Inner Work, Empathy, and Leadership with Jerry Colonna

Many find themselves at the pinnacle of professional success only to discover that the view is less satisfying than as they'd imagined.

In this episode with Jerry Colonna, we discuss how more of us can contribute to a world that cherishes connection and unity above all.

We explore how true satisfaction and leadership arises from self-awareness and we stress the significance of doing our inner work.

We talk about how the recognition of our ancestral heritage serves as a bridge for fostering a sense of belonging and understanding.

An intriguing part focuses on the unspoken, the forgotten, and the truths about societal and familial histories that often go unaddressed.

The conversation is an exercise in introspection,  a deeply necessary step toward cultivating empathy and fostering leadership that seeks to alleviate suffering.

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.

He was a partner with JPMorgan Partners (JPMP), the private equity arm of JP Morgan Chase. He joined JPMP from Flatiron Partners, which he launched in 1996 with partner, Fred Wilson. Flatiron became one of the most successful, early-stage investment programs in the New York City area.

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00:00 Two years since our last episode together (Ep. 84 - Reboot)

01:10 The pain that comes from succeeding

2:07 Success and it’s relationship to some of the challenges people experience

05:00 Face the tiger that is chasing you

08:27 “How have I been complicit in creating the conditions I say I don’t want”?

10:30 One reason to do the inner work on yourself

13:58 The danger of feeling like you have a gaping hole inside

15:12 Proactively creating conditions for systemic love, safety, and belonging

17:43 Deep and powerful leadership goes beyond the realm of creating sound Companies that create meaningful products the world needs

23:13 Taking a stance against Othering and Dehumanization

28:40 Show empathy with people by first understanding the true stories of your Ancestors

34:56 Who gets dismembered from a family tree?

41:56 Who benefits from war, destruction, and dehumanization?

43:54 Why do certain conditions persist?

46:00 We’re all really good at sweeping things under the rug

52:22 Four questions Jerry asks himself and the CEO's or Founders he coaches

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Transcript

Speaker 1: 0:00

Jerry Colonna, it's so good to see you.

Speaker 2: 0:03

A rjun It's great to see you again. As we were saying just before we started recording, it's been about two years since we last saw each other and last spoke Exactly and actually almost two years to the day.

Speaker 1: 0:13

So the universe has brought us together. I've been looking forward to this conversation for a while now. I already had your book Reunion Teed Up and then when I heard you on with Jason Calacanis on his this Week in Startups podcast, I reached out to you. I was like, look, let's see if we can get Jerry back on. And for anyone who actually heard that conversation that you have with Jason, you definitely have this unique insight. You have a unique perspective as someone who can truly and actually talk about and speak about the pain that comes from succeeding. As a former VC, as a coach now, for about 27, 28 years, you come with this experience and so maybe we can start there with just your story around that, around just the pain that comes from succeeding.

Speaker 2: 1:13

Well, part of the how about we just say the pain in general? Sure, and it comes to mind because I was just finished up a coaching call with a client who, wisely, took the month of January off and went scuba diving with his father and took a real vacation for the first time and only to come back to I don't know about nine different disasters in the manufacturing of the product. I remember saying to him would you like a side of nails with that bag of glass you're eating? And we both laughed because it's hard. But to your point, I think that the way to go into the question of success and its relationship to some of the challenges that people experience, I think that the best way to think about it is just how surprising it is for people when they hear that someone is externally successful and they've built and sold a company, they are sitting on a pile of money, that somehow, despite all that we have been taught from fairy tales to religious tracks, despite the fact that we've been taught repeatedly that money doesn't buy happiness, we're still surprised.

Speaker 1: 2:57

Yeah.

Speaker 2: 2:58

Now I wanna be clear money doesn't necessarily buy sadness. But what it doesn't do is it doesn't erase the need to do your own work. And you're right, I mean. The somewhat well-known story for me was that I was immensely successful in my 30s as an early stage VC in New York at the first way of internet investing, which was arguably the most fun because everything we did was brand new.

Speaker 1: 3:40

And we're talking like the Yahoo days for people listening.

Speaker 2: 3:42

the Yahoo days GeoCities maybe before that Pre-Yahoo exactly, and looking at things like being able to sell advertising for CPMs at $15,000, it was crazy. And, despite the successes that I had, the things that drove me to be depressed throughout most of my childhood remain the things that made me depressed, even though I ostensibly had enough money not to worry anymore. Right, and the shock of that and we see stories of this over and over again. You mentioned my conversation with Jason. Jason was particularly close to Tony Shea, for example, from Zappos.

Speaker 2: 4:36

The shock is the thing that actually surprises me the most. Now I mean, I'm 60, now I've been doing this a long time, as one friend said to me just a few weeks ago 40 years fuck you, 40 years. And it just still amazes me that we are collectively surprised that we still have to do our inner work, we still have to do the things. We still have to turn around to use a Buddhist image for a moment we still have to turn around and face the tiger that's chasing us, rather than just keep running and running and running and thinking that a bag of gold is gonna save us. It doesn't.

Speaker 1: 5:41

No, that's true. So I mean in your 2019 book. I mean, the reality is that work on yourself. It takes a lot of effort. It's probably one of the reasons people fail to really explore who they truly are. They fail to explore who they belong to in terms of their ancestors and their lineage, and they probably fail to explore where they come from as a result of it. It's just extra work, it seems like, but the reality is that this is the type of work that's required if you want to go deeper into self-discovery, go deeper into growth and definitely go deeper into leadership.

Speaker 1: 6:16

And in your 2019 book, reboot, that's where you suggest the leaders of today's world are gonna be the people who learn to really do the work on their wounds, because when you do the work on your wounds, you have a smaller chance of taking that out on other people, and so that whole book is about asking yourself, who am I? And really getting into that. And then in this new book, reunion, leadership and the Longing to Belong, you're taking that question and you're going a little bit deeper, because now you're asking, okay, who's am I? And so, again, this question is in the context of self-discovery, it's in the context of leadership. It's in the context of growth, and so I'd be curious, as you did your own work on yourself, how do you, jerry Colonna, address the who's am I question?

Speaker 2: 7:12

Well, can I say a few things before we go to that question? I'm more than happy to go to that question. The way I would reframe a little bit both the description of Rebute my first book from 2019, and then now Reunion. You're right, it's an invitation to self-inquiry, it's an invitation to self-discovery in both books, and you're right that I assert that it's really important. In fact, what I assert in Rebute is that better humans make better leaders. And again, you're correct in the assertion that most people choose not to do this work. They see it as too difficult. But let's go all the way back to even the first thing that you were talking about, which, arguably, is really about suffering. And if you go back, if you remember, from my first book, there's an infamous question that I coined maybe 18, 20 years ago how have I been complicit in creating the conditions I say I don't want? And that question is repeated around the internet so many times that I wish I had trademarked it so I'd make a little bit of money off of it.

Speaker 1: 8:47

I got to say I honestly ask myself that question at least weekly, if not almost daily, because there's so many layers to that question. But ever since reading your book I've been asking myself that a lot.

Speaker 2: 9:02

Well, the thing that people who dive deep on that question, that the thing that I hope that they do, is that they approach the question with compassion and curiosity rather than guilt or shame.

Speaker 1: 9:24

A boy who has self-hate.

Speaker 2: 9:26

Yeah, there is a self-development field, a mantra that actually very subtly conveys a message that you are broken. If you walk through if such things exist anymore physical bookstores I'm teasing, of course they exist and you stop in the self-help section, there's an unmistakable aura of you are broken and read my book so that you can be fixed, whether it's to lose weight or to stop procrastinating, or even to not feel self-hatred in a weird way. And the thing that I think people lose when they come at it from that angle and this is true for both Reboot and Reunion my new book I think the thing that should motivate us to do this work is the wish to not feel bad anymore. If we go back to your first question and we go back to okay, jerry was successful and then he felt suicidally depressed. And again, it's not that for the first time in my life I felt suicidally depressed.

Speaker 2: 10:57

The truth is, I felt suicidally depressed most of my childhood, and so the things that were compelling me to feel these feelings remained, despite the external success. And so questions like how have I been complicit in creating the conditions they say I don't want? And questions like that are really designed, bizarrely, to alleviate suffering. To put it another way, the quest to be a better human, as I talk about in better humans make better leaders is really a quest to alleviate suffering, and the really intriguing thing is, if I work bravely at alleviating my own suffering, then I am less likely to create toxic wastelands around me and hurt other people, which, in a sense, reboot is about alleviating my suffering, and reunion is really about a process, a set of steps that one can take to create the conditions for less suffering for those around us.

Speaker 2: 12:21

Right right Now. You're right, there is this angle in. There's a part of the process that I talk about which is about reuniting with our past, reuniting with our ancestors, reuniting with the truth of what we're about. But the thread that ties both books together and, most importantly, the thread that ties all of that I have learned in these last 30 years, is that if you really want to feel better, you have to go inward. And, arjun, you know what? I use the phrase radical self-inquiry. That's the radical part of this, because we live in a capitalistic society that says, if you really want to feel better by this deodorant, if you really want to feel better, you should drive this car, if you really want to feel better, you should have flat abs. And you know what? It's all a fucking lie.

Speaker 1: 13:36

All of that is external.

Speaker 2: 13:39

All of that. You can literally have it all and still feel miserable.

Speaker 1: 13:48

Like with a gaping hole inside.

Speaker 2: 13:49

yeah, and if you then combine that person with a gaping hole inside with power, look out, look out. I will hurt every living being around me in a bid, unsuccessful, vain bid to make myself feel better.

Speaker 1: 14:21

Yeah, and that even goes to even just the idea of separating from others like othering others. I mean it's all kind of built in. You create separation, you create the toxic puddles around you.

Speaker 2: 14:38

Yeah, You're referencing an important concept in my new book, reunion, in which what I'm trying to do there, what I set out to do, was primarily answer for myself, but then offer this to the world. What is a person's responsibility, beyond doing my own internal work to alleviate my suffering? What is my responsibility? Not just to alleviate the suffering of those with whom I work, but to actively and proactively create conditions of what I call systemic belonging, this sort of root wish that we all have to feel love, safety and belonging, to feel that we are included, that there's an equity yeah, so that those around me can feel worthwhile, safe, that they somehow matter in the world. What is our responsibility as those of us who hold power? Because I'll name it, I'm a white, cisgender, straight man with power and privilege, and I live in a society that really asks very little of me as it relates to caring about other people.

Speaker 2: 16:21

Yeah, interesting and maybe I have a moral and ethical responsibility to give a shit, not maybe I kid. I absolutely have a moral and ethical responsibility to give a shit, and so that's what reunion is about.

Speaker 1: 16:44

Yeah, and that's interesting because in that and picking it up from your book you talk about, maybe in this day and age, a way to measure the success of a leader is to measure how much the people around them feel like they belong. And so, going back to that idea of love and safety and belonging, if you can measure that and people around a particular quote unquote leader can feel like they truly belong, then that might be a reflection of the leader themselves and that might be a way to measure their success in terms of how they're leading and what kind of work they've done on themselves.

Speaker 2: 17:26

Yeah, I think that I want to be clear what I'm demanding demanding is a tough word what I'm suggesting is that, above and beyond the very real and necessary work of building fiscally sound, profitable, sustainable organizations and businesses, above and beyond that is this other realm, and in that realm is a realm of deep and powerful leadership that thinks about the future, that thinks about what I would refer to as our descendants, that thinks about the people who have less power than we do. You know, I've been out talking about this book for a couple of months now and I get a lot of pushback not a lot. I get much less pushback than I thought I would get. But a lot of people will say but that's hard. And I say yes, it is. And I say I believe in you.

Speaker 2: 18:42

I believe in your ability to walk in Chugam, I believe in your ability to build fiscally sound, thoughtful businesses that build meaningful products that the world needs. And I believe in your ability to do that in a humane way that centers your developmental efforts on creating a sense of inclusivity and belonging for everyone. And I understand that you will fail to achieve that goal, and that's okay. You still have to try, because the work is not in always succeeding in everything. The work includes trying. So there's a little subtle distinction I'm making for you Is that it's not people instead of profit, it's both simultaneously, and as a result, you might have to sacrifice a little profit, that's true, but better to sacrifice a point or two of profit than to sacrifice a human heart.

Speaker 1: 20:10

So when you go around and are speaking about this book or coaching people these days and you start to ask them these deeper questions about how they've been complicit in this case now with reunion, it's how have they been complicit and how have they benefited from the systems that are in place that allow for othering? So when you're asking that type of question, what are answers that you're getting? What are people saying to that question?

Speaker 2: 20:45

Oftentimes it takes their breath away. Oftentimes they feel uncomfortable. Oftentimes Dan Harris, who's a dear friend, founder of 10% Happier and the author of that book, wrote in his endorsement something to the effect it's not enough. He wants us to be a better human Now, he wants us to make the world a better place. Yeah, that's true. That's true. So what do they say? I have encountered, sometimes, a defensiveness. I've tried really hard already, jerry, and sometimes though most times I feel relief. I feel like people are saying to me thank you for saying the things that you're saying, because they're not used to someone who walks around in the meat sack that I carry pointing out that I have benefited from the position that people who look like me hold in this American society in 2024.

Speaker 2: 22:25

And I acknowledge that with that benefit comes a responsibility to move what I can move, to try what I can try to speak up and to speak out when I see injustice. Because here's the thing, arjun, and I know I'm particularly strident in this book. I know that some might even call it political. I don't think it's political, as in I'm taking a political party's stance. I'm taking a stand against hatred, I'm taking a stand against dehumanization, because the consequence of dehumanization is genocide. And it is happening on our watch. It is happening throughout the world. It is happening on the streets of the United States.

Speaker 2: 23:43

Here's a fact that many people will not connect there's all this debate about DEI programs and whether they're helpful, and all this. What the efforts for equity are about is to make our society safer, more loving and more capable of belonging for everyone. How can we have that happen when gun violence is the number one cause of death for children under the age of 17? In the United States in 2024. Gun violence, gun is pulling a trigger and killing our children and yeah, I know the impulse is to say I'm a CEO. What can I do about it?

Speaker 2: 24:54

As I say at one point in the book, we who lead cannot heal all that ails us, but we can heal a hell of a lot more than we pretend. And there's a through line here, my friend. There's a through line that links anti-immigration efforts to anti-black racism, to anti-Asian racism, to anti-Semitism, to Islamophobia, to transphobia, to the denial of civil and human rights and the right to healthcare of your choosing, and gun violence. There is a through line, and that through line is the other person who does not look like me is a threat to me, so much so that they must be dehumanized. As I said before, it's just a short walk between dehumanization and genocide.

Speaker 1: 26:15

But a fine line. That's right. That's right.

Speaker 1: 26:21

One of my biggest takeaways from that and reading your book and listening to what you just said was something I've been thinking about is one of the primary reasons people need to read this book is because it's going to connect you with the person that you're looking at. If you do the work on yourself, if you do the work on finding out the truth about yourself and your origin story, you're going to look at the world differently because you're going to look at the person you're having a conversation with as also a person who has ancestors, who has descendants that went through the ups and downs of life. For you to get, for that person to get to that point and for me to get to my point, for us to have this conversation, generations of people had to endure hardships and good times, and just understanding that everyone has an origin story I think is the way to practice the skill of empathy in this case, because I would argue, very few people are really walking around looking at the world and looking at people like this. But if you can actually do that, you will separate yourself as a person and as a leader because you're connecting with people. It's literally just the basic human element of. We are both humans. Let's accept that and understand that we have a line of ancestors that got us to this point and I really find that really interesting.

Speaker 1: 27:47

Maybe you'll find this interesting because in the context of some recent news where 23 and me has lost 95% of its value, I find that kind of interesting because you have a company here who faced financial hardships because people would get their ancestry tests done once and they may not have gotten the results they wanted or whatever the case may be, and so you have a company in the macro that's declining in value. But if you actually did the work yourself in the micro and in the silence when no one's watching, you're actually increasing your value. So I don't know, I was connecting a couple pieces there of just like, look what's going on in the macro with a company like 23 and me, think about what you can do personally and then think about how you can exercise and practice empathy with the person that you're having a conversation with.

Speaker 2: 28:39

Yeah, I am surprised at the response that people have given me in reunion because, as you point out, part of what I call the reunion journey is understanding the true stories of your ancestors, and by true story I mean not just the myths that we spin about their experience, but as much of the reality as you can grasp and to understand the ways they may have lived up to those aspirational, mythological ideals of who they were and the ways they may have come short, fallen short of that. And I'm surprised that people are so fascinated by that aspect of the book because they're taken by the journey that I go on. That leads me all the way back to visiting my biological grandmother, my father's biological mother's grave in Ireland and, as a both, a real journey for me into the past. What were the sights and smells and how did the slant of light look in that small townlet that gave birth to my grandmother?

Speaker 2: 30:14

But you do not have to know the genetic biological connection to those who to what in the Irish Constitution or the Irish Declaration of Independence would say the dead generations. You do not have to know the specifics to connect with the stories of the ancestors so that and you're right you can create the ground of empathy and the compassion. I challenge anyone other than a sociopath to connect with their own kinfolk. You know, there's a section in the book where I talk about. I'm walking through the cemetery and I talk about claiming as kin those dead generations, those dead and buried in this hollowed ground, even if they were not my relatives. Claiming kinship becomes the ground by which on which we can then claim kinship across the divides that lead to children being murdered. Thank you, it is.

Speaker 2: 31:47

If he went on this exit.

Speaker 1: 31:48

Oh sorry, go ahead.

Speaker 2: 31:49

Yeah, I was just going to say it's a lack of empathy and it's a lack of kinship, but say more.

Speaker 1: 31:54

Yeah, no, I was going to say that in preparing for this conversation, I started asking my own parents some questions about, like where we came from. What do they know. I was like who came before you? I don't know Anyone really passed my grandparents, like how did we get here? And I found it was pretty interesting. I don't know how true this is, but from our own personal family experience, like in India, they didn't really have, they didn't really keep records of people, and so the stories and the traditions of former family members is often kept a secret or held back because a lot of people don't really know the details to share. So I found that kind of fascinating, because you might be in a country where, yeah, they don't really have records of the past, so that kind of makes it a little bit more difficult.

Speaker 2: 32:47

Or your ancestors may have suffered in enforced diaspora. If they were enslaved and taken from the continent of Africa, for example, to the continents of North or South America, then the ability to trace yourself all the way back, other than, say, through genetic testing, is really limited. Yeah, but I interrupted you.

Speaker 1: 33:11

Oh, it's okay, it's fine, we're having a conversation and so you know. So I tried to just dig even into like, okay, what caste do we come from? And you know, we come from the warrior caste, and that, just that insight just kind of helps me understand, like, why I'm driven a certain way. I think you know why I feel like I have this strength in me, and so I was just kind of thinking about, like, if I can just ask a few questions about my own history, my own past, maybe that's my way of realizing my own self, worth realizing that there is strength in me and realizing that, like, if I close my eyes and just visualize all my ancestors and the generations before me, then I will always feel like I belong.

Speaker 2: 33:57

How did it feel having that conversation with your parents?

Speaker 1: 34:03

It was. It brought us closer. It felt great because these were questions. They likely unexpected were. You know, it was unexpected for them for me to ask these types of questions. This is the type of conversation that we don't typically have and it kind of got them thinking about like, yeah, you're right, like where, what was our past? Like, what were the early you know ancestors? Like, and you know, kind of pulling from your book, I'm like imagine if we find out that there's people in our family that were left off the family tree for whatever reason you know, wouldn't that be fascinating to learn about? And so it just kind of turned into more of like a fascinating conversation around the possibilities that exist when you try to, you know, look at your origin story.

Speaker 2: 34:49

Well, here's a brilliant, beautiful example of what you're talking about, and I do spend quite a bit of time in the book talking about family secrets and who gets dismembered, who gets unremembered. In effect, in the afterward I had three friends, colleagues, three different women share their stories of belonging and they come from different social locations. And one woman in Virginia writes eloquently about her family's careful tending of a family tree in the form of a Bible that got handed down from generation after generation, and she asks a really profound question relevant to her own identity what happened to my queer ancestors? Were they written about? What happened to the ancestors who may have experienced questions about their own gender identity? See, there's a phenomena going on right now, which is that somehow these feelings are new and is a consequence of kids watching videos on TikTok Other fucking nonsense. Okay, but because we erase people from our own family trees, what happened to the uncle whose mental illness was so profound, whose depression was so profound that he killed himself? We don't talk about these folks, and so part of the reunion process is to reunite, if you will, with all of these people, to, as I say in the book, turn these ghosts from unremembered people who haunt our families and welcome them as ancestors as well, so that we have not only an inkling of to whom we belong, who's are we, as my friend Parker Palmer writes in the introduction to the book, but what is the fullness of that kinfolk Femininity of the negative, so that I can land in my own sense of belonging in a way that is robust and full, and then to turn it outward so that I can hear your story of belonging?

Speaker 2: 38:06

What I'm betting is that if I can induce some few thousand people to do this work, that they will then turn around and look at, say, what's happening on the southern border of the United States, not through the lens of a political machination, not in service to nefarious forces that would drive us apart. I mean, we are talking about civil war in the United States right now. Like what are we talking about? You know, right now I'm in the state of Texas and a taxi driver today asked me what do you think about this conflict between the state and the federal government over who controls the border? But if we can do this work and we see someone desperately trying to cross the Rio Grande, not as a threat but as someone not that dissimilar, not so dissimilar.

Speaker 2: 39:21

I don't mean to say that there's a false equivalency between, say, immigrants who came through Ellis Island and immigrants who have suffered horrendous treatment in a march up through Central America, through Mexico, trying to make it into the United States. But there's enough similarity that we might actually generate empathy. You know, call me a pock-eyed optimist, call me a Buddhist, but the basis of the alleviation of suffering is compassion for other people. I mean, this is the mind blowing cheat code that Buddhism offers you want to feel better, love someone else. It's really that simple and that hard.

Speaker 1: 40:23

Yeah, there's a concept, I think it's called mudita in the.

Speaker 1: 40:28

Buddhist tradition, where it's like if you want to feel joy, feel joy for other people, right, yeah, I mean the whole conversation around the border versus them simply being humans. I think that's an interesting one, because there's elements of both. Right, yes, they are humans, and we all are seeking better, and that's what connects us all, but, at the same time, I can see the viewpoint of how people are being tested and are fed up with the amount of people that are coming across, so it's two different conversations. At the base of it, though, is a human seeking a better life, and that's something we can all relate to.

Speaker 2: 41:13

It's two vantage points on the same challenge. They're not in opposition. As I said before, I'm 60 years old. We have had a crisis on the southern border of the United States for 40 years. We have had a broken immigration policy with half-assed measures for as long as I have been voting.

Speaker 2: 41:42

So here's the question, and this is a question that I insert into the entire dialogue implicit in this book who benefits when the crisis on the border remains unsolved? Who benefits when there's a war in the Middle East that seems continuous and never ending? Who benefits? Because if you really want to understand the way societies work, you have to look at who benefits from war, from destruction, from dehumanization, and almost always it's someone seeking to stay in power. Who benefits when we are at each other's throats? It's neither party, because there's no winning, but somebody and look, I'm not queuing on, I don't have conspiracy theories here.

Speaker 2: 42:58

I don't envision individuals, but in some cases there are individuals who benefit from problems, systemic problems remaining problems, and you know who's not benefiting the average American citizen in El Paso. They're not benefiting. But you know who also isn't benefiting. The average immigrant would be immigrant from Central America trying to cross the Rio Grande. They're not benefiting either. So who's benefiting from this problem that has not been solved for 40 years? Because here's the truth, and this is true at the individual level and it's true at the organizational, systemic level Citizens persist because they need a need. They provide a benefit. Now, the benefit may be neurotic, but the need is being met.

Speaker 1: 44:12

And so the classic follow the money, follow the power. That's exactly it.

Speaker 2: 44:18

Follow the money, follow the power. We're all being subjected to this kind of sleight of hand. Pay no attention to what's really going on over here. Look at this crisis over here. Look at this crisis. Oh, that person's a threat. Oh, no, no, that person's a threat. Stop, you know, it's a threat to all of us. Dehumanization and silence and silence. God bless you for saying that that's right. Silence implies complicity. Elie Wiesel said silence always benefits the oppressor. Neutrality always benefits the oppressor, always. So who benefits from neutrality? Hey, it's just business.

Speaker 1: 45:23

I'm going to take it a couple of beats back, just reflecting on the concept of unsaid things, unspoken feelings, tying it to origin stories. I'm curious your thoughts. So in what ways do you feel like the silences in our family stories is impacting our ability to connect with people? Is it because we're simply uncomfortable with certain truths?

Speaker 2: 45:50

I mean Well, I think, because we're not practiced in the art of naming things, we're practiced in the art of sweeping things under the rug.

Speaker 1: 46:07

We're all really good at that.

Speaker 2: 46:09

We're really, really good at not saying, hey, there's a problem here, right, Especially if that naming that problem might produce guilt or shame. And so we create this sort of collective silence, if you will, and then the person who is suffering might feel erased or annihilated. Now, if we take that activity out of the realm of the family and put it into the realm of the larger family system or our society as a whole, we end up being complicit in the erasure of people, more than not, who have less power than we do.

Speaker 1: 47:12

That's mind boggling to think about, because that reduces their feeling of feeling sufficient, it reduces their feeling of self-worth, it reduces their feeling of belonging. And so all of this is kind of manifesting in all of the challenges that we face, whether we're an individual contributor trying to showcase micro leadership acts from the position that we're in, or we're titled as a CEO or a founder, and I feel like a lot of our challenges are kind of just manifesting themselves from the feeling that we have a lack of belonging, a lack of self-worth and we feel insufficient.

Speaker 2: 47:53

That's right. That's right. And what I'm enjoying about the look on your face is that you're seeing the connections between all of these things. The dots are connected. This was my journey.

Speaker 2: 48:08

I set out to say to myself okay, listen, buddy boy, you think you're so smart, you think you can talk to the world about better humans making better leaders. But, as I wrote about in the book, my daughter called me to task and said dad, it's not enough to be an ally, you have to be a co-conspirator. That process worked its way on me. I'm not saying to you you have to do this work. I have to do this work. I have to continue to lean into these hard truths. If I am going to live up to the exhortation from my daughter to be an active co-conspirator for systemic belonging, then I have to put my heart and my ass on the line.

Speaker 2: 49:12

I would tell you it would be much easier for me to write a book that was called Reboot to more stories that will make you cry. It would be so much easier. I could have done it in a year. It would have been fine. It might not have sold well, but who cares right? Instead, I wrote a book that challenged the hell out of me, because the stakes are that high.

Speaker 1: 49:40

Yeah, it's almost like your ancestors were calling on you to do this, Because most of the book is really just your personal story and your experience. Just think about me reading it. This is the first time I'm really thinking about this concept. I can already imagine, okay, if I really went deep into my history of my family, I might be forced to face some really uncomfortable truths. I know from reading your book you were also in that situation where you had to face some uncomfortable truths about your own family, but you were willing to do it. It goes back to your original comment at the beginning of this conversation around. Sometimes you have to stop and turn around and actually look at the tiger that's chasing you. That's right, yeah.

Speaker 1: 50:27

There's so many elements to you, sharing your story because you did the work versus someone like me or an outside or another person listening who's at the precipice of taking this leap. You're going to have to face yourself, you're going to face the hardships, but it's going to be better for you as a person and then better for you as a leader.

Speaker 2: 50:49

That's a necessary step in the alleviation of suffering, which is our life's work, our job. The reason we incarnate in these bodies is to alleviate suffering, our own and that of those around us. I firmly, wholeheartedly believe that how we alleviate suffering is different for everybody. Build a great company that builds a fantastic widget. The fact that that's what we're called to do, that's why the breath of life was placed inside of us. I'll be damned if I leave this earth not having tried my best to do that task.

Speaker 1: 51:49

In whatever way I can do it it starts with me, and then me doing the work on myself is going to get reflected around the people around me, A lot of this conversation. Also, I'm reminded of concepts from your first book Reboot, because a lot of this is like okay, we are directed in our life by so much of what's going on in our subconscious, so we have to do the work to bring that up, bring it to the forefront, make it conscious. I just think about all of the things that we've talked about. There's also two other questions that you like to ask a lot of people, and that is what am I saying? No, what am I not saying that needs to be said, and what am I saying that is not being hurt? I feel like those are two also equally important questions in this conversation. I don't know if you can just spend a couple minutes and just talk about why you emphasize those two questions and maybe how those two questions have unfolded in your own life and what you've learned from those questions.

Speaker 2: 52:50

Well, there's those questions, and then what's being said that I'm not hearing? I think that those three questions are really key. They have been the undergird of so much of my own personal development, but also so much of the work I do as a coach. Can I add a new question to that list? This stems from something I wrote about in the book where James Baldwin.

Speaker 2: 53:23

At one point I was really struggling in the book, in the writing, and it was James Baldwin's birthday, and it was often the case and social media was flooded with quotes by James Baldwin. One particularly stood out for me and it came from an interview he did with the New York Times and in it he says when I'm writing, I'm writing about things I do not want to know. The question that comes to me is and what is it you don't want to know? What is it that you don't want to know about your family? What is it that your family didn't want to know? What is it that you don't want to know about the world? Because there are things that we will fully choose not to know and therefore not speak about.

Speaker 1: 54:14

Yeah, I mean that goes back to your comment a couple minutes ago. Around you know, there's a high chance that all of us, we might have a queer family member in our history. Just given the statistics and how nature works, there's a high chance.

Speaker 2: 54:28

Yeah, that's right. That's right. And what is it that our family did not want to acknowledge? And the reason I point us in that direction is because, on disconnecting from those facts leaves us less whole, which then makes it really really hard for us to connect to other kinfolk and see the fullness and wholeness of them. So for me and I hope you're experiencing this this has been an unfolding process. So the work I did and I wrote reboot almost retrospectively. This is what happened to me. Here is what I learned, and in this book, this is what is happening to me. Come along on this journey with me, because maybe you'll learn nothing or two about yourself as well, because I'm not some fully enlightened being looking back and saying this is the way I'm, just like you, your story is my story, our stories are the same. I may not be from the warrior caste, but I know those feelings. Not to the same degree, not to the same extent, but I know those feelings and that binds us together as kinfolk.

Speaker 1: 56:17

Yeah, and that's one of the secrets to being able to demonstrate empathy with someone is that ability to say hey, I may not know exactly the experience that you're going through, but I do know the feeling of, whatever the case may be, I do know the feeling of loss, I do know the feeling of grief, I do know the feeling of excitement. So you know, it's just one way of really connecting to someone. The language you can use is you know, I don't know exactly what you're going through, I'll never say that. I do know what it's like to be in your shoes, but I do know the feeling of. And then you fill in the blank and that's how you and I can relate and I can relate.

Speaker 2: 56:56

Yeah, and this is how I relate.

Speaker 1: 56:58

Yeah, so that's like the art and craft of having a caring conversation right there.

Speaker 2: 57:04

Arguably the art and craft of being a human.

Speaker 1: 57:07

Yeah, exactly, exactly yeah. And I think from this conversation and for anyone who picks up reunion, I mean, it's really about taking a close look at everything as you write in the book, examine it all and travel your road again.

Speaker 1: 57:23

And when you think about that in the context of self-discovery, personal growth and leadership. That's what's going to help you separate yourself and be the person who can create the belonging and love and safety that people are really yearning for. That's it. You got it Well, jerry. I really appreciate the time I mean again for someone like you to spend an hour with me again. It's something that I'm truly you know grateful for. It's an experience I'm never going to forget, and I will do my small part to help make the world a little bit better by sharing this.

Speaker 2: 58:07

That's more than a small part. That's the whole point of it all. So thank you for having me on the show and thank you for talking to me, and we'll be in touch.

Speaker 1: 58:17

Sounds good, jerry, appreciate you. Take care, buddy. Thanks, kelly.