Jerry Colonna

Welcome to 100 Stories, the Narrative Intelligence Project. I'm your host, Paige Williams. I'm talking to 100 thinkers, creators, researchers, leader, and people shaped by profound change as I explored the emerging field of narrative intelligence. At the center is one question. >> [music] >> How malleable are the stories we live by, and what does it take to change one? What I learn will help shape the field and the foundational book that I'm writing about it. This is 100 Stories.

Today we're speaking with Jerry Colonna. Jerry is an author and a founder of Reboot. They are [music] an executive coaching firm and his life work is being of service of others and helping others do radical self-inquiry. And I told Jerry as we started years ago when I was a tech founder, he was on an episode of Gimlet Media's show and he was working with the founder through some big issues that happen as tech founders go through what they experience and it really saved my life.

And so I've been following Jerry ever since and I'm grateful you're here and grateful that you're going to share your wisdom with us today. >> I'll share what I can. I can't guarantee it's wise. >> Well, you've spent years practicing what you call radical self-inquiry. And I'm wondering in that inquiry what you've been trying to understand about yourself, not just others. >> Why am I so crazy?

No, in all seriousness, you know, in Buddhism there's a really important concept uh called the second arrow. And put simply, the story goes a man shot with a poisoned arrow. And rather than pulling the arrow out and saving his own life, he spends all the time shooting a second arrow at himself. Who shot the arrow? Why did they shoot it to me? Why do I always get shot by an arrow? What's wrong with me?

And then he dies. And what I get really fascinated by is um what is it that we do that makes our condition so much more difficult? Right? My infamous question, how have I been complicit in creating the conditions I say I don't want is really rooted in not in guilt or self-denigration. What's wrong with me? But it's really rooted in curiosity and ultimately liberation. Why do I do that? How does it serve me?

Is there something else I can do that can give me the feeling that I'm looking for by doing that action rather than spending all the time trying to figure out who shot the arrow. >> Right. >> Take the damn arrow out. That's the lesson. There's poison in your system. Take the arrow out. Heal. Then you'll figure out what happened. >> What work in your life has most shaped how you see yourself in the world?

>> Well, I have been in psychoanalysis now for 34 years. And someday I'll have it figured out. I've outlived at least one psychoanalyst. God bless her soul, Dr. Sayers. I I joke, but um the basis of everything that I try to do is that understanding is that radical self-inquiry. And so when I'm sitting in a room with you know, um senior leadership of a company I try to apply that same thinking and say, "Okay, what's really going on here?"

Oh, what's really going on here is everybody is triggered and acting like children and being deferential to the mama or the papa who happens to be misbehaving and acting out. Okay, now I understand what's going on. And how do I bring forth their adult selves so that all of that triggered family of origin behavior just settles down and I get to be their their adult selves. What I just described in a hypothetical situation, it's what happens when I talk to an analyst, right? It's like, what's going on here?

What's going on here? You know, I'm going to point to my left. Down on the floor is my meditation cushion. And I meditate every day, and I've been doing that for 27 years. And I sit there and it's not Yes, I watch my breath. Yes, I stare at a candle. Yes, I do all those things. But really, I'm sitting there going, what's going on here? Or really, what's going on here? What's going on in my heart?

Why do I feel what I'm feeling? And in understanding that, can I create a sense of liberation from that? So I'm not Trigger warning, I'm about to use a Buddhist term. trapped in the wheel of samsara again and again and again. And then as a business leader or a white straight cisgender man who has power and privilege, if I I don't do that work, I can hurt people all over the place.

So, just settle down. What's happening? Let it go. >> Tell me about a transformational moment in your life that changed how you see the world. Or you're going one direction, [ __ ] happened, and then something shift. >> Of the Saul on the road to Damascus becoming Paul. All right. Probably the most important thing was this this very pivotal pivotal moment when I was 38. And the depression that had really taken over my life and it oh it it it always been in the background even as a kid. I I I'm I've been very open about the fact that when I was 18 I had tried to kill myself and I ended up in a psychiatric hospital and then I got patched together and went

through my 20s and then went through my 30s and became a reasonably successful investor. And as I often say, the more successful I became the worse I felt. Which was a paradox because it went against everything that our society teaches, right? The more money you have, the happier you're going to be. The more title you have, the more status you have, the happier you're going to be.

And boy, that sounds like samsara, doesn't it? And you know, I famously on February 2nd, 2002 was in Lower Manhattan just outside of what has come to be known as the 9/11 Memorial Ground Zero and I was just overwhelmed by the desire to take my own life again. >> Mhm. >> And rather than doing that, which is the pivotal moment, I called my analyst, Dr. Sayers, and she got me in a cab and she said, "Come out to Long Island where she was and come see me." And I did and it was that moment in which I chose to actually stay alive that everything changed.

Because in that moment she wisely sent me to Canyon Ranch, which was where I had my first experience of meditation. Makes me laugh now because it's so secular. But good work. And then I came back and I resolved to leave my job, which was at JP Morgan, and I resolved to do something really brave, which was have the courage to be uncertain about what I was going to do next. You know, again, going against the cultural impulse, which is up into the right. You just got another promotion. Look at you, you know.

>> [gasps] >> Maybe someday you'll be happy. You know. And so [clears throat] I then stepped off that pattern and spent three or four years sorting it out and emerged out of that as a coach. So. That's probably the biggest transformation moment. I call it key zero desperation moment, dark night of the soul, whatever we want to call it, where we decide to live. Mhm. Mhm. The allegory walking out of the cave, allegory of the cave moment.

Changes everything and I'm deeply curious about what it really takes to get there. And from my experience, it seems like it just takes a lot of pain. Is that always the case? Or what have you seen in working and coaching so many people since that moment of what it takes to really change a life? Well, we have to be careful right now in this moment because I don't want to romanticize pain and suffering.

>> Yeah. >> And we can do that again in our society. We we over index on that which does not kill me makes me stronger. Thank you, Nietzsche. Pain sucks. Okay? Pain just sucks and adversity overcoming adversity, overcoming suffering is important and um as the Buddha taught thousands of years ago, life is filled with suffering. But that doesn't mean we should seek it out. Especially if we have this internal sense of our self that we're somehow insufficient, so therefore I have to go I have to put myself through that.

In order to somehow quiet the demons that tell me I'm insufficient. So that's a tricky little thing that we can do to ourselves and that's not what's called for here. But your core question, I think is an important question. Um >> [clears throat] >> is it possible perhaps to do the transformations that we're talking about without pain? Is that a fair restatement of your question?

>> Yes. Absolutely. >> D. H. Lawrence has a poem. I'm going to mangle the words, but he says something to the effect if you are not willing to be crushed made new, you'll never change. And or you know, the overused metaphor of a butterfly, you know, caterpillar transform transforming into a butterfly. What people often forget is that in the middle that which was the caterpillar becomes goo.

Like literally just like a liquid thing as it reforms and I think people are willing to do that. But we're not taught how. In fact as children we're taught over and over again um certain aspects of personal inquiry. We we we we elevate pain in a weird way. We say no pain, no gain. Or we tell often times little boys, but but many times little girls play through the pain. But what we don't really work with is the resilience building capacity of learning to be introspective.

Of valuing the ability to see what's going on inside as as a mechanism for dealing with the existential pain that is inevitable in life. That lack of teaching I think in in Buddhism we have the four noble truths and the first is life is filled with suffering. The second is that which we do to avoid suffering increases suffering. Because we as a society are uncomfortable with pain.

And that sounds silly, right? We're uncomfortable with pain. Of course we are uncomfortable with pain. Sentient beings avoid suffering. We do. But because we don't know what to do with pain, we create pain. One of my great teachers and dearest friends, Parker Palmer, Quaker writer, says, "Violence is what we do when we don't know what to do with suffering." And look at the world, right? We don't know what to do with the suffering of my ego being bruised, so I'll start a war. Right?

It's like, "What?" Or or we don't know Let's make it less Let's make it real. We don't know what to do as young boys. We don't know what to do with the negative self-images and all of the conflicting messages about what does it mean to be a man. So we will sexually assault girls. What the [ __ ] What What What? What happened? And I'm not letting anybody off for their behavior, trust me.

But but when when you when you look at the situation of the world through this lens, there's a kind of moral clarity that comes through, which is that we have an obligation as adults to look pain and suffering in the eye. Not to glorify it, but to do the third Noble Truth, which is to evoke the cessation of suffering, cuz that's the promise. Suffering can end. This is This is the lie that depression tells us.

Suffering will never end. That's a lie. It's a lie. Okay? That's the depressed mind keeping itself depressed. Or I feel bad because I am bad, right? And the the cheat code is of course the Eightfold Path, the fourth Noble Truth, and that you'll have to look up on your own to get all the steps, cuz I can never remember the steps. >> When do we get curious about the arrow and sit on the pillow?

What are we really doing there in that work? >> Well, the first impulse is is [clears throat] again is to shoot the second arrow. And I can't emphasize this enough. My question, how have I been complicit has reverberated around the world. And you know, I'll often get like notes from people, I heard this famous actress on this, you know, podcast quoting you, but they didn't know they were quoting I was like, is that right? All right, whatever. I'm just quoting the Buddha.

But the first impulse is to turn that kind of inquiry into self-blame. And I can't emphasize this enough. Please stop. The point is curiosity. The point is curiosity which then leads to agency. Which is a form of adulthood. Why do I do what I do? Again and again and again. Or if you want to be even more gentle, what need am I trying to meet by staying in an abusive relationship?

Or by uh staying in a position that really doesn't help me. Or by living a life that is antithetical to my values. What What am I trying to soothe? And as I say in my first book, Reboot, it's it typically boils down to one of three things if not all three. Love, safety, or belonging. And of those three, safety trumps everything. I will persist in a bad situation because I think it's going to keep me safe.

I will stay in that relationship that hurts because I am so terrified of being hurt. And I get it. And it's the logic of the child. It's what we learn as children. >> What did you learn about love, belonging, and safety growing up? >> Uh I I can tell you what the opposite of what I learned. What I unlearned, if you will. Uh or what I came to understand was that love, true love, is safe.

And if it's not safe, it's not love. Which is really was a mind [ __ ] for me. Right? Because we can associate familiarity, comfort, a with belonging. This is familiar. I I know what this is like. And so I will stay in this situation because it feels safe. You know, to go back to our cocoon metaphor, at some implicit level, we know that the transformation will turn us into goo.

That that that Saul on the road to Damascus becoming Paul, we know that in that moment God strikes him down and he is blu- blinded. All right, we know that that's a painful moment. So we will stay. We will avoid that which we really need because we're afraid of being hurt. And let's just pause. I don't want to induce, again, negative self-view. I get you. Whoever is listening to this is saying, "Yeah, I I relate to that." I get you.

Okay? When the Buddha taught, "Avoidance of suffering increases suffering." He wasn't chastising us. He was naming something that we do with love and empathy. So please be gentle with yourself. I understand why one would persist in that which is hurtful. I would understand why one persists in hurting other people in the perpetuation of harm. And so take a breath. Get your ash on a cushion.

Stare at a candle. As I have a client who says, "What is What is staring at a candle going to do for me?" And then she comes back 2 weeks later and says, "Like, boy, staring at a candle helps." Yes, because it's that moment of introspection. What's happening here? My goodness. Okay. With love and gentleness towards myself, with loving kindness towards myself, I will endeavor to do better every day.

>> And then as you work with people on agency, what have you seen in your own life and in others that moves us to an enactment? >> Compassion. >> Mhm. >> Compassion towards self, compassion towards others. That's the That's the true cheat code. That's it, right there. You know, I have often said over these last several years that I feel like we are going through a war on empathy.

>> Mhm. >> That somehow compassion is the problem, right? And empathy and compassion aren't the same, but they're related, right? But what? What? Well, as a species, how many millennia? And and reach back in time. Pull up every wisdom tradition possible and tell me the one that says compassion is the enemy. None. None. So, what wounds are you trying to take care of in you? When you assert through your powerful platform and your trillions of dollars, you know I'm talking about, when you assert that empathy is the problem or compassion is the problem.

What are you trying to fix in you that you would criticize me for caring about a 10-year-old kid who doesn't understand or doesn't doesn't can't make sense of their gender. And why does it bother you? Who cares? The Who Who cares? When there's war going on and children are starving. What matters is taking care of each other. That's what the wisdom traditions teach us. All of them.

You have to be careful. If you let me talk, I'm like that that doll that you pull the string in the back and I'll just keep going. >> I'm a I'm an old school documentary filmmaker, so I let people talk. My superpower is listening. Let me ask you this. What happens when a leader's unresolved stories that they carry, the stories that hook them, >> Mhm. >> infiltrate the culture of the company they're leading?

>> I'll I answer that by quoting again my friend Parker, who likes to tongue-in-cheek quote Socrates, who said, "The unexamined life is not worth living." And Parker then adds, "But if you choose to live an unexamined life, please don't take a job that involves other people." >> [laughter] >> Go, Parker. >> So, [laughter] and you know, that's what happens. What happens is people get hurt.

>> Yeah. >> Because when you when you when you take the unexamined life and you map it to power, you get what we see over and over again happening all over all the time. You you get, you know, children being rounded up and separated from their parents under this [ __ ] threat of I don't know. Some 25-year-old mother from Guatemala is going to somehow destroy the United States. I mean, what are we talking about?

Okay? We're still, despite all of our stumbles, the most powerful country in history. And yet we're terrified of of thing and so then we have to pull a 5-year-old out of the arms of the mother. That's what happens. Or or we have, you know, what happens in work all the time, you know, and I see this again and again, especially now in this crazy age of AI. You have to work 996. You have to work 9:00 a.m. to 9:00 p.m.

6 days a week. Like, what? Why? For the accumulation of wealth? Because that's somehow going to ward off what? The big bad boogeyman? Oh, by the way, it doesn't work. Cuz the demons you've been running from, they're going to catch your ass anyway. No matter how many how big the gold brick fortress you've built or the trillions of dollars you have in the bank. They will find you. And so good luck with that.

>> Yeah. How much agency do we have to change our own story when the people or systems around us may still be enforcing the old one? >> Okay, now this is the moment in a podcast interview where I turn the question. >> Okay. >> What is your belief system behind that question? >> I believe that power, identity, and culture influence the narratives that unexamined narratives we're living in our lives.

>> And so, that is true. Not only do they influence it, influence what we're living, but they influence what was implanted. Okay, so answer your own question. >> I think so. >> capacity to change it? >> Yeah. So, that's the whole research field that I'm studying is narrative intelligence. And what is the capacity to examine, understand, choose something different, and enact a new story.

And the capacity is measured by how much I recognize that I have the ability to do it so that I might live free. >> So, two things I would say, two bits of elder wisdom. >> Please. >> Carl Jung once said, "I am not what has happened to me. I am what I choose to become." That's it. Right there. Right on the spot. But that's hard. Because the story grips us and you are 100% right that the culture and our environment can keep us in that.

But when we say when we say the culture keeps us in that or reinforces that, do you see the lack of agency that's implicit in that statement? >> Yeah, our capacity our agency capacity is based on being able to see that. >> Yes. >> And overcome and enact. >> So the second bit of elder wisdom, there's a poem by Adrienne Rich called Diving into the Wreck, which I highly recommend you reading the whole thing.

But she says in effect she visualizes in the narrative. She visualizes putting on your flippers, putting on your scuba gear gear and diving into the wreck. Not the story of the wreck, but the wreck itself. And being with the wreck of our lives. Right? And then resurfacing after that re-examination. She does not say go live in the wreck, which is the fear that we have. [ __ ] if I open up that closet, all that [ __ ] that I've shoved in there is going to come tumbling down on top of me.

Here's another bit of elder wisdom. Eminem song Cleaning Out My Closet. Okay? Clean out the closet. Take all the [ __ ] down. Sort it out. Re-Kondoize it. You know, this does not bring me joy and give it away. But the most important move at that point is to then tidy it all up and put it back in the closet cuz that's the move that keeps us trapped. We are terrified to examine the narrative.

The stories that shaped us because we are afraid that we will be trapped in the conditions that gave rise to the narrative in the first place. And so, what we have to do is examine the narrative. Examine the story. Examine the ways that we unconsciously through a second arrow reinforce the exact story making. Blow ourselves a kiss. Acknowledge that we've been doing that to stay safe. Congratulate the 8-year-old kid who figured out a way to survive. Look at you. You are so [ __ ] brave and strong and resilient. And you don't need to do that anymore. You can let that story go.

You get to write your own story. And Look, I'm a I'm a recent grandpa. I have two granddaughters now. The oldest is just about to turn a year and the youngest is about 6 months and I've got a third on the way. Here's the extra credit impulse for doing it. They need you to do it. Cuz these stories that we've been talking about, they're intergenerational. They get passed down and all with the intent of keeping us safe.

>> Yeah. >> Right? And so, if you want motive if you do not want to do this work for yourself, do this work for your either biological descendants or what are called your storyline descendants, the people who have been influenced by you. >> And what happens as a result of doing the work? >> Several years ago, I was going for a walk with Sharon Salzberg, who's my but his teacher.

And we had been sitting every other week together for at that point about 15 years. And we were walking out to dinner and I stopped at a traffic light and and she said, "Jerry, you seem really happy." And I said, "Well, I should be. I've been sitting on that [ __ ] cushion for 15 years. What was the point of it all not to be happy?" Look, I think the capacity to find joy even in this world, you know, I always say that resiliency isn't isn't the goal.

The ability to take a punch in the face is not what we should be aiming towards. The ability to not get punched in the face is what we should be aiming [laughter] for. The capa- the the capacity to withstand the world and its awful slings and arrows and still find joy and still be able to laugh and still be able to look up. We were talking before about loving the mountains. I can see the Rockies from here.

The ability to look up and despite the fact that there's no snow on the Rockies, which pains me, I can still enjoy life. To me, that is the best way to counteract this painful war on empathy, war on compassion. You know, as we used to say in Brooklyn when I was growing up, [ __ ] them if they can't take a joke. It it's it's like Oh, come on. You think you're going to you you think you're going to send me back into that cycle of self-hatred?

No way. So, you ask what what is at the other side of doing this work? Liberation. And many days I wake up and I am not liberated. And I breathe and as Sharon would teach, begin again. >> Congratulations on those sweet grand babies. >> Oh, yes. >> That's awesome. >> It is amazing. >> Yeah. >> I'm so >> I can't wait. I can't wait. I can't wait. I hope that happens for me. [laughter] If you were defining what narrative intelligence might be in writing the book, what would you say it means?

>> The the the the the fact to be able to distinguish yourself from your story. You know, in Buddhism we are uh uh really one of the things that were emphasis that is emphasized is we are not our thoughts. So, let's expand extend that. You are not your story. We run these regular boot camps and one of my coaches, one of the my colleagues who's a coach now, came to our first boot camp and I said to her, "Who would you be without the story of who you are?"

>> Mhm. >> And the reason I cite that is the result was she had to acknowledge to herself that she'd been misgendered since she was a child. That's how profound the narrative can be. And narrative intelligence is being able to realize that you have been living somebody else's story. >> Thank you, Jerry. It's been a pleasure learning from you today. >> Oh, it was a blast. I'm glad we got to do this. Thank you for inviting me.

>> Jerry's work found me years ago when I was still a tech founder and struggling in ways I did not fully understand yet. So, getting to sit with him today felt like closing a circle. One thing I'm taking from this conversation is Jerry's >> [music] >> insistence on curiosity. When we begin examining the stories that shape us, the temptation can be to turn that awareness into another reason to judge ourselves.

Why did I do that? Why did I stay? Why am I still like this? And Jerry offers a different question. What was I trying to protect? Love. Safety. Belonging. The stories that we carry often begin as intelligent responses to something we needed. And then years later, we may still be obeying them. What struck me most was the tenderness [music] in Jerry's description of what happens when we finally see that. The compassion that it requires.

We can thank the 8-year-old who'd figured out how to survive. We can recognize what the [music] story did for us. And then we can decide whether we still need it. And that feels very close to the heart [music] of narrative intelligence. Jerry defined it today as the ability to distinguish yourself from your story. You're not your story. [music] You can examine it. You can understand where it came from.

You can [music] see how you may still be reinforcing it. And you can go in and clean your closet [music] and choose what happens next. Jerry called what is on the other side of that courageous work liberation. And we never arrive there permanently. Maybe as his teacher Sharon Salzberg says, we simply >> [music] >> begin again. So, the question I'm leaving with today is what story are you still living because it once helped keep you safe?

And who might you become if you no longer had to obey it? This is 100 Stories, the Narrative Intelligence Project. If this conversation gave you something to think about, please subscribe. Share it with someone who might need it. This was a powerful episode. And I believe that narrative intelligence and coming to understand what it is can really change lives and help us live more free and as Jerry said more joyful.

Thank you for being [music] here.