Episode 297

Jerry Colonna On Rebooting Your Life And Leadership

The Elevate Podcast with Robert Glazer | Jerry Colonna | Reboot Your Life


Jerry Colonna is the CEO and co-founder of the executive coaching firm Reboot.io. A highly sought-after coach and speaker, Jerry was previously a partner with JP Morgan and co-founded Flatiron Venture Partners with Fred Wilson. Jerry is also the NYT bestselling author of multiple books, including Reboot and Reunion which is now available wherever books are sold.

Jerry joined host Robert Glazer on Elevate to talk about how leaders can level up, find purpose and leave a legacy.

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Jerry Colonna On Rebooting Your Life And Leadership

Jerry Colonna, top executive coach and NYT bestselling author of Reboot and Reunion, joins host Robert Glazer on the Elevate Podcast

Our quote for this episode is from Ray Kroc. “The quality of a leader is reflected in the standards they set for themselves.” My guest in this episode, Jerry Colonna, is the CEO and Cofounder of the executive coaching firm Reboot.io. He is a highly sought-after coach and speaker. He was previously a partner with JPMorgan and cofounded Flatiron Partners with Fred Wilson. Jerry’s also written a new book, Reunion, which is now available wherever books are sold. Jerry, welcome. It’s great to have you join us on the show.

Thanks for having me. It’s a delight to see you again and to be on the show.

We got a chance to meet and, lucky enough, you’re at my dinner table that the MasterMind Talks about a few months back. I enjoyed seeing you speak and hearing a lot of the material in the books come to life.

It was a pleasure to be there. That dinner was a fun dinner.


The Elevate Podcast with Robert Glazer | Jerry Colonna | Reboot Your Life

Jayson’s a very good matchmaker at dinner. He spends months picking those dinner tables. You start Reboot talking a lot about your childhood and the impact it’s had on you, specifically in the work that you’re doing now. Can you dive a little bit into that for our readers and for those who haven’t read your book yet? It’s your childhood experience and the impact that it had on you. We spent some time talking about the connection that we see a lot in terms of leadership nowadays and things that happened to us in our formative years.

Perhaps the best way to answer the question is I start by talking about my childhood because I believe very strongly that those of us who hold a position of authority or power have a responsibility to go first. By first, I don’t mean grab the microphone and never let it go. To do the interior work, I’m trying to understand how is it that who I am and how I have grown shape how I am as a leader.

It’s because too often, I have found myself working with people who don’t understand the toxicity within our organization or the struggles that they’re going through within the organization. They don’t necessarily understand the connection back to their internal belief systems or, as I describe them, reboot their subroutines. It’s that lower level of patterns that shape everything that we do.

Is it that they don’t want to see it or they don’t see it? I often wonder sometimes when you talk to someone and it’s obvious. I remember having dinner with someone years ago, and she was talking about Facebook or social media. People are talking about their happy marriages and she could tell from a mile away when someone was going to get divorced. I happened to ask the question like, “What happened to your parents?” She’s like, “My dad left and blindsided my mom.” I said, “Have you ever thought about that connection?” She looked at me and she looked stunned. I don’t know who was more stunned, me or her, in that scenario.

You ask an important question. Is it that they don’t want to see it or is it that they can’t? The answer is probably both. To use a phrase, the poet John O’Donohue has a brilliant blessing called Blessing for a Leader. There’s a line in there that goes like this. “May you be surrounded by good friends who mirror your blind spots.”

The truth to the matter is part of the way we contend with the difficulties of simply growing into adulthood is that we place things into our blind spots so we don’t see them. We do that not because there’s something wrong with us. We do that in order to be able to withstand the pain. You talked about your friend. I would probably suggest that the experience that she had of her father leaving the family created enough pain and suffering that she placed the whole experience in her blind spot. However, that doesn’t mean it’s not accessible to her.

No. She developed a heightened sense of pattern analysis and the ability to spot things that looked funky dory.

I would go one step further. I would say that, as a little girl, she probably felt a tremendous sense of empathy and maybe even responsibility for her mother. What she may have developed is an internal subroutine that said, “You better be on the lookout for someone leaving.” Her hypervigilance got tuned into looking for someone who might be leaving and a relationship perhaps being broken up.

You had a difficult family situation. It wasn’t easy. You had a lot of siblings. What number were you?

I was number 6 out of 7.

What got you through into your career? What was the progression of getting through that, getting out into the business world, and starting your career?

I was just thinking about this very issue because I was visiting some family and friends. I was asking myself, “How did I get to where I am?” I revisited a scene that I wrote about in Reboot, which was when I was about 15 or 16 years old and my mother who was mentally ill and my father who is an alcoholic, that’s how his mental illness showed up, we’re yet again fighting.

After everybody had gone to bed, I ran away. I spent the night under the Boardwalk in Coney Island. I grew up in Brooklyn. There was this moment when the sun was rising and my body was hurting because it wasn’t particularly comfortable and I was groggy. I was like, “What the hell am I doing?” I remember feeling so frustrated with my life at that point.

I stood up and I yelled, “This is not going to be my life.” You ask, in a sense, what the trajectory is. You mentioned before that I was a former venture capitalist, I worked at JPMorgan, and I launched a successful firm, but my recollection of that trajectory shifting began under the Boardwalk in Coney Island. In a sense, it was both a declaration of my intention and a decision to not follow the path that was so clearly unfolding for me.

You had no support structures, so that had to come from within. You had to go out there and figure out how to hustle and how to make that happen.

Yes, and even at that early age, what support structure I had was incredible mentors and teachers. I remember one teacher. There was this one moment when I was in high school. I was about 17 or 18 at this point and I had started cutting classes. I was in the top 5% of the students at the school. It was unusual for me to start cutting classes.

I remember one assistant principal seeing me in the hallway, her wagging her finger at me, and going, “What’s going on with you?” I went into her office and burst into tears. A couple of other teachers who were very close to me at the time came into the office. They were all these adults who, in hindsight, cared for me. I left school and they sent me to this therapist who was a few blocks away. It saved my life.

You must have had some teacher or mentor, someone who really advocated for you and saw the potential.

My life has been marked by brilliant wonderful mentoring adults who saw something in me that I struggled to see. I tell this story in Reboot. A professor in college awarded me a scholarship that enabled me to pay my tuition and stay in school, even though I was struggling, which then led to an internship at a small publishing firm on Long Island. It then led to me being promoted and eventually being the youngest editor in the company’s history. It also led to me being discovered by some friends who are starting a venture capital fund, which led me to become a venture capitalist. It led me to discover Fred Wilson, who continues to this day be one of my closest friends. I liken these experiences to asteroids that strike us and set us on the right course.


The Elevate Podcast with Robert Glazer | Jerry Colonna | Reboot Your Life

I mentioned this when we had dinner. It’s funny because I’ve been in and around the venture capital world and a little bit of the private equity world. I would generally categorize the venture capital world as not very interested in culture, breaking a lot of things and a lot of people. You are very successful. Flatirons is one of the most successful firms. Did you have a different mindset then or what was your focus? What was your investment rubric? I’m also curious about what the biggest win was and what the biggest miss was during your investment career.

I’ll circle back and give you examples of what you’re talking about, but I want to respond to the first observation. That is not my experience, but I understand why people have that impression.

There are different believers.

There are jerks in every field. Nobody has a dominant position and has jerks in their field. There’s plenty to go around. I remember early in my career, I was struggling about whether or not I was going to be a good venture capitalist and I had a lot of self-doubt. A fellow who has subsequently become one of my closest, if not my closest friend, Brad Feld, who’s also a very successful venture capitalist himself. We were talking one night and I was sharing my self-doubt.

I said something like, “I can’t be like,” and I would just rattle off a bunch of names. He said, “Stop trying to be like those people. Why don’t you be the kind of VC that you are?” It was like a cheat code. It unlocked something in me. The result was that I was the kind of VC who could peer into the future. One of my earliest investments was a search engine called Lycos.

That’s the first internet craziness. Was that the dog?

Yes, we used the dog as the image because instead of searching, we use that stuff. This was technology that we spun out of the Carnegie Mellon University. In the early days, I remember walking through the halls of the Heinz Convention Center. We were recruiting somebody to come be a top executive at the company. I remember him looking at me and saying, “Come on. Do you think that people are going to sell $100 million or $200 million worth of advertising on the internet?” I looked at him and I said, “You don’t understand. This is going to replace all other mediums because it’s so much more efficient.” It hasn’t entirely come true, but it’s pretty darn close.

You were more right than he was right.

I was certainly more right than he was willing to give me credit for at that moment. He believed me. He joined the company and he made millions, if not hundreds of millions, but the point is that I had a capacity to see the potential. That was the kind of VC that I was. Not every VC does this. Some VCs are much better at structuring a good deal. Some VCs are much better at finding good people.

You were probably a bet on the jockey but not the horse type of person.

I could do both, which maybe was the best thing about me as an investor. I was a tiny early-stage investor in Twitter. This was long after leaving my position as a VC and becoming a coach. I was an angel. The returns on that were great returns because I could look at that and I could say, “This is an experience that will become ubiquitous.” That was one of the keys.

I guess you’re right field and right jockey or maybe more than the horse.

Yes, but I also made some spectacular mistakes.

What did you learn from your biggest mistake in investing?

That I would believe too much in my future forecasting.

Was that a weakness overused?

Yes. I would often overlook red flags because I wanted to believe so much.

You spent some time in JPMorgan. What made you make the transition into coaching?

It was a two-step process. The first transition was out of the venture. It then was this long period of being in this existential desert of like, “What do I do with my life?” and eventually become a coach. To answer the first question, so much of what I had constructed for myself in my 20s and 30s felt false.

False in what way?

The more successful I became and I became very successful, the more I felt like it was a sham and that I was a charlatan. In hindsight, what was happening was that I was living further and further away from who I was as a person. My friend and teacher, Parker Palmer, describes it as living crosswise with oneself. The outer version of me had elements of the true version of me, but it wasn’t a true version of me. That created this existential gap inside of me. Arguably, many people deal with similar issues in midlife, and I happen to be 38.

You were ahead of your time. You said you could see around the corner.

I was always precocious.

You started the midlife crisis a little earlier.

I walked away from the business not knowing what I was going to do next. Slowly doing my work during that period, it became clearer and clearer to me that I wanted to spend my time in the realm that you and I are spending our time in now, like in the realm that you and I spent time even at that dinner. I’m going to ask you something. You tell me if my impression is true. The person that you’re talking to now is the same person that’s next to you at dinner who’s the same person who did that talk at that MasterMind Talks event that we’re at.


I am me.

You are the same. I will vouch for that.

That’s the difference. If you want a visceral expression of it, at about 38 or 39 years old, I saw the falsity of living my life in such a way as to evoke adoration.

That’s what I was going to ask you, and it might be both. Was it to avoid pain in looking inward or was it to get the public acceptance and adoration of others that when you have success, it becomes a little bit of a flywheel?

I don’t think that I was avoiding the pain of looking inward as much as other times in my life I might have. To be clear, when I was telling that story about being in high school, shortly after graduating high school the depression got so bad that I attempted suicide. I went into therapy again. As I’ve often spoken about, I’ve been journaling since I was thirteen. I wouldn’t say that I was unafraid to look inward. I think it’s more appropriate to say I hadn’t yet developed tools to do something with the information that I would get when I would look inward and feel terrible. The corollary was that I was mistaking adoration for love, and that’s a mistake many people make.

It’s because it feels good. In my experience with a lot of entrepreneurs, too, and I don’t know if yours is the same, they didn’t fit into the system early on. They were not colored inside the lines people. They probably had a little ADD. They’re probably getting in trouble in class. They were not winning Most Likely to Succeed awards, and then they finally trip into this thing that they’re good at, which is rewarding creativity in this off-the-wall stuff. They start getting accolades for that and it becomes addictive. It becomes the trophies they didn’t get and the eighth grades they didn’t get. It’s very hard to get off that hamster wheel once it starts spinning pretty fast.

I think you’re right. However, there’s a corollary to that which is, if you describe the person who might not have felt like they fit in, let’s describe the people who are super high achievers who, everything they touched, seems to turn to gold. They also have a little whispery voice inside of the head that says, “BS. You’re faking it,” and then they mistake getting straight A’s for love.

Also, there’s some luck and if everything goes your way early on. It’s probably easier if things don’t go your way or maybe then start going your way then they go your way early and then they don’t.

Let’s go to the common denominator between all of these scenarios we are talking about. What is not encouraged in our children is being yourself.

I was just going to say because that inherently would require being different. Unless you’re in a Montessori school or something that is about that, those systems are about standardization. Seth Godin talks a lot about this. It’s about, “Everyone learns the same thing in the same class. You got to do this thing you hate.” This is what I’ve never understood and having my second kid apply out of college.

You talk to all these schools. They want you to have an A in everything you ever did, even the stuff that you didn’t like and you don’t want to do again. It seems like a false standard. Again, it’s what makes people great, which is they’re like, “I did that and I got a B in it. I had no interest in it, but I love this. I’m doing amazing in it because I’ve thrown my heart and soul into it.”

The same thinking manifests in our inability to teach children what to do with suffering or what to do with negative emotions. What we’re supposed to do with negative emotions is be with them. That’s called compassion. We then look at epidemics of depression and anxiety.

[easy-tweet tweet=”What we’re supposed to do with negative emotions is be with them. That’s called compassion.” via=”no” usehashtags=”no”]

Helicopter parenting is not a good strategy for that.

Helicopter parenting isn’t a good strategy, but neither is not knowing what to do with it and not recognizing that this is what’s going on. We get these people power, agency, and organizations and then we wonder why we have toxic combinations in organizations. The achievement challenge that you talked about, the compliance that you and Seth speak about, that’s real, but even more real is the, “I don’t know what to do with me feeling different.” Forget about being different. We suffer.

Let me ask you something because when you think about before, you talked about the challenges that you had to overcome. Someone could have said, “Poor Jerry. Look at these insurmountable things that he had to face. He could be angry, mad, and all of these things.” A lot of this has popped up in the last month when we’re looking into, understandably, some of the historical injustices and otherwise but some of the things that are going on campuses and stuff now that I disagree with.

I wrote about this is that instead of teaching agencies, we seem to be teaching people to be victims and to be aggrieved. I’m not clear how that solves any of the problems of the world or make things better. I understand why some people feel that way, but if you had that orientation or someone had honed that orientation into you, it would have looked very different.


The Elevate Podcast with Robert Glazer | Jerry Colonna | Reboot Your Life

There are almost two parts to your question and your observation, so I’m going to take each part. One of the most important quotes that I learned in that period of being in the desert after being a VC and before I became a coach, I stumbled upon this quote from Carl Jung, which was, “I am not what has happened to me. I am what I choose to become.”

That’s the agency that you’re speaking about, and you’re right, just like that kid who stood on the boardwalk and said, “This is not going to be my life.” There was a hopeful agency. Yes, you’re right. We’re seeing a response to the violence of the world that denies our own agency, and I am with you in crying that response. There is no excuse for hate, whether it’s anti-Semitism or Islamophobia, anti-Black racism, anti-Asian racism, and anti-immigration feeling.

The truth is there is a throughline that connects all of this. What I am curious about because I am trained to respond to suffering with compassion is what is the suffering that exists in an individual, whether they’re tearing down posters of kidnapped children or calling for the destruction of a particular group of people? What is the suffering inside of them that has been weaponized by truly evil forces because we get so fixated on outrage meeting outrage?

Beyond the problem solving, we’re not even paying attention to the true culprits. Hannah Arendt spoke of the banality of evil in writing about the Nazis. The banal aspect of what’s going on is that there are literally people who benefit from division. Those are the people who should feel it. I’m not excusing hateful violence, but I’m wise enough to understand that hateful violence still serves somebody. When we pretend that there aren’t forces that are benefiting me wanting to kill you or you wanting to kill me, then we are easily manipulated. The merry-go-round goes on and on. This one kills this one and that one kills that one.

Do you think our educational institutions speak for the US but have a more pressure responsibility not to teach the philosophies that are more likely to lead to this? There’s the experience that you’ve had and your lived experience that’s different for each of us. As you said, there’s someone teaching, weaponizing, or trying to tell you that it is most of the people in the world.

The top 1% had a perfect nonviolent and non-suffering life. History has not been easy. Everyone has been challenged. We are a violent species in some ways. You read Sapiens or otherwise. I do find this whole narrative that you should just be angry about everything is not inherently making everything a little bit worse.

There are two parts that I see in your observation question. The first is to look at institutions. If you want to look at educational institutions, we can look at educational institutions. I would ask you to consider all institutions. Remember something, all institutions, educational and otherwise, are made up of flawed human beings. We can decry the lack of sound, thoughtful leadership from “institutions,” but what we’re talking about is the lack of leadership from human beings. What is it that those human beings lack? This is what I wrote about in Reunion. I’m doing this because the book is here.

I was just going to ask you. I’m going to say your mantra of, “Better humans, better leaders,” I love that. I couldn’t agree with it more.

Let’s talk about that. You’re right. My mantra for years has been that “Better humans make better leaders.” In the first iteration of that, it was like, “Of course, that’s true.” Why is it so difficult? It’s difficult because becoming a better human requires that we grow up, and most people don’t want to grow up. The second half of that question is to expand the definition of being a better human. It is to include being compassionate even to people with whom you disagree.

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I’m going to pause. Every wisdom tradition I’ve ever seen says, in a sense, that we need to be compassionate even with people with whom we disagree. Compassionate but don’t be a doormat. The truth is this has been going on for millennia. What we don’t do as a species is listen to our elders. Let’s talk about the metaphorical elders who know better who would slap you upside your head and say, “Sit up straight, eat your vegetables, and be kind.” I understand that you feel the suffering of the world. I understand that you’re outraged at the suffering of the world. Do not meet outrage with outrageous behavior. That doesn’t end the outrage. It doesn’t end the suffering.

If you took all these Ivy League kids and forced them into some think tanks that were only solution-oriented rather than what’s going on, you might have some good come out of it.

I see what you’re referring to when you say all these Ivy League kids. Be careful of the generalization.

It is a generalization. It’s hard not to view.

Think about the experience that you’re having. It’s hard not to see a group of individuals as a nameless and faceless group of individuals and label them. What are we talking about when we do that? We’re talking about this very same behavior that leads to dehumanization, a depersonalization that, in its furthest expression, supports violence. Let’s take a deep breath. Let’s see what’s at play here.

There are evil MFs in the world and they’re pulling a bunch of strings. It’s not based on religious Identity or tribal identity. It’s based on self-aggrandizement, whether it’s the head of a terrorist organization sitting on billions of dollars and hiding out somewhere else while the people that they’re supposedly supporting suffer or it’s the head of a government whose political future is in jeopardy who looks the other way.

The truth is there is a banal evil that is behind the suffering and we are being manipulated when we generalize the other side as understandably reactive as it would be. I have a friend whose sister was murdered in front of her thirteen-year-old child. I understand his impulse for revenge, but God in heaven and every wisdom tradition teaches us that revenge is not the answer.

It’s the same cycle that we’re in.

However, I understand it.

I think this will overlap in the leadership. Why are so many of the leaders, very impressive and highly paid leaders of these institutions have such a hard time finding their footing and their moral compass? You’ve seen the public suggestions and stuff. That seemed like they would be pretty straightforward.

Let’s go back to root causes again. We don’t like to admit this, but the simple but hard is hard to do. It is simple. Hate needs to be condemned in all its forms. There is no equivocation on this. There is no but and what about-isms. Also, historical context matters, and suffering over millennia matters. There has been a global tendency to anti-Semitism possibly for as long as there have been Jews on the face of the Earth. That is a historical reality and we can do both.

We can speak out and speak up with moral clarity. Also, admit nuance and context and reach for deeper questions. Why do I know we can do this? It’s because it was done in South Africa. It has been done in our societies. We have elders in our society. What would Nelson Mandela say? What would Mahatma Gandhi say? Would he say drop more bombs?

This is hard because we’re talking about visceral heartbreaking suffering and we are never going to arrive at what I call a reunion. Whereas the poet, Bell Hooks, said, “When angels speak of love, they tell us all things are union and reunion.” We’re not going to arrive at the place where angels are speaking of love if we’re not responding and overcoming our base impulses with love.

Let’s go into that inner work of the leader because I know a lot of people come to your boot camps and workshops. You have a formula that you like to use. You can talk a little bit about that. A lot of times, they’re looking for practical skills, but I think that’s a small part of your equation. Can you can you go through that equation? I find it extremely informative.

What you’re referring to is the simplistic way in which I present the work that we try to do. It goes like this. Practical skills plus radical self-inquiry plus peer experiences or peer support equals enhanced leadership and greater resilience. The practical skills are the stuff that takes care of the container of the business, “How do I hire people? How do I fire people? How do I grow a team? How do I scale?”

The radical self-inquiry part asks us questions like, “How am I supposed to grow as a leader when I’m terrified? What is it that I worry about that keeps me up at night?” The peer experiences, “How do I overcome my belief that I can’t share any of this and that I am ultimately alone so that I can reach out and receive and give empathy?” that is the core of what we’re trying to do.

What’s interesting is practical skills would come first, “If I know how to do this better, that would be obvious.” I think people then find themselves in some peer support whether it’s EO or YPO.

Also, MMT.

Also, a forum-type structure. Sometimes those structures lead themselves towards some of the radical self-inquiry, but I’m guessing that is probably the most important in that equation and maybe the third one that people dive into and do the work on with that. Would that be accurate?

That’s totally fair. It’s because the presenting challenge is the one that becomes top of mind. However, as a coach what I’m interested in is not solving your near-term daily problem. What I’m interested in is supporting your transformation, so you don’t need a coach and you can solve the problems on your own.

[easy-tweet tweet=”As a coach, what I’m interested in is not solving your near-term daily problem. What I’m interested in is supporting your transformation, so you actually don’t need a coach and you can solve the problems on your own.” via=”no” usehashtags=”no”]

Talk to me about fix or shame. You mentioned that in our species, that’s intended to be a fault. You either fix it or be shamed for something.

Fixing, the way I use it, the way coaches might use it, or therapists might use it, turns everybody’s experience into a problem. You can get a telegraph moment that this is happening when someone says, “Do you know what you should do? You should,” fill in the blank. The problem with that is that it doesn’t create solutions and transformation.

Form structure normally doesn’t allow that. It’s why it’s about experience sharing and not advice giving.

Yes, but it’s hard to untrain.

That’s why there’s training for it.

The corollary to that is that if we don’t keep that under control, what ends up happening to the person receiving the fixing advice is that they start to feel shame because, “Why didn’t I think of that? Why didn’t I think of just firing my head of sales?” The truth is you did think of it. In fact, you lay awake at night for months on end thinking of it, but you also were trying to figure out, “They’re also a high performer. They just piss everybody off within the organization. What do I do?” The radical self-inquiry question is, “Why did you hire the person in the first place? What part of you were you outsourcing in order to get that person or bring that person in?”

When you say what part of you are outsourcing, what do you mean by that? I’ve heard you say that and I can take that a couple of different ways. Could you give me an example of a conversation?

Sure. I tell this story in a Reboot of a CEO who came in complaining about his greedy SOB head of sales. He’s pissed off at me because I’m reading poetry and I’m speaking. He’s like, “I need to get rid of this person.” I convinced him to stay. Two days go by and we’re talking about the disowned parts of ourselves. We’re talking about the parts of ourselves that we don’t want to acknowledge that are there. Again, he’s getting squirmy. He’s getting pissed off. He doesn’t like it.

He said, “I have this greedy SOB.” I stopped him in his tracks and I said, “Why did you hire the greedy SOB in the first place?” He pauses. I said, “What part of you is greedy?” and he paused. I said, “Tell me about greed.” He starts crying and he starts talking about being 15 or 14 years old addicted to alcohol, running away, living under an overpass, and realizing that greed was an expression of himself because he had internalized, “If he has all the toys.”

It sounds like he had a very similar moment that you had.

Exactly, and I could recognize that like your friend who could look on Facebook. I could recognize that, and that’s where I say, “What you did was you outsourced your greed because greed as a word is not something that we are proud of.”

You hired him to do exactly that, which he is doing.

He is being successful. The goal is to take back the wish to have all the toys so he can be free.

I know you like equations too. I heard it on a show. It might have been Morgan Housel who said, “It’s what you want divided by what you need.” For most people, if they can’t reduce the denominator, then the numerator can never keep up.

There’s a wonderful poem called The Tyranny of More.

I’m trying to find the study. I was at a conference years ago and someone talked about a study. I’ve looked for it and I can’t find it. Maybe it was a good story. He said that they had interviewed people with $1 million to $100 million in net worth. They had asked them, “How much is enough for you?” What do you think the answer was in that study?

It was always 20% more than they had at every single level. How much is enough for you?

I’ve thought about that a lot.

I can tell you thought about it because of the questions you were asking.

I think I was on that achievement hamster wheel where the more fulfilled the need and until I identified that and became comfortable with wasn’t getting me what I wanted, I wasn’t able to reverse that. For me, enough is enough. There’s nothing more that’s going to make me any happier. I think it’s figuring out how to be smarter with what I do and my work because I almost fell off that hamster wheel.

Which is why a number of your questions even now circle back to that experience.

That ties into one of your favorite quotes, “Until you make the unconscious conscious, it will drive your life and you will call it fate.”

That’s also Carl Jung.

Explain the fate part of that. These things are doomed to keep happening to you.

It denies our own agency. It’s just fate. It’s just what happens, “This always happens to me.” The truth is that that kind of radical self-inquiry, the kind that you’re doing, the kind that I recommend, and the kind that I have gone through myself puts you back in the driver’s seat. We were joking before about people being reluctant to grow up. One of the things that people are reluctant to do is to take responsibility for their own lives. It’s not because of guilt. I don’t want people walking away from this conversation saying, “Jerry wants me to be guilty.” It’s far from it, but I want you to be able to say, “This is my life and I have many more choices than I pretend.”

Positively and negativity like cause and effect is important. It’s something I talked to my kids about. You do X and there’s an outcome and you learn from it. It could be a good outcome. It could be a bad outcome, but it’s yours. I find that the parenting philosophy of the last many years, which I would call permissive, and overbearing is my name on it, has wanted to take away this accountability. “It’s not your fault and let’s work around bad things.” It’s missing a huge thing.

This is where I think the problem has landed a little bit on a lot of college campuses. I think people are surprised that their behavior has outcomes. The administrators, in some cases, are not following through with the things that they said they were going to do. Remember the bright red line from whatever administration it was. People are surprised if there’s accountability, and that lack of accountability is hurting the agency in some way. People need to feel that. There’s a lot of people who are confused and I’m not trying to make this up. You could speak freely. The government cannot arrest you, but don’t think that it doesn’t have consequences and then they want to be shielded from the consequences.

What you’re pushing up against is immaturity, which can manifest in a sense of entitlement. It’s not adulting. Let’s go back to some of the root causes we were talking about. I’m a parent. I’ve got three kids. They’re all adults. There typically tend to be two images that we as parents carry, stemming in part from our own anxiety. The first image is of the snow plow, which I’m sure you’re familiar with. “Let me clear the path for you so it’s easier.” The second image is standing behind, pushing and driving them forward. Let me offer a third, which is to stand shoulder to shoulder. Occasionally, lean over and say, “If you make that decision, it could be a problem but it’s your decision to make.” You don’t do that to a ten-year-old, but you might do it to an eighteen-year-old.

I love this quote. You probably heard it. The problem now is that we need to prepare the child for the path, not prepare the path for the child.

That’s part of the resilience that I was talking about even with the formula or even with the equation that we’re talking about. Our job as coaches, leaders, parents, and romantic partners is not to do the work that the other person needs to do.

[easy-tweet tweet=”Our job as coaches, leaders, parents, and romantic partners is not to do the work that the other person needs to do.” via=”no” usehashtags=”no”]

I’ve encouraged people who are parents and also leaders to think through the leadership lens. I understand they don’t get 360-degree reviews from their children, but if the micro-management at home, and probably a lot of times, it works, they would be on a performance review and in retraining for leading to not micromanaging more. It’s probably hard to break that. I’m guessing there’s a lot of correlation there.

It’s super hard. I was on the phone with someone sharing another favorite quote of mine, which is being a parent is like wearing your heart outside your rib cage. We love our children. We don’t want them to have any pain, yet what does the wisdom of a skinned knee teach us?

I also heard that he was a roving prefrontal cortex for his own boys. That goes with yours, but it’s a little funnier.

There is something difficult about letting our children, employees, and people make mistakes, and yet that is part of the process.

That’s part of the process to understand the consequence. You’ve seen this. The best sales leaders I have seen will not even get on the call. They will let the salesperson go on the call. They will record the call. The salesperson will fail horribly, and lose the deal, and they will walk through later with them and coach them on the things that they could do better. The not-good salesperson leader will get on the call and jump in and save the deal and that person won’t have that experience. They won’t have that failure. I’ve seen that time and time again.

If they fail to close that deal, does that present an existential risk to the company?

If you fail to close all the deals, maybe, but they’re playing the pound and not the penny.

It’s the same thing with parenting. You give the keys to the car to the kids and then you pray that they stay within the guardrails on the road.

The framework someone once described, which I liked, was military. They are above the water and below the water line holes. Focus on above-the-waterline holes that are not going to sink the ship, but if you think it’s a below-the-waterline issue, then you intervene.

Hopefully, as they age, the vulnerability to below-the-water line bullet holes gets fewer and fewer and lower and lower.

I know a question that you prompt people to think about in Reunion, which I love and I’ve heard you use it a lot. “I’ve been complicit in creating the conditions I say I don’t want.” I’d love to hear a personal anecdote on that if you have one or a friend.

There are so many. I’m more than happy to. That question developed out of conversations I had with my therapists going back many years ago, which is a realization that I have been co-creating and not generating so many of the conditions that I grew up with. A classic example for me would be because I feared conflict as a child because conflict would often end in violence, I might withhold the truth of how I’m feeling about something until I can find the right time to say it to a partner or a loved one the thing that I know would upset them. I might shade the truth a little bit, and what happens is they find out the information and they’ll be more upset.

My experience, when we get these things back, they always come out and they all come out at once.

Also, they always come out worst. However, when you’re five and you first formulate this as a response, that’s not always true. You don’t know that that’s true. With a little bit of empathy for yourself, you understand what’s going on there, and then you start to say, “I’m lying awake at night anxiously anticipating this conversation.” That’s how I have been complicit in creating the conditions I say I don’t want. One of the follow-up questions I often ask is, “What am I not saying that needs to be said?”

Almost invariably, I’m not saying something that’s probably going to piss somebody off, so it avoids people being mad at me. It’s a very particular kind of conflict and I get it. I have a book that’s come out. There’s a part of me that worries that people are going to get pissed off at me, yet what is it that I want? I want people to have a conversation, even if they disagree. That’s one of the ways I continue.

I can continue to do that. When I catch myself, instead of beating myself up, I say, “That’s not the world I want.” Now, I have to lean into saying what I need to say or hearing what I need to hear. Also, seeing that people are speaking even if they’re saying something I don’t want to hear. Those are all important rules for a leader to follow.

The other thing I want to ask you is you discussed how leaders unknowingly fall into the trap of toxic leadership. What are some of the warning signs that I would say they should look for or maybe the people around them should look for that someone is slipping into toxic leadership? It’s because we seem to have plenty of that going on now.

A great example would be this. My colleagues will often be called into an organization because the organization has a “trust issue.” It can show up in things like not being able to take rests and not being able to innovate. I will cut through and I say, “Are you telling each other the truth?” “No. We don’t trust each other. We can’t tell each other the truth.” We’re laughing because they’ve reversed the equation. Trust is an outcome of truth telling not the cause.

This is Lencioni’s bottom of the pyramid.

If you think about toxic organizations, they are implicitly toxic and then they are explicitly toxic. The explicitly toxic organizations put up with behavior that you would never put up with in other circumstances in your life. It’s when those who are in power can’t manage the conflict, “I can’t fire my racist head of sales. They’re the best-performing salesperson. They are brilliant jerks.” There are implicitly toxic situations where people shade the truth constantly with each other. If you haven’t read it, read The Fund, which is Rob Copeland’s book on Bridgewater.

I was hearing anecdotes about it from a lot of people. It sounds like it might dent the sales of Principles a little bit.

Yes. Take a look at it. It’s an interesting challenge.

Jerry, I know we could probably go on for hours, but I’ll bring you to my constant last question, which is multi-variant. It could be singular or repeated. It can be personal or professional. What’s a mistake that you’ve learned the most from?

Not speaking up more often than not, and it roots back into what we were saying before. Ninety percent of the time, the mistakes that I have seen, that I have lived through, or caused are rooted in an unwillingness to say the thing that might upset somebody. I finally internalized that it is the root cause of many of my “mistakes.”

Jerry, thank you for joining us. I hope all the readers will check out Reunion to learn more about your insights and experience.

Thanks for having me. It was a delight having this conversation.

To our readers, thanks for reading. If you enjoyed this episode, make sure to follow the show to be notified about new episodes and have them downloaded and ready to go for you. Thanks again for your support. Until next time, keep elevating.


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