The Tim Ferriss Show - #373: Jerry Colonna — The Coach With the Spider Tattoo

Episode Date: June 12, 2019

"You are not alone. And just because you feel like shit doesn't mean you are shit." — Jerry ColonnaJerry Colonna (@jerrycolonna) is the CEO and cofounder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders.Prior to his career as a coach, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase. Prior to that, he cofounded New York City-based Flatiron Partners with Fred Wilson, which became one of the nation's most successful early-stage investment programs. His first leadership position, at age 25, was Editor-In-Chief of InformationWeek magazine, and now he has returned to the written word with his first book, Reboot: Leadership and the Art of Growing Up.Click here for the show notes for this episode.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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email. I do not publish the content on the blog or anywhere else. Also, if I'm doing small in-person meetups, offering early access to startups, beta testing, special deals, or anything else that's very limited, I share it first with Five Bullet Friday subscribers. So check it out, tim.blog forward slash Friday. If you listen to this podcast, it's very likely that you'd dig it a lot and you can, of course, easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out, if the spirit moves you. Hello, boys and girls, ladies and germs. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job each and every episode to deconstruct world-class performers from all different disciplines. And my guest today has a very, very interesting job. And that is he himself, I would say, deconstructs and helps to reconstruct world-class performers. His name is Jerry Colonna, C-O-L-L-O-N-N-A, on Twitter,

at Jerry Colonna. He is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. Prior to his career as a coach, he was a partner with JPMorgan Partners, JPMP, the private equity arm of JPMorgan Chase. And prior to that, he led New York City-based Flatiron Partners, you may have heard of it, which he co-founded in 1996 with Fred Wilson. Flatiron became one of the nation's most successful early-stage investment programs, and certainly those in the venture game know that is understated. His first ever leadership position at age 25 was editor-in-chief of Information Week magazine, and now, returning to the written word, his first book is Reboot, subtitle, Leadership and the Art of Growing Up. Jerry, welcome to the Written Word. His first book is Reboot, Subtitle, Leadership and the Art of Growing Up.

Jerry, welcome to the show. Hey, Tim. It's great to be here. I'm really excited to talk to you. We have so much we could possibly talk about. You and I have spoken before, had quite a few conversations over the last God knows how many years, with particular density a handful of years ago. And I thought we could start with the spider tattoo, which you just showed me over video. It is not a small tattoo. So, perhaps much like a novel I greatly enjoy, The Girl with the Dragon Tattoo. This would be the coach with the spider tattoo, but I don't know the story. Why do you have a gigantic spider tattoo on your chest? Oh, well, yeah.

So, Spider is a good friend of mine. Spider is my spirit guide. So, in 2007, I went on a retreat led by a Jungian eco-psychologist named Bill Plotkin, P-L-O-T-K-I-N. And, um, on that retreat, this is a long story, Tim, you ready for it? Oh, I'm ready. We have nothing but time. On that retreat, um, I started to go, uh, really deep into some of the important structures of my life. And I had a dream. And it was after a night of ecstatic dancing in which I was supposed to, I was going to a house that I owned on Long Island. And I got to the house and the house was completely white and I

was really terrified. And I went into the house and it was supposed to be my house, but it didn't feel right. And I ended up in the basement. And in the basement, the basement floor was covered with this sort of like the floor of a forest. And these mushrooms were sprouting up. And I got very scared, and I tore the mushrooms from the ground, and I ran out of the house. So the next morning, I went into circle again, and I shared that dream. And Bill turns to me and he says, go leave, leave the circle right now. I want you to go into the forest. I want you to find those mushrooms and I want you to apologize to those mushrooms and ask it what it was that you were

supposed to hear from them that you were too afraid to hear. So I left the circle and I started wandering around and I'm like, what the fuck am I doing? I'm walking around this forest trying to find these mushrooms and I actually have to have a conversation with these mushrooms. And to be clear, I was not ingesting the mushrooms, okay? Because I know who I'm talking to. So I'm walking around and all of a sudden I see on the ground the exact same white, long, stringy mushrooms. And I'm like freaked out. And I dropped to my knees and I start crying and I said, I'm so sorry, I'm so sorry. What were you here to teach me?

And they said, the mushroom said to me, you're too afraid. Go into the forest and find your place. And now I'm like freaking out even more. So I just standing up and I'm like stumbling around. And this is a time period in my life where I'm just a freaking wreck. And I'm crying and I'm wandering through the forest and I find this little sort of indentation, this little spot. And I sit down and I'm like sitting on my rump and I've got my hands on my knees and my head. And I'm just crying. And I look up and off into my right is this gorgeous spider web. And it actually has little dew drops glistening on it.

And it's like, okay, they look like crystals. And this little spider comes walking out it's this virginia garden spider and i look at it and i said okay i give up what the fuck are you here to teach me because i have no idea and the spider says to me you worry too much your children are going to be fine and i just start shaking because there's no message that i needed to hear more than that and so i came out of that forest i came out of there at retreat and a few weeks later was my uh 45th birthday they're about the actual year doesn't matter so much as the fact that it was my birthday. And on my birthday, I got this spider tattoo above my heart so that I can never forget

the fact that I worry too much and that my kids are going to be all right. So, that's the spider. Has it remained relevant to you? Is it something that you consciously notice? Or because it's so continuously present, do you find yourself sometimes losing sight of it? Both. Meaning, I'm often reminded, as I was when you asked and you said oh i'm going to ask you about the spider i'm often reminded so thank you for reminding me um that that the point of that spider's visitation to me was to remember who i am and i can use that reminder every day because

i forget every day. Not only do I forget who I am, but I forget that my kids are all right and that I worry too much. Thank you for the story. And, you know, it makes me think of, given the spider, Lakotaota mythology and ictami there are various names for ictami but ictami is a spider trickster spirit a bit of a hero and uh perhaps one of the ways that you are a productive trickster is by asking questions that are very uncomfortable or that can be very uncomfortable. And I think that's one of your arts. And we're going to come back to that for sure. But I thought we could revisit another perhaps chapter or event in your life that seems to have been very impactful. Could you talk to, uh,

I believe it was February, 2002 after something involving the Olympics or the Olympic bid meeting. If you know what I'm referring to, I am. So, um, yeah. So February,

2002, um, I was working at JP.P. Morgan at the time. I was co-leading the technology investment practice for a fund that was about $23 billion under management, so a large fund. and this was after having left Flatiron Partners in, I think, around the middle of 2001. And just for clarity, that was billions with a B. That was billions with a B. Yeah, that's a large fund. It's a large fund. I mean, but we were very diversified. We did everything from Brazilian railroads to funding the launch of JetBlue

Airlines to the latest web-based startup in some capacity. Anyway, and a few months prior, it had been cleared that my previous fund, Flatiron Partners, needed to be wound down. Fred and I needed to make some decisions about what to do. I was in the midst of trying to sort through what I was going to do with the rest of my life. I did not have the internal capacity to raise a new fund, I know now that I was in the midst of a very profound depression that was exacerbated by the attacks on 9-11. And one of the ways I responded to the attacks on 9-11 was to throw myself into the Olympic bid effort. We were bidding to bring the 2012 Games to New York. And for me, this was a profoundly important effort because, now you're going to make me cry,

my city was attacked. The city that I love. And where you grew up. The city where I grew up, the city of Brooklyn, the place that had so much meaning for me was attacked. And I remember the feeling helpless during the fall following the attack. Anyway, around the same time, I had to decide whether or not I was going to accept an offer to join J the attack. Anyway, around the same time, I had to decide whether

or not I was going to accept an offer to join J.P. Morgan, which had been one of the funders and the funding partners for Flatiron Partners. And eventually, I did that, and Fred linked up with Brad Burnham, and they launched Union Square Ventures. By the way, worst decision of my life, but anyway, to join J.P. Morgan and not go to Union Square Ventures. By the way, worst decision of my life. But anyway, to join J.P. Morgan and not go to Union Square Ventures. Anyway, so he went off and did that. I joined J.P. Morgan. And by February 2002, I was a wreck. And what you're referring to is February 2nd, 2002, I left an Olympic bid committee meeting, which was being held downtown, not far from Ground Zero. And I found myself outside of the stinking, smoking hole that was the pile, as they referred to it, of ground zero. And I remember feeling completely overwhelmed and feeling like there were ghosts flying around that area.

And I wanted to die. And I was obsessed with the idea of running down to the Wall Street subway station and leaping in front of a subway. And I ended up deciding not to do that, but wisely and thankfully instead called my therapist, Dr. Sayers, who said to me promptly, get in a cab and come out and see me. And I did just that and saved my life at that point. What did your therapist do when you arrived? What was that session like?

Can you describe that session? Yeah. So Dr. Sayers was a psychoanalyst. And so I very traditionally, almost like a yorker cartoon would lay on the couch and uh i can't help but think of that and think of like somehow it's a dog sitting in the therapist chair so it's like that's some sort of new yorker thing anyway so i'm laying on the couch staring up the ceiling as i did all the time and i just remember saying to her, just stick a fork in me. I'm fucking done. Put me in the hospital. Throw away the key. And to be clear, the threat was real,

because when I was 18, I did try to kill myself. And so no fooling around here. This isn't just some idle ideation going on here. This was like, I was in it. I was 38, I was being cooked, and I was declaring that I was done. Dr. Sayers, who was also from Brooklyn, said the most magical thing possible. She said, what the hell do you want to go to a hospital for? The food sucks. Go to Canyon Ranch. You'll get a massage every day. You'll be so much better. What is Canyon Ranch?

Canyon Ranch is a health spa, and it's a very nice place. I loved it. It was really sweet um but it's about as far removed from a psychiatric hospital as you can imagine because by the way i i did spend three months in a psychiatric hospital so i sort of knew what i was getting what i was asking for if you will so that's what i did i made plans to go down to arizona think it was the Arizona branch of Canyon Ranch. And yeah, that moved, was the beginning of me being rebuilt. When and why did you spend time in a psychiatric hospital?

Well, I mentioned the suicide attempt. Right. I was 18, and I had, on January 2nd, something about the number two, right? January 2nd, I guess it was 1981. I'm losing track of the time. I had just turned 18, and I tried to kill myself. I cut my wrists and first went to – I was taken to the emergency room, Jamaica Hospital, the Trump Pavilion. That's all I'm going to say. And then I was transferred from there to Creedmoor State Hospital, which is just this side of hell.

And then from there, after three days at Creedmoor, I was transferred to a hospital that actually is no longer a hospital, Cabrini Medical Center in Manhattan, where I was there for three months. I'd love to, I think this is a good point, to come back to questions and good questions. And you're very skilled in this department. So, I'm going to pose one of your questions to you, and you can feel free to tweak it, paraphrase it, correct it any way you like. But if you look back to 2002, how were you complicit in creating the conditions in your life that you would have said you didn't want? Nice turn. Which is a great question. So, maybe you could repeat it for folks because it is so

important and this is something that has greatly aided me when you introduced it to me many moons ago yeah uh and then if you could speak to that as it applies to that particular period in your life yeah yeah so i'll i'll i'll unpack the question so the way i usually ask the question goes like this how have i been complicit in creating the conditions i say i don't want and the reason for the language is very very careful it's very purposeful i like to use the word complicit and not responsible 90 of the time when i first ask that question, people hear the word, how have I been responsible for the conditions? Complicitness is important because it's relieving the person from the burden of feeling responsible for all the shit in their lives,

because that's not fair to carry that responsibility. But it's helpful to think of ourselves as somehow being served by the challenges that we're going through. The second piece of that is that I say I don't want, and that sort of unpacks that notion even further, which is there's something oftentimes about the way in which we operate and the way we set up the conditions of our lives to be in unconscious service to us. The psychological term is secondary gain. But there are ways in which we find ourselves repeating patterns in our life. We always date the same type of person. We are always finding ourselves in the same kind of job. We're always frustrated by the same sorts of situation.

And so it's really useful to sort of start to unpack that. So that's that question. And before I even answer your question, I want to say one other thing. The discomfort of difficult and powerful questions reminds me of something my daughter Emma likes to say about me, which is that he, imagine growing up with a man who asks you questions that you'd really rather not answer. So, shout out to emma so um i think that the way i was complicit i guess we should thank emma for being the crash test dummy for

the questions that you use now in your career you got it. Well, Emma and her brothers, Michael and Sam, for sure, for sure. God love them. They put up with so much with me. Oh my God, dad, stop coaching me. So yeah. So before I can answer that question, honestly, what I would say is Dr. Sayers taught me three additional questions. And those questions are, what am I not saying that needs to be said? What am I saying that's not being heard? And what's being said that I'm not hearing? So, again, what am I not saying that needs to be said? What am I saying that's not being heard?

And what's being said that I'm not hearing? And so for me, the way I was complicit was I wasn't speaking. I wasn't saying what I needed to say. And more often than not, Tim, the suffering that I encounter can almost always be rooted back to somebody not saying something that needs to be said. And if there's a little correlate to that

and not saying it, or not saying it in a way that it can be heard. Because oftentimes we speak without words, but by our actions, and we go unheard. Could you give an example of something that you needed to say during that period of time that you didn't, that I wasn't speaking truthfully, that I wasn't living in integrity, and that I was too afraid of losing the good graces and esteem of everybody around me to actually talk about the fact that I did not want to do what I was doing with my life at that point. Oh, by the way, I didn't know what else I was going to do, but that's a separate issue. Right? I mean, I knew when I decided not to continue working with Fred Wilson, stupid man that I was, I knew that it was actually the right thing for me to do.

But when I agreed to take a job at J.P. Morgan, it wasn't because I wanted to continue doing that work. It's because I was too terrified to do anything other than that. And I certainly didn't want to lose the esteem and the good wishes. I mean, think about your reaction just a few minutes ago when you pointed out that it was a $23 billion fund. And even in that moment, I felt a little bit of that pride mixed with a little bit of the shame because I walked away from that. Right? And I didn't want to lean into that space of like, what if I don't matter anymore? What if nobody calls me? How did you get over that? What are the things that contributed to you making it through those questions?

Because a lot of people seemingly don't make it through those questions, right? They stay in a given track track in a given relationship. They stay stuck exactly for 5, 10, 15, 20 or more years. So what... Or a lifetime. Or a lifetime. What did Emerson say? The vast majority of men, let's update it, the vast majority of people lead lives of quiet desperation.

Mm-hmm. So, you know, how did I get out of it? I guess your question implies an agency that I didn't feel at the time. Meaning, huh, I wake up one day and I decide I'm going to be different. No, it wasn't that. It was that I ran out of the ability to continue to operate anymore. It was that moment above the lip of ground zero and that moment where I chose not to leap in front of the subway, but to get into the cab and go to see Dr. Sayers. And it was that moment where I decided to follow her advice and go to Canyon Ranch.

And it was the series of moments where it was like, okay, I know it's not working. I admit it's not working. I admit it's not working. I don't know what I'm going to do, but what I have been doing hurts too much. And if I have to deal, if I have to suffer the consequence of the loss of status, approbation, affirmation, all the external trappings, so be it. It was like my soul basically said, listen, motherfucker, you better sit down and pay attention to your life because the stakes are too high. I think I read that in the Bhagavad Gita, if I'm correct. Brooklyn edition. It's the Buddha from Brooklyn. Yeah. Now, how did you find your way to, I'll use this term, it may not be the best term, but how did you find your way to coaching?

So on that plane ride from New York to Arizona to Canyon Ranch, I read three books. When Things Fall Apart by Ani Pemachodran. Faith by Sharon Salzberg, and Let Your Life Speak by Parker Palmer. And before fully answering your question, I'll give you this. I must have done something really, really good in a past life because I have the benefit of considering all three of those people, Ani Pema, Sharon Salzberg, and Parker Palmer as my friends. I didn't know them at the time, but I have the good grace and the incredible good fortune to say I'm friends with them. They are my teachers. So what was your question?

The question was, how did you find your way to coaching? And just to reiterate something that you just said, at the time, they were not your friends. That's right. But you had the books. And so I asked how you found your way to coaching. And you went back to the plane ride. Right. And so in reading those books, and those three books were really important because they did lead indirectly to me becoming a coach. Each one of those books presented something different to me. Faith presented this notion of really being honest with myself with what was

going on. When Things Fall Apart was the first laying out of Buddhist Dharma as a path, but it was Let Your Life Speak, which is a brilliant, beautiful, short little collection of essays that really shifted the dialogue for me, partially because Parker is so open and honest and authentic about his own struggles and depression. Okay, so to your question, let me fast forward it. Probably four or five years later, I'm still working my way through all of the issues that I'm carrying at that point and trying to sort myself out. I'm in an office. I'm sharing office space with Fred Wilson and Brad Burnham from Union Square Ventures, but I have a little sub-office within their space. I'm doing a bunch of different

things. I'm serving on a bunch of boards of directors. I'm making little angel investments here and there, but I'm just sort of hanging around the hoop, if you will. And this young guy comes to see me and he says, he's there to, quote, network. This is the thing everybody is supposed to do. Network is way too new job. And you ask about questions. So here's the story. He comes in, and he's a lawyer, and he wants to get a job in the startup industry. He wants to find a way to get some sort of position. I turned to him, and he's probably in his late 20s, and I said, I'm happy to help you, but just answer a question for me. It's kind of my first coaching question. I said, what made you become a lawyer in the first place?

And he starts crying to me, and he starts telling me about pleasing his father and about how it was, you know, his father had taught him that if all else fails, at least he could make a living as a lawyer. And the kid was just miserable, just miserable. And so I reached up to the shelf and I pulled down a copy of Let Your Life Speak. And I said, here, read this. And they get back to me. And then he left the office and I turned around and I said, fuck, I think I need to be a coach. I need to do that more frequently. And so within a few days, I had signed up for a coach training program.

Okay, let me pause for one second. So what did you feel? What did you experience? What was it about that encounter that made you so decisively say that to yourself? A couple of things. I could see relief in his eyes. I could see, I think the first thing I felt was empathy. I knew his feelings.

Because even though the content of the story was different, my experience was so similar. I had been so ruled by fears that I was living in a box. I had lived in a box that was not of my making. It was somebody else's box. It was the wrong box. It was the wrong suit of clothes. It was not me. And I could feel all that. And when I reached for Let Your Life Speak, I was reaching for the very same thing that had gotten me out of the box. And I said, here, here's a path. relief, not that he'd read the book yet, but just relief that somebody actually understood his feelings and had given words to his feelings that he hadn't been able to give to. Remember that question? What have I not been saying that I need to say? There was that going on for him. So then I said, wait a minute, dude, you can do something about relieving suffering.

You're not the mess. and it's not always just your prefrontal cortex that's going to figure everything out because i didn't have an answer for him i didn't say here here's the job you should do that's perfect for you so that you no longer go to bed at night feeling like crap wondering whether or not you should wake up in the morning. I just had to listen to my heart. And I did something completely non-intuitive. I reached onto my bookshelf and I gave him a book. And the feeling that I had was poignant pain coupled with a sense of being able to do something.

I could be helpful. You know, this may be overreaching, but how much of your call to coaching do you think, if any, was finding relief in taking the focus outside of yourself? Oh my God, what a great question. It wasn't just the call to begin coaching. This helps me every day. I mean, this is the craziness about the work that I do, about living my vocation like this.

Even today, in my worst moments, when I can be with another person's pain, by the way, which is the root etymological meaning of the word compassion, to be with someone else's feelings, I magically feel relief from my own unbearable feelings. Because I think that's the essence of being human together. We get to actually, oh, geez, we look at each other across the campfire. I keep imagining us in sort of pre-civilization going, like looking across a campfire, and again, must be in Brooklyn, and going, dang, it's hard. Right? Isn't it hard being human? Yeah, it's really hard.

Okay, let's do this together. So I think the call was that, but if I may, I think the call was also to retroactively go back in time and save myself. Interesting. This makes a lot of sense to me. In saying that, do you mean, and I don't know if you've ever heard of IFS, I think it's internal family systems, in so much as by helping people who are in similar positions with similar states or pains as you experienced earlier,

you are healing that younger version of yourself in some capacity. Well, first of all, to answer your quick question, I have heard of IFS. I have not been trained in IFS, and I know a few of my clients have benefited from it. But broadly speaking, you want to understand Buddhism. It's what we're talking about right now. You want to understand wisdom traditions across the world. It's what we're talking about right now. It's like, you know, even the best of

Christianity, even the best of what Jesus taught, it's like, God, I mean, I just imagine him exasperated, sitting there saying, for God's sake, love one another. Just, you know, come on, can you just stop the nonsense and just reach across and just be with each other? And that there's a kind of, think of it this way, Tim, there's almost like a universal wellspring of pain that you and I share. And in a similar fashion, there's a universal wellspring of happiness and joy that you and I share. And so if you're in this painful spot, I can tap that universal wellspring of happiness and joy and point it a little bit more at your suffering. And you can do the same for me. So let me ask you a question.

And you and I have spent a good amount of time on the phone together. And to those people listening who are self-described high achievers, who don't want to lose their edge, who are looking for the tactical practical. If they hear that and they're kind of rolling their eyes and they're like, all right, you had me at 9-11, you had me at the books, but I don't see how this applies. I'm too busy for that shit. I don't have time to go to Burning Man and do fire dancing. Like, this is serious business. I have serious work to do. Sorry. How do you relate that to someone who in their first meeting fits that profile, perhaps? What do you do with them in a first meeting?

Yeah. So, my job isn't to necessarily convince people that they need help. Right. Right? And so the first thing I say is, and the first thing I would say to anybody who's listening, is if everything's working for you, go at it. Have a great time. Go enjoy yourself. Go ahead.

But, you know, there's a simple little trick. I have this little reputation that I make people cry and all this stuff. You know what I do? I ask them a simple question. How are you? And I often follow it up with, no, really, don't bullshit me. How are you? How are you really feeling?

Because here's the thing. You described this would-be resistant person as a high achiever. Here's the thing about high achievers, in my experience. High achievers early on in their life figure out how to get an A. They figure it out because the whole system is geared towards that grade. Then we take that entire system from our childhood and we move it into work. It's just getting A's, getting A's just getting A's, getting A's, getting A's, getting A's. And the highest achieving people oftentimes come into me scared because there's a little whispery voice in their ear that says, you are a fucking fraud.

You have no idea. And when they figure out that all you're doing is reading the tea leaves and what it takes to get an A, they're going to toss you out of the tribe. They're going to toss you out on your ass. They're going to push you away. Or they say to themselves, because they haven't experienced loss or they haven't experienced failure, they think they haven't experienced loss or they haven't experienced failure, they think they haven't experienced failure, they're just waiting. They're just playing a waiting game. They're just waiting for something, for fate to catch up to them, and bang, the hammer's going to come down. Now, if this resonates with you, you might also then recognize the anxiety that comes in, where you put your head down at the pillow at night and you go, my God, I don't know if I can do it again tomorrow. Maybe they'll catch me tomorrow. and if that's what you're working with, then there's an opportunity in all that we're talking

about. Forget universal suffering. Forget about wellsprings. Forget about spiders. Forget about Burning Man, which I've never been to, by the way, and I don't believe in substances, but that's a whole different issue. Forget about all that stuff. I've been three times. I'm a fan, at least once in your lifetime. God bless. Separate conversation, so continue. The truth is I'm probably too scared to ingest any material inside of my body, but leave that aside for a moment. Forget all that.

Okay, all the esoteric stuff like that. Here's the simple question. How's it working for you? Because if it's not working for you, why are you in pain? Why are you doing it? And would you like a little relief? And you want to know the secret, like, nasty little trick that I play? Yes.

I get them if they either have children or hope to have children someday. I will ask them, what would they like their children to feel when they're at the same age? Because if they would like them to feel something other than what they're feeling, now's the time to start changing the way they organize their lives. That's a really good question. What if, and this could combine with what we're talking about right now, someone comes in, they don't feel imposter syndrome necessarily, but they are simply overwhelmed. You ask them how they are, no really, and they're like, I'm good, I'm just busy, I'm stressed, I just have too much, I'm overwhelmed. If that's the breed of client that shows up,

how do you begin to work with that? Well, once you've established a certain level of trust and relating through empathy, and don't necessarily try to step in and fix it, the first question I would start to ask or elicit is how is that being busy serving you? Remember that how have I been complicit in creating the conditions I say I don't want? Because here's the thing about busyness. Busyness can feel fucking awesome. It can feel so amazing internally. Like,

look at all the great stuff I got done. Externally those voices inside that say, hey, I'm not happy. Hey, I'm serious. I'm going to throw you down on the ground with some sort of somatic illness, lower back problem, irritable bowel syndrome, migraine headaches. That was my specialty. I'm going to throw you down until you pay attention to me. Okay, you're too busy. Okay, I got you. Okay. Because here's the thing too, somewhere around 35 to 50 years old, the systems start to break down. The systems that got you out of childhood, that got you into adulthood, that got you established, that got you to the point where you think you got it all figured out. And then all of a sudden, holy shit, the whole thing starts to collapse. Now what do I do? And when I see someone who's busy, who's kind of in the

early 20s, I see a striver trying to establish themselves. But when I see somebody who's busy, who actually doesn't need to be that way, I get really, really curious what internal need is trying to be met by all that busyness. And that's the place to inquire. What are some of the more common patterns that you see with that busyness? I'm very curious about this. Well, I promise not to coach you, but why is it so curious? No, just kidding. I can tell you. No, I can tell you why it's curious or interesting to me. We can jump into some. I'm game to hit some volleys if you want. Well, for instance, I'm looking at, and apologies to everyone I have not replied to, but that is sort of my

ethos and the gist of everything I've written. So, I feel like I've bought some permission, but I currently have 618,952 unread email and a combination on two different tracks of 165 plus 255 unread text messages. And that's the tip of the iceberg. So, I actually feel surprisingly low anxiety about that. Nonetheless, a small amount of anxiety. And in the process of literally rebooting those various phone numbers and addresses because it's not physically possible to address that. Right. And it's, perhaps similar to many of your experiences, it's given me an opening line or common sentiment of commiseration that opens up the floodgates to similar types of problems in other

people. So, they confess. I'm like the productivity guy in the confessional box for people who want to tell me about similar things. And that is, those are a few things that come to mind when you ask me, why is that curious? And I think think it's very common i just think it's very common i think it's hugely common and i think that you know you you ask the question um by using uh a particular descriptive word you you described it as feeling overwhelmed right and you know if we were to do a dream analysis, we might talk about being flooded. That's typically the psychological signal that the system is overwhelmed. So, again, we use our construction and we talk about complicitness, not necessarily responsibility. And I'm going to use you as an example as a high achiever who is incredibly busy. And so busy that he has over 600,000 unanswered emails.

And we'll just stick on that one for a moment by the way you're allowed to declare bankruptcy at that point okay you're done oh yeah and what i hear you say is i no longer you said i don't feel anxiety just a small piece of it um i i would argue that you probably have have been so overwhelmed by it that you've actually given up feeling anxious about it and it's just like forget it i'm not going to get to it right um so here's the question for you and you don't have to answer it but but hang out with it um a couple questions the first would might be something like um uh when did you start feeling overwhelmed and And how long have you felt overwhelmed? And while feeling overwhelmed, did you take on more tasks, right? In your case, Tim, did you sign up for another book and another show or another thing which only produced more stuff?

Because that's what I do, right? If there's a tiny bit of open space in my life, I tend to fill it, right? And then the magical question is, how familiar is that feeling and how does that feeling serve you? I'm willing to play on this one. And I will say before I get started that I do think I have much better systems and rules and perspectives in place now. But to answer your questions, I'd say it started probably middle of undergraduate college. Right. undergraduate college, this feeling of overwhelm. Or at least that's when it was most noticeable. And the feeling of overwhelm was then kind of ebbed and flowed, but certainly up until at least 2004, my solution to feeling anything I didn't want to feel was to add more activities.

Okay, can you just pause and say that again? Your solution to? Feeling anything I didn't want to feel. In retrospect, I recognize that's what it was. So if I felt anything I didn't want to feel, I would add more activities to drown it out. Some people use heroin. Some people use coke. Some people use work.

And I used activities. At the time I also used stimulants, so I was in fact using both. But that changed quite a bit in 2004 by building in empty space. I think that still now there are vestiges of behaviors that in some sense helped me to find a toehold in financial security that are no longer serving me, that are nonetheless default gears, if that makes sense. Sure. And to that extent, the vast amount of my focus for the last year has been on saying no to practically everything, more than a year. I mean, the last several years. Nonetheless, there is a part of me, I think you had a, was it a crow? A raven on the shoulder? Crow. The crow. We'll come back to the crow.

And no, it's not another dream sequence for people wondering. No drug-induced dream sequence. Correct. We'll come back to the crow. Something on my shoulder saying you might need this person. You might need this person. This person in reference to any given email that might come

in. And so, for what I find in my life is that the vast majority of stuff is clearly noise, and I can ignore. There are categories of activities. I'm not particularly good at moderation, whether that's with, uh, you know, like chips or chocolates or, uh, speaking engagements or fill in the blank. There's certain things where I need to either be considering each, each item that presents itself or not consider them at all as a category. And, uh, so I've decided certain things just from a binary perspective, like speaking, I will not do any of unless they happen to be 10 minute drive from my house and fit 20 other parameters. Otherwise, it's an automatic no, and I don't even see it. Where I think I find more difficulty is where there are people who have been very helpful in the past, who perhaps were very supportive in the early body, it's absolutely not a full body yes. There is part of

me, there's a large part of me that knows I do not want to acquiesce. I do not want to agree. I do not want to accept. I do not want to do whatever it is they're asking me to do because it doesn't feel right and or it's unreasonable. Nonetheless, those are the types of emails that tend to pile up. And those are the types of emails also that even if I have someone like an assistant or multiple assistants filtering, the names are probably noticeable enough or old enough that they'll get brought to my attention. So, let's see here. Is it familiar? Yes, it's familiar. How does it serve me? This I have more trouble with. So, maybe you could walk me through, I would imagine many people, I'm not going to say it

doesn't serve me because I'm willing to, at least as a thought exercise, to accept that if it didn't serve me, I would have already found, at least as a thought exercise, to accept that if it didn't serve me, I would have already found some clean solution, or I wouldn't have any emotional difficulty fixing it. How would you walk me through figuring out how it serves me? Yeah. So the first thing I want to reflect back a couple of things that I'm hearing so that we can just sort of establish it. The first thing I would say is I really admire all the filtering that you've put into your life and the structures that you've put into your life to create boundaries and saying no. And I think that the rules as you define them and they might be rules for like, hey, every morning I'm going to do X,

and every afternoon I'm going to do Y, or I'm only going to work from hours. Those are all important, but ultimately insufficient for complete relief from some of these feelings. They're really, really helpful. They've reduced your anxiety from overwhelming to small, but 620,000 emails, right? And so I want to bring your attention to two other feelings. One was, you said, something about missing something that might be important to you, seeing someone that has been helpful to you in the past, or something that's important to you, that you might miss something. So that's one fear. Is that right? I would say so. I think the greater fear is that people who would at least

believe that they have supported me without asking for a quid pro quo in the past would get upset. And this does happen. It has happened where people take things very personally. And I recognize I can't take responsibility for everyone else's feelings and responses to things. I do think that's a fear. More than missing an opportunity, because I'm not concerned about missing financial opportunities. Not anymore. Not anymore. I once was. But I also stopped startup investing completely in 2015

because the noise simply wasn't worth it. The cortisol-fueled, unnecessary hurrying associated with that culture was causing more harm than good. So, I stopped in 2015. So, I missed a pretty decent bull run, which I'm okay with. So, it's not a financial concern so much as social cost and fallout, if that makes sense. Yeah, yeah. What I'm hearing is a fear of disappointing someone who matters to you. Yeah, yeah. That would be a piece of it. That would be a piece of it. And this is helpful to me to talk through because it's not just disappointment. In some cases, I actually really dislike interacting with some of these more recent acquaintances.

But for whatever reason, they view their position as very entitled in so much as they expect a fast and very compliant response from me on many things. And they know a lot of people in the same circles, and that causes concern. So there's an implicit internal existential threat. I think that's fair. I think that's fair to say. And if I could say one more thing, just so I don't sound totally like I'm living in a land of make-believe. I have run into many, many instances. This is more than a dozen at least where, say, someone will send me an email. They want a blurb for a new book.

They want this, this, this, this, this, and this. And by the way, it's coming out in four weeks or whatever it is. There's some set of requests slash demands. I don't reply. This has happened with journalists as well, where for whatever reason, I won't help them, and then a hit piece comes out. Or then there's some type of blowback slash kind of vengeful behavior, whether that's shit talking me on stage or whatever it might be. So, there's evidence to support the fear, but here I am. I've survived. I'm fine. That is also true. So, I just wanted to add that color. Right. And so, I want to reflect back to you empathetically and rationally. You're not nuts, right? The threats are real.

At least not in that department. That's right. That's right. So what I often say is that there are three basic risks that we're all trying to manage all the time. Love, safety, and belonging. We want to love and be loved. We want to feel safe physically, emotionally, spiritually, and we want to feel that we belong. And what I'm hearing, well, so if you resonate with those at all, the existential threat, and I want to bring your attention to existential, because I think that the threat is to the essence of who you are or at least the perceived threat. And when someone trash talks you on stage,

you know, what they're trash talking is you, right? The you. Not the meat bag, but the essence of you. And so I think that the fear, I know for myself, that the fear of disappointing others is a threat to my belonging. I'm not going to be in my family anymore. My children won't love me. My partners won't love me. My partners won't love me. And so therefore, I will be unsafe.

I will be bereft. I'll be by myself. I'll be alone in the woods, fending for myself. And there are few things that threaten me more than the threat to belonging. I don't know. Does that resonate with you? It does resonate. I think that a lot of what I've done and been able to do has been dependent on maintaining very long-term relationships with people who I enjoy being friends with, who happen to also be very, very good at what they do, whatever that is.

And so I think there's a bit of, you know, what got you here won't get you where you want to go or won't get you there. And that does resonate. And we don't have to jump to this, but what I'd love to talk about or listen to you describe, because I think a lot of people would benefit from it, is when you run into someone who, like me, is fielding a lot of inbound, and it could be from one person, but they, for whatever reason, are having difficulty saying no or establishing boundaries. What are tools or books or approaches that you've found helpful for people in that position,

whether it's nonviolent communication or fill in the blank, anything at all, or questions, anything at all? How do you begin to advise someone like that? Well, there's a couple of things come to mind, and I'm going to reference two friends of ours, Seth Godin and Sharon Salzberg. The first thing was, when I was really struggling with this early on in my career, my adult career, Seth Godin gave me some wonderful advice, which boiled down to this phrase, I wish I could, but I can't. And that became a kind of interesting little fence around my life, a boundary marker. The problem was that it ran out of – and so the idea was that you would be able to say to someone, someone who reaches out, can you do this favor for me, this thing for me? And you get to say, I wish I could, but I can't. So you just sort of pause around that.

The problem is, of course, there's an inauthenticity that can set in, which is I actually don't wish I could. And I can, but I really don't want to. Yeah, that's a whole nother level. I can, but I really don't want to. Yeah, that's a whole nother level. I can, but I won't. And so then it becomes a little bit of like, listen, I'm trying to take my own advice to heart. And the advice I give clients is to take care of themselves first. Right? And so that becomes a kind of useful tool. But then you reference something before about not being responsible for someone else's feelings. And that brought to mind a teaching that Sharon Salzberg gave me,

which goes like this. All beings own their own karma. Their happiness or unhappiness depend upon their actions, not my wishes for them. Say that one more time, please. Yeah. So all beings own their own karma. Karma being the cause and effect,

the consequences of their actions. Their happiness or unhappiness depend upon their actions, not my wishes for them. Or the corollary to that is not the actions that I take or don't take. Now, they may say to you when they're reaching out to you, Tim, Tim, if you don't do this thing that I'm asking you to do, then I will be unhappy. And if I'm unhappy, I will be mean to you. I mean, that's essentially the existential threat. I wish they would actually just send that email, because then I would say, gotcha, bitch. I have a blog. Shouldn't have sent that email.

Which has actually happened with writers from the new york times believe it or not which is horrible to say their threat right oh yeah yeah and then as soon as they realize what they've done they're like ah shit and then they cool their jets but yeah oh yeah so so here's a little tool that i that i have come up with that helps me is I often think of like creating these little fences and I often visualize a chain link fence so that I can see through it and it has a gate in it and the gate only opens one way inward and I get to control whether or not the gate opens and so then I can see someone on the other side and then the phrase that comes up is love them from afar. Be kind to them in my heart, set clear boundaries, right? I have, you know, as your friend, as your guide,

as somebody who hopefully is standing shoulder to shoulder with you is sort of in this crazy journey. I really feel for you, for all the people who have reached out to you 620,000 times in your inbox and all of that stuff. And I feel for you. And I would advise you to delete every one of those things. Yeah. And to basically love all of those people who are going to get unanswered from afar and be kind to them in your heart and recognize that on the whole, you're doing the best that you can because you are. You know, I wish I could give you like, here's the tool, you know, like NVC, Nonviolent

Communications has some brilliant tools, or here's the book that magically unlocks that. To me, the challenge isn't not having the tool. The challenge is in the meaning that we put into the situation that is the hardest thing to come over. And to recognize that you're okay even if you're not necessarily being at your kindest or at your best.

Because like you, like everybody else, like me, we all get resources that are thin at times. My God. My God. And so, you know, if you've not answered a text message from me, Tim, or if you've not answered an email from me, I am never, ever, ever going to think ill of you. Well, I appreciate that. And I wish I could transmit that composure to all of my 620,000 senders. Let me ask you a situational question. And this is true in my life, and I'm sure it's true for many people listening, that I have a handful of people who are kind of close to me, very much in the same circles,

playing at a high level, who tend to reach out to me only when there is an ask of some type. And there tends to be some great degree of discomfort associated with the ask in so much as perhaps they have two or three people who are close friends of mine attending an event of theirs or investing in blah, bitty, blah, whatever it might be. So that it is, there's a great degree of discomfort that I feel in ignoring the email. Maybe I actually get texted by one friend and then the email from this person. There are a few people who are repeat characters, kind of like Newman and Seinfeld and Seinfeld shakes his fist. Newman! Yeah. So, I have at least a half a dozen Newmans who are pretty tough to get rid of. And they're not very good at reading

hints, or they deliberately ignore hints that I don't want to do things that I don't want to respond. Have you coached people through breaking up with friends or having direct conversations with their own Newmans? And then maybe the Newman is a co-founder, maybe the Newman is someone on the board of directors, maybe fill in the blank, for having a really direct conversation about this type of dynamic. Sure. Can we put aside just for a moment co-founder and board member because there are power dynamics there that are different than the Newmans that you've been talking about. Yeah, let's leave out co-founder and board member. I agree that

adds a level of complexity. Or we can circle back to it separately. But here's the thing. If we start with a basic, basic, basic, basic premise, it goes like this. Am I a good person? Am I doing the best that I can? And if I can answer that question relatively straightforwardly and honestly, then I don't have to feel guilty. Because that's what we're talking about, right? That's the emotion that gets manipulated. I don't have to feel guilty saying to somebody, I don't have the space to do the thing that you would like me to do, which might include maintaining this contact. And there's an image that I often use, whether it's with a client or with my own self, and that is, and it's come to me as I've gotten older, and I'm obsessed right now with myself being old.

And the image is of a bonsai tree, which over its lifetime, you can see this one foot tall bonsai tree, and it could be anywhere from 10 years old to 300 years old. You have really no idea, right? And what I see is something that has been carefully pruned into a thing of beauty, and I think that that's our opportunity in life. Now, if we start with the supposition that we are never enough, that we are not good enough, and that we therefore not only, you said before, become addicted to busyness in order to make ourselves not feel the things that we don't want to feel. Remember that? Well, one of the things that we do is we maintain unhealthy relationships in order to not feel the things that we don't want to feel,

even when those unhealthy relationships make us feel other things we don't want to feel. Whereas if we start with the basic premise that we are enough just as we are, and that there is no great loss to you, Tim, if over time you lose some connection, and you use this term several times, to some high-powered person. Oh my goodness, this high-achieving person, this high-performer person. There's no real great loss if – like think of the people that you have interviewed over the years, the people that – for whom – who maybe began in some powerful position and that have gone on to some powerful position. Oh, my God, if I lose that connection that I once had to them, then somehow I'm at a loss. We take a breath. We breathe into that. The Buddha taught us one thing. You are basically good just as you are,

not because of the connections that you have maintained. And those people who love you and care about you and understand the essence are going to be fine, even if you say, hey, I'm sorry, I actually can't maintain this connection. May I ask a question? Sure. All right. So, I agree with what you just said to embodying that in some way that translates to different behavior. Does that make sense? Because one of my favorite quotes is, I guess it's Ted Geisel,

but Dr. Seuss, which is the people who matter don't mind and the people who mind don't matter. I mean, I love that quote. I remind myself of it all the time. Nonetheless, I do have this guilt that crops up on occasion that I recognize is counterproductive. Nonetheless, it crops up and causes me to behave in ways that I know are not necessary nor productive. And I'm wondering how you help people to make that leap from kind of the intellectual, uh-huh, yep, I get it, to the other lily pad

of behavioral change? Well, the first thing I would say is that the practice that you just described embodying the Ted Geisel, Dr. Seuss quote, that is a practice. And the first thing to do is to remember that the thing about the word practice is that we actually never achieve, right? We're always moving towards. We're always going there. But oftentimes, achieving it permanently, sustained persistently, that's a tough one. So in those moments when we fail to understand and remember that those who love us won't mind, when we fail to remember that, it can be helpful to remember what I was saying before about I am enough and I'm doing the best that I can.

Or as Dr. Sayers once taught me, not bad considering, not bad considering how rough you may have had it, not bad considering how hard your life is right now. You're okay. You're okay. And if I can say that to myself every day in one form or another, bringing a kind of mindful attention to the points when I fail with a kind of forgiveness to myself, well then, wow, okay, that can be helpful. Do you use journaling for this? I know journaling is very important to you, and I want to discuss that as a topic. And there are a million and one ways to journal. So I'd like to learn more about how you use journaling, but is journaling one of the ways that you remind yourselves of

these things? And if so, what does it look like? Down to the mundane details, do you write down I am enough as a prompt and then write for two paragraphs on why that is the case? Or how does one implement this? Yeah, yeah, yeah. Thank you. So just for context, I have been journaling consistently since I was about 13 years old daily. And I'm 55. So a hell of a lot of journals. And again, to be consistent,

and I think you do the same thing, I handwrite. I do, yeah. And what may be unusual is I never go back and reread because it's not about figuring shit out. It's about the experience. And so my general prompt,

the thing I almost always start with is, right now I'm feeling, and I simply bring my attention to it. And so I might be feeling, to talk about this very specific situation, guilt, right? So for example, and I'll use this sort of mindful attention, if I were to journal about our conversation, one of the things I might journal is about the guilt that I have felt over the years as to whether or not I was reaching out to you when you might be in trouble or if I was one of those folks who put you in an uncomfortable situation. And I bring that up not to elicit a response from you, but as an example of an exploration of the guilty feelings that I might have. Where are they coming from? What are they doing? Was I kind? That sort of thing. And then I blow a kiss to myself. Easy there, buddy boy. Easy. This is all a journaling exercise. I'm just talking it out. And I remember something that's really important about that word guilt. Guilt is self-focused. Remorse is about the other. Remorse is, oh, I hurt someone's feelings and I would like to not be hurtful. So I'm going

to try not to be hurtful. Guilt is, oh my God, I can't believe this. I'm ruminating, ruminating, ruminating, ruminating. And if I find myself journaling in a ruminating kind of way, I try to bring attention to that. And that's the moment where I say, easy, boy, easy. You're a good man who sometimes fails to live up to your aspirations that's it that's simple i also promised i would return to the crow this might be a good place yeah uh now i'm gonna get the pronunciation wrong mary help me with the last name. P-O-N. Ponset. Poet. Yeah. And it's Marie. Marie Ponset.

Marie. Always a tricky one. All right. So, Marie. Ponset. Ponset. And she's still with us, thank God. And the crow, what does she describe in terms of the crow? That might fit, might not, but I want to make sure I fulfill my promise to return to the crow. Oh, I think it does fit. I think it does fit. So Marie was one of my professors in college. She taught poetry, but I also took a particular track in teaching writing.

And so she was also my mentor. And she used to talk all the time about the crow who sits on your shoulder telling you what a piece of shit you are. That's a piece of shit. I can't believe you wrote that. It's like I hear that voice. And it sits on your shoulder and it tells you all the things that you have done wrong and all the things that are happening. And oftentimes in my journal, sometimes I'll take a second pen so that there are two different colors. I will allow the crow to speak. This is really important.

This isn't a jujitsu move because the mistake I think a lot of people make is they try to throw rocks at the crow and shut the crow up. Right? And that crow is a really interesting voice. That crow tells us all the things that we are doing wrong and the ways in which we are not enough. And that's the linkage back to what we were just talking about. This notion that we are not enough just by ourself,

that's the fuel by which the crow is there. Now, this is the move to make. The crow's mission is to preserve your ability to be loved, to feel safe, and that you belong. What? It makes you feel like shit, though. Yes, it makes you feel like shit. But its motivation is for you not to feel ashamed.

And so the crow is doing you a favor. The crow is trying to keep you safe. The problem is the crow is so attentive and so vigilant that it's a little too active. And so what we want to say at that moment is, thanks a lot, buddy. I really appreciate it. But all those people who might be angry with me because I didn't respond to them or do the thing they wanted me to do, they actually don't really see me. And if they don't see me, they don't know that I'm doing the best that I can.

So I'll blow them a kiss. I'll put them on the other side of that chain-link fence, and I'll love them from afar. Yeah, this is really important. And by this, I mean everything that we've been talking about pretty much since the get-go, but especially I'm referring to the journaling and creating an outlet for the crow or the monkey mind or what Tim Urban of Wait But Why would call the mammoth. And I highly recommend that everybody check out an article he wrote called Taming the Mammoth, which is on this subject, that if you hate that part of yourself and try to contain it, at least in my experience, that does nothing but exacerbate, does nothing but worsen the problem. But along the lines of,

say, morning pages, you know, Julia Cameron and so on, writing freehand in the morning and providing that monkey mind an opportunity to fix itself on paper, at least for me, gives me a tremendous amount of increased levity during the day. It removes a huge burden. Do you tend to journal first thing upon waking up? Could you walk us through when you're at your best, what is your first, when do you wake up, what is your first kind of 60 to 90 minutes look like, or two hours, whatever you choose? Yeah, it's two hours. And when I'm at my best, I wake, I clean up, so I shower and stuff like that. And I have caffeine, because you do not want to be around me without caffeine.

What time do you wake up, generally? Between 5 and 6. Almost without fail, usually without an alarm clock. So I'm really awful around 9 o'clock at night. I'm a very boring person. I do not look at my phone. Let me say that again. I do not look at my phone. I do not look at my phone because it's just too painful. And with a cup of coffee, coffee, not coffee, as I say from Brooklyn, and then I journal, usually for an hour.

And then I sit in meditation, usually for a half hour, sometimes 45 minutes. It sort of depends on how the day is going and what's going on. But the entire period feels like one quiet meditative period. So that's me at my best. The journaling for an hour, I want to dig into that a bit because I think it's such a powerful tool. And I'd like to hear more about how that hour is spent. So, I'm looking at a page in the new book, appropriately named Reboot. And you have in this book different journaling invitations, right? So, you might have, let's give a few examples. In what ways do I deplete myself and run myself into the ground? Where am I running from and where to? Why have I allowed myself to be so exhausted? You mentioned earlier that you often

start the journaling with right now I'm feeling dot, dot, dot. Are there other prompts that you personally tend to use more than others? Well, I would never say that I would use the prompts like I'm going to use the same prompt every time. Usually the one thing that I do consistently is right now I'm feeling. And then generally speaking, I might review the past 24 hours almost in a diary kind of fashion. You know, so yesterday I woke up and then da, da, da. I also don't worry about explaining people.

So I might say, and then I met with Mary Jane and I don't have to explain who Mary Jane is because who cares? I'm never going to read it again and nobody is ever going to read it, right? So I don't, I get rid of all that monkey mind bullshit chatter. And I just go right into it. And I presume that the journal knows all, sees all, has been there with me all along.

That's an important point. Secondarily, I will ask myself many questions like, how long have I felt this way? Which will then bring me back to some early memories, and I will start to be able to elucidate the patterns of my life. And that's really important because it's the patterns that actually point out where we have some struggles. Can I circle back to a point that you were making before about accepting the totality of what's going on? Because the journaling can help me in that. Yes, of course. The journaling can help one in that. So I mentioned before about having, maybe utilizing different pens to speak

for the different parts of ourselves. Before I even go further, let me make this observation. I think it's super helpful for you, Tim, to speak openly about the ways in which there are different parts of you. For those of us who are mildly curious about this space, that's an obvious fact. But there's still very much a point of view in the world that there's just one mind, that there's just one point of view, and all those other voices, we pretend aren't there. They're not part of ourselves. And you are absolutely right. When those voices are not given airtime, they get really pissed off, really, really angry. And the energy that they hold is really important. And so if we go back to journaling for a moment, by giving voice to those other voices, by

giving airtime to those other voices, we get to lay out, in fact, all of the conflicts that exist within us. In Buddhism, we're taught that there are seven layers of consciousness. Seven. There's an observer observing, observing, observing, observing. There are all these layers of what's going on, right? And by taking the time in a good journaling session, you can allow, you don't even have to swap all these pens, you can allow dialogue, you can allow conflict, you can allow argument. And it's in that expression, that's a manifestation of that full acceptance that you were talking about before. Oh, wait, I can contain multitudes.

Isn't that what Whitman said? Do I contradict myself? I do. I am large. I contain multitudes. Amen. And whether we are aware of it or not, we all do. A book that helped me a lot with this, and I found so much value in the first, I want to say 50 to 100 pages that I wanted to get to work immediately. I was like, okay, that's plenty of grist for the mill, let me get started, was Radical Acceptance by Tara Brock. Oh, God, book is so good. And in my particular case, my default emotional home, in a way, was anger.

And the way I dealt with that was by fighting anger, if that makes sense, and trying to cage and contain it. And radical acceptance offered me an entirely different way of relating to that, which I found extremely valuable. Are there any other tools, meditations, books, anything at all that might be helpful in assisting people to accept or reconcile with different parts of themselves, or at the very least recognize different... You know how before you were saying like, you know, you would take a breath because you wanted to jump in? I'm having all those same feelings.

Yeah, so much here. First of all, shout out to Tara Brock for Radical Acceptance. What a brilliant book and what a gift she is as a teacher. Yes, yes, yes, on the acceptance. You talked about anger being your default mechanism. For me, growing up with the violence that I experienced as a kid, rage was a major that i actually turned it into anxiety all the time and so actually you can't see it because because the video is off but on my desk are two little action figures one is hulk and the other is thor and one part of me that i learned to accept was the hulk because the hulk when I was a kid,

I remember this one time, I have a younger brother named John. And in my mind's eye, he's still 10 years old, even though he's in his 50s. So, hey, John. Anyway, when I was a kid, we lived in a part of Brooklyn called Bensonhurst, and we lived in the second floor of a two-family house.

And I remember looking out the window, and one day this kid was throwing rocks over the fence at my brother John. And I went ballistic. And I ran downstairs, and I grabbed this kid, and I pulled him over the fence, and I threw him on the floor, and I pounded the crap out of his face. Because here's the thing. You do not fuck with my people. You do not fuck with Hulk's people. The problem was that Hulk was often dangerous and would often lead to something negative happening to me. So I would shut him up and I'd pretend that he's not there. And he would show up in all sorts of ways, like really cleverly dissecting somebody's argument and being really wordy and verbose and shutting people down and all these awful behaviors. And what I had to do was radically accept that that guy, that big green guy, exists in me for one reason only,

to keep myself and those who love me safe. And by loving Hulk, I transformed him into Thor, who's just as strong, just as powerful, less likely to be out of control, and motivated by justice. Better hair, too. And much better hair, much better skin. So, that radical acceptance, that accepting the fullness of ourselves, oh my God, it's so liberating, isn't it? purpose. Not only did they serve a purpose, but that they were probably in some way fundamental to your survival, whether that's physical, emotional, or otherwise, and that they were incredibly, incredibly important, and may still be very important for certain things,

certain situations., but yeah. That's right. I mean, and that recalls Carl Jung's notion of the shadow, which is the place he describes as the place we put the dismembered parts of ourselves. And this is really important. Not only do we put the parts of ourselves that society may say are obviously not good, let's say a rage-like anger, but also the parts of ourselves that are actually quite powerful and quite positive and quite lovely. But because they threaten, say, our belonging, they have to actually be put in the shadow as well.

Well, they too get really pissed off, right? And they too cause trouble. And so you might put into the shadow your intellect or your capabilities or your ability to write a book. And you might sit for two or three decades knowing that you want to write a book and not doing it because it might threaten you in some way or another. This is a good segue for difficult decisions. And by difficult, I mean emotionally difficult. So, for instance, sitting on the desire to write a book for 10, 20 years, and then finally taking whatever the steps are, the first steps to finally write that book, potentially.

Maybe that's leaving a job. Maybe that's starting a job. Could be any number of things. Could you speak to, and you can choose which of these questions you would like to answer. When did you say no to something that was at the time very difficult to say no to, which in retrospect was very important to your life. And then the other is, when was a time when you decided to kind of block out all the noise, block out everything else, and focus on something very narrowly? And that ended up being extremely important in retrospect.

What occurs to me is that the answer to both questions is the same. Meaning, probably the most consequential career choice that I made, the consequential saying no that I ever did, was to walk away from the venture business and to stop being a professional investor. And the rest of my life unfolded. And I'm sitting here talking to you today. I mean, we might have been friends, Tim. Had I taken that path, who knows? But I'm sitting here talking to you about something that feels like the most profound fruition of who I am, my vocation, my beliefs, all of this, because I said no to the thing that I was actually really successful at,

which is a mindfuck if you think about it. Because if I was failing as an investor, you could sort of say, well, of course, he walked away. Ha, ha, ha, he failed. But I actually walked away when I was successful because it was too painful. How did that, could you walk us through how that happened? Because you had to have this feeling for, I would imagine, more than

20 minutes. Maybe it was days, maybe it was weeks, maybe it was months. What was the 24-hour period, the dinner, the conversation, the 48 hours, whatever it might have been when you were like, enough is enough. I'm actually sending the email, having the conversation, and walking? Yeah. So, it was actually years in the making. And I would have to go back to 99, 2000, right around that time period where, if you recall, the market crashed, the NASDAQ crashed. I forget the absolute numbers because they would be minuscule compared to the numbers we're dealing with now. But the market crashed around March 1999. And I remember it because I was on a family holiday to Washington, D.C. when Fred, I think, texted me, said, did you see the NASDAQ? And I was like, oh my God. And I think it had dropped like 700 points

or something, which at the time was like a phenomenal number. Anyway, right around that time, I started having this, I just couldn't sleep. I was just not happy. And I was 37, 38 years old. So in hindsight, I was clearly entering midlife. And the systems were collapsing all around me. And then I thought I couldn't go out and fundraise with Fred and raise a new venture capital fund for Flatiron. And so I decided to leave the fund. But I decided to leave the fund and go to JP Morgan because I thought that the problem was changing the externalities. And so then I took a position starting January 1st, 2002. And as we were talking about before, by February, it was just not working. And I remember going in to see my boss at the time,

a guy named Jeff Walker, who's vice chairman of the bank. He's still a very, very close friend. And I remember saying, I can't do it. I just can't do it. And I think it was probably a few months after the Canyon Ranch visit. And I said, I'm not going to renew my contract at the end of this year. And he said, well, what are you going to do? And I said, I don't know. But for the first time in my life i'm going to be without a job since first time since i was about 13 and i'm going to be liberated from this definition from this from remember i you know this notion of like wearing somebody else's suit of clothes and uh it was incredibly scary it was incredibly scary. It was incredibly hard.

Was the trigger, I hate to interrupt, but was the trigger that you had a preset scheduled meeting for the renewal of the contract, it was kind of like shit or get off the pot in the sense? No. No, it was a dinner. It was a dinner, okay. It was a dinner. It was like, Jeff, I need to have a dinner.

I need to talk about this. Because the presumption, everybody renewed their contract. Did something prompt, was there like a particular day or moment that prompted you asking him out to dinner? It was a growing sense that, you know, so I went down to Canyon Ranch and I read these books. Let Your Life Speak. Holy shit, I've actually not been listening to my life. And I started to spend the next few months i was the beginning of my meditation practice i first meditated at canyon

ranch and i would argue i first began listening to my life to my heart and over the next few months up until november that year i think we had dinner right around November 2nd or so. There's that number two again. I never noticed that pattern before. We had dinner, and I said to him, you know, it was like one of those moments. Do I say it at the beginning of the dinner, or do I say it at the end? Oh, yeah, just one last small thing before we go. By the way, I'm not going to be your partner anymore, you know.

And I said it at the beginning because I needed to, because we needed, and I knew in my heart that he would still be my friend. In fact, we remain super close. But the fear was like, what was it going to do? And I didn't know. I had no idea. Yeah. Thank you for bringing me back to that time because it's important for me to remember that. I'm feeling that right now.

What was the day after you walked like? Do you remember what you did on the first one or two days after you walked out? I remember starting to tell people. I told the woman who was my assistant at the time, she remains a very close friend. See, there's a pattern. Carrie Racklin. And I said, you know, Carrie, I'm not going to do it. I don't remember all of the details. It was so long ago. This is 17 years ago now. But I remember the feeling, and the feeling was a combination of utter relief and absolute terror. Both feelings simultaneous. What's your advice to someone who's in that position? And I could phrase it as, what advice would you have given yourself when feeling those two things at that point in time,

which you can answer, or since you have experience with so many executives, founders, and so on, when people are experiencing this sense of relief combined with abject terror of facing the unknown, what's your advice? Well, the first thing I would say, and I would have said to myself, is that welcome to midlife, for sure. And I say this often now, because I often can see the connection.

I was talking to the CEO of a very successful company who was just talking to him this morning. He's 39 years old. And it's like, everything's working. Why do I feel groundless? He's like, well, let's talk about that. So what I often say is, remember, you're not alone. And the second is that there are adults, men and women, who are on the other side of that gulf.

And we're fine. And you'll be fine. And they have trod the path before you. And you're going to be okay. How many references to books have you made, Tim? Those were all written by people. Tara's book was written just as much for herself as it was written for anyone else. And all of those people, they're there. They're like ancestors guiding us through that period and saying, come on over, the your worrying, when you transmuted rage into anxiety, or if anxiety bubbled up from other sources, what are some of the things that have helped you most with that? Well, I'll speak about the rage for a moment, the rage and then turned into anxiety.

It would often turn into anxiety, but it would equally as often turn into migraines. And that's when Dr. Sayers first taught me the first of those three questions, which is what am I not saying that needs to be said? And by linking speaking to the rage and to the migraines and to the anxiety, I gave voice to the feelings. And that didn't magically make them go away, but it lessened the power of that anxiety. It lessened the power of all of those feelings. So learning to speak, whether it's in my journal or actually learning to speak like an adult with another human being, hey, that hurt me, or hey, I'm scared. That thing that you said last night scared me. And as a result, I want to do the thing that I would normally do, which is withdraw and cut

off connection to you, but I'm going to stay here and be an adult and engage with you. That move, it doesn't make the anxiety go away, but it puts me back in control. It puts the adult me back in control. The other thing that I do is I start to ask the anxiety questions. Like, you know, you really want to work with what's going on in that amygdala, which is where that source of anxiety tends to be, right? The amygdala. Ask it questions. What's the threat? What am I afraid of? Have I heard this before? Those questions fire off the prefrontal cortex, which can relieve the anxiety. Do you ask, do you personally tend to ask those questions before meditation, in journaling? What form does the asking take?

Yeah, I do. Well, remember, I journal before I meditate. So a lot of times I will be sitting down at the cushion going, oh, this is what I'm working with. And, you know, I'll tell you what happened this morning in my meditation session. I was working with some really difficult feelings that came up over the weekend. And I was sitting in meditation. I had had a conversation with Sharon Salzberg yesterday, and it was really helpful. And all of a sudden, she came back. And just as I sat down,

I'm a very ritualized meditator, right? So I have candles, I have incense, you know, I'm a former Catholic, so I like all that ritual stuff. You know, if somebody could ring a bell, it makes me happy, right? So I'm doing all that stuff. I'm sitting on the cushion and all that's emerging. And all of a sudden, I start visualizing the area of my chest where my heart is. And the object of my meditation this morning was open your heart, open your heart, your heart's closing, stay open, stay open. And in that moment, I realized that what I was continuing to work with was the impulse to close down this weekend, that I was feeling in response to the fears. And so, the naturally arising thought that came from that session in that moment was, open, open, open, which very, very quickly turned into loving-kindness meditation for myself. And for people who

don't know, correct me if I'm wrong here, but loving-kindness meditation, if you want to learn more about it, I would highly recommend diving into that, also known as Metta, M-E-T-T-A meditation. Two folks worth checking out. Jack Kornfield, who's been on this podcast before, specifically speaking about meta and loving kindness. Sharon's also spoken about it on the podcast. And those are good. Those are great places to start.

Very, very effective, short, at least can be short meditation that really punches above its weight class in a sense. And I think in part for me, I'm really glad we're talking about this because it's a type of meditation that I haven't used in a while and I really should, is at least for me, it's a vacation from obsessing on myself, if it is directed at other people. Now, as was pointed out to me during my first ever extended meditation retreat, I was talking about loving kindness and how much I enjoyed it, and they asked on the way out, just a quick suggestion, Have you applied this to yourself at all? And it was so nonsensical to me.

Like, they might have been speaking to me in Klingon. I was like, loving kindness to myself? What? Like, that doesn't make any sense. And lo and behold, I did find it very valuable, but I really enjoy combining that with also loving kindness meditation for other people. And if you're just kind of rolling your eyes at the sort of new age hippie sounding wording of loving kindness, then we can switch to a different language and look up meta, M-E-T-T-A meditation. Same, same, but different. Well, Jared, let me ask you just a couple more questions. We could go for many, many hours more, and we certainly have spoken for many hours before.

But for the purposes of right now, I think we're getting close to a really good getting reacquainted chat and round one of the podcast. I'll ask you just a few more questions. One is, what is the new behavior in the last handful of years, it could be anytime really, or belief that is most, or I should say, greatly improved your life, the quality of your life. New behavior or belief in the last fill-in-the-blank number of years that has significantly improved the quality of your life? The main one that comes to mind is that I am a good man. The belief. That's a belief. I believe that I am a fundamentally good person

and that I accept the fact that I often fail to act in accordance with that. But that feels, to this guilt-ridden, anxious-ridden, angry child from Brooklyn way back when, that feels radically transformative. What? I'm good?

Just as I am? No. Yeah, I'm good. I'm good. I'm good. That's huge. Hard to imagine something bigger. By the way, I have to practice it every day. But I'm a good enough partner. I'm a good enough business person. I'm a good enough coach. I'm a good enough parent. That's the hardest one for me. Have I wounded my children? Yes. Does that undermine whether or not I'm a good man and a good father? No. And that allowance has done something really magical. It's allowed them to accept themselves.

So yeah, it's a big move. That is a big move. The next question might segue, might be completely different. But if you could put a message on a billboard, metaphorically speaking, to get a quote a word a question anything non-commercial out to billions of people what would what might you put on such a billboard i'm going to add two sentences it's a big billboard so there's plenty of big billboard so it doesn't say impeach trump just kidding um it says you're not alone. And just because you feel like shit doesn't mean you are shit. The you are not alone is really, really important. Because we feel so broken, because we question our worthiness all the time,

we exacerbate the feelings of, I must be the only one who's going through this. And this is crazy because despite all the evidence, whether it's myths, whether it's stories, whether it's religions, whether it's philosophical traditions, everybody's saying the same thing. You're fundamentally good. Yeah, there are things you can do to improve your life, but you're fundamentally good. Relax. It's okay. That's that equanimity that I often talk about. It's like, okay. So I guess you're not alone. And just because you feel like shit doesn't mean you are shit. And if I'm not shit, then this feeling of it being crappy right now, well, this will pass. So let's add another one. This too shall pass.

Always. Can I add on to that? You can add. You can keep adding. Tim, think of the times in which you have struggled. You've been very open about your struggles. And by the way, thank you for doing that because you model something that's really important. Think about when you've been at your worst and how alone it feels and how it becomes this self-reinforcing negative view that you must be crap because you feel like crap.

It's like, no, stop. You must be human because you feel struggle. And there are billions of humans and have been billions, and there will be billions more. And struggle is universal. It is part of the amusement ride. That's right. And you bought a ticket so you might as well go for a ride. Can't be on Magic Castle indefinitely. You're going to go through the haunted house occasionally.

Amen. Jerry, thank you so much for taking the time today to share and to catch up and to teach. I always enjoy our conversations. So point number one, thank you very much. Well, thank you.

And thank you for giving me the opportunity. And thank you for asking gorgeous questions that really help me think and feel. And thank you for doing what you do every day. It really means a lot to the world. My pleasure. I really appreciate you saying that. And it helps me as much as I hope it helps other people. There's that weird, crazy, esoteric thing that all those people, high achieving people say, oh, there he goes. Oh, helping me helps other people, helping other people helps me. Yeah, right. Tim's living proof of that. So there.

It's true. It's true. I mean, I think that I've been very fortunate to somehow stumble my way like a drunk in the dark into a career that involves having conversations like this. So, uh, thank you, Lady Fortune for that. And, uh, it's, it's also just a tremendous opportunity to explore some of these things that perhaps aren't explored as often as they should be. And you are a great companion on the path with that. So thank you again. And where are the best places to say hello to you online or to learn about what you're up to? Of course, the book reboot subtitle,

Leadership and the Art of growing up is, uh, is available. And certainly something I would recommend people check out has the, the, the many of the prompts and more that we've talked about a lot of case studies, the personal history and a distillation of a lot of what you've learned working with hundreds,

thousands of clients at this point. And, uh, what else should people know? Anything else? Yeah, I mean, probably the best way to sort of follow what's going on is reboot.io slash book. But also, if you just go to the Reboot.io website, we've got a bunch of resources, podcasts, self-guided courses, journaling exercises, all sorts of things designed to help folks all for free. Because, hey, what the heck? Let's help each other out. And that's probably the best way. You can also follow me on Twitter at Jerry Colonna.

You mentioned that earlier. But pick up the book. I'm pretty proud of it. And I hope it makes a difference, makes a dent in the world. That's the best that we can hope for. And for people listening, I'll link to best that we can hope for. Just search Jerry, J-E-R-R-Y, or Kelowna if you want to take the black diamond route instead of using the easy option. And you'll be able to find it very, very quickly. Jerry, any other comments, requests, anything at all that you'd like to say before we wrap up? No, just that it was a real heart-filled pleasure. It was really a blast. Likewise.

Thanks so much, Jerry. And everyone out there, thank you so much for listening. And until next time, pick up a damn journal. Amen. That's right. And real pens. Real pens. Give it a shot.

It's amazing what you can discover when you take what you think are clear thoughts and put them on paper. And that's it for now. So until next time, thanks again for listening.