047. Jerry Colonna: Why Better Humans Make Better Leaders

[00:00:00] If, as I assert that better humans make better leaders, then what is the responsibility of a better human to create

[00:00:09] what I refer to as systemic belonging?

[00:00:11] We live in society where there is systemic other, whether it's racist, misogynistic, transphobic,

[00:00:22] homophobic, we are constantly turning the other into someone who has less than.

[00:00:29] And to my mind, the only answer to systemic problems or systemic solutions.

[00:00:38] I'm Arandor and this is Remake, a podcast about design, systems and society.

[00:00:44] In each episode, I talk to someone who's trying to change our lives for the better in some

[00:00:48] meaningful way, with a three-year new product, new venture, or new way of looking at the world.

[00:00:54] And I try to understand how they came to it, what makes them tick and what we can learn from them.

[00:01:00] Jerry Colona is the CEO and co-founder of reboot.io, an executive coaching and leadership development firm,

[00:01:08] whose coaches and facilitators are committed to the notion that better humans make better leaders.

[00:01:15] For nearly 20 years, he has used a knowledge gained as an investor, an executive, and a board

[00:01:21] member for more than 100 organizations to help entrepreneurs and others to lead with humanity,

[00:01:28] resilience and equanimity. He's been called the CEO whisperer, and the coach was the spider

[00:01:34] tattoo, and has taken refuge in the Buddhist Dharma tradition.

[00:01:39] Previous to his career as a coach, he was a partner with JP Morgan partners,

[00:01:45] the private equity arm of JP Morgan Chase, and before that, had launched flattiron partners with

[00:01:51] partner Fred Wilson. Flattiron became one of the most successful early stage investment programs

[00:01:57] in the New York City area. Today, he lives in Boulder, Colorado. We had this conversation

[00:02:04] in mid-March 2022 and that's two years into the world-ride outbreak of COVID and a couple of weeks

[00:02:13] into Russia's invasion of Ukraine. I was excited and nervous to talk to Jerry who is famous for

[00:02:21] making podcast-race cry. We've also had a brief chat months before preparing for this interview,

[00:02:27] and I've already had a taste of his radical inquiry approach to coaching.

[00:02:32] So as expected, this did not end up being a regular interview. While we got to explore his

[00:02:39] history and his ideas and his childhood a little bit, Jerry turned his radical inquiry on me

[00:02:46] as expected, and you'll get to hear a pretty detailed coaching slash therapy session on this podcast,

[00:02:52] and dive deeper into my fears and insecurities along the way. I have to say I found it

[00:02:59] deeply therapeutic both at the time and now weeks later when I'm relistant. I hope it will be

[00:03:06] interesting to you who I'll. So we covered many topics here so that we'll give you a little bit

[00:03:12] of an outline. We talked about COVID and how it exposed the interdependence but also the inequality

[00:03:20] of American society. Then we had an really interesting discussion of leadership in the context

[00:03:26] of the Ukraine war, and how when leaders don't address their vulnerable and wounded parts

[00:03:34] that always can express as itself an violence. And we talked about that in the context of

[00:03:39] malignant narcissism with Putin and also with Trump. We covered his childhood and how he became

[00:03:46] keenly aware of how people around him are feeling. We talked about his career in venture,

[00:03:52] and how he veered from that into coaching. Then we go a little bit into my therapy session where

[00:04:00] you start to pointing his radical inquiry, his coach mind on me and we dive into

[00:04:11] my tendency to hide to not want to be very active on social. At least not publicly on Twitter.

[00:04:18] My fear of being judged, my fear of not being seen or not being appreciated. And you really

[00:04:24] get to see Jerry's mind that work and how he works with me and helps me understand and make peace

[00:04:30] with these feelings and find a way to work within them. And we talk about what it means to bring

[00:04:36] your whole self to every challenge in your life at work in any other moment. And we talk about

[00:04:44] how everything is an opportunity for self growth and to practice that.

[00:04:50] Finally we cover his reboot system and method and book. And we talk about how everybody

[00:04:59] life basically is looking for love, safety and belonging. This was a very different, very meaningful

[00:05:07] process for me. And I hope that you'll find it beneficial as well. It definitely affected the way

[00:05:14] that I approach putting myself out there and allowing myself to be more visible on social media.

[00:05:20] And shortly after this interview was recorded, I definitely did start being more vocal.

[00:05:27] And an amazing thing happened as I start being more vocal on Twitter and other platforms.

[00:05:32] We got more and more downloads for this podcast of the podcast that I'm growing very, very

[00:05:36] rapid. And so I guess I owe a big thank you to Jerry for challenging my assumption and helping

[00:05:43] me pinpoint these insecurities. Jerry assured me that this is helpful to other people to hear.

[00:05:50] I really hope that we prove true and that you'll find this episode really helpful to you in

[00:05:56] your journey as well. This conversation with Jerry's one of a dozen or so weekly conversations,

[00:06:04] we already have lined up for you. The thinkers, designers, makers, authors, philosophers,

[00:06:11] entrepreneurs, and investors were working to change our world for the better. So follow this podcast

[00:06:18] on your favorite podcast app or head over to remakepond.org to subscribe.

[00:06:25] And now let's jump right in with Jerry Colona. All right, I'm sitting here with Jerry Colona. Jerry

[00:06:36] welcome to the show. Thanks for having me to delight to see you again. We are in transition.

[00:06:43] So in the recent couple years, I started with like a big COVID exploration and I feel like

[00:06:51] now I have to also add the Ukraine exploration before we dive into our own conversation. So I'll

[00:06:58] start with COVID. I would love to hear how it affected you personally, how it affected you professionally,

[00:07:03] and then what surprised you? Well, you know, we're recording effectively two years around

[00:07:10] two years since the wave really hit the United States. So the last week or so I've been particularly

[00:07:19] mindful of what life was like two years ago. Like a lot of folks, I think it was a series of

[00:07:28] different experiences. There was the belief that it was going to be relatively short time.

[00:07:35] What felt like potentially a long time like a month that we would be struggling with this?

[00:07:40] And so there was a tremendous amount of anxiety wrapped around uncertainty.

[00:07:45] Then it evolved from me into a kind of interesting experience because in the United States,

[00:07:54] in particular shortly a few months afterwards we had the murder of George Floyd,

[00:08:01] which brought into undeniable shocking experience of the reality of so many folks.

[00:08:10] Already, I am a white straight man and I do not experience the sense of authoring

[00:08:20] that many others do. And all of a sudden it became in my mind

[00:08:26] inextricably linked that there was this kind of interesting dynamic going on of

[00:08:33] a profound demonstration of our interdependence because that's kind of what a virus does.

[00:08:40] I could make you sick 5,000 miles away just by passing it from one person to another. And so therefore

[00:08:48] you need me to take care of myself and I need you to take care of yourself. That's a great

[00:08:54] demonstration of interdependence but it also became a stark reminder of the injustice and inequality

[00:09:02] in our societies, especially the healthcare inequities. During that period my part of Allianai

[00:09:08] bought a farm outside of Boulder we moved to a four-acre farm with three horses and

[00:09:16] 19-year-old cat named Ginger. And the like again a dissonant experience I got healthier, I got

[00:09:25] calmer, I began eating better. You know the loss of travel in my life was a net positive.

[00:09:34] And then you know lastly in terms of work the demand for what I and my colleagues do

[00:09:42] clearly went through the roof because it's just so much suffering out there. This week we had our first

[00:09:50] in person all team meeting for the company into and a half years and several team members had

[00:09:56] never met each other before. And I know that's not a unique experience. What surprised you about this?

[00:10:04] Did you feel like you learned anything about people humanity? I think about me personally was

[00:10:11] I realized you know in a book I wrote there's a chapter about needing to stand still even

[00:10:19] where all your hair is on fire. And I wrote that cognizant of my tendency and many people's tendency

[00:10:27] to use motion to cover suffering, to cover up for a sense of inadequacy. So if I move fast

[00:10:37] and it proves that I'm productive and if I'm productive then I'm valuable and if I'm valuable

[00:10:42] then I'm really a love. One of the things that the pandemic did was a kind of slow rolling retreat

[00:10:55] where you had no choice but to sit still, where a choice to actually move and go somewhere

[00:11:05] and do something required to know the enormous amount of attention like am I going to be safe?

[00:11:12] How many people are going to be there? Should I wear a mask? Should I not wear a mask? Will they

[00:11:16] be vaccinated? Will they not be vaccinated? Right. And when I took my refuge vows as a Buddhist

[00:11:23] almost 20 years ago, I added a precept to not eat animals. And not because I have a judgment

[00:11:33] about vegetarianism or not, but because I wanted to slow the heck down and think before I put

[00:11:40] something in my mouth. And in a sense COVID did the same time for me. I had to think before I acted.

[00:11:50] Now it's such a cognitive dissonance where even let it let alone people who are less

[00:11:59] well to do or in countries where there's less of a functioning healthcare system. Even among

[00:12:06] my friends who are in the same theoretically in the same category than me, I had a similar experience

[00:12:12] to yours. I lost weight. I became healthier. I ate better. I read more 19th century novels

[00:12:18] and you know, and then I had friends who were deeply deeply suffering from not being able to be around

[00:12:24] people trying to understand that kind of the same event can have such such a very urgent impact

[00:12:31] on people. That's maybe the thing that I learned the most. And I think that divergence, I second

[00:12:36] that and I'd add to it that that divergence could be within the same human body. Right.

[00:12:42] I can be both healthier and suffering more mentally. It has been a profound experience

[00:12:52] and one that I hope we collectively, societies do not lose the lessons because they were hard one.

[00:13:04] I mean there are a whole generations of children who's learning. It's been set back. There are

[00:13:09] political divisions in the United States that sometimes I wonder if they'll effort be healed

[00:13:14] and it's incredibly challenging. And implicitly that is an opportunity for even greater consciousness.

[00:13:23] Now which leads me to the war in Ukraine, have you been able to process that?

[00:13:31] I have no extra insight into what's happening there. Just people find themselves

[00:13:37] suddenly positioned as experts in pandemics and viruses. They suddenly find themselves experts in

[00:13:45] war. I'm not an expert in that. So I'll put that to the side. But I will say that one of the

[00:13:53] things that I've been saying for many years, and one of the ways in which I dedicate my life

[00:13:59] in support of leadership is that when those who hold power refused to grapple with the parts

[00:14:08] of themselves that really are rooted in woundedness, then violence is the consequence.

[00:14:20] And whether it's quite frankly to get a little political on my side for a moment,

[00:14:27] whether it's Donald Trump really not being able to resolve conflicts with his father,

[00:14:32] resulting in a kind of narcissism that was just awful to experience or Vladimir Putin's

[00:14:40] attempt to somehow assert himself because his reported net worth of $100 billion isn't somehow enough.

[00:14:50] And that there's this gaping hole of need there. And I know we don't want to see that piece of

[00:14:59] it. We want to be angry about what's going on. But the truth is that when we raise children

[00:15:07] without the ability to process their suffering, violence happens, I hope that we come to understand

[00:15:17] that malignant narcissism among readers leads to a kind of horrific fundamentalism

[00:15:25] in constantly making enemies of other people. When a sense we have a collective responsibility,

[00:15:33] not only to preserve democracy against authoritarian structures, but to stand up to kind of

[00:15:43] a belief system that if we imbue the strong man leader with incredible powers

[00:15:54] that somehow we as a people will be safer, we have to confront the fears that lie within

[00:15:59] our societies that have us turned to authoritarian, strong men as leaders and support them.

[00:16:07] So long we did analysis. I said, I wasn't an expert. It's sort of a good idea.

[00:16:12] When it's about leadership and in some ways I look at this and not even falling

[00:16:16] put in for some years, I'm a student of history. And he was to me clearly someone who just didn't

[00:16:26] get what the big fuss is about freedom and individual rights. This doesn't get it.

[00:16:33] In a way I think this is like the world's most expensive lesson that you could possibly have

[00:16:39] for Putin where he just assumed it doesn't have value. And if I come in with some soldiers,

[00:16:47] then they'll give in because that his power is all that matters and suddenly he sees, oh wait,

[00:16:52] there's okay, I have 100,000 soldiers but there's 44 million people saying no. It's a very clear

[00:16:58] case because you know part of the same country just a couple decades ago and now they're like no,

[00:17:05] you're not taking us back. So in some ways I wonder if he's wondering about this. It's like wait,

[00:17:11] is it so different to live under Russia than it is to live in a democratic society that millions

[00:17:19] of people would just make multiple cocktails and go go fight in the street? He must be wondering

[00:17:26] because he wasn't that was clearly that he wasn't expecting that. He might be wondering,

[00:17:30] he might be wondering but I would be surprised if he's wondering. I'm not a psychologist and

[00:17:37] I'm not qualified to diagnose but I suspect that he like a lot of authoritarian figures in those

[00:17:45] drawn to authoritarianism have a profound awakening narcissism at root and narcissism itself

[00:17:55] is rooted in a deep and profound wound. And one of the consequences is that the other person does

[00:18:02] and exists, right? You can always tell you're engaged with a narcissist when you walk away

[00:18:10] feeling annihilated, feeling wiped out. And one of the root causes of this kind of violence is to turn

[00:18:19] the other person into a non-human to not see their humanity. And I suspect although I don't know

[00:18:29] that a young 19-year old Russian soldier hops out of a tank with a rifle drawn and looks out

[00:18:37] and sees a woman who looks like his grandmother. And that kid is not a narcissist,

[00:18:44] then kid might very well be dropping his rifle and saying what the hell am I doing?

[00:18:50] Let's hope that's part of what's going on here. You said it to profound lesson for him.

[00:18:54] Unfortunately, it's a lesson for all of us that we have to consistently and constantly

[00:19:01] elevate our awareness of humanity. That person across from me in my anger

[00:19:14] can cease to be a human being. And once that happens, all bets are off. We have seen this time

[00:19:22] and time and time again. And unfortunately we continue to have to learn this lesson

[00:19:30] that in a blink of an eye, we can turn someone that we think of as a sibling, Ukrainian

[00:19:37] to Russians into non-humans. And then we can pull a trigger. And that's the movement

[00:19:48] that we have to be careful about because that's not isolated to Vladimir Putin by any stretch

[00:19:55] of the imagination. That propends to exist within all people. And that's what we have to push up against.

[00:20:03] That's what the wisdom traditions in every society have taught us. You want to understand

[00:20:10] every single religion, it boils down to one simple thing. See the other as a sibling,

[00:20:18] not as the enemy. And whenever we see the other as the enemy, we are going against

[00:20:28] all of the wisdom traditions that are the best of humanity. Thank you for that.

[00:20:36] So we have kind of a way into, I want to see the meat of our conversation, but the middle

[00:20:43] part of the sandwich of the conversation. I have this question that I usually ask which is what

[00:20:51] something you learned in childhood or early in life that is still guiding you today,

[00:20:58] still very alive in you today. I'll reframe the question just lightly because I don't see it

[00:21:05] so much as a lesson, as much as a skill that I developed. And that is this notion of hyper vigilance,

[00:21:13] but those who are familiar with my work, they'll know that I grew up with enormous violence

[00:21:19] and a household. I grew up with mental illness. I grew up with my father's alcoholism. And one

[00:21:26] of the responses, one of the adaptations I developed was to be keenly aware of how people are feeling

[00:21:35] constantly and keenly. And that permeates everything I do, everything I am as an adult. Even now

[00:21:44] I'm holding the back of my mind, stories you've shared with me of a friend who is suffering.

[00:21:55] When we're talking about universal suffering. So I've got one eye on the universal theoretical.

[00:22:03] Let's talk about the impact of the pandemic and another eye on your heart. And that's the

[00:22:12] positive aspect of that adaptation that I developed as a child. What I've learned subsequent

[00:22:20] to being a child is that I can use that to build an empathetic bridge so that I can be more close

[00:22:29] to the person and feel more connection even if it's just through a piece of software called squad

[00:22:35] cast, which we're using right now. And those are skills that have served you throughout life

[00:22:41] and probably are very much alive today in coaching and working with people and helping more

[00:22:47] alive today and me than they have ever been. Both as a leader, in my own company, and as a coach,

[00:22:55] and as a life partner, and as a parent, and hopefully as a friend. That means that there's

[00:23:02] some hope for people who are left with the similar legacy from their childhood. It is always hope.

[00:23:08] Yeah. There's always hope. Remember this line from Carl Young, I am not what has happened to me.

[00:23:16] I am what I choose to become. It's such a profoundly important statement of agency

[00:23:24] and for those who might resonate with stories of childhood challenges. Take a deep breath.

[00:23:33] The adult in you is capable. Your child survived. You are now an adult and you're fully capable

[00:23:45] of turning all that has happened into you into superpowers so that you can become the adult

[00:23:52] that you want to be. That is possible. It's hard, but it's possible. Yeah. Yeah, I'm sure this

[00:24:02] will be resonating with a lot of people that are resonating with me. Before kind of diving into

[00:24:12] you're doing and the current doing, I wanted to understand that transition because I think

[00:24:20] with those sensitivities and those skills, you actually went into the venture world

[00:24:27] for a while before blending where you are. How did you find yourself

[00:24:33] working at Flatiron Partners with Fred Wilson? I think this is a well-known story. What

[00:24:39] would the first steps that led you to that world and then let you out of it?

[00:24:43] My first job as an adult was working as a technology reporter for magazine

[00:24:50] and I'd gotten that job as an internship and I sort of pearly that until a full-time

[00:24:56] position and ended up staying with that company for nearly 10 years. It was at that time

[00:25:04] that I began to be exposed to the venture capital business really by happens dance.

[00:25:10] And so I actually joined a venture firm before starting Flatiron with Fred and I was there

[00:25:15] for about 18, 24 months. It was a miserable experience. I liked one or two partners but I really

[00:25:22] didn't like working with the folks that I was working with. There was a deep and profound

[00:25:27] values conflict which I internalized to as there's something wrong with me. I don't

[00:25:35] understand the venture business. That's sort of thing. So that was sort of the pathway through

[00:25:40] but I think if you wanted to look at a through line and this was true both in my time as a

[00:25:46] reporter and then my time as an investor and even my time today, I am driven by an

[00:25:54] insatiable curiosity. I mean, I'm the kind of dad that when my kids and I would be visiting

[00:26:00] something I stop and read every damn plaque. If I see something interesting at this point

[00:26:06] and I open up my phone and I go in Wikipedia and I try to find out the email. I just am endlessly

[00:26:12] curious. I'm going to reference the books over your shoulder. I noticed that you've got a copy

[00:26:17] William Blake's poetry. I noticed that you've got a lot of the rings on your other side, right?

[00:26:23] So there's a piece of my brain that's like sitting in saying okay we've got to have a conversation

[00:26:27] about that. We've got to have a conversation about Blake. My friends at Goatens book is over

[00:26:32] your shoulder, right? And it animates me. Even to this day I probably read you know a book a week,

[00:26:38] maybe two and one of the hardest things about reading books on Kindle is that I own immediately go

[00:26:44] and if I find some fact that I think is interesting in the book I'll look it up on Wikipedia.

[00:26:49] So it takes twice as long to read the book because it would normally. So that's really what

[00:26:55] motivated me. And then when I became an investor it was like a kid in the candy shop.

[00:27:03] You know interesting people all day long would give me an opportunity to talk about their best

[00:27:10] ideas. When we just riff, the problem was that by my late 30s that activity which was really

[00:27:21] in live and it was overshadowed by the negative aspect of feeling like I needed to resolve

[00:27:32] some deeper issues within me that was leading me to be outwardly successful but in with the

[00:27:38] remissorable. And that dissonance became unbearable to the point where I was depressed and suicidal

[00:27:46] and needed to make a profound structural change in my life. And so you know I referenced this before

[00:27:55] at 38 years old I had to just sit the hell down and stop moving and figure out my life. In

[00:28:04] hindsight now I see that it was part and parcel of a larger movement which we blindly refer to

[00:28:12] its midlife crisis but it was really more profound than that. It was the existential house

[00:28:19] of cards that I had built to survive my childhood and get into adult head collapsed. Thank God

[00:28:26] because it was inappropriate. And my heart broke open. Yeah. Can I share a bit of wisdom?

[00:28:40] Yeah absolutely. Yeah. So Parker Palmer is one of my teachers and he likes to reference a story

[00:28:50] that Jacob Needleman, the philosopher, shares if I don't get this right forgive me but it's a hascetic

[00:28:56] tale and the tale goes like this. The student comes to the rabbi and says to the rabbi

[00:29:03] rabbi why does the Talmud tell us to place the words of the Torah upon our hearts? Why does

[00:29:08] it not say place them in our hearts? And the rabbi says are hearts being the way they are as

[00:29:17] hard as it is? The words must be placed upon our hearts until our heart breaks open and the words

[00:29:26] can fall in. That story just kills me every time because implicit in it is said the wisdom,

[00:29:36] the divine wisdom can only come into us when our hearts break or specifically our hearts break

[00:29:45] open. Yeah and that openness is the key. I think that's what happened to me. It's beautiful.

[00:29:53] It resonates with me with what the Buddha said. I think there's a place where he says no one comes

[00:30:00] to the Dharma except through suffering and it's definitely true. I never, I know if it says more

[00:30:07] about me or about this but I never fully trust someone who doesn't seem to have suffered in life.

[00:30:14] Like it's like I don't even know how to relate to that. I understand the feeling. I understand the feeling

[00:30:21] if I may, let me talk a little bit like you're older brother. Be careful of romanticizing suffering.

[00:30:32] There is nothing romantic about suffering and I think that the wisdom in both of our stories

[00:30:38] in both of our quotes is less of a prescription than a description. It's not that the Buddha is saying

[00:30:49] in order to become wise you must suffer. I think what the Buddha is saying is suffering

[00:30:59] is a part of life and as we as he taught in the second noble truth, the denial of suffering

[00:31:06] increases suffering. Yeah and so the pathway is to understand that suffering is part of life. That's

[00:31:15] suffering. What do we do? I feel miserable so we tell ourselves or I tell myself there must be

[00:31:22] something wrong with me and so we exacerbate suffering. Instead of seeing the suffering as an

[00:31:31] experience of the universal humanity, you suffer. I suffer. You were wounded in childhood. I was

[00:31:41] wounded in childhood. Now, how do I know that? Because you're a human. Now what you suffered may be

[00:31:51] different from what I suffered but that doesn't mean you didn't suffer. I don't know. Does that

[00:32:01] frame me help? I think so. Thanks, Sam. You're listening to remake a podcast about design

[00:32:16] systems and society. If you're listening on a podcast app, you already know how to follow podcast.

[00:32:26] So please follow this one. If you're listening in a browser, just go to remakepod.org

[00:32:38] to find links to all the major podcast players where you can follow our show. So I resonate very much

[00:32:56] with a lot of the specifics that you share. So I think that high-per-vigilance or high-person

[00:33:03] sensitivity to people's moods is definitely something that I share. I think that for much of my life

[00:33:11] and actually this may be one of the things that are still very active today is really strong

[00:33:16] need that I need to be independent and I can depend on people. You know, I need to be okay on

[00:33:21] my own. I don't need anyone's approval. I recently made the decision to go on be more active on

[00:33:29] social media to promote what I think is great content that we're creating and it was really hard for me

[00:33:34] because I cut that part out of my life very intentionally. I don't want to be too active on social

[00:33:42] media because I don't want to care what people say about me and I don't want to get sucked into that

[00:33:47] realm. I mean in some ways it's avoiding vulnerability but also like I don't want to hear what

[00:33:52] people have to say about what I'm writing. Like, you know, I don't want to hear criticism. I don't

[00:33:57] want to care about criticism and I know that I do want to some level so I kind of show away from

[00:34:03] speaking up sometimes and so I think that's definitely a more challenging thing on the positive side.

[00:34:11] I think having grown up with a lot of disconnection and a lot of resignation, I became allergic

[00:34:20] to these things and it's led me to be one of the most hopeful and one of the most communicative

[00:34:31] people that I know. And you know my life is about design and working together connecting around

[00:34:39] solving things together. And so today I know hope and connection are core to who I am and it's

[00:34:49] because of I think this deep understanding of where disconnection and resignation leads you

[00:34:55] like you have seen the end of the other road and I just have refused to go there.

[00:35:01] May I share what I heard? Sure. I reflect it back to you. I experienced a brave man who showed me

[00:35:10] his tender heart and I am aware of the struggle what seems to be a struggle instead of complex

[00:35:23] for you. Because you care so much what other people say and feel about you,

[00:35:33] you're reluctant to put yourself out there and be vulnerable to that what they might say

[00:35:40] negatively and yet here you are putting yourself out there. Now sure,

[00:35:54] you might project into the guests. A genuine but somewhat defensive curiosity, I'll ask them to tell

[00:36:06] their story but I'll read it into the background to where it's safe. But the craving for the

[00:36:13] connection is quite powerful. Yeah, am I seeing things well? I think so, I think

[00:36:23] there's a longing to share from my own heart, from my own mind and this podcast is a safe

[00:36:40] way to start experimenting with that through other people by choosing the right people to

[00:36:45] bring on the show and asking them question, I don't speak and I am feel it from judgment

[00:36:51] at the same time I am thinking about how to break that barrier and also put myself

[00:36:58] more out there and it's a process so I think you're very much correct. So be careful right now

[00:37:07] there could be a little bit of self criticism that comes in. Sure, I ask these people to be real

[00:37:15] and authentic but I'm hiding behind the question. Easy, easy, your heart is tender. You have

[00:37:28] experienced suffering. You've probably been hypercriticized. You've probably experienced shame.

[00:37:35] This is an awful force in the world. And so that tender part of you needs a little care

[00:37:49] and acknowledging that will call for the adult and realize that in order to create the world

[00:38:00] that we want to exist, we're humans for example. You and I share this belief I think. We want

[00:38:08] human beings to find comforting connection when one another. Now, we want a world of empathy.

[00:38:18] In order to do that, mindful of the tenderness, the opportunity is to be brave,

[00:38:29] is to share. What do I mean by that? When I was 38 and I was entering my second deep

[00:38:40] profound experiences of depression, the books that came to me as life rafts were three

[00:38:50] hemachotans when things fall apart. Sharon Salzburg's faith and Parker Paul Mercellette your

[00:38:57] life speak. And the comment-in-nominated between those three books was the authentic presence of the

[00:39:04] author. There was no BS, there was no hiding. There was no die-dactic, finger wagging. Let me

[00:39:15] tell you how you should live your life, which is a kid from Brooklyn I would find an enathma

[00:39:22] and we're on the other way. The universal experience of all three of those books was that they showed

[00:39:29] their own flaws, their own vulnerabilities. They were real. You know years later, I had the

[00:39:37] great good fortune of becoming friends with all three of them. And in many conversations I've had

[00:39:43] with Sharon, she talked about faith being the most difficult book she ever wrote because she was

[00:39:50] fully present with her own suffering as a means of emotional connection to the other person.

[00:40:02] I offer that because that became a model for me and as a result I know that it has been healing

[00:40:10] for me. I think this definitely is some of the things that I write when I open up they are

[00:40:16] much more powerful. I haven't shared some of these things that outside of my circle friends because

[00:40:24] they're still a working progress, but I think that's absolutely right and that's also the feedback

[00:40:30] I'm getting about the podcast as I need to bring more of myself into it. And at the same time I

[00:40:34] also had feedback of what a wonderful spacious place you create for the other person which I do want

[00:40:40] to keep so there might be other channels. So notice notice the belief system that might be

[00:40:46] there for a moment, which is that if I show up I'm somehow taking space from the other person.

[00:40:56] And I want you to know that as a podcast guest this part of the conversation is actually more

[00:41:02] in lifeening for me. You know I'll take it all the way back to our conversation about

[00:41:09] authoritarian leaders and all that stuff. Let's imagine because I coach leaders. That's

[00:41:16] a magic for a moment that a leader showed up in the similar way that I'm suggesting you show up.

[00:41:24] We're talking about political leaders and we're talking about Putin. What's contrast him for a moment

[00:41:30] with Zelensky? Okay, is Zelensky being a real? Is he being vulnerable?

[00:41:38] I think more than that. He's showing up and saying this is my struggle. These are my people.

[00:41:48] My heart is breaking. Is he angry? Yes, is he flawed? Yes. But that's the kind of leadership

[00:41:59] that we really want to see in the world. When he shows up on one of his videos with his Ukrainian army t-shirt

[00:42:10] and his weeks old beard and his ragged, tired, bags under his eyes. I want to jump in the fox

[00:42:22] holen stand next to him. Yeah, another people do. Right? And it's not just because of the

[00:42:29] wrongness of the aggression that's going on but because there is a sensibility that this person

[00:42:37] isn't I'm gonna curse now, bullshit it. They're real with heartache and pain and suffering.

[00:42:45] It's like, and then it makes you feel like roll it my sleeves and let me do the work with you.

[00:42:54] Now, in a smaller scale translate that to your company. Yeah, I think that I have no problem

[00:43:05] sharing with anyone my anxieties around like, oh, I don't have never done sales before. I'm reading

[00:43:11] a book about it. I'm trying to figure it out. It's not something that's hard for me to share and

[00:43:15] be real about but I think maybe the most sensitive thing for me is like, this is how I see the world

[00:43:21] or this is something I really believe in and maybe it's not something that everybody believes

[00:43:28] and are maybe it's influenced by my perspective or something creative that I wrote.

[00:43:35] When you put yourself out there like that, what's the story that you tell yourself

[00:43:40] before you start feeling you fear? They're not going to get me. They're not going to see me. They're

[00:43:45] going to understand. They're not going to understand you. They're not going to see you. Just hang out

[00:43:51] in that spot for a moment. How deeply held is the belief? Is the fear that you're not going

[00:44:03] to be seen? You're not going to be understood. I think it's very deep in time but I think I've also

[00:44:09] done some processing. I think I'm on of two minds for everything I do and part of me thinks they

[00:44:15] will get it and so part of me thinks they won't get it and I have to be brave in the moment but

[00:44:21] it's not like it's so powerful that it's overwhelming. That's very fortunate for me at this point

[00:44:25] in my life, wasn't always like this but... Right. Let's talk about the time when it wasn't.

[00:44:31] Yeah. So fortunate. What's it going on? Time travel. I've been writing for a very long time

[00:44:40] so I think I was probably 11 or 12 when I started writing poetry. The rawest thing that you could

[00:44:49] do and I wasn't showing it to anybody and I was very lucky to have a teacher who was really kind

[00:44:58] then really encouraged me to submit my writings and we talked to me about them. There is a

[00:45:06] sense that some people are going to be open and some people aren't and so I think what the

[00:45:14] sensitivity now is going public because there's going to be both kinds of people. There's going

[00:45:21] to be the people who get it and the people who don't and do I want to have to deal with that

[00:45:28] basically. Can I just share it one on a lawn or one on a lawn? Certainly you don't want to

[00:45:32] deal with that. When you said to me when you said to me I was 11 and I started writing poetry.

[00:45:42] Go back to that moment just now. What did you hear inside of your head before you said the word

[00:45:50] and the nanosecond before you spoke? Yeah, part of me just saying oh this is really

[00:45:57] it's a really sensitive and personal and I don't usually talk about this and I don't know if I

[00:46:02] should bring it up right but no if I should. I'm more gay via the feeling that maybe I shouldn't

[00:46:08] say anything about this because it shows a much more vulnerable side of me. I much more

[00:46:23] sensitive side of me than maybe I'm comfortable being out there and all of a sudden we

[00:46:30] took away a layer protection and you might be subjected to shame.

[00:46:38] Yeah, because who are you to write poetry? Yeah.

[00:46:45] Or who are you to write poetry or or poetry stupid like poetry,

[00:46:50] or you're just a piece of the right? That really does sound like an 11 year old doesn't it?

[00:46:54] Yeah, poetry stupid. Or it's not it's for girls. Yeah I think that feels right for the time.

[00:47:07] Yeah, all right so that little boy who was trying to connect with his heart and poetry is like

[00:47:15] mainlining feelings. It's like opening a vein and getting an IV of deep sensitivity.

[00:47:25] That little boy I feel for that kid. I have been that kid has an enormously talented and

[00:47:35] capable ally. He has you who is wise and brave and capable and thoughtful and has all sorts of

[00:47:50] agency and when the bullies on the playground laugh at him, it's going to walk over that playground

[00:47:56] and he's going to put an arm around that 11 year old boy and he's going to say you're going to be okay

[00:48:05] I'm right by your side because the bullies can't touch you. Now how does that image land for you?

[00:48:13] It mirrors very well, not in very conscious ways but the process that's going on

[00:48:20] when I'm thinking about sharing something there is a part of me that says I'll be okay. There's

[00:48:25] also a part that's like maybe not so productive and it says I don't care what people think like

[00:48:31] the same part where it's like that's the 15 year old who's jumping front of the left.

[00:48:37] Screw all these people so maybe make more room for the adults for sure. So I'm going to warrant

[00:48:42] and take a guess that those who are listening to us right now can relate to the experience you've had

[00:48:51] and in you sharing the entire arc including the part of you that jumps in the 15 year old I

[00:48:59] called it who jumps in and says that I'll tell with them I won't be on social media.

[00:49:04] Right, I don't care what they think or even the part of them that's the adult

[00:49:10] that says no I got it, I got you kid as well see 11 year old. They're hearing your words

[00:49:20] and just like those who read my words or hear my words and find resonance in the story

[00:49:26] just as I read Parker's words and shareings words and honey penmas words and found

[00:49:32] resonance in their stories. That entire process that's how human beings help one another. That is a

[00:49:41] mix of that is a good deed that is how we make it safe for the next 11 year old

[00:49:49] to say here's my heart I'm going to put words to my feelings. That is the force that counteracts

[00:49:57] the authoritarianism. The not only dominates our political landscape but dominates our own mindset

[00:50:06] the bullies on the playground are nothing compared to the power of love and empathy when we

[00:50:14] stand united and stand together and take care of each other. They don't have stand a chance.

[00:50:25] So when now seeing your radical inquiry process in action,

[00:50:32] well you're right you're making a connection by radically acquiring within land it's radical

[00:50:40] because it means notice what was happening from you. You started to go to those feelings and

[00:50:46] then there are more adult minds that kicked in to reassure yourself that you were okay.

[00:50:55] And I actually pushed that and made you go back to being 11 so that you could actually

[00:51:01] empathetically be connected to that person and then we called forth the adult.

[00:51:08] So take care. To the impulses to be that 15 year old, part of what that 15 year old is doing is

[00:51:18] their feelings about me don't matter. It's a way of being an adolescent and covering our pain

[00:51:29] by saying it doesn't matter and in fact it does matter. It's just not, it doesn't matter as much

[00:51:39] as the 11 year old things. So I wanted to ask you this something that's deeply personal to me

[00:51:48] and it's that meeting place of spirituality, Buddhism like a path or a path of growth,

[00:51:58] path of awakening. I'd like to hope that the business is not an obstacle

[00:52:05] to the path, it can be a functional part of the path and I think you're one of the only voices

[00:52:12] that I hear out there saying that that is so. So I'd love to hear about your thoughts as business

[00:52:20] as a tool for growth, not just psychology but spiritual growth, evolution.

[00:52:27] Yeah, this up title in my book is leadership in the art of growing up. I'll tell you a quick story

[00:52:31] on this. Years and years and years ago, I went to a meditation retreat at a center here in Colorado

[00:52:39] and I went to spend the weekend with Unipenma Children and I had the great good fortune of being

[00:52:45] invited to tea with her on a Sunday. I had arrived on Thursday and on Saturday morning

[00:52:54] the leadership of the center had asked me to join the Board of Directors.

[00:52:59] And leaving aside for a moment my own ego involved in all that. I came to see Unipenma on Sunday and

[00:53:08] I said, I don't know, I just want to be a student, I don't want to sit in the back of the

[00:53:13] classroom and she just laughed and she said, oh boy you've got some ego there. It's like,

[00:53:18] why don't you go, well, you know, you're sort of avoiding the thing that is going on. You're avoiding

[00:53:25] your karma and I just like pulled back and she said, your karma is to combine leadership in the

[00:53:35] dormant and the path to happiness doesn't lie through denying your karma. So with that as context,

[00:53:47] you're right, I do see leadership in business as instrumental in this process of growing up as I call it.

[00:53:57] But I want to be more clear, everything is path. It's not just a tool on the path.

[00:54:05] It's not just a function. It is the path. This is what karma has put forward for you. You have a company.

[00:54:18] You have a merry band of pranksters who want to create magic in the world and they want to use

[00:54:25] their work to express their essence and your task is to create the conditions where great people

[00:54:37] get to do the best work of their lives. How is that not Dharma? See, the problem is that we see

[00:54:48] these things in opposition to each other. It's like seeing work in life as oppositional.

[00:54:56] Pablo Picasso did not say, well, some days I'd paint and do my work in some days I live.

[00:55:04] When you Blake didn't say, some days I write and some days I live, he was his work.

[00:55:14] Now the danger is when that's all that I am. When I sacrifice love and I sacrifice health

[00:55:23] and I sacrifice friendship and I sacrifice family for output. That's dangerous, but I never stop being

[00:55:35] me whether it's Saturday morning and I'm working on my new book or Sunday night and I'm talking to a

[00:55:45] client or Monday evening I'm talking to one of my children. I am me and that is path.

[00:55:58] That is you. So, to me it's quite obvious that karma has said, your path is your business. Right now,

[00:56:11] someday your path might be a book that you write. Some day your path might be this podcast.

[00:56:17] But it's all path. Does that resonate make any sense? Yeah, I think it that and maybe the reason

[00:56:30] it doesn't always feel this way is because in some activities I bring less than my full

[00:56:39] self and then brother. Right? That's right. Okay, in order to for everything to be path,

[00:56:51] there's no holding back. It's not that work by definition is inherently an expression of

[00:56:59] compartmentalized life. It's that we compartmentalize our lives and we put work in that compartment.

[00:57:08] But you're a craftsman, you're a sculptor. The medium that you choose is different than the

[00:57:18] medium that you know where a sculptor might use clay but you're still doing hard. That just

[00:57:25] happens to be this business and you know the sculptor doesn't say I'm gonna hold myself back

[00:57:30] because I'm working right now. You have to be fully present to your life.

[00:57:41] Hmm, that's fascinating. So I want to dig in to make sure that I understand this.

[00:57:48] Hold it more. I feel like okay certain things in a business need doing

[00:57:56] and they need doing for practical reasons. Like you need to do the sales. You need to reach out

[00:58:02] the clients. You need to do you know marketing. You need to do. And some of these things

[00:58:10] you know if I bring my whole self then I don't like that my whole self doesn't really feel like

[00:58:14] doing some of these things or my whole self might prefer to be doing

[00:58:21] something else right now, something more creative. So what is the process of being my whole

[00:58:27] self in those moments? There's an old bit of teaching that's because like this before enlightened

[00:58:34] when chopwood carry water. After enlightened men chopwood carry water. What's that mean? I think

[00:58:46] that the enlightenment what it changes is not necessarily the subject matter it's the perspective

[00:58:51] on it or it's the relationship to it. You're still doing the same activities.

[00:58:57] You may hate making sales calls because making sales calls put you in that place a potential

[00:59:05] shame by being judged. How workable that is, how lovely that experience says,

[00:59:13] how wonderful that experiences because you get to use that experience to explore

[00:59:20] what do I feel shame if I'm judged? Where did that come from? Oh right I'm 11 years old again

[00:59:27] wanting to write poetry. A phrase that the bigger boys are going to somehow find out.

[00:59:36] My blow kiss and let go of that. And let me approach the sales process as an opportunity

[00:59:44] to create an empathetic bond because who am I selling to but another human being?

[00:59:51] Who, by the way, suffered him was wounded as a child. Yeah. Everything that you say I don't

[00:59:57] want to do is an opportunity to practice. Everything that you say I want to do

[01:00:07] is an opportunity to practice. That's the whole self.

[01:00:12] Yeah. It's good. I like this answer. It's feel very practical. So I'd love to hear from you

[01:00:23] about your reboot approach and then also I know you started thinking and engaging with the

[01:00:33] concept of belonging. How does that tie into this approach? Well, I think when I hear you asking

[01:00:40] is sort of my company or coaching style and how we approach things. And I'll just point

[01:00:48] that you experienced it. Yeah. All right let's imagine for a moment that you're a coaching client

[01:00:55] and your CEO of a small design firm and you call me out and say, this boss a job I just don't

[01:01:01] want to do. It's a pain in the ass. And I would have told you exactly what I told you just now.

[01:01:08] Okay. And so implicit in what we do is a kind of deeper questioning than the reflection process

[01:01:20] of looking back and trying to see things from a different perspective. Some of the aspects of that

[01:01:26] are a common to reboot much of that is good coaching, quite frankly, to that's part of what we

[01:01:36] on the question of belonging, you know, one of the core principles of my first book was that we are

[01:01:43] all organized for the pursuit of love, safety and belonging. And that we use as leaders in order to

[01:01:52] turn the challenge of leadership into a path to growing up as we were just described. We use radical

[01:02:00] self-incorrectly. And understand that just like ourselves, everyone around us is organized for the

[01:02:10] pursuit of love, safety and belonging. And so when I ask the question as I do often,

[01:02:15] how have I been complicit in creating the conditions I say I don't want in my life?

[01:02:23] One of the core worries to that is how have I been complicit not responsible for creating the

[01:02:29] conditions in which I don't feel loved, I don't feel safe and I don't feel like I belong.

[01:02:36] Or if I have power, how have I created those conditions for other people? And that leads to the

[01:02:45] new work that I'm doing, which expands that notion to really look at the question of

[01:02:53] okay, if as I assert that better humans make better leaders,

[01:02:59] then what is the responsibility of a better human to create what I refer to as systemic belonging?

[01:03:07] We live in society where there is systemic other, whether it's racist, misogynistic,

[01:03:16] transphobic, homophobic. We are constantly turning the other into someone who has less than.

[01:03:25] And to my mind, the only answer to systemic problems are systemic solutions.

[01:03:31] And so the question then becomes the question of how have I been complicit starts to more

[01:03:35] if into how have I been complicit in and benefited from systemic othering?

[01:03:46] And what do I need to give up that I love in order to create systemic belonging?

[01:03:52] And that is a really challenging question, especially for those of us who hold implicit or explicit

[01:04:00] power as many racially white men do. And I think that's a moral obligation to ask that question.

[01:04:15] So that's where I'm exploring in the new book from MyLips to God's ears of manuscript will be

[01:04:23] done this summer about all my playthrough. And hopefully, it will be out next year which is what the plan is.

[01:04:31] So fingers crossed, that's wonderful. One final closing question. In his TED Talk,

[01:04:38] philosopher Alinde Bouton talks about the difference between a lecture and a sermon.

[01:04:44] A lecture being kind of a dry, secular information all the way of conveying information

[01:04:50] and then you make up your own mind about what you're doing. And what is a sermon is this really

[01:04:55] urgent plea to try to change someone's life. And so if you were to give a short sermon

[01:05:04] today, what would be the one thing that can make the biggest impact in people's lives?

[01:05:12] Well, I hope he, his TED Talk was a sermon and not a lecture.

[01:05:15] Um, I think that the most important thing to hold on to for anyone in all the things that we've talked

[01:05:24] about today is the sense that we're not alone. I think the tragedy of the human experiences that

[01:05:31] when we step into the things that we suffer with, we exacerbate that problem by assuming that we're

[01:05:38] the only one who goes through that. And when we expand our horizon beyond our own experience

[01:05:45] and start to connect with other people's suffering, a magical thing happens, our suffering is

[01:05:51] alleviated. See, when I help you, I am helping me when I help me, I am helping you.

[01:06:01] And that, I think is the most glorious aspect of humanity. We're in this together.

[01:06:10] Thank you so much. No, thank you for asking the question and thank you for having me on the show.

[01:06:17] All right, that's it for today. If you enjoyed the podcast that I would like to support it,

[01:06:23] please consider writing a five-star review in Apple's podcast app or wherever you're listening.

[01:06:29] It helps many more people discover the podcast and also makes us feel good.

[01:06:35] Current support for the podcast comes from my own design company, remake labs.

[01:06:39] We run design sprints all over the world and our goal is to improve outcomes of whether in business

[01:06:46] or various organizations through repeated and rapid design interventions. Now, until next time,

[01:06:54] be well everyone. See you next week on remake.