, dang, it's hard. Yep, dang, it's hard. You want some gelato?

Yeah, let's go get some gelato. I mean, if we could just pause and do that a little bit more often, a little bit more frequently to the loves in our lives, to our children, to our parents, to our friends, to our colleagues, just makes life a little bit easier.

I think it's what you do, Jonathan, with this show. I think it's the presence. Yeah, I think it's part of it. It's interesting. We both are strong believers in the fact that belonging is an essential part of the human experience and the research is straight there to back that up as well. I often wonder if part of a fundamental ingredient of belonging, yes, is shared values and interests and all this other stuff, and is shared commiseration.

Sure. And that's where I think your point about it doesn't have to be a coach. It doesn't even have to be somebody who is higher or further down the road from you. It could be somebody who's going through their own thing. I almost think that just sitting by somebody where you both know that we are going through something, but circling all the way back to what you said you want on your gravestone. That's right. But we are not alone.

Not alone. That alone is so powerful and transformative. I think that's right. I think, you know, this is called the Good Life Project. I think that's actually the essence of the good life, is to know you're not alone. I can kind of withstand anything if I know I'm not alone. And that makes it all good.

So normally the last question that I struggle around with is, what does it mean to you to live a good life? But I think we just got the answer. Oh, look at that. I may have internalized that. Beautiful. Thank you so much, Jerry. It's always such a pleasure.

Oh, thank you. And thank you for making me laugh so much and making me feel at home. Thank you so much for listening. And thanks also to our fantastic sponsors who helped make this show possible. You can check them out in the links we have included in today's show notes. And while you're at it, if you've ever asked yourself, what should I do with my life? We have created a really cool online assessment that will help you discover the source code for the work that you're here to do. You can find it at sparkotype.com. That's S-P-A-R-K-E-T-Y-P-E.com. Or just click the link in the show notes. And of course, if you haven't already done so,

be sure to click on the subscribe button in your listening app so you never miss an episode. And then share. Share the love. If there's something that you've heard in this episode that you would love to turn into a conversation, share it with people

and have that conversation. Because when ideas become conversations that lead to action, that's when real change takes hold. See you next time. Mayday, mayday. We've been compromised. The pilot's a hitman.

I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him, we need him. Y'all need a pilot.

Flight risk. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you eight hours of charge in just 15 minutes.

The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary.