#099 Wisdom from the CEO Whisperer with Jerry Colonna

#099 Wisdom from the CEO Whisperer with Jerry Colonna

"How have I been complicit in creating the conditions I say I don't want?"

Many of us find ourselves trapped in patterns we claim to hate - overworking while craving balance, tolerating bad bosses, accepting toxic work cultures.

This question cuts right to the heart of it. It's not about blame. It's about awareness. The word complicit cuts deeper than responsible, because it asks us to look inward, without self-attack.

This question comes from Jerry Colonna - former JP Morgan partner, co-founder of a top-tier VC firm with Fred Wilson, now known as the CEO Whisperer. He coaches Founders and CEOs at Etsy, SoundCloud, and Fortune 500 companies.

I've wanted this conversation for years, ever since hearing him on the Tim Ferriss podcast. When he agreed to come on How to Live, I honestly couldn’t believe it.

In our conversation, Jerry opens up about his journey from massive Wall Street success to a near-suicidal moment on a subway platform, and how radical self-inquiry saved his life.

We dive deep into self-growth, leadership, practical journaling techniques, managing the voices in your head, and why the most successful people often create their own suffering without realizing it.

If you're exploring the next frontier of growth, it might not be outside.

It might be within.

This conversation will help you start the work.

Shownotes

https://howtolive.life/episode/099-wisdom-from-the-CEO-whisperer-with-jerry-colonna

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Sharad Lal: Meet Jerry Colonna. He was a partner at JP Morgan, then co-founder of a top-tier VC firm with Fred Wilson. But despite all his external success, he was depressed inside. He had a major breakdown one day at the Wall Street subway station, almost taking his own life, but he worked through that breakdown and chose a different path. Today, he's one of the most influential executive coaches in the world, working with founders from Etsy, SoundCloud, and Gimlet Media, and also with CEOs from Fortune  companies. 

Wired Magazine calls him "the coach who makes founders cry," empowering them through vulnerability and radical self-inquiry. 

I've admired Jerry's work for years, ever since hearing him on the Tim Ferriss podcast, so I'm extremely thrilled to have him on the How to Live Podcast. We dive deep into suffering, purpose, how coming home to yourself not only transforms you as a human, but also your leadership, what journaling really means, and how to face your inner demons with courage and compassion. 

Before we jump in, thank you for making How to Live one of the top % of all podcasts globally. This is episode , and it's one of the most powerful conversations I've had on this spot. Here's Jerry Colonna. 

Sharad Lal: Hi, Jerry. Good morning. How are you doing today? 

Jerry Colonna: I'm doing very well.  Thank you. It's a beautiful morning here in Colorado. 

Sharad Lal: Welcome to the How to Live Podcast. It's a huge honor, Jerry, to have you on our show. 

Jerry Colonna: Well, the honor is all mine. Thank you for doing this. 

Sharad Lal: Jerry, I thought a good place to start is . You were externally successful, but there was internal pain. There are many folks who listen to this podcast who are in a similar place where they've done well externally, but internally something's not quite right. So I'd love to hear you talk about that time so we can take some lessons on how we should go about those times in our life. 

External Tragedy, Internal Shift: A Workable but Unsatisfying Life

Jerry Colonna: I really appreciate the way you describe it. It shows that you have your own sensitivity and your own awareness of that kind of challenge. The depression became most pronounced in , really began in , and as  unfolded, two things were going on. One was externally, the venture capital firm, Flatiron Partners, that I had co-founded with my partner Fred Wilson in , was undergoing a significant change, in part, because there was this collapse in the market known as the Dot-com bubble.  And really on September th, , there were, of course, the attacks that really devastated New York City. These things were sort of happening simultaneous with a kind of internal shift that had really begun.  And the way I often describe it is because I had struggled with depression throughout my childhood. I had a suicide attempt when I was . I had constructed this workable but not fully satisfying life, starting in my twenties and thirties. So the entirety of everything kind of collapsed right around the same time. 

After the attacks, I joined the New York City Olympic bid committee. We were trying to bring the  games to the city partially as a response to what was happening. And on the morning of February nd, I left an Olympic bid committee meeting, which was taking place downtown right close to what we refer to as Ground Zero, where the Twin Towers had been. 

A Call to Dr. Sayers Saved Me That Day

Jerry Colonna: And I walked past the smoldering pile, and I was so overwhelmed by the sense of death, destruction, despair, that it triggered my own depression or made it more manifest. And I really was confronting the suicidal ideation that sort of plagued me since I was a teenager. And I thought about going down to the Wall Street subway station and jumping in front of a train. But instead, I called my therapist, who's a nice Jewish lady named Dr. Sayers. And she said to me, "Get in a cab, come out and see me right now."  And that's what I did. And the reason I get that specific is because I want people to understand, if you are confronted with this kind of a moment, you have a choice.  And the most important thing is to understand my story. Whatever it is that you admire about me stems from making the life-giving choice that I made in that moment: get in a cab and go see Dr. Sayers. I want people to understand that as bad as it can feel, you have no idea of the positive impact that you can have if you are able to get in a cab and go see your own version of Dr. Sayers. 

Sharad Lal: Hmm. Thank you very much, Jerry, for painting that picture and that very powerful message. That is a prime example of how you can use that choice. Jerry, as you reconstructed your life, what was the process of discovering yourself and figuring out how you want to live from there on? 

The Three Books and One Life-Changing Flight

Jerry Colonna: In that session with Dr. Sayers, I said to her, "Put me in the hospital." I wanted to go into the hospital, and she said to me, "What do you want to go to the hospital for?  The food sucks. Go to Canyon Ranch," which is like a health spa.  "You'll get a massage every day and all." So I made the decision to go to Canyon Ranch, and as I was on the flight down there, I took three books with me. One was

Let Your Life Speak by Parker Palmer. Another was

When Things Fall Apart by Pema Chödrön. And the third was

Faith by Sharon Salzberg. I have become good friends with all three of those people. 

Sharad Lal: Hmm. 

Buddhism and the Most Powerful Message

Jerry Colonna: In reading When Things Fall Apart, I discovered Buddhism. It kind of opened a doorway, and the most powerful message was the first noble truth, which is that life was filled with suffering. 

Sharad Lal: Hmm. 

Jerry Colonna: When I got past that depression, that nihilism, I began to realize the universality of suffering. One of the lies that depression tells us is that you are in pain because you are broken. And I want to be really clear: you are in pain because you're human. 

Sharad Lal: Hmm. 

Jerry Colonna: And there's a profound distinction. If I'm broken, then all hope is lost. But I am in pain because I'm human, and as the Buddha taught, only humans are capable of enlightenment, then there has to be a way out. 

Sharad Lal: Hmm. 

Learning the Eightfold Path

Jerry Colonna: So what I began studying was the way out. 

Sharad Lal: Hmm. 

Jerry Colonna: Called the Eightfold Path, which is the path to ending suffering. 

Sharad Lal: Mm. 

Jerry Colonna: And I don't mean to be reductionist, or even dogmatic, but I will just tell you from my experience, when suffering comes back, and boy, is it an old friend, and it comes back regularly, but when it comes back, I can find ways to soothe my own soul, my bruised and battered soul, and come back to myself. And the last thing I'll say is the most important way to come back to myself is to be in service to others. 

Sharad Lal: Hmm. You talk about suffering brings you back home to yourself, and when you come to yourself, you go out and serve others.  What is it like coming home, coming back to yourself? What is that process like? How do you do that? 

Be Excessively Gentle With Yourself

Jerry Colonna: Well, I remember saying, in the years following the work that I'd begun, I felt like I had come home to a house that had belonged to me since I was a kid, but I had never occupied. David Whyte has a beautiful poem called

The House of Belonging. I won't quote it, it's way too long, but it's like coming home to the place that was always yours in the first place.  And how do you do it? With gentleness and kindness. You know, I'm very famous for my question,  "How have I been complicit in creating the conditions I say I don't want?" One of the reasons I use the word complicit is because I really want to push back against the notion of responsibility. So I need to parse that a little bit. When people start to do the work that's necessary to come home to themselves, a work that I might call radical self-inquiry, when people start to do that work, one of the ego defense mechanisms is to start attacking oneself.  "I suffer because I'm an idiot." Literally, that's the inner critic, right? "I'm in pain because I'm bad."  So the most important thing is to approach oneself. John O'Donohue has a quick line, which is, "To be excessively gentle with yourself." 

Coming Home to the Self

Sharad Lal: The work of coming home to oneself is provocative. It's challenging.  Why do we leave our home? And we do that to avoid guilt or shame or the criticism of others. 

Jerry Colonna: To fit in. A beautiful phrase. 

Sharad Lal: Hmm. 

Jerry Colonna: You read my second book, Reunion. The original title:

The Homecoming

Sharad Lal: Hmm. 

Jerry Colonna: So you got the sensibility that the reunion itself is maybe the most important reunion, it's a homecoming. 

Sharad Lal: That's beautiful. Many people listening would love this concept of coming home, that home that was always yours, but you'd never been to, to find that place and that safety and that comfort and that love. And you said gentleness and being compassionate with yourself is a good way to do it. How else should, at a practical level, people figure out, "Who am I? These radical self-inquiry questions. What's important to me?" 

Learn the Art of Daily Presence Practice, and Start to Cultivate That

Jerry Colonna: The reason I call it radical is because we tend not to do it.  We tend not to notice things. People who are fascinated with meditation and psychedelics and all, it can be intellectually and emotionally intimidating, but at its root, meditation is about awareness. The word Buddha means "the awakened one." Waking up to oneself, paying attention to one's own life, it can be really challenging. But what you want to do is to start to cultivate that. This is why a daily meditation practice is important. This is why a daily journaling practice is. 

Sharad Lal: Mm. 

Jerry Colonna: You listen to a lot of podcasts, and a lot of people will say, "I do meditation and I do journaling. I wear an Oura Ring." But  we have to hold onto the point of all that. When I sit on the meditation cushion, what I'm practicing is the ability to be present with you right now by being present with myself  minutes ago. I get to come onto the call and clear all the thoughts from yesterday, all of the — this is a good Yiddish word —

mishegas, craziness, and I can just be here with my friend and talk about things that matter. 

Sharad Lal: Hmm, it's beautiful.  It's like most of these practices, both meditation and you talked about journaling. It's about emptying. It's about removing this noise, and once you remove that surface noise, you're more present in life. You're present to every experience, and being in that state over a period of time starts giving you more information about yourself. So you're canceling out that external noise, increasing the internal noise, and moving towards that. Is that how the process works? 

Journaling, Story of Milarepa in Reboot, Meditation, and the Process of Mental Stillness

Jerry Colonna: The description that you began with, which is about emptying,  I think sometimes trips people up. People will say to me, "What am I supposed to journal about?" Because they're fixated on the outcome, not the starting point. So just like in meditation, sometimes when I journal, the first thing I will notice is, "How well did I sleep the night before?" So there's no emptying out when I start writing with a pen. 

Sharad Lal: Hmm. 

Jerry Colonna: Some journaling sessions, I literally write one or two sentences of every single thought that I can think of, and after about  minutes, the thoughts slow down.  When you start to journal, it is entirely human to be filled with thoughts and feelings. Don't believe that just sitting for the first moment, the noise is going to go away. 

Sharad Lal: Mm. 

Jerry Colonna: What happens is, when we pay attention to the thoughts, they disappear a little bit.  Do you know the story of Milarepa in

Reboot? The famous Buddhist teacher, the story goes that he'd spent  years meditating in a cave. And one day he leaves the cave to gather firewood, and he comes back to the cave, and the cave is filled with tiny demons. And Milarepa starts trying to push them out of the cave, but they just multiply. So then he says to them, "I will teach you the Dharma." And they quiet down, but they actually are still there.  So then he says, "What are you here to teach me?" And one by one, they start to disappear.  He's noticing them. And then finally, there's one big, hairy monster. He puts his head up to the mouth of the demon, and he says, "Eat me if you wish."  He surrenders to the worst possible thought. The monster disappears. 

Sharad Lal: Hmm. 

Jerry Colonna: The peace of mind that we're seeking only happens when we put our head up to the mouth of the demon. 

Sharad Lal: And then we can settle in and come home to ourself.  That's so beautifully described. It's a process which takes time. That's right.  Maybe to some people who don't know your style of journaling, I don't want to miss the opportunity for them to really understand how you journal, because it's extremely powerful. So if you can describe your method of journaling and if you could talk a little bit about that, that'll be very powerful to people listening. 

My Way of Journaling: Journaling as a Meditative Descent

Jerry Colonna: I feel it's a little too dogmatic to call it my method of journaling,  'cause I resist methodologies. I handwrite, and I will acknowledge that I have terrible handwriting, so I can't even read it after I write.  So the process of handwriting does something physiologically for me. And it's almost what's called automatic writing. So I don't journal the way a lot of people might, where they type in a computer classic thoughts and they might upload them to ChatGPT and ask ChatGPT to tell them what they should be. It's not for me, because for me, it's the somatic experience in the moment.  What is the first thing I write about? And I often will say, "Right now I'm feeling..." That's it. "Right now I'm feeling..." And you let the pen guide you. The first few lines tend to be very pedestrian, uninteresting. But then what's happening is you start to settle the mind down. If you're still paying attention to the mind, interesting thoughts arise, stuff that were there, but you weren't paying attention to it. 

Sharad Lal: Hmm. 

Jerry Colonna: "I notice that tightness in my chest  every time I think about the argument I had with my wife. I thought the argument was over, but it turns out that it's actually still going on inside me." "Boy, I don't want to be passive-aggressive later. So I really need to talk about this." You see what I'm doing? 

Sharad Lal: Yeah. Yeah. 

Jerry Colonna: It's kind of meditative in the sense that when we sit to meditate, we might start with just focusing on a candle flame or our breath, and then what starts to happen is things start to arise.  Tiny little demons. "I can't believe that stupid guy next door. He is, you know, playing that music and blah." And then, "Oh, I'm really, I need sleep. No, I'm working too hard. I'm really scared about money." "Oh, that's something I grew up with," and we go deeper and deeper and then we let it go. 

Sharad Lal: Hmm.  Thank you for describing it. Something additional in that method, which I found even more powerful when you spoke about it separately, you talk about having different color pens for the different voices in your head. This inner critic, maybe an optimistic voice, a nasty voice. We have all these kind of characters inside us, and when you use different pens to write it, you give that voice an outlet on paper so it doesn't come out in real life.  Did I understand that right? Because I found that again so powerful. 

Inner Dialogue and Journaling: Using Different Pens for Different Voices

Jerry Colonna: You did. And in fact, sometimes many people are familiar with what's called Parts Work,  Internal Family Systems Work developed by Dick Schwartz. This is my version of that. And by using different pens, you can actually visualize a dialogue with the different parts of yourself. In some cases, I like to change the ink color so that I can visually see the difference. I actually have been spending time with what I call the inner accuser, which is different than an inner critic.  Almost like a prosecutor who will put me on the witness stand, and I'll say, "But you did this in ." And it's like, "Whoa, where's this coming from?" And I play with it, and I listen to both sides of it. 

Sharad Lal: Hmm. 

Jerry Colonna: You're right, because by giving voice to that, you are creating space for the wholeness of you. As I wrote about in

Reboot, my first book, a lot of that, what we call the inner critic, in the book, I call it the Crow. The purpose of almost all of these voices is to make you safe. 

Sharad Lal: Hmm. 

Jerry Colonna: And you can start to create a dialogue with that voice, by creating spaces, you make friends with those voices, and the urgency with which those voices find the need to speak dials down. 

Sharad Lal: Jerry, with all this work, as you're coming home, getting to know yourself better, you're becoming a better human being. I love what you said about once you become a better human being, you become a better leader. You do better at work, and I know a lot of your work is to do with executive coaching. How do life skills come into play when you're thinking about the corporate world and being a better leader and doing better at work? 

Connecting Personal Growth, Leadership, and Emotional Maturity

Jerry Colonna: Imagine for a moment that we raise generations of children into adulthood who don't know how to deal with suffering, who don't know how to deal with the inner critic or the inner accuser.  And then we'll give them power. And what happens is they start to create toxic situations around themselves. 

Sharad Lal: Hmm. 

Jerry Colonna: I wrote about this in

Reboot.  I started with the question of what does it mean to be a better leader? I don't mean by "better leader" someone who creates the greatest possible shareholder value, the greatest return on investment, or the best revenue numbers, or the best profitability numbers. And so what does it take to be the kind of leader for whom the best people would like to work? Because what I'm interested in is coaching leaders who want to build not only fiscally successful businesses, but businesses that they would be proud to be a part of, their children came to work for them. And what that takes is being a better human. 

Sharad Lal: Hmm. 

Jerry Colonna: To use the language of

Reboot, "growing up," becoming the adult that they were born to be, means putting the head up to the mouth of the biggest demons in their life and saying, "Eat me if you wish." It means being unafraid to confront the fact that unprocessed pain and suffering from my childhood, more often than not, results in toxic behavior in my adulthood. So I have to sort the unsorted baggage of my childhood and thereby become a better human being, not only so that I can be a better leader, but so that I can have a healthier relationship with my own self, so I can come home to myself. 

It Relies on What Kind of Leader You Want to Be

Sharad Lal: That is so powerful, bringing that to the corporate world. And like you said, it's not for all leaders, but there are a fair number of leaders who are looking at this. And then your style of coaching, executive coaching, is the human in them, which then comes out in the corporate world. 

Jerry Colonna: I would say that it is for everybody, but  I am not going to assert that doing this work immediately results in a better profit and loss statement. Okay.  The question really is, what kind of leader would you like to be? What would you like your legacy to be? "He was a terrible person, but boy, he created a lot of profit." "He hurt people, but he created a lot of shareholder value." "She built an amazing machine that produced a lot of money, but she destroyed people along the way."  That's not the legacy I would like. That's the challenging question. 

Mission, Integrity, and Pitching Inner Work in a Corporate World

Sharad Lal: Jerry, I'm going to ask something for mentorship for me, as I'm starting out and I want to create my own business the way you did it.  There's always the temptation of the entrepreneur in you to just go and do work, but how do you stay true to this mission that this is the work I'm going to do? You're talking about being a better human being. How has that experience been, and how have we been true to the mission that you've tried to accomplish in the corporate world? 

Jerry Colonna: So the fear that you have is that you're going to pitch a potential client, and they're going to say, "What? This is nonsense." Tell me what that voice that you're hearing is saying to you. You know where I'm leading you? 

Sharad Lal: The voice that I'm hearing in my head, it's conflicted. There's an entrepreneurial voice that has always been an entrepreneur that's saying that, "Alright, this is what the client needs. Just give it." And there's the other voice,  "No, this is not what you set out to do." Because I want to work with people. My approach is such that I want people to be better humans and then becoming better leaders. 

The Entrepreneurial Drive and the Deep, Voice-Based Inner Dialogues

Jerry Colonna: Let's go back to what we were saying before. You have a journaling exercise you need to do, and I want one pen to be in blue and one pen to be in black ink, and I want those two voices in dialogue with each other 'cause you can feel the conflict. But now I want a third pen. 

Sharad Lal: Mm-hmm. 

Jerry Colonna: And the third pen is the voice of the client who's responding to you.  Indulge me for a moment. What is the voice of the client saying to you when you are trying to pitch and, quote, "be true to yourself?" What's their resistance? 

Sharad Lal: The resistance would be, "All this spiritual kind of stuff doesn't work here. We want to use, like, how do you actually get people to be better leaders in the corporate world? There's politics, there's all these things." That's the resistance I feel. 

Jerry Colonna: Okay. Pay attention to that voice.  What does it sound like? Who might it sound like? It's a very critical voice. 

Sharad Lal: Mm. Yeah. 

Jerry Colonna: Okay.  Have it use your name. Speak aloud. What's it saying? 

Sharad Lal: "Sharad, you're not going to be able to make it." 

Jerry Colonna: "You are not going to make it with this kind of what?" 

Sharad Lal: With this kind of approach. 

Jerry Colonna: What does that voice feel about you? 

Sharad Lal: The voice feels that I'm in a hurry as an entrepreneur to just get going. And yeah, I think I've just kind of out of the voice, just come up with something that it's like normally as I'm as an entrepreneur, and for me also, it's a journey.  A little bit like yours. I've had a moment where I was pursuing achievements, and now I'm going towards a purpose-oriented path, a more meaningful path. That old thing still keeps coming back at times. That voice wants to protect me. 

Jerry Colonna: That's right, but it's using a kind of criticism 

Sharad Lal: Hmm. 

Jerry Colonna: to protect you.  Remind you of anybody? Mom and Dad? 

Sharad Lal: Critical self. My critical self as well. 

Jerry Colonna: Right? Okay. So I love the laughter here. 

Sharad Lal: Hmm. 

Jerry Colonna: What's happening is you're giving voice to it.  So there's an entrepreneur that wants to go ahead. "Come on!" 

Sharad Lal: Hmm, hmm. 

Jerry Colonna: "We got to build this business. If the client wants you to do X, you have to do X. The client says, 'Jump,' you say, 'How high?'" 

Sharad Lal: Yes. 

Jerry Colonna: Because that voice is afraid that you're not going to be financially successful. 

Sharad Lal: Yes. 

Jerry Colonna: Then there's the other voice, "Hey, dude, we worked so hard.  We went through so much suffering. What does it profit a man to gain the world if he loses his soul in the process?" 

Sharad Lal: Yes. 

Jerry Colonna: Right? Then there's the voice of the external voice, which is, "What is this stuff that you're trying to make me conscious? I what?" And then there's this other voice, which is, "I just want you safe." Okay? So in a journaling session, you might bring all these voices together and realize that every single one of those voices 

Sharad Lal: Hmm. 

Jerry Colonna: wants you to be safe. 

Sharad Lal: Alright, I'll stop with the coaching session for a second. You ask how about,  thank you very much for that, Jerry. Thank you very much for that. 

Jerry Colonna: It's my pleasure. I appreciate your willingness to go there because I can talk about it theoretically, but when you start to experience it, you see the difference. 

Sharad Lal: %. 

The Profound Wisdom, Emotional Truth, the Buddha Nature, and Universal Humanity

Jerry Colonna: And what we just did is a kind of radical self-inquiry, is like, "What is actually happening here?"  And you sort of, all those tangled voices, we just tease them out to sort of un-knot them. Okay.  And you asked about how I do it. I have had the great luck, the great good fortune, the great privilege, especially in the last  years, of being able to stay true to what I believe. And in fact, I would argue that after

Reboot came out and it was so well received, and I wrote about this in Reunion, and so many people, in responding to my first book, said, in some form or another, "Your story is my story."  It kind of blew me away. Right? I mean, you're nodding because you read my book, and you're like, "Wait, he was in my living room when I was a kid."  Well, remember my comment before about the universality of suffering. Turns out that so much of the human experience… I mean, where did you grow up? 

Sharad Lal: I grew up in India. 

Jerry Colonna: You grew up in India.  I grew up in Brooklyn. Turns out that we were neighbors, that we're kinfolk, right?  And in some ways, we may have had the same parents. Like, what, what, how? It turns out that we're both human. 

Sharad Lal: Hmm. 

Jerry Colonna: I mentioned that in response to this, and I wrote about this extensively in

Reunion because part of what the subtitle of Reunion is, Leadership and the Longing to Belong. And I seek to answer the question, what is a leader's responsibility in a world where babies are shooting babies?  You know, India's almost at a nuclear war with Pakistan. Again, they're brothers. 

Sharad Lal: This is the world we live in. And no one has monopoly on hurting other people. 

Jerry Colonna: We're forgetting the universality of suffering. We're forgetting that you grew up in India.  I grew up in Brooklyn. We're brothers in this vast expanse. What I try to do is never lose touch with that. So if I'm talking to the CEO of a company with , employees, I remember that. 

Sharad Lal: Hmm. 

Jerry Colonna: If I'm talking to a podcast host, 

Sharad Lal: Mm. 

Jerry Colonna: who's trying to build his entrepreneurial business in Singapore, 

Sharad Lal: Mm. 

Jerry Colonna: I don't lose touch with that. Try to stay as connected to that as possible so that the human-to-human connection, which is something that I fundamentally believe in, is available to us.  Good coaching is not like consulting. Our job is not to provide the client answers. 

Sharad Lal: Yeah, that does. 

Jerry Colonna: Right?  It says, "Just tell me what to do." Our job is to create the conditions for them to figure it out on their own. In a sense, our job is to work ourselves out of a job. It's that old adage, you know, "Give a man a fish, feed him for a day; teach a man to fish, feed him for a lifetime."  Our job is to feed them for a lifetime. We do that not by providing answers, but by asking powerful questions that teach them 

Sharad Lal: Hmm. Hmm. 

Jerry Colonna: that they know how to get to the answers themselves. Right. That consistency is based on the fundamental belief that all humans are basically good. 

Sharad Lal: Hmm. 

Jerry Colonna: Which is basically Buddhism, the land of your birth. 

Sharad Lal: Yes. 

Jerry Colonna: They forget  their basic Buddha nature. They forget their basic goodness. They forget the basic goodness of the other person. 

Sharad Lal: That was beautiful, Jerry, as you were talking, that I was processing it, like you look at everyone as a human, whoever that person is, and the universal suffering that we all go through. Like you have compassion for that person, but you also think of that person as a good person, and through that, connect like you said, they're a kin, you can have a better bond and a connection with them. That's the premise of your coaching as you work with people. 

Jerry Colonna: Yes. Isn't that what the Buddha taught? 

Sharad Lal: Absolutely. Right. 

Jerry Colonna: Most wisdom traditions teach that. 

The Art of Powerful Questions

Sharad Lal: Yeah. Then about questions, you've got the most powerful question, like we talked about. One of the questions that, "How have I been complicit in the conditions that have been set for me?"  "Not responsible." How do you think of questions?  Because one of the things you're known for is the quality of questions you have. How do these questions come to you? Have you arrived at them? 

Jerry Colonna: I ask myself those questions first. So one of my other famous questions is, "What am I not saying that needs to be said?" 

Sharad Lal: Yes, that is a beautiful one. 

Jerry Colonna: And think of the universality of that. "What am I not saying that needs to be said?" 

Sharad Lal: Hmm. 

Dr. Sayers' Question That Changed Everything

Jerry Colonna: And as you know from

Reboot, that question came to me because Dr. Sayers asked me after I was hospitalized with a migraine, she said to me in exasperation, "What are you not saying that you need to say?" Because I'm not saying what I need to say, I have a migraine. 

Sharad Lal: Mm. 

Jerry Colonna: You talk about closing the gap between the unconscious and the somatic body experience. 

Sharad Lal: Mm. 

Jerry Colonna: We spent all this money and all this time measuring our bodies. We've got our Apple Watch to measure our heart rate, and it's like, what if we just slow down and paid attention? 

Sharad Lal: Mm. 

Jerry Colonna: We're measuring these things, but we're not asking the core question, which is, "How is the way I'm living my life contributing to, or impeding, my health?" 

Sharad Lal: Mm. 

Jerry Colonna: I'm about to be a grandfather in November, my daughter...  Thank you. My daughter is expecting our first grandchild, her first. 

Sharad Lal: Hmm. 

Jerry Colonna: I want to be alive to dance at my granddaughter's wedding, 

Sharad Lal: Hmm. 

Jerry Colonna: to watch her graduate college. 

Sharad Lal: "What will it take for me to take care of myself to get to that place?"  These are the kinds of things. So you ask, "How do I come up with these questions?"  I use these questions all the time. A lot of time, I use these questions in a journaling session.  "Why did I get so triggered at this person?" "Oh, he reminds me of my brother when I was  years old, and he did this and this and this." 

Jerry Colonna: "What am I doing to myself? I'm making my own suffering." 

Sharad Lal: Yeah, I just remembered another question you had, which stayed with me for a while.  "Whose approval do you crave?" I think you had a question like that. If I'm not mistaken. 

Resilience Is Withstanding What the World Stirs Within

Sharad Lal: Jerry, you also talk about resilience in a big way. What does resilience mean to you, and how do you create that in yourself? 

Jerry Colonna: I want to be very specific. I don't think about resilience as an objective. I think about resilience as a mechanism, as a means. The objective, as I often say, is equanimity, 

Sharad Lal: Mm. 

Jerry Colonna: right? Resilience is the capacity to withstand that which the world is creating inside of us.  But the objective is to withstand the world as it is. My sister once asked me, "What does equanimity mean?"  And I said, "The world is terrible, and I'm okay." "The world is great, and I'm..." 

Sharad Lal: "...I'm okay." 

Jerry Colonna: It's literally this capacity to be able to return to oneself in a calm and calming way. And resilience is the means to get there. 

Sharad Lal: Hmm. 

Jerry Colonna: And the reason I make this distinction is that sometimes we can get a little too fixated on resilience as the goal. 

Sharad Lal: Hmm. 

The Conclusion

Jerry Colonna: Jerry, as we close out, for people listening, is there any final bottom-line thoughts that you'd like to leave people with?  Be excessively gentle with yourself. The world is a really hard place, especially right now. 

Sharad Lal: Hmm. 

Jerry Colonna: We're in this strange, dark age time. Be kind to yourself and to one another.  This too shall pass. If we're lucky, we will be kinder to one another at the end of this time period. 

Sharad Lal: Thank you very much, Jerry, for so much wisdom. 

Jerry Colonna: Thank you for inviting me on the show. Thank you.