Most of us have gotten pretty far by moving fast, doing more, and striving for the next achievement. But when you’re called upon to lead, it’s time to look in the mirror, face your hard stuff, and grow into your full self or you’ll never lead others to do the same. To get there, you might need a reboot.

Jerry Colonna is an executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. This episode has Sean discussing a lot of the struggles he personally faces with Jerry asking provoking questions to get to the root. You will not want to miss this!

Sean DeLaney: Jerry, welcome to What Got You There? How are you this morning? 

Jerry Colonna: Doing great, Sean. Thanks for having me, and it’s a beautiful day here in Boulder and watched the sun rise and I’ve got a cup of coffee with me so I’m good to go.

Sean: Few things more enjoyable than an unbelievable morning in Boulder. I used to live in downtown Denver, and would travel to Boulder quite frequently, so, I’m very familiar. I’m glad you’re enjoying the aesthetics there, but I wanna know typically how do you start your day? What does it look like?

Jerry: Uh, groggily.

Typically I wake usually without an alarm somewhere between 5:00 and 5:30, which is odd when you are shifting time zones and you still wake up between 5:00 and 5:30 regardless of the time zone. And then I make coffee, that’s kind of my ritual, and then I journal and I journal and then I meditate and this morning I was meditating on the back porch, which is not something I normally do. Normally, I meditate, I have actually a dedicated meditation room, and I’ll journal anywhere from 45 minutes to an hour, an hour and a half, and so my morning ritual, takes about two hours. It was a little cram this morning, but it normally takes about an hour and a half to two hours before I really do things like think about my day and look at my phone and all of that nonsense.

Sean: The journaling process, I’m always intrigued by people’s process. Mind has been one that’s been refined throughout the years. What does your journaling process look like when you sit down with your notebook or your journal what do you start doing?

Jerry: Well, I’ve been journaling since I was about 13 pretty much every day. There was long stretches of my life where I wasn’t, but pretty much every day I journal and I typically do kind of quick inventory. It reminds me a lot of what I do with meditation, which is the first two breaths of meditation and sitting posture I will just sort of scan how am I doing, or what’s going on.

So when I open up the page, most often, I complete the sentence that begins with “right now, I’m feeling” or some variation of that, I might then go into a dream that I just had, or I might do a kind of diary “yesterday this is what was going on.” And it feels like a very completing process. It helps me process all that, I’m caring positive and negative, happy, sad. It just feels like it’s a very clearing process. 

Sean: It’s just a great way to put it. That really does sum up, I feel like, many times, how I feel once I’m journaling and you bring up the power of questions, and questions it’s gonna be a reoccurring theme throughout this conversation, but a lot of questions I receive and I’m always dealing with is the rest of the day. It seems like you’ve done a great job structuring those first two hours, but what about when the chaos starts to ensue? Is there anything you typically have set up on-going throughout the late morning, afternoon and evening?

Jerry: You mean like in a ritualized way, like at lunch, I’m doing x or mid-day kind of thing?

Sean: I guess my question stems from many times there’s just a million things thrown at me and I can just spend the entire day consumed in reactionary things. Do you schedule time alone for yourself at other points in the day, so you can reflect, think through problems, anything along those lines.

Jerry: I typically don’t although there’s two reactions I have. The first is to go back to meditation for a moment.

Okay, so, why do we meditate?

Right? We meditate for life off the cushion not for life on the cushion, and sometimes a meditation is so popular right now, I get a little nervous because this seems to be so much emphasis on technique and it has the unintended consequence of getting people to focus on those 30 minutes that they may be sitting in a lotus position in the posture and that is important, but that’s not the point. The point is to strengthen the muscle that you’re gonna use throughout the day, which is that when life is thrown at you, four hours after your meditation session you’re able to reach back in without a pre-planned experience and take a breath and say, “Okay what just happened? Oh, I’m triggered. I’m going into my old pattern, I need to take a walk right now.” Rather than perhaps setting up these breaks throughout the day.

Now, that was my first reaction.

Second reaction I had was I really, really resonated with your question about taking some time alone. I’m a profound introvert. I’m not shy, I enjoy people and I enjoy meeting people, but I am often overwhelmed by larger groups of people. And for me, large as anything more than three.

And so what I think that I have hit upon without a lot of conscious thought, about it is that I spend a lot of time alone, and that feels really nourishing and so it’s not something that I’ve consciously said, “Okay, from four to six every afternoon, I’m alone.” It just evolves. So yesterday, for example, I had two calls scheduled with friends to do sort of a check-in and I woke up and I just needed time alone so I wrote to them and I said, “Can we reschedule? I’m good, I just need time alone.” And so that’s what I took. I hope that answers your question. It was a very full answer.

Sean: No, I love the answer, it really helps me think through things and understand. Well, I guess I’ll circle back to understanding, strengthening your muscle, so that way you’re able to adapt and evolve with the situations at hand. So how far long do you feel like you are in terms of strength in your muscle to be able to handle new scenarios thrown at you?

Jerry: I love the question, so let’s go back to the word practice. Or even the word art, okay.

Practice implies it’s something that we do without actually achieving the outcome and I think that that’s a really, really powerful and liberating framing. Art implies experimentation. It implies moving and trying things without art as a verb, not as a noun. It implies a kind of trying without necessarily focusing on achieving something.

And so what I think the muscle that I have practiced well, and spoiler alret, the last line of my book is something like, “And with that I mastered the art of growing up,” and the word is growing up, I don’t say, “And with that, I’ve grown up.”

And so to go back to your question, I think my muscles for trying and practicing the art of being human are pretty good right now, but I’m not there yet.

And what’s most important, I’m never gonna be there and that makes me laugh and smile because it look gives me the freedom to fail without producing shame.

Sean: It’s a fun journey, isn’t it?

Jerry: It is indeed it is. You get to work on things that are important with a kind of consciousness that allows a bit of humility, and humor, and love to come into the process.

Sean: So, at this point in your life, what are those big pillars, what are you viewing is most important that you’re spending the most amount of thought? 

Jerry: My relationships.

We’ve got the video turned off, but I’m looking off to the left and I’m staring at pictures of my kids who are all, by the way, adults not in the pictures, right? And the pictures, they are like munchkins, but the Rugrats. But thinking about those last night, my oldest son and I, when for a long drive, just outside of Boulder, just to appreciate the sunset just to talk. So relationships are important, taking care of my health, making sure that I am working on the issues that hold me back and create my own sense of suffering. We have a phrase in the company that I think is a good model for life in general, and we’ve taken it from the poet David White, which is, “Good work done well for the right reasons.” And I kinda like to use that as a guide for each day. “Good work done well for the right reasons.” And the right reasons are typically things like kindness, compassion. I desire for my own internal growth because I know that that’s the surest way to contribute well to the world. 

When I pass as will happen at some point. I want people to say, “Here was a good man, he did, he did his best.”

And so, that’s the commitment that’s what I’m striving for. 

Sean: A lot stood out in those past few minutes. Two things that are really standing out for me is, you mentioned holding you back and just that desire for internal growth.

So, when you’re assessing yourself and that desire for internal growth, how are you doing that? Is it a very meditative practice that you’re sitting back and kind of assessing the 30,000-foot view of your life?

Jerry: Your question implies a kind of intellectualized consciousness around it. It’s a little bit more felt sense than that. Like so, for example, at 2 or 3 o’clock in the morning, I woke up from a dream last night with some anxiety and what I did, it was in my journaling, a session this morning, I noted the anxiety and the noted the dream and I’ll continue to work with the dream because the dream is a kind of a gift for my unconscious telling me, “This is where you are or this is what you’re holding, this is what you’re feeling.”

Because oftentimes were disconnected from the feeling and noting the anxiety that I felt overnight enabled me to spend some time with the content of my life.

Right, which is where I would say is holding me back. And so I have my oldest son is moving from Colorado and I’ll miss him and that’s the feeling and I am super proud and I’ll miss him.

And so allowing myself to explore that creates the space for me to be able to respond and be connected in a more human way, but doing so means that I have to touch upon feelings that are, “That hurts,” but there’s love behind that feeling and so it’s a great little spot to go to.

Sean: Can you expand upon going to that spot?

Jerry: Sure, I think that we’re socialized to avoid pain, in fact, you know I’m a Buddhist and the four Noble Truths, which is what the Buddha awakened to from his first profound experience of meditation.

The second, the first two Noble Truths are really interesting. The first is that life is filled with Dukkha, suffering, and the second Noble Truth is that, “That which we do to push away suffering, increases suffering.”

Now, if you just stay with those two thoughts for a moment, think about how our societies are organized, how our belief systems are organized. I know a lot of your listeners are entrepreneurs. We believe that there’s some magical land out there, some magic startup playbook-driven land where nobody’s suffering. We believe that. We’re socialized to think that that place exists and as long as we hold on to that belief, we actually suffer because our firm hope in the belief that being a leader means I don’t have to grow actually increases the pain of being a leader. Just like my experience of not wanting to touch into feelings of anger, feelings of sadness, feelings of shame, feelings of guilt. Yet every one of those feelings, there’s a wisdom behind them and it’s a hard process because you have to feel the anger without acting out the anger, and you do that with very, very curious questions like, “Wow, why does this hurt?” Oh, because it reminds me of when I was seven and such and such thing happened to me. Oh right, I’m not seven anymore. The feeling is still there, but the whole circumstance is different.

How can I grow from that point?

So I’ll pause. I know I said a lot of words there, so.

Sean: No, a lot to think about right there. And I’m thinking a lot about the questions. And is that something that it’s more important you’re asking yourself, or is this someone else asking you these questions and having someone who’s capable of going deeper with you?

Jerry: That’s a great question. I think that one of the reasons why community can be so powerful for us is that you and I could go for a walk one day, and I can ask you a question that allows you to sort of go deeper within yourself, and that process creates an intimate bond especially if you turn around and ask me a similar question. And then all of a sudden there’s this connecting point that happens. Once we are sort of practiced in that art, we can ask ourselves those questions or conversely, you could start by asking yourself those questions. 

In the book, I end each chapter with a series of questions that are designed to just prompt people to explore deeper. If they stop at those questions, they’re not fully experiencing what is available to them. So the whole idea is questions lead to more questions which lead to more questions.

Now, if we just pause and hold on to that thought, there’s something really important that is behind all of this, which is, “Wait, Jerry. Are you saying you should ask questions, even though you might not get the answers?”

Yes, that’s right.

We live in an outcome-oriented world. We live in a world in which our worthiness is measured by what we have accomplished. And the challenge with that is that if I start to ask these probing questions, these curious questions, these open, honest questions, and I don’t arrive at an answer, the danger is that I will judge myself poorly. I will judge myself a failure because I haven’t figured out the answer, which reminds me of that famous Rilke question, his advice to the young poet in Letters to a Young Poet, in which he says, “Live the questions now.” What he’s really saying is there’s a power in contemplating questions and maybe I just gave you a very long response, here’s a simpler response.

If you were to journal with a set of questions, a question like, “what do I believe to be true about being an adult?”

Okay, if you were to journal that and then go back a year later and journal the exact same question, I guarantee your answer would be different.

And that difference is what’s interesting, ’cause that’s growth, but if we approach that experience saying I have to come up with the once and for all answer, we will then end up exacerbating the anxiety and the suffering and the self-criticism that is such a hallmark of our experience as human beings right now.

Sean: You make it sound much simpler. I feel like, can we make it out to be so many times?

Jerry: It is simple!

Sean: I mean, any recommendations, Jerry, for someone who, who has a very difficult time asking themselves those questions but more importantly, letting the question be, and continue on with more questions as opposed to looking to that finality? 

Jerry: Yeah, thank you for making me laugh, Sean. 

What I often say is, “It’s not complicated, it’s hard, it’s not complicated.”

What makes it complicated are our expectations. And so, if you can relax the expectations, which are internally generated, we’re the ones who are saying to ourselves in this experience we are supposed to have the answers.

Now, we may have internalized messages from our parents, from the society that I guarantee you we’ve internalized those messages from our larger society, but they are internal, which means that they are under our control. And if we can relax those expectations and realize that we’re gonna ask ourselves a whole bunch of questions and that even if we manage to come up with an answer, the answer will shift. Then we’re liberated from this notion that we have to have measurable progress every single step of the way, that every single day I’m supposed to be marginally better than I was yesterday.

That’s like a jail.

And that, I think, exacerbates the suffering. It means we miss the beautiful sunrise. It means we miss the whiff of lavender in the air. It means we miss the smile on our son’s face, when as he did last night, he let loose on my very, very fast car and experienced being thrown back into his seat and accelerating. Shh, don’t tell the police.

I mean, I don’t ever wanna miss those moments. Not even just a moment of the acceleration but the little smirk on his face when he felt what I had been feeling ’cause I’ve been driven this car for months, right?

To me, that’s the point of it all. Those little moments.

That’s why we strive so hard that’s why we work our tail off. That’s why we build companies. That’s why we… So that we can have those experiences.

Sean: You’ve talked a lot about your kids. I just celebrated my son’s first birthday and I…

Jerry: Mazel tov!

Sean: Well, thank you! I feel like I’ve never been at a place where I’ve worked harder and I’m assuming a lot has to do with setting an example for him, making him proud, setting a foundation up. How do you balance those moments? ‘Cause while you were in the car driving with your son, my son is pushing his Mickey truck, and I do not ever wanna miss those moments, but at the same time, I’ve gotta provide for him. 

Jerry: Right there! Right there, Sean, right there.

But at the same time, what’s that? What happened?

Sean: Expectations?

Jerry: Just stay right there, no judgement.

Just notice that moment, what your son’s first name? 

Sean: Daxton.

Jerry: Daxton. Daxton’s on the ground. He’s pushing his Mickey truck. You’re noticing his Mickey truck. All of a sudden, a paternalistic voice comes in and says, “Take care of him. Keep him safe, warm and happy. Be a good father. You’re with him? Be a good father.”

The duty and the presence. Is there a tension there? 

Sean: At times. So at times, I can fully enjoy that moment for everything that it is. And then there’s other times, and I feel like it’s times where I lose hold of my day, that tension is there.

Jerry: Okay, so I’m gonna speak a little bit like your older brother, ’cause my children are 29, 27, and 22, so I’m at that end of the spectrum. You’re at the beginning of that.

Here’s a framing I would suggest you hold on to. Be the adult, the adult that you would like Daxton to be when… I’m imagining you’re in your 30s?

Sean: Yes, I’m 32.

Jerry: Yeah, there you go, okay. So when Daxton is 32 we want you to be the man that you want Daxton to be at 32 and hold that frame.

And so one of the challenges is I talk about leadership as an opportunity to grow up. Here’s the truth of what you’re experiencing. Being a parent has an opportunity to grow up.

We’re called forth to be the adults that we needed as children. Not to say that the adults who raised us were bad or good, they just were who they were. But we are now presented with an opportunity to grow even further to be even more. That bitter sweet tenderness that you feel around your son, use that as a motivation to grow into your fullest stuff and that means holding the tension between love and presence and duty and that duty is… It can overwhelm us, it can drive us to work harder than our children actually want us to work, which is converse, perverse, right? We’re doing this, to create love, safety, and belonging for our children and yet what we’re doing, we may at times do is actually undermine their sense of safety, their sense of love because of our lack of availability to them.

And so, it’s simple, but it’s damn hard. What’s hard is holding the balance, let’s call it between presence and the call to take care. And by the way, this is something I still have to struggle to balance because there’s a whole world of people that would like me to help them, and I get affirmation and approbation, out of being able to step in and take care of them. Modeling for my children what it means to be a good citizen in the world to compassionately be there for someone else.

And yet, I need to also be there for them.

Sean: And that’s such a powerful framing. No wonder you’ve been coined. The CEO whisperer.

I’m intrigued and you mentioned being pulled in multiple directions and I just saw what you were able to do for me so quickly. And so what do you think it is about what you’re able to do? Why can you do this so well and pose these questions, in such a way that just seems so simple, but goes so deep?

Jerry: Well, the first thing I have to do is acknowledge something that you just said which is that I do it well. If I may, I don’t know, I suppose I do it well. At this point, I can internalize that, but let’s drop the adjective or the adjectival phrase, I do it so well, how do I do what I do, why do I do what I do?

Well, for me, what occurs to me is that I listen. So if we go back to that moment before the moment and where I just sort of yelled into the phone and said, “Stop right there!” It was the moment of the word “but.” That word and my body winced, because you were enjoying this beautiful memory of Daxton pushing his Mickey truck or his car and I had this picture of you hopefully on the ground next to him. Going “Vroom, vroom, vroom.” And the sweetness of that. And it was interrupted for the “but.”

“BUT, you better grow up, buddy, boy, you better be…” All of that follows from that word “but.” Now in coach facilitating schools, they always teach you to work with teams and to help them insert the word “and” in place of the word “but.” And it’s a cognitive thing, but I’ll do that right now. I wanna be on the ground with Daxton pushing the Mickey truck going “vroom, vroom.” And I want to keep him safe. And all of sudden what we do is we remove the tension from that place.

Now you asked how do I do that? I do that by listening, actually tuning into how my body was reacting. If we go back to the meditation and we go back to journaling for a moment, strengthening the muscles of paying attention to my own body allows me to then turn around and pay attention to you.

There was a hitch in your voice when you said, “But.” And I’ve heard that hitch, and that tension tens of thousands of times in my career, and that’s the moment to pay attention to.

So that’s what I do. 

Sean: When did you discover your ability to do this well, ’cause your career did not begin this way?

Jerry: I think that this intense listening, conscious listening, which is what I would describe it, it’s like a full body listening, I actually developed as a childhood survival strategy. Because I had to navigate my mother’s mental illness, and my father’s alcoholism and it created a tension in my body where I was kind of, I was always hyper-vigilant, paying attention to everybody else’s feelings.

That experience is quite familiar to people who grow up with parents who struggle with their own emotional well-being and their mental health. It’s one of the ways in which we navigate that experience.

I think what is different about me was that at some point, it became less of an obstacle in my life and more is what I often referred to as a superpower and I think I began practicing it even as a reporter in my early 20s because if I look back, I can see conversations I had with prominent figures in the technology industry where I was hearing things that other reporters were not hearing. And so then therefore following up with questions that other reporters were not following up with and then, therefore, getting answers that no one else was getting. And then over the next 20-30 years, I just refined and refined that process to the point where it’s the most natural thing in the world to make.

Sean: That must be a fun place to be at, where it’s so natural at this point. 

Jerry: It is and I’ll acknowledge that it can be really annoying for the people in my life. 

My daughter once famously said on Facebook about me, “Yeah, can you imagine what it’s like to grow up with a man who asked you questions you don’t wanna answer?”

Sean: So any advice then to those people who are similar, who probe those closest to them, with certain questions that might be incredibly difficult and could create tension in that relationship?

Jerry: Yeah, so remember the phrasing to use before “Good work done well for the right reasons.” The “for the right reasons” is a really important experience here. 

Sometimes I will use that superpower to defend against what I perceived to be an attack. And so then it becomes prosecutorial. Sometimes I will use that to ward off self-inquiry, okay.

And so, my obligation and the obligation of anyone who is looking to enhance this capacity, the obligation is to be acutely responsible and the deployment which means that if someone comes back to you and says, “Hey! Back off I’m not your coaching plan,” and you gotta listen.

Or even more, and I didn’t ask permission of you, one of the nice things to do would be to sort of say, “Hey can I give you an observation or can I respond with a question that might be helpful?” Right? And to create a little bit of permission around that, that’s something that I’m still working on because my impulse tends to be the jump in a little quickly inn those instances. 

Sean: What gets you the most excited when working? It doesn’t necessarily need to be a client. It could just be a loved one. What is that moment that really just makes your heart beat a little faster?

Jerry: Can I tell you a quick story? And it’s from a client engagement. Last week I did a fireside chat with a former client, Jeff Lawson ,who was the founder and CEO of Twilio, and he had read my book, and I think we last worked together maybe two years ago, but we had worked together for a long time, and in the early, early days of the company we became working together. And at one point he had read the book and he said, “Oh, I get it. Now I understand why you never gave me answers but you asked me all these questions all the time.” But I said, I said, “Jeff you had no idea how much I wanted to give you the answers, but I knew that my job was to ask questions so that you could arrive at your own answers.” And he sort of looked up and goes, “It was such a pain in the ass.” But now, I understand what it was you were doing, you were helping me grow and so you asked the moment that I love, like I love that moment where I got to look back, and I just felt such a deep pride and understanding that his growth was not something I did. His growth was something he did, but I was a witness to that. I was a questioning companion on that and that made me not responsible for his success or failure, but a deep, deep soul companion and that just indescribably beautiful.

Sean: Is the importance for you giving the person the space to discover on their own?

Jerry: Yes, yes. See when we give the answers we actually undermine the person’s belief system that they have the answers themselves and our job, our work to do in relationship, is to support each other.

It’s not to make it happen for each other.

And listen, my young father friend, this is something that will be hard for you because we watch our children stumble and sometimes we do have to step in and say, “This is how you tie your shoe,” but we also… Our job is to support them not only in tying their own shoes but in discovering how to tie their shoes, because there will be a day when you won’t be there, or you’ll be there in an internalized way. Not physically there. And our job as parents is to leave the world with adults.

Our job as leaders is to leave the company with leaders and other adults, that’s good work done well for the right reasons.

Sean: Once again, you’re able to say such a simple phrase, that’s so powerful. And going back to children, one of the things I love most about being a father is just seeing that childlike fascination and they’re discovering and it could even just be a box that cardboard box is endless in terms of what it could be to that child. Do you find yourself still having that childlike fascination with things?

Jerry: Yeah, yeah, it tends to be out and about around the natural world, but yeah, I do.

Sean: It’s fun to see that in adults and the interesting places that might lead to when they go about the world in those ways. I’m also thinking about what you were just talking about your time with certain CEOs and entrepreneurs, are there vast commonalities you’re seeing amongst these people in recent times?

Jerry: Yeah, to go back to an earlier statement, many, especially first-time CEOs walk around with the belief system that there’s a secret list of answers, there’s a secret book and that the world is just keeping it from them, and that they are not either worthy of, or smart enough to know those answers and so they furrow their brow and they dig in and they sort of say, “I just have to work hard to get this all right.” And what I would say is I appreciate the love that’s behind that wish for learning. But there is no secret textbook that has all the answers. 

There are some really, really good sources of information about those things, but in a similar fashion, if I were to write a textbook for example, and say, “These are the 15 things to do,” I would kind of leave you bereft because you could only internalize one or two of them and then you would walk around absolutely convinced that you are shitty as a CEO. And I think you can collect a lot of opinions and use that as data but data in wisdom are not the same thing, and wisdom has to come out of your own unique experience and that’s what makes that leadership journey so hard and ultimately so rewarding. 

Sean: With the leadership journey, this is something I’ve dealt with and I’ve seen others around me, the combination of ego and optimism, and I’m trying to discover that it seems like there’s a lot of entrepreneurs, a lot of CEOs, who are incredibly optimistic and they almost don’t think things can’t happen or could be impossible. And I’m wondering how do you combo that optimistic view but don’t let the ego blind you?

Jerry: Maybe seven or eight years ago, I frequently used a phrase pathologically optimistic. And I think we’re hitting upon the same thing, which is that it’s a way of using optimism actually as a way to dilute oneself and to not soberly assess our lives. So imagine if you will, that what I just said is true, and that’s the condition that we’re talking about. What’s the feeling behind that pathology once a fear of failure?

Oh okay, so if I can address the fear of failure, I can arrive at a healthy optimism because healthy optimism goes like this: what we’re about to attend, launching a business, launching a new product or service, is hard. We may fail and if we fail, we are A-OK as human beings. We may stumble, we may have to work doubley hard to put more money in the bank and that sort of thing. That’s not to be taken lightly but it doesn’t mean my self-worth is shattered and I have assembled a good group of people. Our ideas are smart, our thesis, our questions, our persound. Let’s go for it, and if we fail, we’ll pick up the pieces and figure out where we go from there.

That feels like healthy optimism.

And the turn is letting go of an unhealthy attachment to achieving an outcome, allowing whatever outcome will happen and being convinced in the belief of the values of yourself, in your team, so that you can go forward.

Sean: I’m assuming you did this assessment or a similar one over the past year. Your book Reboot has been out for a few months now. Can you describe what it’s like leading up to the launch of the book and then what it’s been like? The following months? 

Jerry: Yeah, you touch upon some really good nerve there.

In terms of leading up to the launch of the book, one of my dear friends, an incredible supporter in the whole process, some what I’ve known since 1996…23 years, anyway, Seth Godin early on the process said to me, talked about how writing and being a writer can expose a kind of nerve, nerve endings. And he talked about the thinness of with which writers sort of approach the world and the ease with which they can feel judged, and criticized.

And so, there are several parts of this process that were hard. One part was the writing, which meant really excavating my experiences, my memories, my belief systems that was hard and then turning it in and working with my editor, and not hearing back for a week to two weeks and I was very, very lucky ’cause I had amazing editor, who just responded so well and quickly but still like the stories I would tell myself, which was, “She’s rethinking the whole contract, she’s completely decided that I’m an idiot as a writer.” And she can’t figure out how to tell me, right, so all that’s going on and then the manuscript is done, and it’s being edited and all that’s going on. And then I have to begin the process of building the startup known as the book, which is a completely different experience of talking to lots and lots of different people about the experience of that and then worrying about, like for me, I wanted to do a good job and I wanted to hit the numbers not because of my own, I guess there’s some ego involved in it, but because I wanted to prove that the publisher was right in believing in me. And so there’s a very regress childlike belief system, right?

So there is that experience. Then the book is out in the wild, and there’s a completely different experience, which everyday I’m getting people right to me in one form another saying some version of this book has changed my life and not just because I’m giving off a list of leadership principles, those are implicit in the book, but because of the very thing that I set out to do, which was to show up and be present myself in the book. 

Now, it’s not a book for everybody, I understand that it’s a challenging book in the sense that it will challenge you to grow, for sure, but those people who are sort of leaning into that are coming back to me and saying not only is this a book for me, as the CEO, but I’ve given this book to my children, I’ve given this book to my family, I’ve given this book to my friends and that experience, I wasn’t prepared for. The sense that there is this deep connection that people are feeling. It’s quite moving, it’s a little scary for this introvert.

My friend and mentor, Parker Palmer said a few weeks after the book was launched I was talking with him about the experience and he said “You know, Jerry, you have to understand there are 10,000 copies of you out in the world now, and people are reacting to that and they’re having their own experiences with your words and taking that in.” It’s not unlike what you will experience when Daxton is older, which is you feel the connection to this person this thing, and then it starts to have its own life, and I’m watching and being a witness to that unfolding in a way I never anticipated. 

Sean: So that’s a pretty powerful line from Parker. 10,000 copies of you out in the world. I can only imagine, grasping that. And then, like you mentioned, this is a constantly evolving thing you now have. I have just a couple of quick questions for you, that I’ve been very intrigued to ask you. And you’ve worked with a lot of talent to the individuals in the past.

Sean: When’s the last time you’ve stopped in your tracks? Just being impressed by someone? This doesn’t have to be someone you’ve worked with, it’s about seeing talent and just being truly impressed by the capabilities of someone.

Jerry: When was the last time? Thursday, just a few days ago. Today is a Monday. 

In all seriousness, I work with a company I’ve been working with the CEO for a number of years, I’ll say, four years, and I’ve been involved with the senior leadership team now for about eight months and just helping them grow as a team. And a few months back, I started working with two individuals in the team who are having tension.

And one of the two, I’m gonna describe him as a young man in his late 20s, came in and my preconceived notion of the challenge was that he was really struggling to understand what his role was. There was a lack of clarity, lack of… There’s a lot of conflict avoidance in the organization.

And he sits down and he says, “I’ve been thinking a lot about our meeting and I listened to your podcast,” and he named one of my podcasts, “and I was reading your book and I realized that I am a source of a lot of lack of clarity because I’m afraid to clarify what my role is, ’cause if I do, then I’m afraid I will fail.” 

And my jaw dropped.

Because that’s the kind of insight that is exactly what I’m hoping to prompt.

And then we had this amazing conversation, and then literally just last week I was back visiting the company and there was a similar kind of simultaneous recognition of the reality of the conditions of the company and his own contribution to kind of the mess that is a normal mess.

And I looked at him and I said I can’t wait for this guy to be a CEO, because there’s growth right there, that’s leadership. And he feels a complete a total mess and I just smile and I know I can see 10 years into the future, when he’s gonna be running a kick ass company where people get to do the best work of their lives because he is willing to look fiercely in the mirror and to borrow another phrase from Parker, “Be fierce with reality.”

Sean: This is so fun for me, getting to have these conversations. Ask a question, have no idea where it’s going and then to hear a story like that. I’ve got one final one for you before we wrap up. What’s the kindest thing someone’s done for you?

Jerry: Well, what comes to mind there? Many, many can I just give you a recent kind thing versus the kinds… 

Sean: I’d assume you’d go with with the recent, so yes. 

Jerry: So a few weeks back, just after the book launch, I was struggling, I was having a hard time. And I reached out to a dear friend who doesn’t need me to be their coach, and doesn’t need me to be wise, I could just be a complete mess with him and we had a video call ’cause he’s not local, and I was just a mess, and he just wasn’t and he was with me and I cleared the air and I felt better about a week later. He just sent me a note, and he said, “Just checking in, how are you doing?”

And I was in the midst of being there for so many other people and that little act of kindness, that’s all it was, was just like, “Hey how are you doing? Just checking in?”

I know the world wants a lot from you and I just want you to know I’m here.

That just means so much. It’s like, it’s like a hand on the shoulder that says, “I see you, I hear you, I love you.”

That’s what it felt like. 

Sean: I don’t think there’s a greater closing loop on our conversation than that final minute, so thank you for that. That was truly remarkable and incredible. I know you’ve got the listeners engaged much like myself right now, I know you have a lot going on with the business, the book, the podcast and some of the other endeavors you have, where do you want the listeners going, where can they stay connected with you, Jerry?

Jerry: They can either go to the book website, which is rebootbyjerry.com or reboot.io, which is the company site, and if they go to the company site, one of the nice things about having built a company and then the book, there’s a tremendous number of resources available to people from our own podcast, who we’ve actually developed free courses for people that can really help them in their journey, and nothing makes me happier. Then to know that there are people, even if they can’t afford individual coaching services and all, that they’re out there getting help just by doing some of the stuff that we do for free, and make it available for people. So those are the best ways to follow what we’re doing and really use that to grow in their own process.

Sean:  Well, thank you for making that available to people as always, that will be in the show notes and even more on Jerry and the work he’s doing at whatgotyouthere.com, but Jerry, I cannot thank you enough for joining us and taking me on my own journey into fatherhood. So this came in a great moment in my life, so thank you for that as well. 

Jerry: It’s my pleasure, and thank you for such compelling questions and make sure you get down on that carpet, and push those cars around.

Sean: Vroom, vroom.

Jerry: You got it.