July 8, 2019

The Scared Child Inside Every Leader

by Without Fail

Background show artwork for Without Fail

Jerry Colonna was a high-flying venture capitalist in New York City at the height of the dot-com boom. He looked like the picture of success—but as time wore on, he felt more and more like a fraud. And when the boom went bust, it all began to unravel for him. Alex talks to Jerry about that struggle, and about how it led him to his current life as one of the most in-demand executive coaches—who just happens to be Alex’s own executive coach. 

This episode discusses suicide and mental illness. If you’re feeling depressed or you just need to talk to someone, you can call the National Suicide Prevention Lifeline. The number is 1-800-273-8255. 

The StartUp episode referenced in this conversation — the episode that includes one of Alex and Jerry’s sessions — is called “Shadowed Qualities.”

Without Fail is hosted by Alex Blumberg. It is produced by Molly Messick, Rob Szypko and Heba Elorbany and edited by Alex Blumberg and Devon Taylor. Music and mixing by Bobby Lord. 

Where to Listen


From Gimlet, I’m Alex Blumberg and this is Without Fail, the show where I talk with artists, athletes, entrepreneurs, visionaries of all kinds, about their successes and their failures, and what they’ve learned from both.

Back in 2015, not long after my cofounder Matt and I started Gimlet, the company that makes this podcast you’re listening to right now as well as many others, we got a really great piece of advice from one of our investors. He told us that before his company invests in any startup with two founders, he advises the co-founders to hire an executive coach. Someone who can help them deal with the problems that inevitably arise. One of the biggest predictors of early stage startup companies falling apart is founder conflict. 

So Matt and I went looking around, and eventually we came across this guy, Jerry Colonna, who seemed like he might be a good fit. Although I did have some reservations...

ALEX BLUMBERG: There were two things that gave me pause about you. One was the price tag.

JERRY COLONNA: I am very expensive.

ALEX BLUMBERG: And two -- two was -- and I'm sure I'm not the first person that -- to have told you this, you can come across as somewhat woo-woo.

JERRY COLONNA: Oh yeah. I don't come across nearly as woo-woo as I really am.

ALEX BLUMBERG: [laughs] You tone it down.

JERRY COLONNA: I do! [laughs] 

Jerry’s woo-woo-ness takes many forms. He wears a Tibetan bracelet of wooden beads and doesn’t shy away from quoting Buddhist teachings whenever he thinks the moment calls for it. He hosts executive retreats where it’s not unusual for participants to play with clay or talk to plants or read poetry aloud to one another. And weep. There’s lots of weeping. 

But he works with some of the least woo-woo, most powerful people in business and tech. High profile CEOs, executives, leaders. And he himself has a very non-woo-woo background, as a successful venture capital investor. And so, he’s got this woo-woo non-woo-woo thing going on that really works for him, and really works for lots of his clients too, including me and Matt. 

One of the most powerful things that I’ve taken from Jerry is this notion that the psychological baggage we carry with us, if it’s left unexamined, can lead us into destructive behaviors. And that, as a leader, it is vital to deal with that baggage. Because the baggage you don’t deal with in yourself spills out and replicates through whatever organization you’re running, causing pain and chaos and strife for everyone who works for you. 

I found out from Jerry firsthand how that was happening to me at Gimlet. And I found that out during a session that I happened to record with him. We ended up taking that recorded session and turning it into an episode of the Gimlet show StartUp. And so, as an example of how effective Jerry is and why he earns the big bucks, I’m going to play a clip from that episode now. And to set it up, I'd had this surprisingly emotional reaction to some seemingly innocuous feedback around the office, about how I had to devote more time to preparing for meetings. And so Jerry and I, in that recorded session, we explore why that feedback had upset me so much, and we ended up going deep – into my childhood, my father's patterns of behavior. And we arrived at a sort of classic therapy breakthrough: 


ALEX: It is scary to think, like, “Oh man, could I be self-sabotaging in some way that I'm not aware of that like -- just like my dad?”

JERRY: Uh-huh. I'm gonna read you a quote. Bear with me, Jung said something like: Until we make the unconscious conscious, we will be dictated to by it and call it fate.

ALEX: Right. Whoa. Why is that making me so upset?

JERRY: Perhaps it's that word "fate." I'm fated to end up like my father.] 

So, that’s Jerry. Woo-woo. But man is woo-woo what you need sometimes. 

Over the course of that work that Jerry and I have done together, I’ve learned some things about him, but we’ve never gone too deep the way he does with me. I never learned how he discovered the stuff he was teaching me about the connection between your own unexamined emotional baggage and the toll it can take on you and your organization. 

Well, Jerry has just written a book, called Reboot, about all this stuff. And so, it seemed like the perfect time to get him into the studio. And just a quick warning...There is some swearing during this conversation, and also, we discuss  suicide and mental illness. So if those subjects can be difficult for you, skip this episode, or take care while listening. 

So back to my conversation with Jerry. I told him I wanted to do version with him of what he does with me and Matt. 

ALEX BLUMBERG: A lot of what we end up talking about you and me and me and Matt is where we come from, and how where we come from affects where we are today. And that, my friend, is what I want to do with you today. So I want to start um -- how did you get into the world of investing, and the world of fancy, rich people doing fancy, rich people things in the first place?

JERRY COLONNA: So, my first adult job was as a reporter for a magazine, a technology magazine out on Long Island. Along the way I got a series of promotions and eventually I became a vice president in charge of a division we called electronic media at the time or even new media, which these terms seem so arcane now.

ALEX BLUMBERG: And what year was this?

JERRY COLONNA: Probably '93-'94?

In other words, the early years of the internet. And Jerry was in the middle of it, overseeing a team of people who were figuring out what the internet meant for their business -- publishing. Jerry gradually moved from internet media to internet investing, and eventually started a VC fund called Flatiron Partners. Its mission was to invest in New York City-based tech companies. And his partner was Fred Wilson, who these days is one of the most well known and well-respected tech investors out there. And their timing...couldn’t have been better. 

JERRY COLONNA: I mean, it felt like everything we touched turned to gold. You know, it felt like we were smart. It felt like we knew what we were doing. I remember feeling like I was moving at the speed of light.


ALEX BLUMBERG: When you said that you -- that you -- everything you touched turn to gold, give me an example.

JERRY COLONNA: One of the first investments we made was a company called Yo-Yo Dyne, which was founded by Seth Godin. And, I think within 12 months of making that investment it was sold to Yahoo for maybe three or four times our money. But during the lockup period in which we held on to that stock, because we were -- we were unable to sell our stock, the stock you know, tripled or quadrupled again. And so our tiny investment became worth, you know, well over $100-million. And that was, like, our first investment. That was quickly followed by companies like Geocities which we invested, I don't know, $2 or $3-million and it became worth, a half a billion dollars inside of 24 months, maybe 30 months. Yeah. And it was just -- it was like -- it was like we would invest and then all of a sudden the company would be bought. And, you know, it felt like this -- not quite a Ponzi scheme, but it just felt like this was just unreal. This was Monopoly money. 

ALEX BLUMBERG: What was your life like at this point? How were you -- if I saw you on the street or if I met you at a party would you have felt like the same Jerry that I know?

JERRY COLONNA: Probably not. Probably not.

ALEX BLUMBERG: What would you have been like?

JERRY COLONNA: I often think of, like, the guys who did the land speed tests where their -- where their cheeks were blown out because they were moving so quickly.


JERRY COLONNA: I remember, you know, the -- I think it was the FT did a profile piece on me.

ALEX BLUMBERG: The Financial Times.

JERRY COLONNA: Yeah. The Financial Times. And they showed up at my house at 6:00 in the morning so that they could watch me train with my personal trainer and then, you know, watch me get on the Long Island Railroad to travel from Port Washington into Manhattan, and just trail me throughout the day. And I remember that the last event I went to at the end of the day was a fundraiser for Hillary Clinton's Senate campaign. And, you know, I look back and, like, the whole thing was just a blur. It was just a blur. I'd be walking around with a backpack on my back and sweat constantly pouring off my head. And it just -- I mean -- I was smiling, I was a nice guy, but I was -- I was disassociated. I was not in my body. And I was floating.

ALEX BLUMBERG: What do you mean by that? Disassociated from what?

JERRY COLONNA: From just like how I was feeling and what was going on. I mean, as you are getting me to recall those memories, I have an image of myself hopping into the back of a yellow cab. You know, I was always polite, but kind of feeling like I was barking out an address that I needed to get to, pulling out my phone, tapping very very quickly on the phone, moving to this thing, moving to that. Like, feeling -- I don't know. Bizarrely self-important. It's like the only existence I had was from the neck up, right? No connection to, like, I'm hungry, I'm thirsty, I have to use the bathroom, You know, I'm tired. None of that. And not even just the head up, it just like the pre-frontal cortex, the front of my brain. And that's it. Forward motion, forward motion. What's next, what's next, what's next, what's next. And it's like, "What the fuck are you doing? What are you doing? 

ALEX BLUMBERG: When did the what are you doing question go from something that was sort of buried to something that became actually real and in your mind?

JERRY COLONNA: I would say it really began in the fall of 1999. I remember vividly, there was a moment when the S&P listed Yahoo as one of the S&P 500, which meant that every index fund in the country needed to own Yahoo shares. And because we had earlier in the year sold Geocities to Yahoo, I personally was sitting on a lot of shares of Yahoo. As it went up 10x, I think, in the space of maybe 24 hours.


JERRY COLONNA: Yeah. And I'm sitting -- and so that the shares are not fully locked up. I can only sell a few at a time. But I'm sitting there going, "What just happened to me?" 

ALEX BLUMBERG: You just got 10 times richer. Sort of.

JERRY COLONNA: And I did -- I did nothing. I did nothing to deserve that. I mean, I had backed a brilliant young entrepreneur named David Bohnett who had -- has a heart as wide as the world, who had a service that -- that gave a voice and a platform for people who felt voiceless. I mean, one of the first pages on Geocities was being written by a man who was slowly dying of AIDS. And he was daily writing about his struggles. And that felt really, really important at the time. I mean it was. It is. And great. So I was a good consigliere to David, and I helped that company go from a small little company to something meaningful, something that made a difference. But -- but all of a sudden there's this, like, wealth, and people are listening to me like, you know, Hillary Clinton, are listening to me on policy issues. And it's like, I don't know shit. I'm just a kid from Brooklyn. What the hell do I know? And then it's just building and building and building, and over the course of 2000, really into the spring of 2001, the "What are you doing" voice just got louder and louder and louder. And, um... yeah.

ALEX BLUMBERG: Until -- until what?

That what… it’s coming up after the break. 


Welcome back to Without Fail and my conversation with executive coach Jerry Colonna. My executive coach Jerry Colonna. Before the break, Jerry was living the life of a high-flying VC, but that life was feeling increasingly wrong for him. 

JERRY COLONNA: It was the spring of 2000 when all of this is just sort of coming to a head, and I remember ...

ALEX BLUMBERG: All of this -- all of what? 

JERRY COLONNA: All of this sense of disassociation and this sense of, like, not -- this is not my life. I'm not living...the life that I'm supposed to be living. That -- that outwardly, it's all successful, but inwardly...I mean, in a sense Alex, what you're asking is when did my depression really begin? You know, uh, I remember when the Nasdaq crashed. It was like March of 2000. And it -- and internally what it felt like was the whole house of cards was starting to crumble. 

ALEX BLUMBERG: They're finally -- they're finally onto me.

JERRY COLONNA: They're finally onto me. They're finally onto the -- the fact that all of this is just a shell game. It's all monopoly money. None of this is real. What began as, you know, "Hey, isn't this cool? Look what we can do on the internet," to "We're gonna create, like, these massive companies." All of that started to crack and fall apart. And people began attacking those of us associated with quote "the dot-com era." You know, when the market started to crash, the Schadenfreude that was in them -- in the society was just so pronounced, that we became these visceral targets. And the more that I felt that, the faster and faster I would run. I mean, I've -- I've often told the story of flying back and forth to the west coast from New York during this time period. And um I fly across the country to fire somebody in the portfolio...

ALEX BLUMBERG: And who, who… So, wait. So this all culminates in this moment when you're -- when you have to fly across the country. You had to fire somebody in the portfolio. What does that mean?

JERRY COLONNA: Yeah. I was a board member at a company and, you know -- the CEO needed to be fired because the company was a mess. And I was the nice guy on the board. So the task went to me, and I had to fly across the country to California to land in this guy's office and tell him he was being fired, because I wasn't going to do it over the phone. 

ALEX BLUMBERG: How did that go?

JERRY COLONNA: It -- it sucked. You know, I had to confront the fact that I had failed as a board member. You know, and I was still in that phase in my life where I was not recognizing my own failings. I was masking those with a kind of false aggression. And like, you know, "Hey, I'm gonna be the big powerful guy and I'm gonna come into the room and I'm gonna fix it. I'm gonna save it." And it was all bullshit. And then I fired him. Elevated the COO. Got on a plane, flew back to New York. Walked into the house, dropped my bags, sweat again pouring off my head. And I look up at the top of the stairs and my daughter is up there, and she says something like, "Hi Daddy." And I spin around and I fall down on the floor and I smash my head against the wall, and I hear her saying, "Daddy, daddy!" "Mommy, mommy, daddy died!" I mean, as I often exhort my clients, you know, our children don't sign up for this. And I'm pausing man, because I feel shame.

ALEX BLUMBERG: About what?

JERRY COLONNA: I feel ashamed that I was that guy. I knew better. I always knew better. 

ALEX BLUMBERG: Knew better than what? Like what -- what guy?

JERRY COLONNA: The guy who would fly across the country and fire somebody. The guy who would pretend that he hadn't failed as a board member. It's the responsibility of those who hold power to be human and humane. 

ALEX BLUMBERG: What do you think -- what do you think happened when you walked in? Like, what -- what made you collapse?

JERRY COLONNA: I was physically exhausted. I mean, I weighed 75 pounds more than I weigh today. I was unhealthy. I was depleted. 

ALEX BLUMBERG: I have had these feelings where I get, like -- where there's something that's on my mind that I'm not fully aware of. Something that my subconscious is doing. And then there'll be a moment where something somehow activates that feeling. And then I get dizzy. I've never actually fallen over from it, but I've had that feeling of like, I start to swoon a little bit, and it makes you realize like, oh there's all this turmoil that I'm repressing and all these conversations that I'm, like, trying not to think about. And -- and I wonder, like, if that -- was there something in that conversation that you had with the CEO that, like, was emblematic to you of, like, some of that, here's what I'm doing that I don't want to be doing, or here's a way I'm behaving that I don't want to be behaving, that was sort of like on your mind but not on your mind at the same time.

JERRY COLONNA: Well, what occurs to me was that I felt a certain amount of pride in being able to fly across the country and do that. I felt so important. I felt so full of myself. And then there's this other layer of awareness that was sort of operating which was like, "What the fuck are you talking about, dude? That is not you." And okay, here's an association I've never made before that just popped into my head. One of the most profound memories from my childhood. Fuck! I was 10 years old. And it was just a couple of weeks before Christmas when my father got fired. And it was the first time I ever saw him cry. And he had worked at that company since he was in high school. And I remember being so terrified, because he said, you know, "Kids, there's no Christmas this year." And as God is my witness, this is the first time I've made this association, Alex.I became that guy. You know, the guy who fired my father.

ALEX BLUMBERG: We're doing some good work here, Jerry.



JERRY COLONNA: You know, the number of times that I've told that story, I've always focused on what it did to my kids. And I've always glossed over the fact that I'd flown out to California to fire somebody. Yeah.

ALEX BLUMBERG: Well you know. One of the things that I think about you is that you are so good at detecting that exact moment when other people talk to you, that exact moment where it's like, "Oh, you're focusing on this part of the story, but this part of the story you've glossed over." 

JERRY COLONNA: The truth is that -- that like any other human being, I am wired to keep things from myself, because that keeps it safe. And like any other human being, I can feel relief when I look in those places. But I don't want to look in those places. So  you actually helped me, because you helped me make an association that I was blind to. And I won't be blind to it anymore. 

ALEX BLUMBERG: What does that -- what does that association make you -- do -- do for you now, though? 

JERRY COLONNA: Well it actually helps me understand what 'that guy,' that phrase 'that guy' means. Because the truth is, I don't know who it was that actually fired my father. So there's a lot of stories I tell about that. And when I think about the things that motivate me and the things that define me as a leader, there is a profound sense of I don't want to be that guy. And that guy is somebody I've made up in my mind. 

ALEX BLUMBERG: So what finally propelled you to -- to leave -- to leave investing?

JERRY COLONNA: Well, you fast forward a year or two. Flatiron Partners is dissolved. I agree to join JP Morgan. It's shortly around 9/11. I made that agreement. I'm to start in January, 2002. The fall between September 11th and that January was just a sort of bizarre time of, I was trying to work and help some of the financial recovery efforts in New York City after the attacks. I was working on the Olympic bid effort for the 2012 games. And go ahead to February, 2002, and the depression is really peaking, and I am not well. And I ended up feeling depressed and suicidal. And I remember coming out of an Olympic bid committee meeting in downtown Manhattan. We had free office space, because nobody wanted to be down there at that time. And I remember walking by the pile. 

ALEX BLUMBERG: The rubble from the buildings.

JERRY COLONNA: Yeah, it was the rubble, it was buildings, but it was human beings. Remember there were human remains in there. And it was still smoldering. And I wanted to go down to the platform at Wall Street Station and jump on front of the train. Um, yeah. I called my therapist instead.

ALEX BLUMBERG: That sounds really … scary.

JERRY COLONNA: Well, you know it was -- it was more visceral and more real, because when I was 18 I had tried to kill myself, and statistically, you know, those who have those feelings a second or third time are more likely to complete. And um… 

ALEX BLUMBERG: I didn't -- I didn't -- I didn't know about that until preparing for this -- for the -- for the interview with you and going through your book, that that was something that you’d -- that you'd grappled with. Do you know -- when you had that feeling at 18, and then when you had it later at the period you're describing, like -- why those two points do you think?

JERRY COLONNA: Hmm..Well, I think some of the common things was that -- that again, the same feeling of the house of cards falling apart, you know? That -- that I was done pretending. At 18, it was a similar kind of disassociation from how I was truly feeling. I remember fighting with my parents when I was 13, 14, 15 years old, and -- and I remember feeling that I wasn't talking about what was going on. I wasn't actually sharing how I was really feeling. I remember being so terrified of upsetting everybody. And I remember, like, watching my brother Dominic, for example. He fought much more. And he said things that I wanted to say.


JERRY COLONNA: Like, it was unacceptable that my father was drinking as much as he was drinking. That it was not right. And that they had to get their shit together. Or even worse that mom was crazy. That mom was, you know -- like, we would sit there and we would watch my mother who was mentally ill talking to people who weren't in the room. Talking to Bobby Kennedy, talking to Art Garfunkel, talking to people. And, like, sitting in a room and collectively not saying, "This is crazy. This is wrong." And so we would just sort of sit there in silence and just let it go on. And -- and just bury it and bury it and bury it and bury it. And then really starting in, in senior year of high school, it just started to -- it was building and building and building. And I remember cutting classes, which is something I never would have done. I was a straight-A student. I would ride the subway past Avenue M on the M-train in Brooklyn and keep going, and go down to Coney Island. And just cut class and spend the entire day at Coney Island. And I remember teachers going, "What the hell's wrong with you? This is not you." And I remember, like, not -- not really trying to fill out college applications. And, like, ignoring that whole process. Until finally it -- you know, I did end up at Queens College because they would just accept anybody. And I registered for classes the day before classes were to begin. And, you know January 2nd I cut my wrists. 

ALEX BLUMBERG: I think the thing that you said about that you -- you couldn't keep pretending. Like, this inability to keep pretending. There's -- there's the partner to that feeling is that some part of you needed to pretend something. And not pretending was scary. What was driving the need to pretend, do you think?

JERRY COLONNA: Well, I think -- I think it was a learned behavior from when I was a kid which was, you know, the way I -- the way -- I remember being convinced that I could break the spells that would grip my mother in these sort of psychotic episodes if I could just get her to remember that we kids existed. And I remember pretending to be sick a lot. And I remember laying in my bed. She would -- she would be sort of ranting and walking around the house, and -- and I just remember saying, "Ma! Ma! I'm sick!" And sometimes it would work. Sometimes it would break the spell. And it was like -- like, looking backwards it was like the maternal feelings that she had would just take over the psychotic feelings that she'd had. And she'd come in and she'd put her hand on my forehead, and she put the back of her hand on the back of my neck because somehow that was going to tell her whether or not I had a fever. That that was enough to just call her back. And I got really good at pretending to be happy. I got really good at pretending to be sick. I got really good at pretending. And so, you know, fast forward 20 years later, it was -- it was a very similar feeling of, like, the whole house of cards just coming down and none of it makes sense. And   I remember my therapist famously -- you know, we were talking before about somaticized feelings and you feeling dizzy, and I remember my therapist working with me about migraines that I had had, which was -- you know, the question she asked me that liberated me was, "What are you not saying that needs to be said?" And there was a whole bunch of shit that I was not saying that I needed to say. And, you know, in a sense that whole sense of the house of cards falling apart was a -- I couldn't keep it in anymore. And I thank God every day that I made the right choice to call my therapist.


Coming up after the break, how Jerry learned to say the things that needed to be said, and how he started helping other people do the same thing. 


Welcome back to Without Fail and my conversation with Jerry Colonna. When we left off, it was 2002. Jerry was in the midst of a severe depression. And after placing that emergency call to his therapist, Jerry began making serious changes. He quit his job. And dedicated himself to his mental and emotional health. 

JERRY COLONNA: I think what I did was I started supercharging everything. I did art therapy. I did dance therapy. I read books. I sat in meditation. I went on retreats. I first started traveling in Tibet. I did stone-carving workshops with a Jungian analyst.  I -- I needed to reduce the suffering. Like, therapy alone wasn't working. So I was -- I was searching. 

ALEX BLUMBERG: And out of that experience, it seems like that led you to your current vocation, which is how we started this conversation, which is being an executive coach. How did that idea first come -- come across that like, I can help other people deal with their baggage and be effective leaders? How did that first come to you?


JERRY COLONNA: It was that -- it was during a time in which I -- I was engaged in a lot of boards of directors and that sort of thing. And a young man came to see me about a job. You know, he was doing the thing that you do, which is kind of network your way. And he was a lawyer and he wanted to get a job in a startup. And I remember asking him a question, which I thought was relatively innocent at the time, which was, "You seem miserable. Why did you become a lawyer in the first place?" And that's when he started talking about pleasing his father. And he started crying. And we had a -- you know, our conversation continued and I gave him a few books to read. And it was that moment that I realized that this was something that I could do, all of a sudden, I realized that -- that I could help people. I didn't set out to say, "I'm gonna coach CEOs in how to be better leaders." I was really focused on somebody who might be struggling right there in front of me.


JERRY COLONNA: And that was the primary focus.

ALEX BLUMBERG: It wasn't a calculated question. Like, so tell me about your father and I will parlay this into a career for myself.

JERRY COLONNA: No, no, no, no. 

ALEX BLUMBERG: When did you -- when did it go from, like, this is something that I could do to this is something that -- that I am doing?

JERRY COLONNA: Well initially, I was just a solo practitioner, and I would actually coach maybe a day or two a week.

ALEX BLUMBERG: And who are your clients at this time? Who are they. Like I mean, not names obviously, but like -- like what kind of -- what profile?

JERRY COLONNA: It was a mix of people. There were some non-profit executives, some individuals in midlife. I remember a guy who was in his 60s who, not unlike my father had just lost his job. And then there were -- there were more than a few first-time CEOs of local startup businesses. And, uh, did I ever tell you about the office in the back of the baby furniture company?


JERRY COLONNA: [laughs] So one of my clients had built a company manufacturing and selling furniture made of sustainably-harvested woods and non-toxic glues and finishes and that sort of thing. And they had a very, very popular line of baby furniture. And… Anyway, he came to see me and then I had to find a new office. And he said, "Well, we have some office space that you're welcome to use." And so they carved out a little space way in the back of this furniture showroom. And my clients would sit amidst, you know, cribs and baby gliders and rockers and that sort of thing. And they would come in and then the door would close and they'd be -- they would cry. And they would sit on my couch and we would talk.

ALEX BLUMBERG:  In the beginning, did anything strike you about just -- just about that? Like, about how much everybody was carrying with them? Was that something that was surprising to you or not? 

JERRY COLONNA: There were a few things that were surprising to me. One was how universal the feelings were. That regardless of the size of the company, regardless of how successful they were, they were scared. They were squelching those feelings and not letting people know that they were scared. They felt incredibly alone, because they weren't sharing the fact that they were scared. You know, they were all worried that there was a house of cards and that somebody was gonna figure it out and blow on the house of cards and the whole thing was gonna fall apart. And I was also surprised that the feelings that I had had for so long, I kept hearing out of the mouths of the people that I was working with. And I think that part of what started happening for me was I started, instead of responding from a place where I was going to tell them what to do like a mentor, I started responding from a place of empathy. And like, "Oh, boy. I know how that feels." 

ALEX BLUMBERG: Working with you is -- is a lot of sort of like you're putting us through sort of I guess what I'm putting you through right now, which is trying to figure out what-- 

JERRY COLONNA: Turnabout is fair play.

ALEX BLUMBERG: Why are you doing the things you're doing?


ALEX BLUMBERG: And a lot of the reasons that you're doing the things you're doing go back to things from your childhood, things that you learned long, long ago. Patterns that were established long, long ago. One of the perverse realities of -- of being an adult is that these -- these -- these behaviors that you develop when you're a child, when you're little and scared and defenseless, can become harmful to others in adulthood.


ALEX BLUMBERG: So you need to, like, address them. 

JERRY COLONNA: Right. The point of doing this kind of work isn't to unearth new sources of shame. The point is to relieve yourself from the burden of those patterns so that you can actually transform them. By being gentle and recognizing that, we did the best that we could. We all just did the best that we could. You know, as my therapist used to say to me all the time, "Not bad, considering." Right? Considering everything? Not bad! Okay? So you resolve to grow up. You resolve to find new ways of doing it. And you let go of the need to beat yourself up. 

That was my conversation with Jerry Colonna. His book is called Reboot: Leadership and the Art of Growing Up.

If you’re feeling depressed or you just need to talk to someone, you can call the National Suicide Prevention Lifeline. The number is 1-800-273-8255. 

Without Fail is hosted by me and produced by Molly Messick, Rob Szypko and Heba Elorbany. It is edited by me and Devon Taylor.

Music and mixing by Bobby Lord.

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