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You’re listening to Insights at the Edge. Today my guest is Jerry Colonna. Jerry is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm whose coaches and facilitators are committed to the notion that better humans make better leaders. For nearly 20 years, Jerry has used the knowledge he’s gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, equanimity, and a whole lot of heart. In this conversation with Jerry, I really felt his tremendous warmth and generosity, and the vision that he’s offering that we can define success for ourselves and be true to that in how we build organizations of aliveness, generosity, and kindness. Here’s my conversation with Jerry Colonna.
Jerry, in your book, Reboot, you share a lot of your personal story in a very vulnerable and raw way. You talk about your family upbringing, one of many children with an alcoholic father and a mother who developed a mental illness. You talk about your early suicide attempt as a teenager and being in a locked psych ward for three months. Then you continue about how you achieved early success in the magazine business and then worked as a venture capitalist in what was then the beginnings of the tech industry. The part of your story that I want to focus on is what comes next—how you achieved a level of worldly success, but then realized it wasn’t actually fulfilling you, that you felt a kind of hollowness, and how you left that world of being an investor and went through your own, shall we say, reboot, the title of your book, reboot process. What happened to you? What needed to be rebooted and how did you do that?
Jerry Colonna: Wow. Thank you for that. There was this moment in February 2002. The location of the moment is important. I was, at the time, working for JP Morgan, and at the time, running the New York City Olympic bid effort. We were trying to bring the 2012 games to New York. There was a whole lot of emotion associated with that because the 9/11 attacks had happened just a few months before. I was all bound up—in the sense that my home had been attacked. I came out of an Olympic bid committee meeting and I stood across the street from the pile, as they referred to it—Ground Zero, which was still smoldering. It all felt like it was falling apart. It felt like there was a complete charade.
In the book, I describe it as being hollow and empty. Our mutual friend, Parker Palmer, in a brilliant interview that you guys did, talked at one point about [An Undivided Life]—living a life of divided . . . where the inner and the outer were not in alignment. It was so clear that I had reached that point. It was also clear that I basically had a choice. I could follow my impulse, which was to run down to the subway station at Wall Street and leap in front of a subway train, or I could do what was the wise thing to do, which was call my therapist, Dr. Sayers. I chose the latter.
In hindsight, it was a very, very particularly challenging moment because it really felt like I could’ve chosen either way. I was at this bottom point. I chose to live. Choosing to live, when I think back on it now, and thank you for bringing me back to it, choosing to live is empowering. I slowly began to build a life that was actually more in alignment, more true, more authentic, more real, more “me” than I’d ever lived before. Yes. That was that moment.
TS: I think for many people it’s not a decisive one moment like that—either I’m going to throw myself in front of a moving vehicle or not—but it’s a gradual dawning of a sense that my life doesn’t have the richness and fulfillment that I want. These are the people, many of these people you work with in what you call these Reboot camps. I’d love, as a way of setting the stage for our listeners: What happens in a Reboot camp? Here you get people who say, “My life is somehow not . . . I know something’s off. I’m not quite sure what it is. Help me, Jerry.”
JC: Yes. What I often advise other coaches, and it’s something that I’ve learned from many of the therapists in my life, which is that the coaching process, the therapy process, the rebooting process actually begins longs before that first encounter. It begins with someone basically saying, “Enough is enough.” I often think of that St. Augustine quote, “My soul was a burden to me. It had grown weary of the man it carried.” Admitting that is a powerful first moment. What the folks who come to our camps, what happens is that even before they’re showing up, when they’re applying, when they’re reaching out and inquiring, they’ve already started a process. The process is, “It’s not working. Whatever it is that I’m carrying, whatever it is that I’m doing, it’s just not working. I need something else.”
Now, many times, they will start to take a step and then take a step back. That’s A-OK. That’s more than OK, because this is scary business. But that process of just pausing, listening to, say, a podcast conversation or listening to a recording or reading a book or something, that process can take years. I focus on that one moment, that singular moment, but the truth is, it was years in the making to get to that point. That’s when it begins.
TS: Yes.
JC: Then, at the first night, generally speaking, what they encounter is a safe container, where I often say the spinning and the delusion stops and they’re called to just look at their life as it is. I remember one person just was sitting in a circle. I remember looking and I just said something like, “Who would you be if you no longer carried the story of who you are?” He looked up at me with terror and relief all at the same time, because we don’t often talk about the fact that we walk around with the stories and persona and that sort of thing.
TS: Yes.
JC: Then it unfolds from there.
TS: I know, Jerry, in your work, that one of your areas of specialization is working with startup CEOs and business leaders. What are the special challenges that these high-achieving types bring to the process of inner discovery? I think a lot of people come to a place where they say, “Enough is enough. I’m going to leave my husband or wife or partner. I’m going to move to a different place.” But it seems like people who are these high-achieving types—running companies, big ambitions—have a particular set of inner demons, if you will, that they have to confront. I’d love to hear more about that.
JC: Yes, they do. I think it’s . . . One way to think about it is the cumulative effect of—with a kind of fragility—holding the possibility of failing at bay for most of their lives. Often times, I will start to—someone might start to laugh because I’ll say—start to describe what they’re going through. I’ll say something like, “Oh, never got less than an A before, did you?” Then they sort of startle. “Well, what’s that like?”
What happens is that it starts very, very early on in the socialization, which is, “Don’t make a mistake. Don’t make a mistake. Don’t take a misstep. There is no coming back from failure. There is no coming back from disappointment.” What starts to build up inside their minds is a kind of whispery voice that says, “You’re just one step away from the whole thing falling apart.” The more success that they have, the louder that voice gets, which then increases the anxiety and often turns that into an aggression, where they’re violent to themselves or violent to the people around them, because they cannot withstand the fragility of impermanence, or the fragility of disappointment, or, effectively, the fragility of life. Then you layer on top of all that the expectations, the burdens, taking care of all these people.
You’re an entrepreneur. You know what it’s like to worry about payroll, to worry about whether or not one of your employees is going to be able to pay their bills. That’s an awful burden.
TS: You know, quite honestly in listening to you, I’m relating not so much to the entrepreneurial burden of payroll and stuff like that, but I’m very much relating to this idea of being that type of all-star student who just doesn’t have a lot of space to make a mistake, or a misstep, and then engages in a lot of self-aggression if and when that happens. Of course it happens. We all make mistakes. The more you put yourself out there, the more likely it is you’re going to say something weird or foolish or that you regret later—the more of these broadcasts I do, et cetera.
JC: Right.
TS: When people are out there, they’re taking a lot of risks, but they have this high-achieving mentality. How do you help them be OK with all of the mistakes that happen? Of course. I’d love if you could maybe give an example of someone you’ve coached through a process like this.
JC: Sure. First of all, laying it bare, just the way you’ve described it, just the way we’ve been talking about, is often helpful because one of the self-reinforcing negative phenomena is that folks often believe that they’re the only one who has these voices in their head. Now, it’s illogical, and when you begin to speak about it, their adult brain kicks in. The adult brain says, “Well, of course.” We can describe this, but more often than not, they’re being dictated to by their childlike brain. The childlike brain says, “You’re the only one. Everybody else,” for example, “seems to have it all figured out.” I might start a talk with something like, “Who here is brave enough to admit that they’re making everything up every day?” Everybody laughs.
Once we sort of normalize it, then we start to go a little bit deeper. I start to ask questions about the roots of that belief system. What was it like? How was failure continent in the family structure? At what point in a child’s life do we start to internalize these messages? Whose messages are they? Whose failure are we so worried about? Then, if they are in a relationship of some sort, of if they’re a parent, I might do a little dirty trick where I say, “How would you like your child to feel about themselves if they made a mistake?” Then, all of a sudden, compassion opens up. I suggest to them if they would like their child to feel otherwise about themselves, then they need to start to model that for themselves.
I find that trying to cultivate empathy and compassion for ourselves is really, really hard. When we can do a little mental trick and say, “I’m cultivating compassion for myself to be a benefit to other people,” well, then that starts to break down some of those barriers.
TS: Jerry, just in this conversation with you, I feel your warmth and your openheartedness. I can hear it in the sound of your voice. I know in your own personal story you’ve done a lot of work to be able to embrace yourself in such a way, with the kind of warmth that I can hear, that you help your clients develop toward themselves. Help me understand your own process of accepting failure—your own mistakes—how you came through that to where you are now.
JC: Well, thank you first of all for hearing that. It is a daily struggle. It’s a daily practice. I’ll tell you a different story in response to what you’ve asked. Just the other day, I had to give a talk—one of these Ted-like talks where you step out into that red circle and there’s a big spotlight. I was a wreck. Two or three days beforehand I couldn’t sleep. It’s one thing to talk in front of a bunch of people for 45 minutes or something like that. I can meditate beforehand. I can do all sorts of things that will sort of calm me, but to give me 10 minutes, that’s enormously different. How am I going to make a point that has some relevance? All of these stories were just spinning in my head.
Just before I had to go out on stage, when I was at my most nervous, I was at the hotel and I ran into somebody outside of the ballroom. He stops me and he’s very timid. He says, “Are you Jerry Colonna?” It’s like, “Uh, yes I am.” He says, “Oh my. I was so excited to see you. Unfortunately I’m not going to be able to come to your workshop this afternoon because I had a secondary workshop later on in the day.” I said, “Oh, don’t worry about it.” He says, “It sold out.” I said, “Well, if you’re willing to sit on the floor, you just come in anyway. Don’t worry about it.”
As I walked away, I realized that he was excited because I had somehow touched him in the work I had done. Just before going out into that incredible, charnel ground of “dun dun dun!”—all this noise and the lights and the glare and “I’m supposed to perform” and “I’d better not fail” and “Oh my God, the book’s going to be a failure, my whole life is going to fall apart,” I just paused and I thought of this young man. The only thing that matters is that heart that sits there. When I spoke, I spoke to him. To go back to your root question, which was the process, I’ve done a half dozen different forms of therapy over my life. I have sat with and trained with many, many different teachers. I have read hundreds of books from various wisdom traditions. Every single person says the same thing. The only way to be with the pain that we have is to open your heart to others’ suffering. That’s it. That’s the hardest thing in the world, but it’s the only thing that I think gets us through.
I remember one time seeing Ani Pema and lamenting my life and talking about the pain and suffering of my childhood and the ways in which I had been abused in different forms. She was with me compassionately, but she challenged me to think of the millions of children—past, present, and this is heartbreaking, the future—who have [suffered] and will suffer. Not to make myself smaller in comparison, but to feel the humanity, the universality of “we all go through this,” this being human. Being human is hard. Therefore, it’s glorious.
TS: There’s a quote from Reboot, “Better humans are better leaders.”
JC: Yes.
TS: In a way, I had a little chuckle when I read this because I thought, “Well, of course. Do we want a leader that’s not a decent or reasonable human being? Of course a better human would be a better leader.” It’s interesting that you even need to write or . . . What’s happened—I’d love to hear your views on this—in contemporary leadership that it’s trained out the humanity in us?
JC: Well, I don’t think it’s conscientious or consciously trained out, but I think it’s de-emphasized. Of course, that’s part of the reason why I play with that term. Its simplicity is designed to get people to say, “Well, of course.” Then, of course, the follow-on question is, “So then why do we have such trouble with leadership? Why are our political institutions led so poorly? Why are our corporate institutions led so poorly? What is going on?” The only thing that I can come to is this: being human is hard. This being a better human is really difficult. It’s so difficult, in fact, that I think people seek shelter in the doing of being a human, rather than the being. Then you look at business schools or you look at leadership training schools and you get this emphasis on practical skills. You get this emphasis on technique and not this emphasis on presence. What’s lost is the heart—all at the altar of the prefrontal cortex and outcome and output and efficiency. Then, the art of being in community is lost.
TS: One of the ways that you help people move into their interior life is through something that you call self-inquiry and asking self-inquiry questions. Help our listeners understand how you approach self-inquiry, how you teach it.
JC: Yes. Here again, I try to play with words. I actually describe it as radical self-inquiry. That’s a little bit designed to poke fun at it. It’s radical because we don’t do it; it’s rare. For example. A little tactic I will use is I will ask somebody to consider how they really are. Alright. I’ll take a phrase that we often use. You and I meet each other on the street and I say, “Oh, how are you?” Your first response tends to be a bit of a persona. “I’m busy. I’m fine. I’m this. I’m that. I’m off to this.” No. No. No. No. No. No. No. Stop. Slow down. Pay attention. Notice your heart. Notice your breathing. What was your morning like? Did you sleep well last night? Just simple little tactics to sort of bring it down.
Then, to go a little bit deeper, to ask myself questions like, “What do I believe to be true about the world?” For example, if I believe it’s a dog-eat-dog world, then I will tend toward a self-optimization. I will build a company or an organization or a community that takes care of itself first. If I believe that human beings are basically, fundamentally good, and that they’re just obstructed and obscured in their ability to live that way, then I will seek to find common ground. All my actions will flow from one of those two choices.
How do I define success? How do I define failure? What is it that I’m aiming to become, because we’re all always in a process of becoming? When you started off and you noted that you were feeling some sense of presence and heart that I had, well, I was glad, because that’s what I aim to be every single day of my life. I know that I fail every single day of my life, but I also know that my life is better. I believe that our lives are better when we aim to do things like that. That’s a fundamental belief system that I carry. That’s what I’m really reaching for with this notion of self-inquiry. It’s a way in which all of those persona, all of those stories, all of those delusions that we carry about ourselves are kind of stripped away. With love and compassion, we’re just sort of staring at us. Who are we and what do we believe about the world? What makes my heart go pitter-patter?
TS: You brought up an interesting radical self-inquiry question, “How do you define success?” Let’s take a moment. How do you define success, Jerry, at this point?
JC: Have I been kind? Have I been kind to myself? Have I been kind to others? I told that story about that man who stopped me at the hotel before I went onstage. Part of the reason that made such a difference to me was that I knew that his having listened to some of my podcasts had eased his heart. What a gift. It’s a gift to be kind.
TS: Yes.
JC: I’ll just note that.
TS: Let’s talk to that person who’s listening who says, “Truth be told, there’s a gap between how I’m living my life and what I really think a true definition of success would be. I’m living my life over-working, over-giving. I feel under financial pressure . . .” whatever it might be.
JC: Whatever stories . . .
TS: Yes, but hey Jerry, these stories are real.
JC: Yep.
TS: “I’m under real pressure, real external pressure.”
JC: Yep.
TS: My real definition of success might be taking time to walk in the woods and kayak and spend more time with my kids, but I’m under external pressure. There’s this gap here. What would you say to someone who reports that to you?
JC: Well, there are two steps to be aware of. The first is that when we pause, when we stand still, when we sit still and start to pay attention, one of the things that I have noticed happens is that another set of self-criticizing, self-critical voices come up. Those voices tend to say, “Look at how terribly you’re living your life. Look at what’s wrong with you.” Or, they might say something like, “Oh, how self-indulgent is it to try to define success as being able to kayak every day or be home?” All these other confusing voices come up, perhaps. That’s step one.
The second step is the most important step. The second step is to understand that the reason we have persistently lived a life out of alignment with who we truly are, and the reason that all of those self-critical voices exist—the reason is kind of surprising and perverse. They’re there. Those choices are made to keep us safe. They’re actually coming from a place of love. The voice that says, “It’s self-indulgent to pause and look at your life and to design your life in such a way that you have hours each day for loafing,” well, it’s probably trying to protect you from being humiliated for being found out or called lazy.
There are all sorts of these structures that sort of form early on to keep you safe, to protect you. The third step is to then love those voices, is to love that part of you that is trying to keep you safe, even if it’s doing it in a way that is painful. The magic moment is to turn around and say, “Thank you, but I actually don’t need you to tell me that anymore because I’m an adult and I’m safe. I know how to love. I know how to belong. If you could just stand down, I got this.” That’s the maneuver I always recommend.
TS: Jerry, what if the person still feels a gap of some kind between their deep inner values and the structure of their life and they say it’s because the structure of their life is—by X, Y, Z necessity—coming from the outside?
JC: Well, oftentimes there are necessities. We do need food, shelter, clothing. We need to take care of our physical expressions. Oftentimes, there’s an over-the-top adherence to the implicit threat to those things that may be operating. Another good move at that point is to ask oneself, “How has that belief system been useful to me?”
For example, one of the things that I carried was the belief that I had to have a certain amount of money to feel safe. Now, again, logically, there is a certain amount because we live in a particularly capitalist kind of society. There is a certain amount that one needs to be whole in one’s body. That is a truth. Inescapable. The attachment to it was much greater. It was out of proportion to the reality, to the logical reality. We kind of know that. We operate it and we feel it. It goes down to, “Well, I need this.” We look at that structure and we turn it around to ourselves. We say, “Well, how has my belief that that is true served me?” In my case, the belief served me and got me out of Brooklyn, where I was born. It did create a certain amount of physical well-being and safety, not only for myself, but for those I love.
“How has it impeded me?” Because it has also impeded me. That’s that kind of radical piece of this is to turn around and say, “Well, wait a minute. There’s a superpower implicit in that belief system,” but as Marvel comics like to teach us, every superpower has a negative dark side, especially when it’s inappropriately applied.
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TS: One of the images that you introduce in Reboot, in the book, is this image of the leader as an open-hearted warrior. Talk to me some about the warrior qualities that you think are needed here.
JC: Sure. I learned that image from my lineage, from my Buddhist lineage. We often speak about the warrior stance. The warrior stance, to be clear, is an open heart, but a strong back. When I first heard that imagery, I immediately applied it to business because it makes so much sense to me. From where I sit, I think that the strong back of that warrior leader is someone who can hold fast to values, hold fast to integrity, and also understand that things like clarity in organizational structure is incredible important because it calms the nervous system of people who have to operate within that. “Oh, I know what success is. I know what failure is. I know what my job is.”
Another aspect of that is a kind of fiscal discipline. I make a dollar, I don’t spend more than a dollar. There’s a strength in being able to do that. Oftentimes, that strong back is not coupled with an open heart. You can see kind of stultifying, fear-driven, closed environment that’s going on. That’s partially because to keep your heart open as a leader means to subject yourself to the projections of those who ask you to lead them. You become their parent. You become their disapproving or approving parent. You become every past poor leader that they’ve ever had. You become every potential great leader that they could be. You become a role model.
To hold your heart open means that you will suffer in many ways, but of course, you’ll also feel joy. You’ll feel happiness. You’ll feel love. Another way to think about this is I often will put a coffee cup or something in front of a client. I will say, “It’s like this. The mug is the container. A container without content is meaningless. Content without the container is useless.” You actually need both. We need both the strong back and the open heart as adults, and we absolutely need that as leaders. Even best of all is when our organizations and our communities can hold that. Then that means, if we take it to the community for example, then the well-being of all the participants is cared for. The physical well-being is cared for. Then the existential/spiritual well-being is also cared for. Both are taken of. That, to me, is the highest expression of adulthood.
TS: I love this image of the open heart and the strong back. I totally love it, and yet I imagine someone listening said, “OK, a strong back. I’m a leader. I’m with you, Jerry. Check. Open heart, I want that, too.” Then you said you’re going to have to suffer, feel suffering. That’s where I imagined someone saying, “Uh, can’t I be an open-hearted, strong-back warrior leader without suffering. I want to be a happy leader, a positive leader.”
JC: Yes. We don’t get to cherry pick emotions and experiences, do we? If you’d like to feel joy, you have to be willing to feel pain. It’s really that simple. I think the choice is: numb or not. That’s it. Unfortunately, we’re so afraid of suffering that we choose to numb. There are a bazillion ways in which we numb, but the opportunity to feel it all . . . What did John Cabot say? He called it the “full catastrophe living.” It’s just like everything. Bring it on.
TS: I can imagine in your work with people in leadership roles that consciously feeling that suffering that comes with the open heart is really a part of your—a deep part of your coaching work. Because I don’t think, especially in our sunshine-y culture, that that’s often what we think we’re supposed to be as leaders. We’re supposed to be the optimistic one, the positive one, the one who’s always shining the bright light of the possibilities.
JC: Yes. What comes to mind is something Parker Palmer says in Let Your Life Speak. He talks about leading from within in one of the chapters in that book. He talks about what he calls “functional atheism”—when the leader puts themselves in a position where they’re supposed to always fill in the blank: have the answers, be optimistic, be the eternal source of sunshine and brightness and answers. The truth is that nothing could be further from the truth. When somebody who holds positional power, structural power, role power, holds that false view of themselves, it actually has an unintended negative consequence throughout the entire organization. It instills distrust, because everybody knows when they’re faking it. Everybody around them knows that they’re gritting their teeth and saying, “I’m fine,” and they’re not.
In the book, I tell this story of going to a movie with my youngest son, Michael, who yesterday turned 22. In the story, he was about 13, 14 years old. The movie itself was very upsetting. It provoked childhood memories. I was surprised. I was so surprised that I broke down into tears. I was just bawling. I couldn’t move. Michael sat next to me. Now, understand this. Dad and his son—and dad is just a blubbering mess. He sat with me. You could feel it. He was confused and scared. Then he said one of the most magical things anyone has ever said to me. He said, “Dad, you might as well tell me what’s going on.” Because I was going to protect him; I wasn’t going to tell him what’s going on. He said, “Dad, you might as well tell me what’s going on, because if not I’m going to make shit up and it’s going to be negative about me.”
The brilliance of that assertion—because when I think that the leader is walking around pretending to only see sunshine, pretending to only be positive so they are some sort of source of never-ending happiness, they’re not really telling people what’s going on. In that distrust and in that gap and in that dissonance, people are going to make shit up. What they’re going to make up is going to be negative, usually about them.
I’m not suggesting that the leaders should walk around and say, “I’m a mess. I’m filled with anxiety. I don’t know what to do.” Because that’s projecting all of your stuff onto other people and asking them to solve it. To calmly, self-soothingly acknowledge that you don’t have an answer, that today’s a hard day, that you’re scared, that last night you hadn’t slept, to acknowledge all of those things creates the space to be met by another human being. Isn’t that wonderful?
TS: I’m glad, Jerry, that you brought up a sobbing incident and this idea of the power of tears to . . . it’s really part, in a way, of the warrior leader pose of having an open heart, at least in my experience. As I was reading Reboot—and there were a couple of instances where you shared tears in your own life, including this sobbing incident with your son—I remembered the time when I met you. It must’ve been, I don’t know, 10-ish years ago when we were in a car together. I don’t know if you remember this, but at one point, and I can’t remember what we were talking about, but your eyes welled up. I think a tear might’ve even dropped out. I was like, “Oh my god. I’m in a car with this high-powered investment guy and I think he just shed a tear.” I almost fell off the seat, the backseat. I couldn’t believe it. It was so inspiring to me, actually, that people could be in such high-powered positions and also be tender-hearted.
JC: Well, first of all, thank you for remembering that. I remember it. It means a lot to me that you remember that. Part of the dissonance that I experienced that led me to walk away from my experience as a venture capitalist was—in the year or two previous to that famous incident outside of Ground Zero that I was describing before—was that I was, for years, working with, in a relationship with depression. I would go to my office at J.P. Morgan and I would pass the desk of my colleague, Carrie Rackland, who remains to this day a really dear and close friend. She’s a soul sister. She’d look up at me and she’d say, “Bad day, Jerr?” I’d say, “Bad day.” She’d say, “OK. I’ll cancel your meetings.”
I would go into my office and I would close the blinds and I would cry. I would hide and no one knew except Carrie. That was part of the suffering, the needless suffering that I would put upon myself, because I would tell myself that I had to put this false front on, that I had to change the experience that I was having, and that I had to cherry pick, as I was saying before. Cherry pick. I’m only going to have positive experiences. In effect, I was saying to myself, “To survive, to make it through, to get through, please stop being a human being. Oh, and by the way, don’t feel pain because you’ve put yourself into that box.” Well, that’s absurd.
Now, fully feeling my feelings is so a part of who I am that I don’t even notice sometimes. Even in our conversation, I’ve teared up. I’ve welled up. I’ve thought of this person. I’ve thought of that person. I’ve felt joy. I’ve felt laughter. For me, this is the definition of aliveness. You asked before, “What’s the definition of success?” I said, “Kindness.” Here’s another one: alive, full—the whole megillah.
TS: One of the things I’m reflecting on is how our corporate cultures don’t really invite the kind of aliveness that you’re describing. Here, in the spirit of the vulnerability of our conversation and the truth telling, to share that this year my 93-year-old mother transitioned out of her body. Leading up to that process, I felt like I had maybe 25% of my normal energy for creativity and productivity. I was really in a deep inner space. You mentioned your analyst and now I’m going to bring up my therapist—and we’re going to talk more about your analyst in a moment, Dr. Sayers, because you share some great teachings you received from her.
Anyway, I said to my therapist, I said, “How do people do it? Here I work with 120 people at Sounds True. I know many of them have had parents and grandparents die. How did they make it through the workday like this?” “Just like you are, Tami. They’re at 25 percent their capacity, but you don’t know it.” I thought, oh my gosh. All of these people are coming to work not really being comfortable saying, “I’m only at 25 percent of my normal capacity, and guess what? It’s lasting for more than the three days off I was given for my grievance allowance. It’s going on for months. This is a really deep process I’m in.”
JC: Right.
TS: The question that comes from that is if we want to create corporate cultures, organizational environments, that actually welcome our full aliveness and full feeling, we have a long way to go. What are we going to do to go from where we are to a place like that?
JC: Well, the wisdom of our friend Parker comes to mind again. He often says that violence is what we do when we don’t know what to do with our suffering. First of all, I want to just acknowledge your suffering.
TS: Yes. Thank you.
JC: I have been in those experiences that you just described. Yes, at any given moment, some percentage—10, 20, 30 percent—of the people you encounter every single day are carrying a broken heart. Every day. Every day. If it’s not ourselves, the people we encounter have a broken heart, but we don’t have systems that allow the recognition or acknowledgement of that. The thing that always strikes me is when I—I live in these worlds, these intersectional worlds where I’ve got this Buddhist side of me, I’ve got this technology/company side of me. I’m this. I’m that. I’m all in these different places.
Almost always, when I am working with folks who might define themselves in a more spiritual context, they look at me a little scant and say, “Well, those corporations, they’re awful.” I want to bring their attention to the fact that because we don’t know what to do with our suffering in our systems, our organizational systems, our organizations then perpetuate violence: violence to the planet, violence to the community, violence to ourselves. I’m reminded of something that happened. I was a guest on a documentary that CNN produced. It was on mental health in the technology industry in Silicon Valley. There was this moment where—it was a really intense encounter I had with the correspondent, Lori Siegel. She was in tears because we were just feeling her feelings right there.
Anyway, a few weeks later I got a phone call from the head of HR at a very large software company who asked me to come speak to the senior team. When I probed and I asked why, she said that health care claims for depression and anxiety among the children of their senior executives had gone up 70 percent in the previous two years. The children, they didn’t volunteer for this. They didn’t sign up for that. Because that organization at that point didn’t know what to do with the inherent suffering that comes from being humans in organizations. There was a violence that was being perpetuated down to their children, simply because the bereavement policy calls for three days of grief. What fucking nonsense. Excuse my language.
TS: It’s alright.
JC: We’re better than that. The Buddha taught: we are the sentient beings capable of enlightenment. Holy mackerel. We’re better than this. Can I hold your heart because your heart is broken because your mom has transitioned to another phase of life? Isn’t that more important? I don’t know any wisdom tradition, and you folks at Sounds True, you know all the wisdom traditions, I don’t know any wisdom tradition that says, “Grief, yes, get over it. Be done. There’s work to be done.”
TS: Now, Jerry, let’s say someone’s listening and they’re like, “I want to create a culture where I work,” whether they’re in a senior leadership position or another position of influence, “that welcomes real feeling and the aliveness that comes with that.” Where do you think their point of power is to do that?
JC: With themselves first. With themselves first. I recognize structural power. I recognize, too, that I identify as male. I identify as white. I’m cisgendered. That creates all sorts of opportunities for the things I’m talking about that are not available to every single person, however they identify. That gives me certain kinds of access to experiences that are just not available. To recognize, first of all, that that is a truth is important.
There is an opportunity to look at our own experience and our own relationship first and ask: How am I leading my life? How am I living my life? How am I responding to the inevitable ways in which I disappoint myself or do not live up to the aspirational goals that I carry? What am I working with, with regard to that? Then, in those moments of encounter in which I might have temporary power, I might have temporary agency to change culture, what can I do to lean into that place?
We were talking before about questions to ask. I often will ask folks that I work with, “What kind of organization do you want to work for?” Because you co-create that every single day of your life, from something as simple to—if you work for a large corporation and some percentage of the staff might even be contract employees because they’re emptying wastebaskets, how do you greet them? Do you look somebody in the eye? When you hop into a cab, or I guess an Uber, or whatever, do you ask a genuine, “How are you?” Do you listen?
You asked about the company, but I would expand it and say, “What kind of experience do you want to have every day?” Every single human encounter is an opportunity to practice. Every single one, including the one you have with yourself every single day.
TS: Now, I mentioned that I wanted to speak more about Dr. Sayers, the analyst that you write about in Reboot. You tell a lot of great wisdom teaching stories that involve Dr. Sayers, how much you learned from your work with her. The part that really got my attention was when you were writing about the migraines that you were experiencing. You were unclear what the cause was, and how she helped you identify three questions that could unearth what was going on underneath these migraines. I wonder if you can share those three questions with our audience.
JC: Sure. Thank you for bringing Dr. Sayers back into my heart right now. For context, she is . . . I worked with her for 27 years. Shout out to her. She’s a true boddhisattva. She grew up in Brooklyn. Nice Jewish lady from Great Neck, Long Island who could call me on my bullshit faster than anything else, including the self-denigration and things that I would sort of put myself through.
What you’re referring to is this moment when I was sort of struck down by this overwhelming migraine/cluster headache that actually sent me into the hospital. I had grown up with migraines. The breakthrough question, the first question she taught me, she asked me was, “What are you not saying that you need to say?” I turned that into, “What am I not saying that I need to say?” That’s a powerful question. “What am I not saying that I need to say?” Here again is another instance in which we tend not to pay attention. We know that we’re not saying something that needs to be said. We just don’t acknowledge it. In my case, I somaticized tension that would arise from that.
Then that led to two corollary questions, which is, “What am I saying that’s not being heard?” Which I think is a tremendous source of suffering. It’s important to recognize that we often say things without words. We might be saying something with actions. Then, equally important because it’s empowering, not because it’s designed to produce guilt, “What’s being said that I’m not hearing?” Because the people around us speak to us all the time. Sometimes they speak to us with just a look, with a raised eyebrow, with a wince, with a felt sense, a whisper. Sometimes they actually talk to us and we choose not to hear what they’re saying, or to take it in.
If we have positional power in any structure, and we are doing it—we could be a parent not listening to our child, we could be a partner not listening to our life partner, we could not be listening to ourselves—to the point where our bodies actually have to grab our attention by somatically sending us an unmistakable message, like a headache that throws you on the ground and says, “Pay attention. I am in pain. If you no longer pay attention to me, I will grab your heart and I will throw you to the ground and I will make you wake up.” That’s what Dr. Sayers from Brooklyn taught me, among many things.
TS: Those are three powerful questions. There’s another powerful question that you bring up in Reboot that I think will help me a lot. It already has. I can complain about different things, different people, different things that are happening at Sounds True. You have this great question. “How am I complicit in creating the conditions I say I don’t want?”
JC: Yes.
TS: That’s a question I just . . . I think I’m going to have to . . . I don’t know where I look every day, put that on my watch or something like that.
JC: Yes. It’s a fun question. First of all, I’ll break it down a little bit. It’s really important not to use that question to evoke guilt and more self-criticism. It’s really designed for good discernment, clear seeing. I’m going to go back and break down the question. I choose the word complicit, not responsible—50, 60 percent of the times that I first say that question people will hear the word, “How am I responsible?” I actually think that’s another ego trick, because the ego wants to either be completely unresponsible for the conditions of our lives, or totally responsible. The truth is, it’s neither. “How am I complicit in going along with the things that are happening in my life?” I think that’s a really important question.
Then, the second half that I think is equally important is this notion of, “I say I don’t want this, and yet situations, conditions persist. What’s up with that?” I’ll often make somebody laugh and I’ll say, “You ever date the same person three or four times even though the meatbag of who they are changes? What’s up?” It goes to the heart of something I was saying before—oftentimes the conditions repeat themselves in our lives. The conditions in our lives repeat themselves because they’re serving some sort of hidden purpose. It’s not like Groundhog Day—there’s a lesson. Sometimes there’s a lesson, but it’s because there’s a system that needs to be maintained. My partner, Khalid Halim, likes to say that the conditions we survived as children become the conditions necessary to our survival as adults. I’ll say that again. The conditions we survive as children become the conditions necessary to our survival as adults.
For example, in order to feel safe, I may need to feel financially threatened, because I grew up in a family where that was the norm. If I don’t feel financially threatened, I feel out of sorts. I feel really confused. I feel like I may not belong. Just when I get everything settled and I’ve paid all my bills, I go out and overspend, thus being complicit and creating conditions I say I don’t want. When we explore that, we get to unpack some really juicy tidbits about how are we actually organized. Or, we start to make conscious the parts of ourselves that it has served us to be unconscious to. Then we get to choose. What kind of adult do I want to be?
TS: I love the question, Jerry. There’s something about this word complicit. I don’t hear it as responsible. I hear it as even a small amount, I’m definitely contributing to this and there’s something I could do about it. How am I? Oh, OK. I feel like it really opens up a creative response. I’m very grateful to you for the question.
JC: Oh, thank you. Yes. Yes. There’s agency in that word, isn’t there?
TS: Yes. Exactly.
JC: You have power. You can do something about this. You can choose not to be complicit.
TS: I have one final question for you, Jerry, which is . . . Someone’s listening and they’re inspired: strong back, open heart. This is the kind of leader I want to be, but there aren’t that many examples in our culture of people who have done this successfully, run big companies. When I think of the leaders, they’re people whose hearts seem, I don’t know, a little armored. Strong back, yes. Do you believe, truly, that this is a recipe for success for future leaders?
JC: How do you define success? If we define success as aliveness and kindness, then the answer is yes. If you define success as becoming an adult, as using the process to become an adult, then the answer is yes. I find it curious that people need to see a model of someone who has done this to be assured that it is possible. I understand it, but I don’t know that that’s necessary.
I think that we can imagine a world in which leadership is like this. As long as we can imagine that, then we can move toward it—as long as we’re willing to forgive ourselves when we fail, because we will. I’d rather live in a world in which people who have power are moving toward that kind of experience than not bothering at all.
TS: There was a section in the book where you share a lesson that you learned from your co-founder at Reboot, Ali Schultz, and it’s about the wisdom of horses. You write, “Horses do not base their choice of the leader of their herd on strength or intellectual wisdom, nor is the choice based on which member might keep the herd safe from a predator wolf. They choose the one who feels the group best and who cares the most.” I thought, that’s really interesting. What if we chose our leaders, whether they’re political leaders or organizational leaders . . . Quite honestly, Jerry, it inspired me to be one of those people who feels the group best and who cares the most. I thought, I don’t spend enough of my attention on that, “feels the group best and cares the most.” We can learn from horses.
JC: We can learn from horses. Ali is the one who taught me that we can learn from horses. When we work with leaders, and Ali does this better than anyone I’ve ever encountered, when she lets people feel their horse body, as she calls it—and it’s important to understand that a horse is almost this magnified limbic nervous system—it just feels the world somatically and it can sense another horse’s emotions, or another mammal’s emotions just by standing next to them. When we allow that part of our mammalian structure to connect with one another, then we can move in a sense of belonging and safety that I would define as love. What if your organization was a source of love? Yeah. Yeah. Yeah. What if we defined success is that, at the end of the day, the people with whom I work may be tired, but felt better about themselves than they did at the beginning of the day?
TS: Jerry Colonna, I’ve loved talking with you.
JC: Oh, we’ll I’ve adored talking with you, Tami.
TS: What a successful conversation we’ve had.
JC: Kind and caring. That’s right.
TS: I’ve been speaking with Jerry Colonna. He’s the author of the new book, Reboot: Leadership and the Art of Growing Up. What a mensch and kind human you are, Jerry. I’ve really enjoyed talking to you.
JC: Thank you.
TS: Thank you so much.
JC: Thank you. Tami, let me just say, thank you for reading the book so closely. It means a lot to me.
TS: Thank you for listening to Insights at the Edge. You can read a full transcript of today’s interview at soundstrue.com/podcast. If you’re interested, hit the subscribe button in your podcast app. Also, if you feel inspired, head to iTunes and leave Insights at the Edge a review. I love getting your feedback, being in connection with you, and learning how we can continue to evolve and improve our program. Working together, I believe we can create a kinder and wiser world. SoundsTrue.com: waking up the world.
