Ten Percent Happier with Dan Harris - 192: The Art of Growing Up, Jerry Colonna

Episode Date: June 19, 2019

Jerry Colonna is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm committed to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, executive, and board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, and equanimity. Colonna is a certified professional coach, who draws on a wide variety of experiences to help clients design a more conscious life and make needed changes to improve their performance and satisfaction. Plug Zone Company: https://www.reboot.io/ Book: Reboot: Leadership and the Art of Growing Up: https://www.rebootbyjerry.com/ Event at the Rubin Museum with Dan Harris & Jerry Colonna 7/10 https://rubinmuseum.org/events/event/jerry-colonna-dan-harris-07-10-2019 Twitter: @jerrycolonna Ten Percent Happier Meditation - Sharon Salzberg's Dressing Up The Inner Critic: https://10percenthappier.app.link/2sFkPUVNiX ***VOICEMAILS*** Have a question for Dan? Leave us a voicemail: 646-883-8326 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Before we jump into today's show, many of us want to live healthier lives, but keep bumping our heads up against the same obstacles over and over again. But what if there was a different way to relate to this gap between what you want to do and what you actually do? What if you could find intrinsic motivation for habit change that will make you happier instead of sending you into a shame spiral? Learn how to form healthy habits without kicking your own ass unnecessarily by taking our healthy habits course over on the 10% happier app. It's taught by the Stanford psychologist Kelly McGonical and the Great Meditation Teacher Alexis

Santos to access the course. Just download the 10% happier app wherever you get your apps or by visiting 10% calm. All one word spelled out. Okay on with the show. For ABC, to baby, this is Kiki Palmer on Amazon Music or wherever you get your podcast. From ABC, this is the 10% happier podcast. I'm Dan Harris. Hey guys, we've done a bunch of episodes, great episodes in my opinion, about how to bring meditation into the workplace. But in this episode, we're going to go quite a bit deeper than issues of focus and productivity

and lower emotional reactivity, which again are all great. But now we're going to talk about how work, which is where many of us spend most of our lives, frankly, actually gives us an opportunity, if you want to call it an opportunity, to see stuff about ourselves that we may not want to see. If you do this work though of looking at your stuff and I'm speaking from some level of personal experience here, it can actually make you better at your job and not for nothing a better person. My guest is a guy named Jerry Kaloana who is both an executive coach and a practicing Buddhist. He's also had a significant impact on me personally.

Regular listeners may remember that a few months ago had something called a 360 review. That's when you hire a firm, in this case Jerry's firm, to interview people who work before you, work with you as your peers alongside you as your peers, or your bosses. In this case, we also interviewed some people in my personal life to get a sense of where I'm at my best and where I'm at my worst. And the 360 was quite surprised to me in many levels in that it was humbling.

And Jerry's firm, reboot, did the 360 very sensitively. And Jerry personally coached me pre and post the 360 in ways that have been quite transformative and we're still working together in that capacity. So in this episode, we're gonna talk about things like, what are the demons that sometimes drive us in our professional life, and how do they show up at work? What's our relationship to money?

How does our unexamined stuff bleed out throughout the organization in which we work? So pretty heavy stuff and really interesting and useful stuff. That's all coming up first though just a quick pair of business items. Speaking of Jerry Kelona, he and I are going to be doing a live event in New York City on July 10th at the Rubin Museum from 7 o'clock until 8.30. That's July 10th at the Rubin Museum and there's a link in the show notes. And one quick note about the 10% happier app, one meditation we're featuring this week is from Sharon Salzberg, the eminent Sheridan Salisberg. It's called dressing up the inner critic. It's all about her little technique for managing your inner critic so that it doesn't own you. All right, back to Jerry

Kelona just quickly his CV. So you have it. He is, as I mentioned, the founder of a company called Reboot.io. He's the founder and CEO of Re of reboot.io, he's a certified professional coach. Before he got into that line of work, he was a hotshot venture capitalist at places like J.P. Morgan and Flatiron Partners, quite a legendary venture capital career. And now he's kind of legendary in Silicon Valley where he's known as the CEO whisperer. He works with all these high tech hot shots and is known for making them cry and stuff like that. And if you want to know more about his personal story

and meditation practice, you can go back to listen to episode 68, which was the first time he's on the show. In this episode, we're gonna do a deep dive into his new book, Just Out. It's called Reboot Leadership and the Art of Growing Up. Here he is, Jerry Colona. Let me get something out of the way first. This is a book about leadership, but a lot of people, I wonder if people in the audience are going to say, well, I'm not a leader, I don't run anything, I'm just a worker, I'm a parent, or whatever. Therefore, this book is not

for me. How do you respond to that? I think, well, two things. One is that we all have moments of leadership regardless of whether or not we have structural positional power, which is normally the way we approach it. You know, when a mother is organizing the family and working with, say, their teenage is broken heart, their leading. When a child is sort of stepping into trying to figure out, well, I'm going to go into that recital, and I'm really nervous. That's a leadership moment.

And so, yeah, I'm playing with that positional definition of leadership, and really going at it. But the truth is we all have that opportunity for leadership in that way. And then secondarily, I think that because of that core message of the book, which is that the leadership journey, the journey of really challenging ourselves to grow is an opportunity to really confront the things that we have that we're carrying, the unsorted baggage of our childhood. So I think everyone has the capacity to lead and everyone has the opportunity to use those challenges to grow up.

You think most leadership, I mean, I haven't read, even though I'm nominally in the world of business, I haven't read a lot of how to be a manager of books, but you think most of these books, I'm sure you've read more than I have, are telling people about, you know, you get to dive into the deepest abyss of your personal damage and work from there. Or you're an outlier in management advice.

I think I'm an outlier except that I have good lineage, even amongst the well-thought-out leaders or the well-regarded leadership pundits and thinkers. In the book, I use a phrase called the Crucible of Leadership, which is that moment, those moments in our adulting journey are work journeys where we are really confronted with a challenging moment. And how we choose to respond to that moment really determines the whole trajectory of our leadership path. Well, that phrase comes from Warren Benes. And Warren Benes is considered one of the most thoughtful and intelligent writers on leadership of the 20th century. You know, the leadership writers I admire would recognize what I'm trying to do.

The difference is that I think that I am trying to drop the trappings of the language of leadership so that it's more personal, more visceral, and more accessible to people. Peter Drucker, for example, is very accessible once you get past. He's just a people. He's a well-known management. That's right. But if you pick up a Peter Drucker book, your impulse might be, well, I don't have an MBA, so I can't read this.

And so the whole idea for me has always been to bridge different worlds, whether it's the Dharma world, whether it's just the language of every day and traditional leadership thinking. Now that said, there's a whole bunch of how-to leadership books, which are good, but insufficient, leadership books, which are good, but insufficient, because they don't really get at the core challenges of leadership. They tell you, you know, the best ways to run your weekly sync meetings with your employees, but they don't actually give you any advice on how to grow up yourself and how to grow into your own leadership. But just to be clear, this is a book that you think could be read by people who don't have any employees.

Yes. I didn't start out thinking that, but those who have read the book so far, I've heard from a wide variety of people who have shocked me, who have shocked me with this notion that this book is really relevant for them. I have, I encountered this young woman who's 21, who read the book over the course of a week as part of our social media campaign, and she came back and she said the book gave her permission to be herself. That's not what I expected. But on the other hand, I did write the book with the intention that my three children, Sam

M. and Michael, would be able to read this and sort of carry it forward. So I guess it's not that surprising to me. What would you say is the core thesis of the book? The challenges of leadership and the challenges of work represent us with an opportunity to confront and work with the parts of ourselves that we'd really rather not. And that if we choose to do so, not only will we become a better leader, but will actually grow up. And my general belief is we spend the vast majority of our lifetime in this thing called to work.

Why not use it to grow up? Why not use it to become a better person, rather than seeing it as an opposition or an obstacle to our path to actualization. How do we do that? Well, we look at the challenges that we're confronted with. Every day you've got somebody who walks in and sort of questions your authority or questions your thinking about things, questions your values or questions your integrity. Every single day we're presented

with those kinds of challenges. And we can either shut it down, bully our way through things, white knuckle our way past our fears, our self-dance, our sense of impossess in room, or we can lean into those moments. And we can say say what is really going on for me. In the book I talk about the notion that a Joseph Campbell quote in which the treasure you see is in the back of the cave. Are you willing to go way into the back of the cave and retrieve that parts of yourself, those parts of yourself that you'd really rather not think about. And then pull them out and see them as the source of your strength, rather than necessarily something that you should be ashamed of. Well, obviously, well, maybe it's not obvious, but to me, that sounds really

wise, at least in theory, but in practice for the regular person. So I have Jerry Kologna as my coach. So you take me to the back of the cave all the time. Right. And I'm guided there and supported, et cetera, et cetera. But how does the average person go to the back of the cave and emerge as a better worker, leader, whatever you want to call it? Well, you know, the first step is to actually recognize that there is, in fact, a back of of the cave or that there is even a cave to begin with because so much of us So much of our life is organized around denying that these things exist and that we have these

challenges that we're working with the second is to do what I often think about is what I often refer to as radical self-inquiry and you know, we've Radical self-inquiry is a term I coined to refer to a fundamental Buddhist principle which is to sit still and look at what's actually going on and sit still and look at what's actually going on. And to use the practice say of meditation, to use the practice and to just standing still and looking at your life and ask yourself a series of questions, why am I upset in this moment? What's the threat that I'm feeling? Is it true? Is that threat really true? And that simple act of asking yourself these open questions and being willing to listen to the answer,

you don't even have to talk to anybody about it. I think the journaling about it can be really powerful. But if you just sort of sit there and you look at your day and you review your reactions in a situation, I'm in the middle of a meeting. Why am I getting upset? Sure, the person across from me is a jerk, but really? Why today?

Why is that bothering me? And what can I learn from that? That's a practice that you don't necessarily need a guide that said every, at the end of every chapter in the book, we added a series of journaling questions, prompts, really. These are the questions themselves are less important than the act of actually pausing and asking yourself what's really going on here. So I think that answer will land with a lot of listeners of this podcast, the vast majority of whom I suspect either have a meditation practice or a spire to establish one. So just to put a fine point down it, you're saying if I'm hearing you correctly, you can use your meditation practice as a vehicle

toward this radical self-inquiry that you're describing and recommending. You can do journaling, which doesn't cost anything beyond having some paper and a pen. And I suspect a lot of people listen to this show avail themselves wisely of psychotherapy. Right. And that's another place you can do it. And they may not be management experts, but you can talk to them about what's going on at work as a way to explore the fact that since we spend so much time at work, it's going to trigger lots of stuff from the back of our cave.

Yeah. I mean, look, I'll tell you a funny, I think it's a little funny little story from my work in workshops and boot camps and boot camps is our term for these sort of multi-day experiences that I run. I always stand up and I have this reputation for making folks cry. And I don't think I've actually made you cry yet. Why is that such a big deal you making people cry? It's not. It's not. It's not.

But it's the thing that people talk about me. And so I actually use it. What is important to me, and this is the point I often make to people, is because I have that reputation, I try to turn it on its head, and I say, you know how I actually do that? The very, very simple technique, I ask people how they really are. I just ask people to stop, sit still, look in wood, and ask themselves how they're feeling. And Dan, it's heartbreaking. But most people, when they pause and they listen to the chatter inside,

they start to feel sad. What's going on with that is because we're, I think it's because we spend so much time in a kind of fast-forward leaning in, running up the stairs, you know, life at the speed of light, that when we actually pause and someone guides us to just say, hey, how are you? No, really, how are you? The minute that happens, all of a sudden, I can see it in your eyes, it's happening to you. The minute that happens, we start to drop away all the nonsense of our day.

And then what I often advise it, whether it's a client or in a large setting, is what if we spent our days from that place? And you can do it for yourself. And you can do it for yourself. You don't even have to see it out loud. You can sit on the subway and you can do it for yourself. You don't even have to say it out loud. You can sit on the subway and you can say, okay, I'm seeding, I'm seeded, seeded. The train is rushing by.

How am I feeling? And rather than, you know, to put it in this in a leadership context, in a business context, rather than rushing to fix the problems which are relentless and never ending. We started off by saying, I'm not feeling well right now. And because I'm not feeling well right now, the answer that I'm going to come up with is probably not going to be a good answer. And may even be inhumane to the people around me because I'm thrusting myself into a situation. I'm forcing it. By starting off from that place and it's caused nothing and it's available to everyone, imagine you sit down with your life partner and you're about to have a meal.

And before you launch into a recitation of the day or the lamentations of life, you just said, I'm not feeling well right now. I'm scared. I'm sad. I'm angry. Or I'm joyful. Or I'm happy. or I'm anxious. And then you connect. So we start some of our meetings at 10% happier and I think you do this too. You may have recommended it to us. I did. With Red Yellow Green.

Can you talk about what that is? Yeah, so it actually comes from a psychological theory called polyvagal theory, which folks can look up because I don't know enough about it. But it's a simple technique, and it's just a way to use colors to identify emotional states. Why do we pick colors? Because sometimes we're socialized not to be able

to talk about feelings. And so by using the words red, yellow, and green, and then allowing the space for people to define any color in between while I'm orange trending towards fire engine red to describe my emotional state, you also get people to be able to connect both internally with themselves and with each other without going into the story behind why. Because the big fear when we teach this, the big fear is, oh my God, we're going to turn a business meeting into a therapy session. No, no, no, no.

All we're doing is grounding ourselves. It's kind of, to me, it's very much a mindfulness exercise. I'm going to sit on the cushion and I'm going to pause. And I'm going to see how I'm doing. And then I'm going to go to work. So that's what we do with red-yellow green. Red is, I'm kind of here, but when red is, I'm totally in the red.

I'm anxious. I'm not really here. Yellow is, I'm sort of in between. Things are OK. Green is, I'm not really here yellow is I'm sort of in between things are okay Green is I'm fully present. I could be green at home and red at work. I could be red at work and Yellow at home and it's just a way for your colleagues to sort of understand where you are as well. I of course You will be 0% surprised to hear that I resist some of this stuff because I'm like, you know, I'm, Gen X raised by a bunch of militant, hierarchical,

baby boomers here at ABC News, and back when this was a pretty toxic environment, I've been here for 19 years, it's much less toxic now, but I come out of that. And so the whole red yellow green thing for me, I still approach it with some trepidation because I'm like, oh my god, is this going to devolve into some combaia session. But the rational part of me sees that it has the benefits that you just described. Well, and I totally understand your hesitancy. And I smiled when you describe the old toxic ways. You think that was an accident.

Right? In the old toxic ways, it was, you leave your life, you leave your reality at the door when you walk into business. And the truth is, none of us do that. All the best we can manage is to suppress it. That's the best that we can do. And in the most extreme version of that, we suppress it to the point where we're no longer cognizant of it consciously. And then we just act out all over the place. And your point, the point you've made to me individually many, many times is the more you rise, so to speak, the more you become a leader with people looking to you, the more all of this unexplored pathology bleeds out and affects and infects everyone. I used to work down the hall from here.

There was a guy you may have heard of named Peter Jennings. Right down the hall from here. On the second floor of our building here at ABC News. And an incredible human being, an American icon, even though he's actually Canadian, but also incredibly difficult. Really difficult. Had some, I don't know it intimate.

I don't know his personal history. Intimately, I know a little bit about it. Difficult relationship with his family. And I think specifically his dad. And that played out here all the time. And it was everybody was walking on eggshells all the time. Cause you never know. Peter walk in red, he wouldn't declare it.

You'd be able to tell from his body language, but he would just start saying incredibly mean things because he was so smart. He could really just cut to the core of whatever your insecurities were. And that was that affected everybody. And then I see it playing out of my own leadership, but with your help of, I'm bringing some of that into my leadership here at ABC News or at 10% and so yeah, this stuff, if you don't look at it, it's not like it goes away. No, and in fact, it amplifies throughout the organization. I mean, that's the really sad part of it is that when those who have position on structural power within an organization, whether it's our community, whether it's our politics, whether it's, you know, non-profit organization,

when those who have that power, a family, a family very much of family, when those who have that power don't do their work, don't take responsibility for the un-sorted baggage of that they're carrying since childhood. They infect and affect everyone throughout the power structure. And maybe when the saddest things that I've heard over the years in my career was, I got a phone call once from the head of talent for a very large company, thousands and thousands of employees.

And she called reaching out because she needed for a very large company, thousands and thousands of employees. And she called reaching out because she needed to break through some of the habits, some of the toxic habits in the senior leadership at this company. And the catalyst, and this breaks my heart, that health care costs for mental health claims for the children of the employees had gone up 70% in the previous two years. Yeah, just like that sink in, okay? There's some 15 year old kid who is depressed to the point of being suicidal. Indirectly, because of the toxicity of that parents work environment,

stemming from the fact that it's too soft to pause in a business meeting and say I'm in the red and what I'm about to say is probably not Grounded in a healthy place That's just both that's really unfair That kid did not sign up for that job and I think that we have a moral responsibility to do our work because the people around us pay the price. We just say more about doing our work and his meditation enough. No, meditation is not enough.

But meditation, so let's break down what do I mean by doing work. I mean stop, stand, still, slow down, check in with yourself, pause. There are a million stories you tell yourself about the lamentations of your day. Are they true? Because if they're not and you act from that place, you're going to hurt somebody. So slow down, stand still. Check it out. Ask yourself a series of questions Am I leading the organization that I want to work for?

One of the challenging questions I often ask people is if my child were to come to work for my company Yeah, that got you How would I feel? Because if I don't feel pride and happiness, then I'm not leading well. So meditation becomes the ground upon which you begin this process. And by the way, it doesn't have to be sitting meditation in a lotus position on a cushion. It's that moment of meditation where you just pause and you slow the chatter down and

you say, is this who I want to be? Is this the adult that when I was five and I was laying on the carpet, pushing a matchbox car around, saying to myself, when I grow up, I'm going to be toxic, hurtful, bullying, suppressed, repressed, angry, anxious, of course not. How do I get back to that? How do I lead from that place. Responsibly wield my power. And if I do that, I create the space for everyone else around me. You were telling a story about Peter Jennings and how everybody walked on eggshells. I can only imagine what the second and third in commands, those who were in those

command positions, how that just ran down the hill. And they made sure that as soon as you walked into this environment, you knew that you had a walk on eggshells. Now, before we get all, we gooey on this. Tell me how that's productive. I can make a case for it. I mean, he did Peter forced us to operate at the highest level. He asked in size of questions. We knew we weren't going to get away with anything with him. It made me sharp and ready and awake. So here's the question. Yeah, I'm not I'm could could that quality of that work have been delivered Without your sense inner sense of worthiness

Having been challenged every single day. Absolutely. Right. So that's that's the hard work of leadership How do we lead in such a way that we inspire the best in our people without using fear to drive them to do extraordinary work? Because occasionally, we're not talking by the way about hard work versus soft work or easy work. What we're talking about is having a shared sense of commitment to the actualization of every individual so that the work environment becomes a place that demands the best of us, but allows each of us to grow up. To use the terminology that I use in the book to allow each of us our best adult selves to come forward. Now, might we not squeeze every ounce of profit out of that? Yeah, that's possible. Well, but I was just my mind was just going to self-interest

here because whether you're the leader of an organization or a leader of a unit or just a member of a team which does require being a leader or whatever. In a business context, can't you just make the case that, you know, I think science is making the case for us that happy productive teams do the best work? I think the, I can't put my fingers on the data right now, but I think the data is out there and irrefutable. Well, I'm doing a do something dangerous because I'm going to try to work from memory here, but I believe Google did a study of the best teams. They're trying to figure out what's the common denominator among the best teams?

Charles Doohig wrote a piece that wrote about this in his most recent book, and there was a piece in the New York Times magazine if anybody wants to go look it up, it was from a couple of years ago. And what they found was, took him a long time to figure this out. What they found was, if I'm remembering this correctly, the common denominator among the most successful teams within Google, and by the way, we are increasingly working in teams, right? This is relevant to everybody. That's the way the workplace is trending these days. The common denominator was something called psychological safety, right?

Meaning it was okay to speak up. You weren't operating in an atmosphere of fear. There was equity, all voices were being heard, et cetera, et cetera. And that can look in a lot of different ways. And that's why it was so hard to figure out what this common denominator was because these teams can have all sorts of different cultures, some are really humorous, some are not, but the common denominator was psychological safety. Which seems to me is when you're talking, that's where the rubber hits the road. That's right. And it's psychological safety coupled with the joy

of excellent work. Right. Now, that's an unusual phrasing. We don't often think about the joy of a well-crafted piece of work. Right. Those are not in opposition. They're not in opposition. Right? Those are not in opposition. You know, they're not in opposition. This is hard work for a leader because that means they have to model creating psychological safety within themselves. It means that they have to constantly check into a sense of purpose and vision. This is who we are. This is how we are different. It creates a sense of connectedness and a spree to core where really talented people get to do the best work of their their lives and then leave feeling energized and feeling that they grew. Imagine if that was our model for leadership. Imagine if after spending four or five years working for a company, we

walked away saying, I am a better person for having had that experience. not boy, I survived that experience. Right? Look at the battle scars I have. Demanding excellence in that environment. Well, if we dropped the word demand and we said that all leadership models excellence. Then what we're doing is we're creating a, we're living into the wish that we all have to belong to a tribe that feels safe, that where we feel loved. And that's deep in our evolutionary wiring. You know, in the book I talk about the fact that all,

that we're all wired to seek love, safety, and belonging, to feel that we can love and be loved, to feel physically, emotionally, and existentially safe, and in doing so that we belong, we know where we belong. This is my tribe. This is who, who, no matter what, they will have my back. And if we can create work environments and communities and families that are organized for those three things. When we do, let's put it this way, when we do this, because we do. We create truly extraordinary and sustaining work. Would you say your goal is to remake the workplace?

You know, the first time I came on this show, one of the things I said was that I was uninterested in enlightenment per se, that I was really about alleviating suffering. It's the same goal. I want to participate in a movement to make it less painful to go to work. You know, you've heard me say before in coaching conversations that phrase that we've taken from David White, the poet and philosopher, good work done well for the right reasons. I want to encourage people to end their days, put their head on the pillow saying, good work,

done well for the right reasons. We will sleep well tonight. And tomorrow morning, I will get up and I will have the joy of hard work all over again. I think if we do that, then work becomes not the means for suffering and hurting ourselves, but the means for our full actualization and becoming the people that we were born to be. I remember when you first quoted that we were in a coaching session, which for the uninitiated means you and I were talking. And within the under the rubric of you being a coach and me being your client, and you use that quote with me, and I remember saying, I'm not sure I've ever put my head on the pillow and felt that. I definitely think there have been times

I've done good work. I have some questions about whether it was done well in the fact in the sense of, did I not hurt myself or anybody in that process. And then it gets really dicey when you get to the right reasons and sussing out what exactly are my motivations here? And is, can I say with confidence that there wasn't a ton of ego in my reasons? No. Or can you say with confidence that there wasn't a ton of fear in your reasons?

No. Right. What drives us to work? Right. I don't think we ever fully remove those childhood survival structures that we carry forward. If I don't have enough, if I don't work hard enough, then I won't be worthy enough.

I don't think we entirely remove those. But if we can bring forth our adult sensibility to examine those, we can lessen that as a driver and therefore lessen the toxic effect of that old childhood structure, so that when we have power where no longer asking those around us to make us feel loved, safe, and that we belong. More 10% happier after this. Like the short, and it's full of a lot of interesting questions, what does happiness really mean? How do I get the most out of my time, you honor, and what really is the best cereal? These are the questions I seek to resolve on my weekly

podcast, Life is Short, with Justin Long. If you're looking for the answer to deep philosophical questions, like, what is the meaning of life? I can't really help you, but I do believe that we really enrich our experience here by learning from others. And that's why in each episode, I like to talk with actors, musicians, artists, scientists, and many more types of people about how they get the most out of life. We explore how they felt during the highs. And sometimes more importantly, the lows of their careers. We discuss how they've been able to stay happy during some of the harder times. But if I'm being honest, it's mostly just fun chats between friends about the important stuff like if you had a sandwich named after you what would be on it. Follow life is short wherever you get your podcasts. You can also listen to ad free on the Amazon music or wonder yeah.

I was thinking recently as you were talking and I've been thinking about recently the context of our coaching relationship about the hotel Regina and Paris France. My parents when I was 10 maybe took us for a couple of week vacation in Europe because they didn't have a ton of money. They were they were doctors. A lot of people think when you you know doctors make a ton of money but they don't, especially not in the context of academic medicine, which my parents are both in, meaning they worked at Harvard, and they treated patients who were worked on the, who are patient care teams, but they also did a lot of academic research.

That's very prestigious, but not very well paid, as opposed to being in private practice as a physician who's just billing the insurance company or their patients directly. And they took us on this trip in part because I think one or both of them was speaking at academic conferences in Europe and that sort of underwrote the expenses. And at one point we're in Paris and the, I believe one of the organizers of this kind of a conference that I want to one wonder both of my parents are speaking at, put us in a hotel called the Hotel Regina. And I remember walking in there

and thinking, this place is nice. And this is how I wanna live, as opposed to my parents, who raised me in Newton, Massachusetts, and my mother's a flinty Yankee, and my dad's Jewish guy from New Jersey, both very careful with money. We didn't often keep the heat on and the winter, and so we had to wear vests around the house. And a lot of my friends lived in these big fancy houses, and we lived in what was by comparison.

Not that nice of a house, and my parents didn't drive super nice cars. And I walked into the hotel Regina, and I was like, no, no, no, this is living. This is how it's going to be done. And I was thinking about your exhortation for all of us to think about what's our relationship to money, why do we work and that kept coming up for me. Well, and I love that image. And as your coach, I'm going to hold on to that because hotel Regina is a powerful symbol. I mean, it, you know, I'm going to project into that. You tell me if this has any relevance for you, but you were aware as a boy before Paris that

you didn't have as much money as others. Yes. And when you stepped into the hotel Regina, for a brief moment in time, the shame of not having as much was lifted. And so money became a means to creating hotel Regina for you as much as you can, which meant leaving behind the shame of not having as much money. Does that have any resume? No, it's 100% accurate. And so, if we look at your relationship in your, say, contract negotiations, you might get a little more edgy when someone says to you, well, we're not going to pay you that because very, very quickly, your effort to leave behind the shame of Newton Mouse is threatened. Yes, 100%. And that happens

for most of my life happened outside of conscious awareness. That's right. And so then it just made everything worse. That's right. Still happens much of the time outside of conscious awareness, maybe 10% more aware of it and therefore 10% less driven blindly by it, but it's still there of course. Yeah. I'll tell you a story about my lemon drops.

Yeah, I was going to get you to tell that story, so go for it. So, I grew up with an enormous shame around money. Um, uh, six siblings, um, parents who struggled with alcoholism and mental illness, and, um, a deep dependency upon my mother's father, my grandfather, Dominic Guido, who remains to this day, the image of what an entrepreneur should be. He was an iceman in Brooklyn as most Italian immigrants from Bari were and he had only a six great education but nevertheless he still managed to create a business, whereas I often say there was more money at the end of the day than there was at the

beginning, which is the basis of all business. And he would distribute ice and coal throughout the, throughout Brooklyn and the joke in the family was in a legal homemade wine all year long, right? On his route. And the thing about Dom and a Guido, you know, in the chaos of my childhood, which was extraordinary, we would, especially my brother John and I. Kind of just a turbulent,

because you had chaos in your childhood. Not, I mean, your mother had mental illness and your father was an alcoholic. Correct. I just want to add some color here. And in fact, my mother had what's called Skitzoid Effective Disorder Bipolar, which included her having lots of delusions

and talking to people who weren't in the room. It was a really painful and challenging experience. And you watched her carted away to the hospital on many occasions. On many occasions, she spent most of the 1960s in and out of mental institutions and hospitals, the phrase 47 shock treatments, rings in my consciousness all the time, 47 electro shock therapy treatments to break the grip of the depression that she had.

And this is back when the medications that they use were just like shotgun to the brain, rather than the much more skillful medications that they have now to deal with things. And so we grew up with a constant sense of tension. My father's depression, which was really manifested around his alcoholism, his relationship to my mother. There was always this seeding relationship to your grandfather because there was resentment

there about your grandfather. There was subsidizing. That's right. My grandfather would, We lived in an apartment that my grandfather owned and we were the supers in effect of the building and cleaning the hallways, taking care of the building. And there was always this consciousness

that we were dependent upon grandpa. I remember my father bristling if my grandfather showed up with food and food was an issue. Food safety is a core issue. It's a core threat for human beings. As I talked about before, the sense of love, safety, and belonging, all of it was challenged. Thank God I had six amazing siblings, and I love my parents, but thank God I had six amazing siblings because we were kind of like a a thorough group of cats who just took care of each other. Anyway, grandpa always seemed to have enough.

There was always enough food, there was always enough. I remember the smells of fresh picked figs from the tree that grew in the backyard, or the ground coffee that was always there. And one of the things that I really connected to was that they had this green, dored pantry in the hall of their house, and Beverly Road in Brooklyn, just off of Nostran Avenue. And there was always a canister of lemon drops in there.

And like the hotel Regina, lemon drops became a symbol. And so years later, when I struggled in my thirties, and I had my breakdown in my thirties, I just can I just explain that with those? So you're in your thirties after, if people haven't listened to your prior podcast, you're in your 30s after in the midst of a very successful career as a venture capitalist here in New York City and yet found yourself not long after 9-11 feelings suicidal. That's right.

And again, I tell that story with more detail in the book, but Finding myself at ground zero Wanting to leap in front of a subway and this is no idle threat. I had had a suicide attempt when I was 18 and so My dance with depression was lifelong and so in the midst of all of the External wealth, external approbation, I was Hearding deeply again in my late 30s And it was at that point that I really began to unpack my relationship to money

Which sounds that I really began to unpack my relationship to money, which sounds surprising when I say it out loud again, because, huh, money, why? And it's because I was driving myself to answer the question of, do I have enough lemon drops? And with that mindset and with that attitude, no amount of lemon drops in the world would be enough. At one point your shrink asked you what would be enough. At one point Dr. Sayers, my shrink said, when is it going to be enough? How much do you need? And I found myself saying, Bill Gates.

And I was shocked. I needed to have what I referred to as Gatesian-like wealth in order to feel safe. And you know, there are seminal moments in our lives where you begin to see with clarity, the structures of your childhood, as they are driving your decisions in the present. And that was one of those moments where I said, that is not who I am, that is not the man I want to be. That is not the father I want to be. That is not the father I want to be. That is not the adult that I want to model myself. After and it's not the model I want to be for my

children, someone who is so afraid to not have enough as to risk his personal well-being and drive himself to the point of suicide. And that was the feeling. I had to drive myself to the point in order to feel safe, and the irony is, the more I drove myself, the less safe I was. And that's an example of what I would call an adult, a kind of wake-up call, into adulthood. I no longer am as driven by those fears. I still occasionally worry about, do I have enough? Will I be safe?

And external exogenous events happen to me all the time to trigger those fears. But I have now the resiliency to return to an equanimity, to be able to come back and say, okay, the story I'm telling myself is I don't have enough lemon drops. So maybe there are some things I can do or maybe I actually have enough just as I am. And so this is you post throughout the book post, when I'm talking about the internet here, you pose throughout the book a series of provocative questions that you're hoping to get people to journal on and relationship to money is one of them. You are now intuiting what my desire is because you've just picked up your phone to look, and go ahead, keep looking at all Phil Muster. Before we start a rolling, ask Jerry

to pull up a copy of the book because there are a bunch of other questions that I think are really useful for people to take as journaling prompts or even just prompts for your own internal exploration as you're walking around that will get you toward the back of the cave so that you can be a better functioning grown up. Do you want to, Sure, think of, post some of these other questions. Sure, and what I would suggest is, see, I think of my meditation sessions as inclusive of both sitting meditation and my journaling and I journal every day. And you know my morning don't really begin until I've done both of those things and it may take me an hour and a half to hours to just quietly go through all of that. And

so for your listeners many of whom have a practice or a thinking met a practice a lot of these people might say to themselves, I don't have an hour and a half to do all that. Right. And so my sitting practice is only 15, 20 minutes. My journaling practice could be as little as 15 minutes or it could be as long as an hour and a half. It sort of depends on what's happening.

But the reason I was making the connection is that I think whether it's just prior to sitting practice or just after sitting practice, it might be kind of interesting to then sit with pen and paper. And I really recommend pen and paper because of the visceral physical nature of it. Because we're not writing and journaling for someone else to read. It's not note-taking. It's not performative. It's the process of actually looking inward. I, of course, you know, because I'm always trying to monetize my own inner experiences. I'm thinking, well, I could journal and then... And then turn into a book. Yeah. Yeah, I know. That's not the point. Yeah, that's right. So here are some questions for folks to consider. How did my relationship to money first get formed?

How did that relationship shape the work I've chosen and my definitions of success and failure? How does it shape my view of the quality of others' work and contributions? What was the belief system around money and work that I grew up with? And how does that impact my own view of my own worthiness? I think that if you can ask yourself questions like these and then sit with the answers that arise. Understand that the answers are probably morph and change as your mind goes down the rabbit hole of your past or goes into the back of the cave and kind of retrieves memories.

We just started talking and you brought up the memory of the hotel Regina. Now that's a piece that was in the back of the cave. It wasn't so far back that you couldn't access it, but it was in the back of the cave. It wasn't so far back that you couldn't access it. But it was in the back of the cave. And then you bring it forth. And you sit down and you say, well, how does that how old were you in that moment? I think ten.

Right. So imagine how was ten year olds dance reaction to the lobby of that hotel?, how does that show up as you try to navigate all the different pressures that you work with today, you and Bianca work with today? And we sort of give a nod to that. And then we carry forward. That's a really helpful piece to carry. And for me, meditation becomes the ground upon which we do that work.

Before we wrap up, can you go back your phone there for a second and pull up just randomly at some another provocative question about anything, just as another example of the type of stuff you get us to do in your quest for radical self inquiry? Who is the person I've been all my life? What can that person teach me about becoming the leader I want to be? What was the story my family told about being real, being vulnerable, being true? What do I believe about vulnerability, and how might that actually serve me? And then let me give some of the concluding questions. How would

our organizations respond? Were we to hear all the things that are being said? What does it mean to be a leader at our organization? And what does it mean to be a grown, fully actualized adult? How would we feel if our children were to work for the company we've created, or the team we lead? How is the unsorted baggage of what has happened to us shaped who we are as leaders? What do we believe to be true about the world? Is it a doggy dog world? Or is it a world where people can be mutual in support for each other?

And I guess the final questions I often ask are, what kind of leader do I want to be? What kind of adult do I want to be? What kind of adult do I want to be? Because that's our opportunity to look at who we are and to consciously move into creating that. And I think that's in the end of the most radical act of adulting is to choose who we want to be. And when we fail to live up to that aspiration, we blow ourselves a kiss, we dust ourselves off, and we pick ourselves up, and we try again the next day. And it's key to know you will fail all the time.

All the time. And so there's a question, how do we respond when we ourselves fail ourselves? Do we use that to beat ourselves up? Or do we use that to grow? In a similar way, how do we respond when people disappoint us? John O'Donnelly, the poet, the late John Adani, he says, may when those who fail or disappoint you, may your response be their stairway to renewal, mean, that's our opportunity.

That's the adult I want to be. By the way, because I'm always thinking about the pleasure centers of the brain, it's in your interest as a leader to be building that stairwell for people who fail you. You're just going to have better functioning team. And it's in your interest to be that kind of adult. Yeah. To go home and when your spouse hurts you because they're carrying their stories about the world or when your child disappoints you or when you disappoint them

or when you hurt them to allow that renewal to come forward. If this is deeper than forgiveness, this is empathetically stepping into the fact that we all disappoint and hurt each other. And in recognizing that, we get to grow up. You know, in the end, that's the message that, you know, Dr. Sayers, my former therapist, she passed just about a year ago at 93. I worked with her for almost 30 years. That was probably the greatest gift that she ever gave me was the ability to accept myself totally down to my bones.

What she used to say to you all the time you're you're incorrigible. You're incorrigible. And she used to say it at first and I used to feel really really resentful about it but then eventually I heard her love and acceptance and all of that. And then it was okay. It's okay that you fail. Yeah, I mean, if I hope I'm not veering away from accuracy here, but I think there's a concept in psychotherapeutic traditions of what's called unconditional positive regard. Yes. So a great therapist, well, every therapist should do this, but a great therapist really embodies that idea of unconditional positive regard vis-a-vis their patients or

clients. And so calling you incorrigible within that context is basically you just giving you permission to be to fail and dust yourself off. And to be worthy nonetheless. Yes. Yes. And to be worthy nonetheless. Yeah, yes, yes. And to be lovable nonetheless. And so unconditional positive regard it sounds still complicated. But what we're really talking about is unconditional love. Mm-hmm. Yeah, it's a way to make it sound a little bit more clinical.

That's right. And by taking it out of the clinical, what if we could love the people who disappoint us even when we have to terminate or fire them? What if we could love the person even when we have to end a relationship? What if we could love that entirety even when it doesn't work out? What if we can love ourselves down to our bones despite our being incorrigible? Comedian Tracy Morgan or Tracy Jordan?

I can't remember because he goes by Tracy Jordan on 30 Rock, but it's real life. He once said, I love you and there's nothing you can do about it. Very cool. Well, I love you and you've done a great job on this interview. I think the book is going to help a lot of people. You individually have helped a lot of people, including the person, the hammering into this microphone right now. As we close, well, before you close that, I want to say I love you too. No, thank you.

And one of the things that I've enjoyed the most over the last few years is actually getting to know the whole of you. And the more I know the whole of you, the more I love you. You know, you're no longer just this guy behind the mic with a really deep voice. You're this really wonderful human. And I'm just, I'm really proud that you're in my life. I appreciate that. And now I have to do this awkward transition of asking you to do something super crass,

which is can you just plug the hell out of your book? It's really uncomfortable sure the book is called reboot Leadership in the art of growing up published by Harper Collins. Thank you Harper Harper business and it's coming out June 18th and Or it was released on June 18th and I'm super excited about it. It's, you know, as I write in the book, for a boy who suffered a sense of not being heard to finally have his words being read, is exciting and terrifying. And my deep wish is that somewhere down the line, five years from now, someone comes across some tattered paperback edition that's all marked up and says this book is really making a difference in my life. So that's the

best I can do for craftness. There you go. Well done. Thank you very much. Thank you, sir. Again, big thanks to Jerry Colona. As as I said, he's had a big impact on me, so I really appreciate him coming on the show. And if you want to see us together live, that's coming up July 10th at the Rubin Museum right here in New York City. Time now for your voice mail. Here's number one. Hi, Dan. I have a question regarding the recent podcast with Daniel Ingram.

He talks about two kinds of practices, emotional work, and insight practices. And he says both are important, but should be done separately. And I feel like I understand what is meant by insight practices, but I don't know what is meant by emotional work. So I was wondering if you could maybe clarify specific techniques for both, particularly the emotional work. And he also cautioned against spiritual bypassing. And I'd be interested to know more about that because I wonder if by just doing insight practices, I

am also doing spiritual bypassing. Thank you, thank you, thank you so much Dan, I love your work, thank you very much, have a great day, bye bye. Okay, so those are great questions, I'm really glad you asked them because these are important things to be able to disambiguate. Insight practices are, as I think you said, you know this, but I'll just say it for anybody who isn't clear on this, insight practices generally refer to meditation practices,

where you get insight into the nature of your mind and the nature of reality, if you wanna be a little grandiose about things. And that is actually quite different from, there's a difference between looking at the process by which your mind works. In other words, seeing how rapidly things come and go in your mind, seeing how you can get attached

and caught up by passing emotions, it's that that's looking at the process of the way the mind works. Emotional work is looking at the substance of your emotions. And we deliberately, in insight practices, in mindfulness practices, try not to get overly analytical about the substance of our stories of our life, the stories we're telling ourselves, et cetera, et cetera, because we're really trying to create a healthy,

non-attachment to that stuff so that we can see it come and go. But of course, our lives, our psychological lives are real and are really important on some important levels. And so we do need to also work with that, the our childhood, whatever may have happened to us and our childhood, what is the happened to us in our childhood, what is the nature of our relationships right now. And so that would be emotional work by which I believe Daniel is referring to things like

the kind of coaching I do with Jerry or just straight up psychotherapy, which I also highly recommend to anybody who believes they could find value in it. And so, again, insight practices would be like the straight up mindfulness meditation that we talk about a lot on the show, emotional work would be probably, I think, the most common example of that would be psychotherapy. Spiritual bypass is when we use our spiritual practice to avoid feeling into the difficult aspects of our experience. So one example, and this comes from Ray Houseman, who's the head of our coaching department, a 10% happier. One example of this would be using loving kindness practice or meta practice, which we've

talked about a lot on the show, as some sort of defensive strategy in order not to feel the discomfort of your anger or distress. So this is a really important concept, the idea that we can use meditation as a way counter intuitively, as a way to kind of avoid dealing with the substance of our lives. So both of these are important tracks that should be worked on. I hope that clears things up. I'm really glad you asked and I hope this was of use. Let's go to voice mail number two.

Hi Dan, this is Yardan, calling you from Brooklyn. So I work from home and like a lot of people these days, I've gotten used to sort of judging my own value by how much I do. So when I work myself as a bone, I feel like I've accomplished something. But when I rest or take the day off, it's really hard not to feel guilty. And I've been doing my best recently to be nicer to myself, so taking breaks when I need to, slowing down, meditating, taking care of myself.

But the problem is I'm so used to rewarding myself for hard work. So on a day that I'm tired or anxious or not feeling well, and I make the conscious choice not to work so hard, I'm not sure how to treat myself. Like have I done enough today to justify this cookie, or the snap, or lying down on the sofa and reading a book? So my question is how would you go about changing that mindset and giving yourself little treats without having quote- quote unquote earned them? Thanks so much for everything you do.

Lots of love. Bye. All right, so I really relate to this question. I agreed to, you know, they sent me the questions beforehand and the Samuel Johns, who does the work of fielding the voicemails. He sends me the voicem and my are the Samuel Johns who does the work of fielding the voicemails. He sends me the voicemails in advance and I agreed to take this question, not because I think I have some silver bullet answer for you, but because I just this is something that I see in my own life on the regular. There's a great term for this. I heard it. This

is podcast I like and the host I hope to have on the show at some point. The podcast is called Hurry Slowly and the host is named Jocelyn K. Gly. G-L-E-I Jocelyn K. Gly. Anyway, she had an episode recently about something I politely called it Productivity Shame that we that many of us in the, and I certainly feel this way, beat ourselves up for not being productive enough. And her answer, one of her answers was that the way we get into this situation where we're feeling all of the shame about our lack of productivity,

or perceived lack of productivity, is that we take on too much. It's like it starts right from the beginning. We think we can do or we should do more than we can or should be doing. And so it's looking at like, what are your basic expectations for the amount of work you can or should be doing?

This is more art than science. And your specific question was, how do you know when you can give yourself a little treat without having, quote unquote, earned them? And this is, I can't give you some silver bullet, so you can figure out, yeah, this is my night for a pint of ice cream. I don't know exactly how you get to that, but I think it's really about

using mindfulness as a way to see what is, when have you worked too much and when do you need a break and also noticing how really nasty your inner narrator can be and hopefully using mindfulness self-awareness to see oh yeah I'm in a spiral here of productivity shame I can change the channel also I invoke the name Ray houseman she is as I said before the head of our coaching unit at 10% happier app where we have all these amazing coaches who can answer your questions pretty much on demand through the app. This is what she replied to the question, and I'm quoting here, this is a fairly common experience. She said it can be helpful to simply sit with the awkwardness of not knowing how to be when we're not engaged in agenda-oriented activities.

So that's just kind of like a better version of what I was saying, which is, you know, use mindfulness. If you're in one of those moments of thinking, oh man, should I be doing more? Can I take a break? Did I get enough? What's my point?

What's my use on the planet? Might be worth it to actually use that as a cue to sit and meditate for a minute and think of, and just be with this not knowing. I regret your end that I'm not going to be able to give you again some sort of really easy formula for figuring this out and it's I expect maybe just annoying to hear that the answer to everything is meditation. But in this case I believe actually a little bit of meditation in those moments when you're having this struggle can be useful.

One other little thing I'd say is since there's a certain sort of, and I may be reading this into what you're saying, maybe I'm projecting based on what's happening in my own mind around productivity shame, but there's a kind of nastiness in my own inner weather when I'm worrying about this stuff. And the aforementioned loving kindness practices, where you repeat these phrases, may you be happy, may you be healthy. If you can do a version of that for yourself in these moments, if you can deal with the sappiness

that some people, myself included, perceive in this practice, if you can get over that, there's a lot to suggest that that can make a difference. So I've thrown a lot at you. Hopefully it was helpful. Again, I really appreciate the question. Now, at the at the point in the show where I say a lot of thank you. So I want to thank our listeners. I met somebody the other night. I want to say a woman named Liz, who was part of our podcast Insiders Group. It was really cool to meet Liz and that the reminds me, I just want to thank all the folks who every Friday,

take time out of their own lives to give feedback on the show. It makes a huge difference. I see it personally and it informs how we change as we move along here. I also want to thank the folks who put together the show, Samuel Johns, Ryan Kessler, Grace Livingston, Jonah Haskels on the board tonight. Thank you, Jonah, appreciate that.

Thank you, of course, for listening, and we'll be back next Wednesday with another show. [♪ OUTRO MUSIC PLAYING [♪ Hey, hey, prime members. You can listen to 10% happier early and ad-free on Amazon Music. Download the Amazon Music app today. Or you can listen early and ad free with Wondery Plus in Apple

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