Ten Percent Happier with Dan Harris - Deep, Provocative Success Strategies From the “Yoda of Silicon Valley” | Jerry Colonna

Episode Date: November 15, 2023

How getting your sh*t together can make you a better leader in your own personal orbit. It can maybe even change the world.Jerry Colonna is a leading executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. He is a co-founder and CEO of Reboot, the executive coaching and leadership development company, host of the Reboot Podcast, and author of Reunion: Leadership and the Longing to Belong, and Reboot: Leadership and the Art of Growing Up. In this episode we talk about:How to avoid the pitfalls of virtue signaling and self-righteousnessThe term, “reunion” and how it relates to the stories of our ancestors What he means by, “the longing to belong”How we can learn to “do our first works over”The difference between equality and equity And his framing of, "content and container" to help guide good leadershipRelated Episodes:Jerry Colonna, 'CEO Whisperer' and Reboot.io FounderThe Art of Growing Up, Jerry ColonnaFull Shownotes: https://www.tenpercent.com/tph/podcast-episode/jerry-colonnaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This is the 10% happier podcast. I'm Dan Harris. Hello, my fellow suffering beings. Today, we've got some deep and maybe for some of you, rather provocative success strategies from the man who's been called the Yoda of Silicon Valley. Jerry Kallona as a former venture capitalist, turned, practicing Buddhist, turned, leading executive coach, his co-founder and CEO of an executive coaching firm called Reboot, where I'm a long time client. Jerry's also a friend of mine and a repeat guest on this show. He's out with a new book called Reunion Leadership and the longing to belong to be super clear right from the jump.

Jerry has a very broad view of leadership. So you don't have to be a boss to benefit from his advice, whatever professional role you play, or even if you don't work and are a parent or a volunteer wherever you're coming from, you do have a sphere of influence. And if you don't get your shit together, Jerry's argument is that you're going to pass your pathology, your ancient tramas, your ancient storylines, along to everybody else in your orbit. Jerry calls his process radical self inquiry, and it's made a huge difference for me. One of his signature questions has long been, and I love this, although it's been painful to mull it, but I love it anyway.

How are you complicit in the conditions you say you don't want? It's really such a compelling question, and it's not about victim blaming. It's about taking a look at whether you're contributing to the stuff you're complaining about. And if you're really wrestle with it, you might not like what you see. As the old saying goes, self-knowledge is always bad news.

Jerry's new book is all about adding a new and broader question on top of that. Already pretty tough and touchy one. The new question is, how have I been complicit in and benefited from the conditions in the world that I say I don't want? In other words, Jerry's now arguing that it is not enough for us to just get our shit together, but that we also have a responsibility to address the problems in the larger world. Jerry freely admits his new thesis, made draw some criticism, and that his suggested remedies are also quite experimental.

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Jerry Colona, welcome to the show. Thanks Dan, thanks for having me. Pleasure to have you. Congratulations on your new book. Thank you. You know, book is always a labor. And this was really a labor of love. Yeah. This was a hard one.

Yeah. But it feels really important for me. Well we're getting to it. Before we get into it, let's just lay some groundwork or level set for people who might not know much about your work. I'll put links in the show notes to your previous appearances, but in case people haven't had a chance to digest that. Let's just start with some definitional things.

You talk about leadership. Does that include everybody or am I only in the target audience if I'm a boss? Oh, it definitely includes everybody. By including everybody, it's a subtle way of taking our standard definitions of leadership that is association with power and helping people realize that we each have the possibility of leading. And what does that mean? It means being able to affect those around us in some capacity. And even at a minimum, we have the possibility of leading ourselves. And that's a very broad definition. But thanks for that. This is not just for CEOs. Right. This is good to get that out there. Right at the jump. I'm not a CEO and I've found

your work to be incredibly helpful. So let's talk about some of the, and again, before we dive into the new book, because the new book really builds on your prior work, including your last book, what is radical self inquiry? Yeah, that's a sort of catchphrase I developed to describe in some ways. Well, maybe because of this audience, they'll get it. The kind of overlap between deep psychological understanding of oneself, but also the insight that comes from a dedicated practice, sometimes showing up as meditation. The working definition I play with is the process by which the mass that we wear are slowly and compassionately stripped away so that we have no place left to hide. And I focus on the radical piece of the self-inquiry process simply because we tend not to do it. We tend to wear a persona and whereas yet we tend to believe that persona.

And then we get into a lot of trouble. Yeah, I know people who do that. Yeah. Yeah. Yeah. So how do you do radical self-angry if you're not a Jerry Kalona client? Well, there are simple questions that I often encourage people

to ask of themselves. My most famous question, the one that almost invariably provokes tears, is simply to ask somebody how they are. And what I always add as a caveat is, no, really, like, stop bullshitting, stop spinning, stop telling me what you think I want to know. Stop telling me what you tell yourself, but just pause and take a look at yourself. That's emblematic of a process. Yes. If we think about what happens on a meditation cushion, meditation in effect is an act of inquiry.

I'm noticing stuff. I'm noticing what's happening. I'm not becoming attached to that which I see, but I'm noticing stuff. I'm noticing what's happening. I'm not becoming attached to that which I see, but I'm noticing it. I'm not looking away. So shame arises. I look at it. Guilt arises. I look at it. I have a negative thought. I look at it. And then imagine carrying that not so distractedly, but a carrying that throughout your day. So that when someone turns you and says, how are you? You actually can answer honestly. The how are you question is very powerful when you administer it and follow up. I think there's

another question you ask that people can self administer that that really. I find it extremely provocative. And this is like, I think, in my view, your signature question, which is, how am I complicit in the conditions I say I don't want? That's a powerful question, right? I mean, I learned that question in psychoanalysis. And to be clear, I've been in psychoanalysis now for 30 years. And you're still so fucked up. I'm right. Someday I figured it out. And when I talk about that

question, there's two parts of that question that are really, really important. The first is complicit as a word. Oftentimes this question gets misinterpreted as how am I responsible for the conditions in my life. And I want to talk about why that's misinterpretation. Complicit, it relates to the word accomplice. You are driving the getaway car. You're not sticking up the bank teller. And that's a really important distinction, because as you know, from our work, the things that set us up, the things that sort of start to

define our character, the things that in my techno babbles speak, I start to call things like subroutine, right? The technical code that runs beneath the surface, we didn't invent that. We were given that. And that's a really important distinction. For example, I might have been given the belief system that anger is such a negative experience that it should be wiped out. What do I do with that feeling? I become anxious.

Anxious is better than anger. That's a belief system. We're complicit in that. The second half of the question is super important as well. I say I don't want. Not I don't want. Now why do I make that distinction? Because most of the time that we walk around with, let's call it that kind of whiny complaint that we have about the world. We don't tend to look at the benefit of the behavior we say we don't want. So classic example is, I am so busy. Dan, do you know how busy I am?

I am so busy. Ugh, the world is such a pain, right? And a radical self-inquiry question is, well, what benefit do you get from being busy? And you can see the looking people's eyes when they answer it honestly. Oh, you mean, I'm complicit in this? Or even more, oh, it's kind of a mask, isn't it?

I'm busy, busy, busy, because if I sit still, I may not like what I hear. Right. For me, I use how am I complicit as a nice little riddle or a colon or something to puzzle on and wrestle with in my own life and to usually apply it to this very issue. Right. I've quit so many jobs. I was a quit nightline, I quit ABC News altogether. Now I'm mostly just focused on the podcast that I keep quitting things.

And I'm so busy. And so I like to ask myself what's going on there. And I think this is a thing that's helpful to be in line of yours, but I think this is a thing people can do at home in their own lives. Absolutely. Absolutely. And the inflection point is that moment when we start complaining, quote, again, and we start repeating the patterns. You know, for me, I use journaling as a way to sort of notice what's going on inside of me. Even though I've got 30 years of practice of like looking inward, I still need to

set the day with like, okay, what was happening for me yesterday? Why is I feeling this way? Takes 20 minutes. It's not a big deal. But in that space, I start to create a sense of understanding. God, this is happening again. Maybe I should spend some time with that. Get curious about it. Yes, get curious about it. That is a quick tour through your previous over what's the new book? How does it build? Well, one of the fundamental belief systems that I have about leadership and those who hold power is that when they don't use, say, radical self-inquiry to examine their own structures, they run the risk of, dare I say, bullying people or

spreading their toxic shit all over people. Yeah, he emphasized bullying because that's a problem that I've had in my own work life. I'm bullying myself and then taking it out on other people. That's right, that's right. Because early on you learned to be bullied. Yes. And so you then internalize that as a means of relating to the world.

Yes. So that's the basic supposition is that in order to grow as an adult, really, not just a leader, but as an adult, we need to start to understand with curiosity these structures so that we understand why and who we are. And that leads to the second declaration that I often make, which is a kind of obvious statement. Better humans make better leaders. And it's an obvious thing, of course.

And yet we don't really understand why we don't have good leadership. We just think of people as like, you know, good or bad, good or bad. We don't really understand what's motivating them. And that is a really important understanding. I think it's been very useful for myself and for those who follow the work. But what I've come to understand is that that's insufficient, that it's not enough. And that there's a corollary to that first complicity question, which is how have I been complicit with and benefited from the conditions in the world, I say I don't want. And that in the world is a really important flip because as every wisdom tradition has taught us, we don't live in a bubble.

We interact. We have responsibilities, call it our into beingness, call it our into dependence, but what happens in one continent impacts another continent. What happens in another person impacts me. And what happens with me impacts another person. And so I started looking at the question of how have I benefited from conditions, I'll use a term I use in the book, systemic other.

The process by which, whoever it is, however they identify, doesn't fit a normative structure, the dominant normative structure of whatever society, whatever grouping of people. How do I benefit from that? Because I don't want to see that happening. And equally important, what might I be willing to give up that I love to see the changes that I actually want to see? All right. So you just said two really important questions there.

I think we should double click on them to be a little, sure. Isn't this douchey? The, I, not my favorite. We've been hanging around too many startups. So many board meetings. Double click on that. Yeah, exactly. Yeah, now next time you get close to something,

like you get close to the point that I want to make, I'll say, yeah, you're in the fairway. Another common expression I hear in board meetings. Anyway, how have I been complicit and how have I benefited from the conditions in the world that I said I don't want? Let's just start there. How do you answer that for yourself?

A good example would be when I was 18, 19 years old, I almost dropped out of school because I couldn't afford to pay my tuition. And in reboot, my first book, I tell the story of this really kind English professor, Robert Greenberg, who I was crying to one day. And to be clear, my tuition was $750 a semester. I went to Queens College, City University of New York. And I said, I have to drop out, I can't continue. And he said, well, that's not going to happen. And he awarded me a scholarship.

He was the sole judge, and the scholarship paid my tuition for the next two years. It's a great story. It's a true story. It's a really powerful story. I earned his admiration. What did the fact that I looked like him? How might that have impacted his decision?

And I'm not saying it was the only reason. He was an older right man, I was a young white man. I'm not saying that that's the reason. But isn't it important? Isn't it incumbent upon me to ask the possibility that there may have been somebody else equally deserving? And why did they not get that? And for what reason? to ask the possibility that there may have been somebody else equally deserving and why did they not get that and for what reason? And that's just a simple little way of saying, wait a minute, I might have benefited because

if I didn't get that scholarship then I would have dropped out. And if I had dropped out, I wouldn't have been your coach at any point in your life because it would have been a very different trajectory for me. So once you answer that question, then what, how does it change how you do life? Well, the second half of the question, right, what is it that I want to see in the world? What do I want? I have a colleague. She is a brilliant coach. She doesn't feel comfortable traveling to the state of Florida. Because in the state of Florida, she could be arrested if she doesn't use a

particular bathroom. What the fuck? Why? Because somebody somewhere thinks this is a threat. That's not a condition in the world I want to see. And yet I can walk into many different spaces without worrying about whether or not someone's going to call into question my belonging in that space, my safety. I have a colleague who can't travel to one of the 50 states. What? And we all have colleagues, friends, family members who have experienced variations of this same theme, whether it's anti-black racism, anti-immigration feelings, anti-Semitism, transphobia, homophobia? What benefit do I get from identifying as white,

as male, as straight, as cisgender? Just to ask that question is radical, isn't it? And what kind of world do I want to see? You ask, what do you do that? How about that second question? What would I have to give up so that my colleague can travel to the state of Florida and feel safe? What would I have to do to make that world to at least try? I think these are morally profound questions to ask. I think it's a responsibility that we have. What have you done about your colleague?

What have you given up? She would say to you, this is Virginia Bowman who contributed an essay to the book. The afterward of the book takes a turn that is somewhat unexpected. I had three different friends all identifying from different social locations, right about their experience of belonging. And I think that there are many things that I have a responsibility to do. One of them is to do what I'm doing right now, is to speak up, and to speak out,

and to raise questions. I've earned a certain amount of credibility in the world. I've earned a certain amount of trust from the work that I have done, from my being. I could choose to continue to do what I've always done, become this like, why is elder sage on the stage, or I can lean into a very, very difficult space? And I've chosen to do the latter. That's one step. So in terms of giving up, there's a kind of giving up of comfort

by waiting into these issues of... Or status? Yeah, well, status how? Well, I could be canceled, right? Right, well, who's gonna cancel you? I could say it wrong. I see, I could be canceled, right? Right. Well, who's going to cancel you? I could say it wrong. I see. I see.

I could be waiting into his base that other people would not be comfortable having me speak about. We're doing this interview a couple of weeks before the book comes out. We'll post right as the book comes out. But are you nervous? Maybe between now and then you're going to get canceled. Is that what's on your mind? It's on my mind, clearly.

I wouldn't have brought it up, but it's... I was talking to someone yesterday and she said to me, I'm going to ask you a question that is really difficult for me to ask, what right do you have to speak about these issues? And it's a great question. And then I said, I want to reframe the question if you don't mind. What right do I have not to speak about these issues? Yeah, good reframing is what responsibility do I have? That's right. That's right. Because I know where the problem is.

The problem is not on the people who bear the burden. And yet part of our structured response in order to maintain a certain safety, and existential safety, part of our structured response is we make those who bear the burden to the labor. So what's the risk, and my worry about being canceled? I may be, I don't know. You know what's a really precious thing for me that I worry about giving up?

I sit down and you tell me if this is true. My understanding is that for some bizarre reason, I start talking and people calm down. You're nodding, so it makes sense to you. I like that about me. I like being seen as the guy who makes people feel better. It answers some really deep, profound, existential questions of my own. Am I worthy of love, safety and belonging?

Oh, look what I do for this person. That's great. That's how my ego goes out for a dance. What if I lose that? I thought a lot about that. More during the writing than now. Now I'm in like, come on, LFG, let's fucking go. I'm not backing down, you know. But that's the fear. Yeah. Yeah, I mean, my fear, we talked about this privately. My fear for you with a book

like this isn't that you get canceled because I think the folks who generally lead the charge on cancellations, you're talking about the stuff that they agree with. Right. My fear would more be that some percentage of the population is just tired of having this conversation. I mean, I see it because- You get tired. No, well, yes, but we do a lot of stuff about race and gender

and social justice on this show. We get it hardcore during BLM and we continue to do it, but we get negative comments every time. And this audience is, you would think, would be very open to this stuff. And I'm sure there are plenty of people who are. Yeah, but I do see in my personal life in the people I know a real fatigue around this.

And so that I think is the risk. And that may happen. I run the risk of being corrected. I run the risk of being told I've got a completely wrong point of view. But what's going to happen is going to happen. Coming up, Gary Cologne, it talks about how to avoid the pitfalls of virtue signaling and self-righteousness. It talks about the term reunion, what does that mean and how it relates to the stories of our ancestors and what he means by the longing to belong.

I'm Rob Briden and welcome to my podcast, Briden and. We are now in our third series. Among those still to come is some Michael Paling, the comedy duo Egg and Robbie Williams. The list goes on, so do sit back and enjoy. Briden and on Amazon Music, Wondery Plus, or wherever you get your podcasts. We can't see tomorrow, but we can hear it. Tomorrow sounds like hydrogen being added to natural gas to make it more sustainable.

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Join the challenge right now by downloading the 10% happier app today and starting a free trial. You get very practical in the book and we're going to go there. We're staying at a bit of a high level here, but we will get to that. How do you manage talking about the stuff without the pitfall of virtue signaling or self-righteousness, which is so often a turn off. Like I've mentioned this before in the show, but there's a TV show that I love called Letter Kenny.

It's a obscure Canadian sitcom. Have you seen it? No. Okay, it was very funny. And there's actually a sequel on the air now. You can see it on Hulu called Shorze. Many of the main characters in letter Kenny are white farmers. But the has this subtle, very stealth and skillful

social justice. Part of his character name, Squirly Dan, who every once in a while in conversations with his other beer drinking buddies will talk about something he learned from his feminist studies teacher. And he does it in ways that are like utterly unpretentious. And I always think of like, let me be squirrely Dan. Like, I care about these issues. But I wanna do it in a way that isn't like, oh my God, like this guy's showing off

or he's trying to show what a good person he is. And do you think about that and how do you manage it? I don't. And maybe as a result, I come across not like Swerley Dan. I don't worry about it, but I see it. And I know what you're talking about. And maybe I'm guilty of it. And if I am, I'd like to know if I'm guilty of it, because I think that performative

allyship does a real disservice to what it is that we're trying to create. And I'll go back to something, this is a quote from the book. And I tell this story about my daughter, who very powerfully once said to me, Dad, it's not enough to be an ally. You have to be a Coke and spiriter. And Emma is fierce as fuck. So I maybe is the benefit of having children who just cut through your bullshit. And I grew up, or they grew up, calling me out. But look, the fear of that, I think, first of all, we should be aware of it. But the fear of that should not let us stop us from saying what needs to be said. I a thousand percent agree with that. And, and I have no, I'm not in your mind, so I'm not speaking for you at all. But I can tell you from my own mind, from reporting live on the scene, and my own psyche, that

there have been times where I've noticed on the show or in meetings that I'm showing off because I'm looking for some sort of ego gratification. I am to use the term of art in social justice spaces, cookie seeking. I'm looking for that cookie that that hit of ego gratification. Where people around the table in a meeting are like, that's a good guy. He's, you know, I've just given some lecture about how we got to do the right thing.

And, but part of me is looking for something instead of actually trying to help. I'm just as guilty of that of cookie seeking for all aspects of my life. Not just in this area. So guilty as charged, because I'm a human being, right? I mean, I want to be loved. And I can just as easily confuse and conflate a cookie with love. But I'm also pissed off. I'm also sincerely worried.

I'm also wondering what the hell is going on with our world. And those are genuine feelings. Let's just say as well. And when I say as a parent, I do not want my descendants to think that I didn't try. You know, the descendants I'm worried about aren't in a position to give me cookies because they're not even born in it. I'll be long gone when the people I'm most concerned about are looking back on my efforts.

Those are great points. So the book is called Reunion. What do you mean by that? And I would love to talk about this process as something anybody listening could do, whether they have a coach around. I think it's precisely that. So Reunion is the term that I came to describe what I think is the pre-work that needs to be done. And the pre-work is reuniting with what I refer to as the,

not just our ancestors, but the real stories of our ancestors. What was their experience like? Re-uniting with the dismembered, unremembered parts of ourselves that we sort of lock away, so that we can then move towards reuniting with the rest of us. See, I suspect that a lot of efforts, especially within corporations, to create what I would refer to a systemic belonging fall short because the people who have the power actually don't do the work.

They take the actions, they take boxes, they complete surveys, but they don't actually look at themselves, and they don't look at their own experiences. We've had conversations about this before. Understanding from whence we came and how that influences who we are is absolutely essential in this process. For example, as I write it about in the book, I have two sets of ancestors, one acknowledged that I grew up with understanding, which were my Italian American or Italian ancestors. And the other were my father's biological parents, Irish immigrants in the 1920s in New York, and his mother gave him up for adoption.

Now there's a whole subplot in the book about the fact that my father didn't discover this until he was 21 on his wedding day. And so I asked the question quite deeply, how could he know to whom he belonged? If the woman who gave birth to him and who was his mother for 18 months gave him up, for whatever reason, and how could he belong to the people who adopted him when that mother was the one who screamed at the back of their wedding church? You're not my son, you're not my son because you were so angry about who he was marrying, my mother. Whoa. Yeah. And what did that do to his own sensible longing. And consequently, what did it do to my sensible longing? Because I grew up knowing this, but I denied it. I didn't want to know it. And I make the

point that I think that there are stories like this in many, many families. Stories of what our ancestors did and did not do. What happened to them and the story that they madeist, or the great grandfather who was a fascist. We don't talk about that. We don't talk about what their experience was like. We don't talk about, I have an ancestor who may have been transported to Australia as a convict in 1804, leaving a five-year-old son and dying there. We don't talk about that. And the lack of talking about that

undercuts our ability to do what our teachings tell us to do all the time. Which is to be compassionate and to be empathetic. Same more about exactly how we would do this work and how that work would lead to being more compassionate. So I want to be clear, not everyone is going to have the capacity to figure out the stories of their ancestors, but everyone has the capacity to imagine certain things. I was talking about my colleague, Virginia, who offered an essay. She asked a very, very powerful question because she spends time in her essay talking about the family tree and

how obsessed the family was. They had this beautifully bound book that linked all the answers all the way back to Switzerland. And she asked a simple question, who were the queer members of that family tree? Yeah, you just smiled because guess what, dude, we both the queer members of that family tree? Yeah, you just smile because guess what, dude, we both have queer members of our family tree. It's as if being transgender is something that just got invented or as if being queer is something that just got invented. Okay, that's bullshit. That's what I'm talking about is being able to connect that. Okay, so let's just expand our imagination and imagine that 10% of your ancestors,

just like 10% of your ancestors may have had mental health issues. 10% of your ancestors may have experienced some form of other now. Talk to me about trans rights in the United States. Talk to me about your obligations as someone who might hold power to think about that. And just for a little extra juice, think about what life you would like your son, who is still forming, who he is. What if what

emerges is an identity that doesn't fit a norm. How would you like him to feel 30 years from now? Okay, now do you feel the empathy? Just put a fine point in it, by getting a sense that your family tree consists of people who were either a deeply flawed and conflicted or be part of marginalized groups and may have suffered as a consequence, you can take all of that information and extrapolate it out into your view of the world where you feel empathy for people who are making mistakes or you might disagree with, and of course empathy for people who are currently being persecuted in one way or another. I think for me, because again, I put myself through a process that, because you know me,

I can't ask you to do something that I myself have not done. It feels false and out of integrity. And I put myself through this process. And I, using an active imagination, using some research, imagine what my mother's mother, an immigrant from Pallodical and Puglia in Southern Italy, what was her experience like coming through Ellis Island? How close was she to having a wrong checkmark on her lapel that said, you have to go back because you might have TB?

And what's the difference between that person and a mother from Guatemala or then as well or on the southern border of the United States? What's the difference between those two? Yeah, yeah, yeah, we have a broken immigration policy. Yeah, yeah, yeah, the system is completely screwed up. But you're a long time journalist. Do you remember 20 years ago talking about the gang of eight and immigration reform? Yeah, I do. Never happened. Never happened. And yet there are actual human beings, including children on the border right now, suffering. And you can look at them less as statistics,

wherever you are politically, and more as actual human beings, if you could interpolate back into your personal and family history to get a sense of the fact that people whose DNA you were carrying around right now had the exact same experience. That's right. Or close enough, maybe not exactly the same, but close enough, because we

got to be careful of false equivalencies, but close enough to be able to see the interrelationship between us too. You talk about belonging before. So in one level right now, we're talking about looking back and seeing that we may have had people in our family trees who are dealing with versions of the struggles that other populations in our culture right now are dealing with. We also talked about belonging, which is a more diffuse idea. And you talked about your father's feeling of belonging on his wedding day as the woman he thought it was his mom is shrieking from the back of the church. What is it about this interpolation of this going back and looking at your family tree that can teach you about belonging?

And why does that matter now today? Well, very specifically, the subtitle of the book is Leadership and the Longing to Belong. And I speak about the longing to belong because I think it's one of those base universal experiences. So when we encounter someone saying, this is unfair, this is unjust. If we put it through the lens of, wait, just like me, they want something, just like me. What do they want?

They want to feel loved, they want to feel safe, and they want to know that they belong in some place. Even if I disagree with what they're saying, they want those same things, right? Because we're all human. Okay, and we start from that proposition. And then we start to explore, who am I? And in the forward to the book, Parker Palmer, my friend and teacher, wrote the core secondary question, is who's am I? To whom do I belong?

Because I would argue, having cut ourselves off from that story, having cut ourselves off for this myth of resilience. My ancestors made it through. Why can't you? We actually cut ourselves off from the true story of to whom we belong. For good and for ill, or admirable people or not admirable people. By reconnecting and reuniting with that my hope and I don't know

this is an experiment my hope is that we can create the conditions for the longing to belong to be answered in whatever sphere we have would have us yes it could be a family it could be a business it could be a volunteer organization, a classroom. Exactly. So let me just talk about how this could work. I've done a little bit of ancestor work, just looking back at my family, which is populated by a remarkable amount of crooks and cowards.

And I find that intriguing and a little funny, and but also poignant. And I can look back at, you know, especially the Jews who came over from Russia. And I think about a lot about my great grandfather who, and this is sort of sad and poignant in a way is like, his name was Libowitz, but he changed it to LaBalle, L-E-B-A-U,

because he thought it would sound French. And he ended up being a criminal and went to jail and then took his own life. But there's a way in which you can shove that into a larger narrative of, well, generally speaking, these scrappy Jews from Eastern Europe came over and by the time my dad's generation hit, they were mainstream, very successful. White. White, at this point, they'd achieved whiteness. And there's a way in which you can like get up onto the highest

rungs of the ladder and forget about all the struggles. Like, I'm here. I'm done. Like, we did this. Yay. And why can't you? Yes, exactly. Exactly. So instead, what you're saying is look back at all the messiness and the grit of this whole story. And then you can look out at folks who you might be tempted to say, well, what are you complaining about? We did it and be like, no, no, no, no, no, no. There are reasons baked into the structure of our society that have held people back. Well, and just look at the whole question, when did Jews become white? Yeah, I actually know some Jews now who still don't consider themselves white because of the amount of discrimination. Right. Right.

Yeah. I consider myself white, right, which means to use a term I use in the book. So you became racialized as white. Yes. Which means to use a term I use in the book, so you became racialized as white. Yes. At some point, that wasn't true. Yes. And at some point, I mean, just to get pointed about it, your son carries the DNA of people whose status was ambiguous.

Yes. And I think that there's a moral responsibility to not forget. I think there's a self-interested case for this, so let me just make the case, see if I can build the case. In Buddhism, it's often talked about, in psychology too, that the root to compassion, or one root to compassion, is to see your own suffering and learn to get comfortable with it.

So for my son, is to understand that in his four bears include a lot of messy characters who were struggling to fit in in this country and weren't considered a mainstream. And to get comfortable with that and to be able to have some equanimity with his own family's history of suffering and hopefully with his own messiness too, and then to be able to use that tenderizing, like we do with meat, to be able to look at other people with some degree of empathy and compassion. Oh, yeah. As you said before, just like me, they are struggling, whether it be with interpersonal stuff or with social, political, cultural stuff. This process of, I like to think of it as inexorable,

although it can get interrupted, of getting cool with your own stuff, and then leading to you being cooler with other people's stuff. And I think the self-interest there is that, we as humans and people have heard me bang on about this a lot, we know the thing that makes us happy, is the quality of our relationships.

And so if you do this work, the quality of your relationship with other human beings in your orbit, and also with the culture and the world writ large and how you view things on the news and on social media will warm up. So I think this is all to the good. It's not like you have to wear a hair shirt and suffer just focus on the jerry's giving things up. No, no, no, no. You will improve your life. It will improve everybody's life. Yes.

Well, because your life is part of everybody's life. Yes, yes. When I work to alleviate my suffering, I alleviate other sufferings. When I work to alleviate their suffering, I alleviate my suffering. Correct, because we're in a double helix. Thank God we are.

It's part of what makes us human. Right. But this is my attempt at squarely damn. Because I like to inject self-interest in because- Because you want to acknowledge that is a motivation. Yeah, well, I mean, because I see my own greed quite clearly. Sure. But I don't, to use Jerry's turn, I don't make it bad.

Exactly. I was just going to use Jerry's term, I don't make it bad. Exactly. I was just gonna jump on the word greed. You taking care of you is not greedy. Well, it's a term of art within Buddhism of, you know, just desire or... Sure, yes. So, then I can see impulses that go beyond just taking care of myself and my family.

I can see impulses toward world domination. I can, you know, all of that. That's just part of the human repertoire. You don't have to make it bad just see that it's there. It's the organism trying to protect itself and so on. Well, you know what makes it bad? Pretending it's not there.

Yeah, yes. Yes, acting it up blindly. That's right. That gives it all the power in the world. And we all suffer as a result of denying those impulses. Coming up, Jerry talks about how we can learn to do our first works over the difference between equality and equity and his framing of content and container to help guide good leadership.

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So in order to do this reunion process to make peace with our ancestors, you and I have plenty of financial advantages that allow us to hire people to help us learn about our family tree, but it could be just as simple as talking to your parents or your grandparents, it could be as simple as, as you said before, just making imagination leaps. It's worth saying a lot of black Americans

don't know much about their ancestors. Because of the diaspora. Yes, because of the diaspora. Absolutely. It might be just that you do this work through your imagination or you do this work in simple conversations I mean I had a client come up to me at one of our boot camps boot camps are these immersive experiences that we do long weekend kind of experience and it was early on in writing the book and I was describing what was going on to

and he pulled me aside and he said, he was from the Dominican Republic and he said, Darrym, I'm having an insight. I have grown up my entire life with a sense of overwhelming guilt and I said, okay, tell me about this and he said and what keeps flashing through my mind is that my great-grandfather raped my great-grandmother because he had enslaved her or as part of the consequence. And he just starts weeping. Now where do those tears come from? Right? You can argue epigenetic trauma. So I said to him, he quieted down. I said, what was her name? So, I said to him, he quieted down, I said, what was her name? And he said, my father never told me.

I said, I didn't ask you what your father said. I said, what was her name? Because that woman was dismembered from the family tree. And part of bringing all of these connections back is to reunite the dismembered parts, not because we can turn around and go back in history and make something apparent, somehow acceptable, but to acknowledge the truth of that. So when you talk about reunion, I mean, sometimes the term ancestor work gets thrown around and for somebody like me who doesn't like jargon, I can be like, what's this now?

Is this going to be like an horror? How many times a day do you raise your eyebrows and get to this? A lot. That is like my resting face. And so like I hear ancestor work, I'm like, oh, is it like an aura reading or a adult and healing or whatever. No, I know. I actually think ancestor work

is incredibly important because it is, it's the same as doing like internal family systems therapy. You're based in peace with parts of your own personality. That's right. Ancestor work is just looking at like who you are because of course you're carrying around all this stuff from your forebears. That's right.

And you wanna look at the stuff that your parents never really wanted to talk to you about because that's the shit that's in the, some crevice in your brain. That's right. Driving your actions. So for me, the guy who put his head in the oven after he lost the family fortune, because he became a crook after changing his last name to fit in and all that stuff, that's in me hustling now in lots of ways.

Okay. So looking at that seems really helpful. Okay, so let's look at that just for you. And you don't even have to answer this question. But here's a question for you. Why did they become crooks? What benefit were they seeking? Belonging on it.

Belonging? They wanted safety, they wanted to belong. What were the conditions that those crooks were leaving? Oh, absolutely. Yes, pogroms genocide in Eastern Europe and then they came here and they were treated like shit. And this guy, I think it's so pointy that he changed his name to LaBao.

Yeah. My assistant Amy, who was a amateur geneologist, she found newspaper articles about this guy. And the FBI was on him. He was like, it was nuts. And you know, you can view it as mildly amusing and it is, but also there's something deep there and it fits into the category of reunion

or ancestor work. That's exactly right. I'm just trying to help you make your point. That's what I'm telling you. Well, you're actually making it better than me, which is great. I don't know about that. I would recommend James Baldwin's essay,

The Price of the Ticket. And I quote, just a little bit from the essay in the book, but The Price of the Ticket refers to The Price of the Ticket of Whiteness. And that the price is a disconnection is a lack of remembering from when she came. It's a transformation of the names. It's the movement towards safety.

Yep. And the result is what you actually lose, I think it's fascinating. I mean, for me, I did the work of saying, oh wait, so in all of my lineage, this famine, that's fascinating. I don't know the ways in which that shows up in my life right now

But I'm really curious about that and being aware of that makes it really hard for me to look away from famine We have flotillas of refugees around the world Just like me Just like my ancestors You know you asked me about virtue signaling before. I think that doing some of this work might undercut the virtue signaling. Because, oh, wait, no, this is real stuff for me, so that I can then turn around and use the power and privilege that I have been gifted

to actually make a difference on the southern border of the United States in the state of Florida on the streets of New York. Because what's the point if you're not doing that? What's the point? So we can have more toys at the end of our life. That's bullshit. No, I grab smiling just because sometimes somebody will say thank you for something I've done and I'll be like there's no point making money if you can't spend it on your friends. You know, absolutely. Which means you're gonna take me out to dinner. Sure.

We are having dinner tonight. There's another phrase you're using the book, which is, do your first works over. What is that all about? That comes from James Baldwin. And it comes from the price of the ticket. And what he says is that it is incumbent upon us, all of us, but especially those who do not attend the church that he attends,

meaning especially those who identify as white to do our first works over. Because you look, we create these structures, we create these understandings in order to become adults in order to move forward, right? Okay, so the family story is with laughter, our family tree is filled with crooks and cowards. Okay, but maybe asking why is an expression of doing your first works over? Why? Were they born that way?

Chances are probably not. That, to me, is what do your first works over? To go back and reconsider things. Not to get stuck in the past, but so you can move forward with more clarity. So if some significant number of people do this work, the work that you're recommending, in particular, I think giving your platform, you're going to reach a lot of people who have a lot of power, what's the impact? What do you want to see them do once they've done the RSI, the radical self inquiry, and

then the reunion? From that place to then begin to do equity work so that equity work gets transformative. So it can actually stick. Look, this is quicksotic. I get it. But I literally think this is the most important work that we can do. This and saving the dam planet from climate change. The epigraph from one of the chapters is from the Talmud.

And in it Rabbi Tarfren says something to the effect, it is not your responsibility to complete your work, but neither are you at liberty to ignore the work. It's like the Dalai Lama talks about how you got to think about the impact of your work over multiple lifetimes. And you have to do the work. Yes. Yeah. Even if you will not see any difference in the world, what would I like? I would like.

And by the way, doing the work will make you happier. Doing the work will make you happier. I would even expand and say even more content. Yes. Yeah. Have you ever brought that into your study? even more content. Yes. Yeah, that's your brother that understood. That's right. Yes. That's right.

We could give up because the work is so hard. But again, I think about my grandchildren and a great grandchildren. I don't want them sitting on a podcast with Dan Harris and them calling me a coward. I want them to look back and say, he may have failed, but he tried. That's the attitude I want to go out with. Or he helped build what eventually became a more equitable culture. That's it, belonging for all.

What's the difference between equality and equity? I always get confused. I know this is controversial, but we've moved in our vernacular from equality of opportunity to equity of opportunity. Equity addresses disproportionate opportunity equity addresses disproportionate power. So if we look at for example, and I am not a DEI expert by any stretch of the imagination and I am not positioning myself as that. I am a curious human when it comes to all of that.

not positioning myself as that. I am a curious human when it comes to all of that. But my understanding would be that the language around equality can get subsumed into numbers. How many of this demographic versus how many of that demographic, whereas when we look at, well, who actually holds power in an organization? Then we start to look at the question of equity and equitable opportunity for advancement. How do we create a leveling of that opportunity? Right. So you can be a major corporation, say, we've got equal employment because we've got X number of people of color, but they're all in the mail room. Correct. That's not equity. That's right.

How many are in the board room? Right. And we have huge problems with equity in corporate America. Oh, yeah. Yeah. I mean, how many CEOs are women? Well, I was just going to say it's not just people of color. It's under two.

No. And I've seen some data that CEOs of public companies who are female have better stock price performance than the men. I've seen the same data. I don't know the stats behind the data. I don't know the sources of the data, but I've seen the same data. It's interesting. I just interpolate back to my own life.

Many, if not most, of my best bosses were females. So if people have listened this long, they're buying Jerry's message. They're going to do the RSI and they're going to do the RSI, and they're going to do the reunion, and they're going to try to create more equitable either workplaces or homes or classrooms or organizations or whatever their sphere of influences. Having said that, sometimes even as you try to increase the sense of belonging on a team, which I have in fits and starts, spent a lot of time thinking about my own little world.

Sometimes somebody's got to go. You have to let somebody go because they're underperforming. So you're not saying, you know, you're wrapping everybody in a warm blanket of, you can do no wrong. You still have clear eyes. You still are trying to hit your KPIs

to use another douche business term, your key performance indicators. You're still trying to hit your revenue goals, but you're doing it with a different lens. But that doesn't mean you're letting people off the hook forever. Right. So, a simpler way to understand this is, I often talk about content and container. Every person who runs a business has a responsibility to create a healthy container. That means physically sound that

the business can operate in a sustained and self-perpetuating way. And in a similar fashion, that means holding people accountable to their own aspirations to do their job, to creating the conditions for them, to do really excellent work. But if we only focus on that aspect, then we create a container that is meaningless. We also have a responsibility to create the content in a way that gives meaning and purpose to the container. And we can apply this thinking to how we lead, how we work with our colleagues. Right. Belonging doesn't mean you're not

expected to do your job. In fact, you could argue that holding people to the standards that are out there about doing that job is really important. And it helps them. But an important version of the content is, where am I creating these contents, these standards of behavior? Where do they come from? What are my expectations? Is there an unconscious bias that exists within that? And even more, am I overindexing on say, profitability because I have unresolved fears about money?

I'm laughing because that's exactly the kind of shit I would do. Sure, but here's the thing, Dan, all of this is hard. All of this is hard for business people. I get it. But as I like to say, I believe people can walk into go. I was just going to say that you can build a profitable company that doesn't treat people like shit. That's right. And you can be a really good leader without being an asshole.

Yeah. These are not mutually exclusive objectives. Well, actually, I think they're mutually supportive objectives. Well, that's because you've had a good coach. That's actually true to give you credit, because I don't think I viewed the world that way before I met you. But I think that none of us viewed the world. I mean, we were socialized to think it's an either or kind of construct. It's either this or you're that, you're this or you're that.

And I think human beings are much more capable than that. They're much more complex and they're much more pleasant. And so you might sacrifice a little profit. Okay. But it doesn't mean that the ability of the organization to sustain itself goes away because you somehow made it safe for everybody to belong. You've given me slash us a lot to think about. Is there something I should have asked but failed to ask in this discussion? No, you're pretty good at this. No, thank you. I can get mad at myself actually as I think back during this interview because I interrupted you a few times

so I apologize. Oh, I loved it. Okay. I try not to do that usually, but maybe it's because I'm so comfortable with you that I did it. Well, it's it's our friendship. Yes. Yeah you that I did it. Well, it's our friendship. Yes. Yeah. Before I let you go, will you just shamelessly plug reunion and reboot and anything else is what people know of it? Thank you for giving me the permission to be shameless because that overcomes my separate taste.

Yeah. So reunion, leadership and the longing to belong. And the first book was called Reboot. Leadership in the art of growing up. And all of this is really emblematic of the work that we do at reboot.io, which is a neat little band of happy warriors who are trying to make a positive dent in the world. Definitely made a positive dent in my world. Thank you.

Thank you, Jerry. Thank you, Jerry. Thanks again to Jerry. Always great to see my man, Jerry Kelona. Thank you to you for listening. Please go give us a rating or a review. I know I say that all the time, but actually it really does help. Thanks most of all to everybody who works so hard on this show.

10% happier is produced by Lauren Smith, Gabrielle Zuckerman, Justin Davie, and Tara Anderson. DJ Cashmere is our senior producer, Marissa Schneiderman is our senior editor, Kevin O'Connell. He's our director of audio and post-production, and Kimi Regler is our executive producer, Alicia Mackie, leads our marketing and Tony Maggar is our director of podcasts, our fearless leader,

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