Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year | The Tim Ferriss Show | Transcription

Transcription for the video titled "Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year | The Tim Ferriss Show".


Note: This transcription is split and grouped by topics and subtopics. You can navigate through the Table of Contents on the left. It's interactive. All paragraphs are timed to the original video. Click on the time (e.g., 01:53) to jump to the specific portion of the video.


Intro (00:00)

Hello boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show. I'm going to keep my preamble short. My guest today is Jerry Colona, C-O-L-O-N-N-A on Twitter at Jerry Colona. He is the CEO and co-founder of, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. Now, for those of you who don't know, Jerry's already been on the show. It was an excellent episode and it was named the coach with the spider tattoo. We're not going to have time to get into why we chose that title necessarily. But suffice to say, very, very detailed, very, very tactical and I wanted to have him back on for reasons that will be clear shortly. For nearly 20 years, he has used the knowledge gained as an investor, one hell of an investor, an executive and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience and equanimity. Prior to his career as a coach, he was a partner with JP Morgan Partners, the private equity arm of JP Morgan Chase. Previously, he led New York based Flatiron Partners, which he co-founded in 1996 with partner Fred Wilson. Flatiron became one of the nation's most successful early stage investment programs. Jerry's first leadership position at age 25, a young and a young whippersnapper, was editor in chief of information week magazine. He is the author of reboot, subtitle, leadership and the art of growing up. As I mentioned, this is his second appearance on the podcast. Definitely also check out his first, which goes deep into his bio and all sorts of topics. Again, one more time, C-O-L-O-N-N-A. You can find him on Twitter as mentioned at Jerry Colona on LinkedIn, of course. Reboot's Twitter is @reboothq. And the website for all things Jerry and reboot is Jerry, welcome back to the show. Thanks for having me, Tim. You know, it's a bizarre experience hearing your life played back at you like that. I'm sitting there listening and I'm going, "Damn, I'm old." You're practicing something from 1996. And I know that's in my bio, so... Oh, man. Yeah, when I ever hear my bio read back, which, you know, I've usually crafted carefully in third person.

Understanding And Maximizing Sabbaticals

How the first sabbatical became a continued practice. (02:34)

I'm like, "Wow, well, that's the highlight reel. It's all downhill from here." So it was a very terrible way of setting expectations. So Jerry, I want to explain for folks how we came to be here today talking again. And we're actually recording this episode about five feet from where we recorded the first in Austin. And I remember it very, very clearly. And we reconnected, I want to say, a month, six weeks ago. Yeah, something like that. And we were covering a number of different things, but it quickly came up that you had just finished a two months sabbatical. And then you've sort of casually mentioned that you'd done that for how long, roughly? Would you say? Well, I interrupted it last year because of the disruption that was 2020. But previously, it was nine straight years, so that was my 10th two months sabbatical. Okay. So 10th two months sabbatical. And I wanted to hear all about this. I wanted to dig into this and thought it might be a great bridge and launchpad for discussing all sorts of things. So since we covered so much of your bio and background and trajectory, the ups and the downs. Let's just jump right into it. Can you perhaps begin at the beginning with the first sabbatical that you took and how that came about? It's like it. And if we were a TV show, you know, the image would get all wavy as he flashes back in time. Okay. So I've been a coach now for about 17 years. And I came to coaching on the one hand very much having been trained and gone through methodologies that are known as coaching. But it would be dishonest or not completely honest if I didn't also say that I modeled myself after my psychoanalyst. And as every good New Yorker who's in therapy knows, August is when all the therapists go on vacation. And so you don't want to be in New York in August because not only does it stink to high heaven, it's also when all of our therapists are gone, right? Home alone in New York City. For more on this, watch the movie, What About Bob? Which is a very good, anybody who watches the movie will get the reference. Is this corn hand-shucked? I continue. Indeed. Excellent, excellent movie. Excellent movie. Bill Murray in search of his therapist. So, you know, when I started doing this work, one of the things that I found myself doing was feeling the repercussions, if you will, of being fully emotionally present. More fully and emotionally present than most folks are in a given conversation. And I also found myself terribly depleted, terribly exhausted on a regular basis. And I remember talking to my therapist with the idea of at first taking four weeks off. And what I started to do, though, was I started to realize that I needed longer than that. Because I know this is going to sound really intelligent. But I also wanted to take a vacation during the middle of sabbatical. I know that's a bit of a controversial statement. But I would do things like go to Tibet for two weeks and help build an orphanage. Or I would take these monumental trips. I rafted the Grand Canyon for the third time in 2014 with my son. And so what began is, well, maybe I'll take a month and then take two weeks of vacation, started to morph very, very quickly into, you know, modeling myself after my therapist, morphed very, very quickly into, no, I actually need to take a pause. I need to take a break. And a funny thing happened on the way to the forum.

The first (or sometimes second) sabbatical: wrestling with questions and self-doubt. (07:20)

A funny thing happened on the way back. I found myself being a better therapist. Oh, did I say that out loud? A better. Freudian slipped there more ways than one. A much better coach. A much better coach because I was rested and I could be there more fully for my clients. So what did the very first sabbatical look like? Did you have any internal conflict or pushback? Oh, yes. I laughed. It doesn't have to be the very first. It could be one of the first, but one that comes to mind. Well, the first one that comes to mind is, can I afford this, right? Which is crazy, but it's the thing that we're programmed to think about. The second is, if I go away, will everybody leave me? Right? Which is a variation on a theme, which is, will I become irrelevant? What if it turns out that all my clients decide, hey, that was great. Thanks very much. We'll see you, buddy. So there were those feelings and those feelings can still arise for me, which is why I think when we were talking on email, I was like, yeah, of course, Tim is kind of interested in this. We can get to that. That's what prompted you. And then the other thing that happens, and I think a lot of folks can relate to this based on what I offer from clients, even just about taking a long week in our vacation, there's the hot and cold boredom that can set in. We often live with a forward momentum inertia, if you will, just pushing forward, pushing forward. And when you suddenly stop, it's a mixed metaphor. It can feel like musical chairs, and the music is just stopped, and you're standing there, and you don't have a chair. And that's really disconcerting. Because part of what we do, which I think leads to a significant amount of burnout and existential struggle, is we take meaning from motion. We take meaning from performance. And then when I take away the motion, what happens to my meaning? So like a good Buddhist, there's a piece of me that goes, oh, very good. That's perfect. That's exactly what we want to have happen. But it's challenging.

Is a sabbatical a 1% frivolity or can it be both meaningful and eminently doable? (09:58)

I want to touch upon something that you mentioned briefly for folks, and that is, can I afford it in this question? Because on one hand, depending on your expenses, one could argue that a sabbatical is a very indulgent 1% activity. But you can also take a different perspective. And it makes me think of a book called Vagabonding by a now friend after I read the book and gave it to many, many, many, many, many, many, many people. I later became friends with the author Rolf Potts, but Vagabonding was one of the books I took with me when I took my sabbatical of sorts in 2004, I want to say, 2004, 2005, about 18 months. And did work at points throughout that period, but it was largely a walkabout. And one of the points that he makes in his book with a story is recounting part of the movie Wall Street with Gordon Gecko with the brick-sized cellular phone walking on the beach in this iconic film, Greed is Good, et cetera. And the Charlie Sheen character at one point is asked by, I want to say his girlfriend or his love interest, what are you doing this all for? And he's like, well, someday I'll have enough where I can just pack it all in and ride across China on a motorcycle. And Rolf, who's done a lot of traveling, said you could work as a toilet cleaner for six months and save enough to ride across China on a motorcycle for a year. Particularly if you put a pause on some of your other expenses. And I think about a lot of people over the pandemic, including family members of mine, who packed everything up or put it into storage, canceled their leases and ended up traveling around the country trying different cities. And it cost a lot less than their previous fixed expenses. So depending on how you approach it and depending on how you organize the rest of your life, hit pause or don't hit pause on certain expenses, a sabbatical can be something that's very, very expensive. And it doesn't have to be, it can also be something that's very, very achievable. And I just wanted to mention that. I think that's a really, really important conversation. We are too relatively well off white men, yackin' away on a podcast, right? I mean, it's almost a trope at this point. And so we have to be very, very conscious and mindful of the fact that we often have choices that are not available to everyone. And whether it's a two months sabbatical or an 18 months sabbatical or two months sabbatical every year for 10 years, those are choices that are afforded us. Sometimes by external forces, sometimes a combination of what we ourselves, the choices that we make, we choose to spend less money. But I think what we're also talking about, Tim, is something really important, which is behind all of that, which is a mindset. In the mindset, I think not to be too playful with my own work, the mindset is the mindset behind rebooting and resetting. Let's go back and think about that word sabbatical for a moment. And swapping notes with the producer, I was saying, to recall the fact that sabbatical as a term actually is related to the same root word of sabbath. And this is why I'm playful as well when I talk about sabbatical, taking a vacation in the middle of my sabbatical. Sabbatical is also a time of thinking differently, of considering things differently. I think it was Bill Gates who popularized a term think week. It's the same impulse, which is I'm not working. I'm just working on something other than what I have been compelled to work on for the rest of the time. And for many of our friends who are in startup land, the thought of taking a weekend off is as terrifying as my thought of taking two months off. And that's a problem. That's a problem that not only affects them physically, it's a problem that affects them mentally. It's a problem that actually I would argue undermines their leadership capabilities and creates toxic environments. And so what we're really talking about in this way is this notion of can I afford myself a moment to pause, stand still, and think a little bit differently and see the world a little bit differently. Do you mind if I ask you some mundane questions?

How setting business expectations is the first step toward an effective sabbatical. (15:30)

I would like to look at the plumbing inside the cathedral for a moment. And by that, I mean, we have a rare opportunity. We am using the royal. I mean, Tim Ferriss. This is a rare opportunity. King Tim, who has deep pockets and short arms. So he gets a therapy for free on the podcast. Would like to ask you tactically and practically what you have learned about making sabbaticals work. What do you set up in advance? What are some of the mistakes you made early on? What are some of the things you've learned? Because we're going to get into much more of the deeper first principles, philosophies. But I want to front load some tactical stuff to kind of lure people in as a honeypot. So let's, if you don't mind, focus on some of the tactical practical, anything that comes to mind in terms of what you've learned about making sabbaticals work for yourself. Well, you know, you raise a really good point, which is to think about it in advance. And I would argue that a corollary to that is to set expectations. And so a good example of this from my own life was that when my three co-founders and I set up reboot in 2014, two of my co-founders had previously been clients of mine. So they were aware of this. But I said to them, whatever budget we model for this enterprise, if it cannot afford to have me not working, not bringing in revenue for two months a year, then I don't want to do it. And so if you think about it, you think about me not as a coach, but as a CEO, stepping into the launch of a business. And from the beginning, we modeled in the notion of taking time off. Now, as soon as I said that, my co-founders were like, "Hey, I like that idea. I'd like to take December off. I'd like to take this time off." And so we built a financial model, presuming not two weeks vacation, but sabbatical time. And I think that that's really critical because that was me being in conversation with my co-founders. Now they could have said, "We can't afford to do that." And I would have said, "Okay, that's great." But that's how important that is for me. So we have to do something else. That's that setting expectation. And if someone out there listening is privileged enough to be able to say in stepping into a new position. We have this funny notion, especially in the tech community, of unlimited paid time off, unlimited PTO. And studies have shown that the more unlimited it is, the less time people take. Because there's no sensibility around it. But I think that if we start to build into our companies, and many companies do this, when we say, you know, after one year, you get a week of sabbatical in addition to your vacation time. After two years, you get a month of sabbatical. Something along those slides. If we build that into our models, we start to change the perspective about EBITDA, about profitability. And if we start thinking about this as simply a cost of doing business, it builds into the structure of the business, a humane working part. By law, you have to build into the structure of the business, sick time, vacation time, parental leave, all sorts of policies. And then periodically something awful happens when we say, okay, let's build in some mental health time. But it's always after some sort of horrible event.

Managing your email during a sabbatical and beyond. (19:56)

Wow. Jerry, may I double click and zoom in a little bit? Sure. To look at the sealant on the plumbing. Just to come back to your personal experience, what were some early mistakes, if any, come to mind that you made or cases where you back slid to default behaviors and how you perhaps counteracted those when you were kicking the tires and first taking sabbaticals? So I wouldn't say that there was a mistake that I encountered as much, but there was a heck of a lot of backsliding. And there still can be a heck of a lot of backsliding. So I guess one mistake is I said to myself, I was going to be completely off the grid and not answer any email. And that's just not possible. I just don't do that. And so what I did early on, the first thing I did, which kind of didn't work, was create all sorts of rules. I'm only going to answer email this time or this time. You're smiling because you know your rules, right? And you create all these structures around the rules and I'm going to do this. And for me, that just doesn't work. All it did was engender a sense of self-criticism, right? Because I would quote unquote backslide. I remember, I always do an away message and I always try to do an away message that in some way or another inspires other people to think about these things, right? So I remember one away message I did on sabbatical where I talked about my plan to go to Italy for a couple of weeks. And I did that and I said, you know, my plan is to eat more gelato than to read email. And so if you're actually getting an email from me, I failed. And that tends to make people laugh. But what it does is it also helped me in managing expectations. So you know, a mistake or lesson I learned was to not turn the sabbatical into another source of self-criticism. So how did you decide to then handle say email? So it's easy to get pulled into the vortex and time dilates and you realize four hours later, holy shit, I've been looking at my inbox for four hours and I'm supposed to be eating gelato. Yeah, you know, it's so funny when I was thinking about our conversation today, I was thinking about it yesterday. And if I remember correctly in our first conversation, you also asked me about email, like, how do you handle email, Terry? And or some point in our life, you asked me this question. And I gave you the perplexing answer of just don't respond. You know, like, no, that's in there. Well, we'll come back. It's it's it's I was slightly like Rashomon, perhaps slightly different remembrance, but we can dig into that. But to go back to your question for a moment, I look, I think the way I handle email and that is I will scan it. And I feel super liberated if I decide not to respond because I've already given them a response that says I'm not going to respond. And so and yet there are times where it could be really important to respond. And so for example, this this past summer, I think I did probably six or seven sessions while I was on sabbatical. When you say sessions, what do you mean? A session is a coaching conversation. And there was genuine crises that needed that my clients needed some help with. And I consciously said, yes, I can do that, you know, two o'clock and such and such afternoon kind of thing. Boring process question, how did news get to you that that was a crisis and important to handle? I will allow people to text me and I allow people to email me. So I don't, as I said, I scan things, but I don't and I don't have anybody answering my notes and stuff like that. I need to have a direct relationship with people. So does that mean that you're scanning each day? Yeah. As the spirit moves you or is. I think you know that I have a fairly healthy morning ritual where I don't really, for the most part, check email. Why don't you remind people, I do recall us discussing this in episode one, but just for people who don't have that context? Yeah. So I'm a really early riser. Pretty much regardless of time zone, I'm up between five and six a.m. every day. My morning consists of a little caffeine and a lot of journaling and meditation. And when I'm at my healthiest, I don't really glance at the phone until my brain is ready. And so generally speaking, it's usually the third or fourth thing that I'm doing and it's a glance. And then if there are things that I can respond to quickly, that just sort of clear it out and I clear it out. I'm a zero inbox kind of guy anyway. And I suppose that all sounds quite disciplined. It doesn't feel disciplined. It just feels normal to me. And the people I'm most responsive to are the people I love. So my partner, Ali or my children, and they always get responded to, even if officially I'm off the grid. But the other thing I will do is I will say to people, I'll be unavailable next week.

Norm's tips for effective recovery. (26:02)

And then I'm really unavailable. When you look back at the sabbaticals you've taken, it's nine or ten, two months sabbaticals now, when you look at the sabbaticals that have recharged you the most versus the sabbaticals that have recharged you the least, do you see any patterns or do you see any characteristics that have some explanatory power for you? That's a really, really great question. This past sabbatical was incredibly recharging. And it came after the year that time forgot 2020. And in 2020 I got into cycling. And as I said in my away message during this past sabbatical, I said something like, may your summer be filled with fireflies and s'mores? For me, I hope to have it filled with weeding in my garden and cycling in the mountains and writing and working on a new book and working on my new book. And I slept well. I ate well and I rested well. And I exercised my mind with a new book. And I traveled. I saw a family that I hadn't seen in 18 months. I spent two weeks on the coast of California in a lovely beach house. And my kids each came to visit and cycle through, which was lovely. So if I would say there's a pattern of sabbaticals that are done right, it's a focus on mind and body. And it's resting both and taking care of both for sabbaticals that did not go so well. I would say the pattern is to load it up with expectations. Like I'm going to finish a book or I'm going to read these 10 books or I'm going to write a new business plan or I'm going to travel to Europe and see all these friends and then travel back. So all examples that my clients have given me and the number one rule in sabbatical is sabbat. Rest. Rest. The body needs rest. The mind and heart need rest. Right? That's the simplest way I can put it for you.

Positive epiphanies coming out of sabbatical. (29:14)

Do you have, or could you tell us if there are any examples, any examples of epiphanies or breakthroughs, aha's of any type that resulted from being fully rested when you came back to quote unquote normal life. Epiphany could have happened during the sabbatical but let's just say something. What I'm trying to do here is speak to people who have disallowed themselves from taking breaks to try to sell. This might be the wrong way to approach it but some of the payoff of resting. Does that make sense to me? It does. It does. And I'm looking away and I'm getting uncomfortable in my body because what I'm feeling is the impulse which I think you're giving voice to which is to make sabbatical productive. Right? And if that all feels resonant, that's the problem. You know, when I was saying before, let go of those expectations. That's part of what I'm talking about here. Okay, so there's an image that I write about in my first book, something that occurred to me in 2001 when I was lying on the ground, the bottom of the Grand Canyon, which by the way, if you really want to disconnect, go to the bottom of the Grand Canyon. You're four billion years into the past. It's an extraordinary experience. And I'm lying on the beach. There may or may not have been some alcohol involved. And I'm staring up at the sky and someone lying next to me says, "Oh, shooting star." And I begin trying to stare at the shooting stars. And I'm looking and I'm looking and I'm looking and it's driving me crazy because I can't see them. And then finally someone says, "Stop looking for them." And I rest my eyes and with peripheral vision, this is true fact, all of a sudden I start catching emotion. And that's an image I would give you for sabbatical. People who go into sabbatical with the plan to, A, I'm going to lose 10 pounds. B, I'm going to get into real good shape. C, I'm going to finish that book. Typically after farting around for a week, not getting anything done, start to feel terrible. And then it becomes this voice of your wasting time, I can't believe you did this, what's the matter with you? You're failing at sabbatical, which is insane. But if we go back to that notion of Sabbath, which is in Jewish tradition, disavow or disconnect from anything that is electrical, put your keys down, put your money down, rest. There's something very, very profoundly holy in rest. Now, I know I'm swimming upstream. Everybody wants to be productive. I could also just, if you don't mind me playing stand in for the listener, I could also say, well, you spoke about this hot, cold boredom. And even if you don't say I'm going to finish the book, the fact of the matter is you were writing, working on a book, and likely on some level feeling productive. So if we removed that, would you have needed an alternate activity, which I don't make wrong, by the way. But one could say, hey, you're a writer, you're working on books, you're saying we don't need to be productive, but I bet you feel productive after a good day of writing. What if I'm not a writer? There may be people who would say something like that. Sure. And I get that. When I felt good working on the new book this summer, it was when I let go of the production goals. Some writers like to say, you know, thousand words a day, you know, 500 words a morning, something like that. And I went into this past the badical with a little bit of that mindset. I'm going to get part one. It's all mapped out. I'm going to get part one done this summer. And I did hand in 15,000 words of what will eventually be a 70,000 word manuscript do next summer. And they were kind of a mess, as Annie Lamont would say, the shitty first draft. But my editor was able to sort of pull it apart, break it up into two chapters, which is a more appropriate status. So it was productive. But I was at my most productive when I stopped trying to be productive. I mean, I hit the sound Zen like here, but you know, it's all of the emotional load that we put into that notion of productivity that actually exacerbates the stress and tension that causes us need to take the rest in the first place. Yeah.

Zero sum games and targets for anxiety. (34:40)

Well, let's, if I may, we can make this personal on my side and we can explore those muddy waters for a minute. So I have been able, over the years, to take many trips and disconnect. And typically for particularly since I'm in an intimate relationship with my lovely long term girlfriend, we don't like to be a part for long periods of time. She has a job that doesn't totally disallow, but largely disallow her to take the type of time off that I might want to take off for a sabbatical, let's say. Nonetheless, we're able to take trips. We took our first trip post COVID just a few months ago and I was effectively offline for three weeks, which was wonderful. And I will take shorter trips and be typically completely in the wilderness or the jungle or somewhere with nothing, no electronics for a period of time. I do that generally at least once or twice a year. Nonetheless, what I have found for myself and some people may resonate with this. Actually, I'm going to give a few examples of friends and then I'll give my personal example. So there are friends who have been in zero of some games for so long that that lens has become their default. So I would argue that in some startups at certain stages, if you're the CEO and you took a week off, things would blow apart. I do think there are certain scenarios in which that's the case. However, let's say you ride that 100 foot wave, you have some wonderful exit in the case of a founder, they think they will just be able to turn off that script. And I have seen close to zero examples of them being able to, right? It's very common. Before I have a friend, I shant name, but very good friend and we've known each other very long time. And I've watched as his magical number, right? This number, once I hit X, then I'm going to build a workshop in my garage and make artisanal rocking chairs or whatever the hell. And I've seen that number move and move and move. So every time he gives me some new number, I'm like, yeah, I've heard that before. Great, where I was talking to a friend who said, I'm never starting X type of podcast again. He's done this twice now. And I'm like, yeah, I've heard that before. And he said something to me, which I thought was interesting. It's not totally germane here, but maybe we'll tie into it. We were texting and he said, I suppose that I just need a target for my free floating anxiety. Yes. And I identified with that quite a bit. I said, you're right. I mean, it's a lot. It's reassuring in some perverse way to have an external object or circumstance you can point at and say that explains why I have this really uncomfortable feeling inside. Right.

Refining self-exploration. (38:06)

So I'm going to park that for a second. Because this is all a way of me sort of backing into my own personal experience. So when we last spoke and I thought, hot damn, this is something we should talk about on the podcast, what I had realized for myself is not that I can't take time off or that I can't ignore the inbox or refuse to reply on the vast majority of things that come in. What I simultaneously have realized is that over the last say 10 or 15 years, there has been a creep of complexity. So when you have dozens of different entities, LLCs and so on, when you have hundreds or at least 100 different investments and funds and capital calls and this, that and the other thing and you've added people to your organization. So you have more headcount. There is a certain amount of complexity that comes with that. So while there are a million emails, I feel like I can safely ignore there are certain others from whether it's a tax authority or some registered agent or an employee that I do feel like I should keep track of or there will ultimately be some consequences to ignoring those things. And so this is a very roundabout way of asking how you have seen people either reframe the complexities so that it has less of a fearful impact on them or end or reduce complexity in a way that lessens this sort of internal drama that they experience going along with it. I love the way you framed that question. And there are tips and tricks and hacks that you can do to reduce the complexity. But the complexity will creep back. And I think you know this because you've experienced this and we've had conversations over the years about that tension between those two spaces. I hire an assistant and then all of a sudden I need to and then I need five and now they need to be responded to. And it goes. And so let's take us all the way back to one of Jerry's very, very famous questions, which is how have I been complicit in creating the conditions I say I don't want. I like that you just referred to yourself like the Hulk uses a third person. Hulk mod. Hulk smash. Jerry ask. Jerry ask a question that calls here. How am I complicit in creating the conditions I say I don't want. Right. And so I'm going to alter that just slightly. What benefit do I get from the conditions I say I don't want? What benefit do I get from the conditions I say I don't want? And so let's turn it back to the question. So you create these really complex structures and you probably spend an enormous amount of energy sorting them out, responding them, maybe even use auto responders, tax person go here kind of thing. So if you want to alter that behavior, you have to understand what the benefit is to you. Right. The payoff for the secondary payoff. That's it. What's the secondary payoff? What's the secondary benefit? And for you, what does it make you feel like living a very complex life with hundreds of investments and lots of fingers and multiple pies and doing all sorts of things? What does it do for you? So I've thought about this and I would say that I think the complex structures are a side effect of something else. I don't think that I actually get much payoff from the complicated structures, but I think they're a symptom. And I would say that for much of my life, I had competitive athletics and other things that consumed in a very good way, I think, a lot of my focus and provided a lot of excitement, just as important excitement. And I haven't had that in a very long time after a shoulder reconstruction and then elbow surgery and twisted ass eye joint and all these things. I'm like, you know what? Maybe I don't need to get heel hook today. Maybe I don't need to get thrown on my head in judo class this week. And I've stopped a lot of that. And I think in lieu of that, I enjoy competition. I enjoy it. And I don't think there's anything inherently wrong with that. I actually really, really enjoy competition. And I think I'm a good competitor in a lot of ways. So I've shifted the arena from sports and all these other things, art, although I haven't treated art competitively, but these activities and substituted in investing. And I've substituted in different types of projects that often have some creative component, most always they do, whether it's deal structuring or a podcast episode or a preloading podcast that I can do A, B and C elsewhere. But very often, I would say the investing side in particular is related to excitement. I would say that's what I get from it. And the side effect of having lots of investments and lots of things that come along with that is this complication, the complexity and the systems.

Boredom is the opposite of excitement? (44:22)

That makes sense to me. What's the opposite of excitement? Opposite of excitement would be boredom, which is why I wrote down this hot and cold boredom for you that you mentioned earlier. I think it's boredom. I think it's, and I'm not, you know, I used to be more, maybe optimistic about this. I mean, I am sure fundamentally it comes down to not wanting to be alone with my own thoughts and certain feelings that might come up. Right. So the question of, you know, what is it that you're unwilling to feel? Yeah. I think it was Tara Brock who said, you know, one stage said, there's only one question that matters. What are you unwilling to feel? And I've spent a lot of time thinking about that. I've spent a lot of time working on that. And I've also arrived at a point where I've looked at my family, you know, like family wedding recently, and I'm like, okay, this could all be nurture. Maybe it's just behaviors that have been passed down the bloodline. That's one explanation. It could also be that our code, our DNA just leads us to have a certain baseline of anxiety or depression or any number of other things. And maybe I'm exerting a lot of calories trying to prove to myself that that is not the case. You know, Tim, the thing that occurs to me every time we talk is how much self-work you've done. And I'm going to make you feel really uncomfortable because I'm really fucking proud of you. Thank you, Jerry. You go there. So we're going to go there. You know, the proclivity to anxiety could have a genetic component here. But the proclivity to be uncomfortable with what the Buddhist would call hot boredom is not DNA. It's, you know, to use the term from my first book. It's a subroutine. It's programming. It's nurture. And you said kind of offhand, but really with a kind of self-awareness, okay, so I'm uncomfortable, perhaps, with boredom because I don't like to necessarily be alone with my own thoughts or to face those things. And God bless you. You've done a fantastic job of learning to deal with your own thoughts. So let's imagine, if you will, that the learned behavior was boredom bad, hulk, boredom bad. Well, the learned behavior may just as equally have been the family saying, we don't want to actually be with these questions. We don't want to be alone with our thoughts collectively because when we're alone with our thoughts, bad things happen. So let's get busy. And let's make sure that we're competitive and complicated and busy with lots and lots of different things so that we don't have to feel those things over here. To go back to Tara Brock, family systems can reject feelings, not just individuals. Yep. Right. It reminds me of a, I remember sitting with a group of executives at a company and they asked me to just observe their executive team and I was watching and something came up. It happened once, it happened twice, it happened the third time. And what it was, was anytime that there was a really moment of tension, somebody would make a joke and the whole energy would dissipate. And when I called it out, the CEO said, "That's just like my Sunday afternoon family dinners." And sometimes we get really complicated and busy because we don't actually want to feel what those thoughts bring up.

Hot vs. cold boredom. (48:29)

And there again is a reason why sabbatical can feel really challenging. Because if I pause, I'm going to feel really uncomfortable. I'm going to feel hot bored. Can you expand on hot boredom? And then I'm going to come back to what we're talking about. But could you just explain the difference between hot boredom and cold boredom or the spectrum of boredom? Yeah. Yeah. So hot boredom and cold boredom is really great framing to think about. We don't really do this so much anymore. But imagine you're online at the post office or online at the DMV and it's just an interminably long line and you've got to be someplace else and there's nothing to distract you. And that discomfort, that's hot boredom. That's like literally my body starts to feel achy and all that stuff. But contrast it to cold boredom. And I know you've done meditation retreats. Imagine not the first three or four days of meditation retreat, which often provokes hot boredom. Right? What the hell am I doing here? I can't even sleep. It's in it. But by the day four, day five, day seven, day 10, you're sitting there and literally there's nothing dramatic going on in your mind. There's no drama and you're okay. And all of a sudden you catch a glimpse of a bird that's really interesting. It's cold boredom. And I would argue that the mind needs cold boredom. It needs those days of simple, you know, my therapist calls it just simple stern oatmeal kind of morning. Here I am, doo doo, just stern the oatmeal. Because that's a moment of rest from which we can then go about the rest of our time, the rest of our day. I have many questions as one would expect if I invited you on the podcast to talk about this.

A client who won't make time for fortune-telling boredom (50:55)

Let's start with hypothetical situation. So I'll tell you something that I haven't talked about much. Maybe not at all publicly. But I've spent the last, I would say, year sitting with a lot of void, very deliberately, not committing to any big projects. And it has been one of the most difficult, painful experiences in my life. And I threw every tool in my toolkit at it, meditating, do it twice a day, do it three times a day, take two weeks in the wilderness. I threw everything I had at it and ultimately decided sitting with this void for this long is actually not good for my mental health. And still haven't prematurely committed to something huge, just commit. But I got to a point where sitting with that void felt unhealthy. And so my question to you, and I'm not, I'm not at the point of total burnout. But if you're talking to a client who like it or not is not going to get to a place of comfortable cold boredom before they burn out and you jointly decide or he or she decides they're going to take a sabbatical. So they have yet to become sort of comfortable stirring the oatmeal, but they're going to take a sabbatical. What advice do you give to that person? Start small. Start with tiny steps. When you were talking baby steps. Yeah, how about starting with a weekend? How about starting with one evening? You know, I mean, literally you were you asked me before about the when I started sabbatical rising. And it feels so long ago and it feels so natural to me that I actually forgot what really began this. And it was something that you said where you talked about going off into a jungle, going into a forest and things like that. For the 10 years previous to me taking two months of atticle, I would take monumental off the grid trips. Why were they monumental? Because that was the only way I could really break being attached to the grid. Because if you go to as I did, you know, across the polar ice cap in Greenland, for some reason you don't get a good cell signal. It's like it's amazing. You are forced or you know, I went rafting the Fudalafu River in the Chilean-Pedagonian area. And there really isn't a good Wi-Fi signal. And it's beautiful. And so those small little steps, I have a client I just started with in September and he's taking his first vacation two weeks in Namibia, first vacation in 10 years. First vacation in 10 years. And it was only because his life partner recently sold her business and that they feel like they have the time. That's not healthy. And so practical advice, start small, start where you are, start with a day. Our mutual friend Brad Feld was the first person I know who used the notion of digital Sabbath. Right? I'm going to turn off the devices from Friday till Sunday night. And just I'm just not available. And train the people in my life to know that that is happening. Just start there. Just start there.

Peer Experiences And Alternatives To Sabbaticals

Pub during the workday: Where the (seemingly) insane gather (54:47)

So let's say you've taken some baby steps and I'll tell you what I've run into when I try and I have, I've taken time off of my or away from my normal routines in Cia City, like Austin. Here's what happens to me. Let's just say, so I'm sitting downtown in Austin right now. I take, I decide I'm going to take a couple of weeks away from my normal routines, but I'm going to stay here in so-called civilization. My girlfriend, meanwhile, is going to continue with her normal routines. Most of my friends, at least here, are not going to be coincidentally taking a Sabbath that's sabbatical at the same time that I do. And so I go about my day and ultimately A, it's very lonely. B, I end up feeling unemployed/insane because if you go to the Starbucks or you go to the library or you go to any number of other places, you end up surrounded. In fact, by a lot of unemployed and/or crazy people. I realized this in San Francisco, actually, when I was like, "I'm going to take a break and I'm going to go to the library and read." And I was like, "Wow, this is actually very disturbing because this is sort of the halfway house during business hours for a lot of unstable people." And I found that pull towards the river edge of chaos, not good for me. Well, what I also hear you doing was then deciding that you were one of those people. It's not so... I mean, there is that... I mean, you know you're not unemployed if you're not working. I know I'm not that, but it's... I think we're all affected on some level by the people we spend time around. Like if somebody were... This is an extreme example, but just to kind of play out the point. If somebody actually were sitting inside an insane asylum, I know that's probably not the politically correct term these days, but like one flew over Cuckoo's necks and you weren't like working behind the desk. You're actually sitting in there and playing just with these people all day or whatever it might be. I think that would affect just about anyone if they were exposed to that, right? So when you go into some of these public spaces or semi-public spaces during business hours in a place like Austin, that is also the case. That's not limited to Austin. If you want it times 10, go to San Francisco. Sure. So I don't automatically assume I'm one of those people, but my instrumentation is very sensitive so I do feel impacted by being in those settings. I think we could treat these two things almost separately. There's being in those settings and being affected by those settings. There's also just a genuine sense of loneliness. I know a lot of people who are quote unquote free, right, who can work whenever they want on some level, even if they're still paying the bills by working consistently, but they are working from a laptop somewhere without people around them who are in a similar situation that it can be agonizing how lonesome that feels. So that's a big mouthful. I don't know if you have any thoughts.

Introversion, loneliness, and being socially around unhealthy people (58:33)

Yeah, I'm glad you circled back to the word lonely because you went lonely, unemployed, insane, and I zipped in on insane. But I think the lonely is-- We don't have to rule out that I'm not insane. I mean, leave that on the table. But I think the lonely is really important. And what you're helping me see is that my lens is very much affected by the fact that on the spectrum, I tilt toward its introversion. So I don't quite have the same reaction to the word lonely or alone as, say, my daughter, who is very much an extrovert. And during the lockdowns, she would really yearn to be outside with other folks. May I interject for one second, Jack? Yeah. So I would actually consider myself very introverted, but I would also recognize myself as someone who almost killed himself, had a date on the calendar to do so in college. I think, in part, as a byproduct of certainly lots of factors, but one of them being, I was alone and isolated way, way, way too much. So I would consider myself an introvert. And yet, at the same time, I have a lot of fear around feeling alone, which is actually very different from being alone. If I do one of those extreme trips, which I don't consider that extreme, I actually consider it a real return to fundamentals, but where I'm in nature by myself, I don't feel alone in the same way that I feel alone if I'm sitting in a Starbucks with a bunch of unstable people sitting around me with no friends who are following any routine that's similar to mine. I appreciate that distinction. I think that that's really helpful. What I'm feeling my way to, and I can relate to this, is there are certain mental states that are reminiscent of the past states. As we've talked about before, I actually attempted suicide at 18. And in an odd way, I make my bed every day. And I make my bed every day because that's what I learned when I was in the mental hospital, was that you make your bed every day, even if you do nothing else, even if you don't shower, you make your bed every day. And so I make my bed still to this day. Because if I don't, it starts to bring up those feelings that I might end up back emotionally in that place. And so what I'm hearing you say is the fear isn't about being alone so much. It's about feeling lonely because that's the association back to the depression. That's right. And this suicidal impulses. And that's a really good observation about yourself. And so I applaud you being able to say to yourself, okay, as an alcoholic might say, I'm going to stay out of a bar. You're going to stay out of those situations that can be triggering for you and bring you back to some of those states. And I like where we are right now because what we're seeing is that perhaps there's a little fear of cold boredom because it might remind one of feeling lonely. Maybe, maybe I, maybe, maybe I think that there could be some overlap.

Cold boredom (01:02:26)

But for instance, if I go on a, I'll tell you one of my happy places and maybe that will be a contrast. So one of my happy places would be I go into the wilderness with a handful of close guy friends and we have the shared privation of like sleeping in a freezing fucking cold tent, waking up and having shitty instant coffee in the morning, which is like the best feeling in the world. And then hiking at altitude and feeling like I'm just getting punched in the lungs for like 12 hours, taking a nap on a mountain top and having a fire at night to like thaw out your feet and then going to bed. And the majority of the day, there is no talking. Right. That's great for me. And you're not lonely. I'm not lonely. I'm also not hyperactive. Right. So it's like left, right, left, right, left, right kind of march. So I would consider that maybe I'm just not understanding the terminology correctly, but I would consider that that would seem to me to be a form of cold boredom. That is definitely a form of cold boredom. And I love that. I find after four or five days of doing that, even if I'm getting the shittiest sleep, you might imagine, right? Three hours a night.

The bear encounter (01:03:50)

Sleeping on a rock. Side note. Can I tell a funny story just for a diversion? So I went on one of these first outings with a couple of guys who were very experienced outdoorsmen. Like also a number of them, former professional level sponsored athletes. So I was already intimidated and that was a sea level. The San Francisco resident at that point going up to high elevation. And I asked about bears because they were all eating candy bars and all this garbage inside the tent. And I said, "Shouldn't we be concerned about bears?" And they said, "Ah, no." And one of them said, "They're just black bears." "Just." And they're more likely to lick you to death than hurt you, relax. And I was like, "Okay." And sort of shamed into silence. So we go to bed and we're sleeping all around the perimeter of this large tent. And I wake up and it's close to a full moon. I wake up and the tent's about four inches from the side of my face. And there's literally a huge nose pressed to the tent, four inches from my fucking face. And it's this gigantic bear. I'm not kidding. First night. First night. And I don't know any of these guys except for like one, one and a half, let's call it. And so I think to myself, more likely to lick me to death, if I wake these guys up on the first night, I will just be, I will be shamed to death for the rest of this trip. And so I don't say anything. I'm in full prey mode. Every single corner of my psyche just lit up on fire. I can't sleep, not surprisingly. I comes back a few hours later. And then in the morning, we're having our coffee. And I mentioned this and the same guy who told me I would lick me to death. It's like, Jesus fucking Christ, man, you gotta let us know. That kind of shit happens. And nonetheless, after that trip felt like I had taken a six month vacation. Well, that, you know, I mean, you just said it. I mean, the experience of resetting for you wasn't something that's time to limit it. Right. There were some, some, some core components of it off the grid is a really key component of it being with people that you can physically be with for several hours, but not have to entertain with dramatic thoughts and talk. That nourishes you. You know, being in the land nourishes you, being physically in your body nourishes you. That is a sabbatical, dude. Yeah. So should I just keep it at that? Or should I be able to do this in Austin despite the fears of sitting in these sort of third non-home locations? Because I can, I can convince some friends to go into the mountains for a week. I can't, it's harder for me to convince friends inside a city to be like, hey, let's just not do our usual stuff for a few weeks. I totally get that. And you know, changing physical location is really important. I just put a reservation down on a sprinter van, you know, from Winnebago, the Revel. I can't wait to be able to climb into that. And I live in a 40 acre farm. Right. So, you know, with the woman I love and three horses and an 18 year old cat, right? Coyote is running across my, the pastures and hawks and birt and eagles and stuff.

What to do if you cant take a long sabbatical (01:07:40)

But sometimes you need to change the venue. Sometimes you need to change it up. And I get that. I pause and hesitate it, Tim, because she said, should I? And you know me well enough to say, I'm not so sure I can answer a show. I would. Should you? Yes. Should you know? I think you have to go, you have to design it for yourself. You have to sort of tune into what you know and you know, collect the information as you have been doing and design your own retreats. I find it enormously helpful to be able to periodically, even within the envelope of my normal days to be able to cut the chatter. Right. I often say that, you know, I sit on the meditation cushion because during the morning, because I need to be able to meditate throughout the day. I need to be able to return to that state of mind. So, you know, go to the mountaintop for a week at a time so that in an afternoon while stuck in the middle of Austin, you can go for a bike ride. You can go for a hike. You can go to a park. You know, you can take a dog for a walk. You can do the things that nourish you. If you can't be off the grid for two months at a time and very, very few people can, then go off the grid for hours at a time. That's all. You know, I think ultimately take the sabbatical with you. Take that mindset with you and live it into your days. Thank you, Jerry. That resonates with me. And I meditated this morning. 20 minutes. Nothing fancy. No drama. Just TM repeating some sound in my head so that my monkey mind has something to do. Climb up and down the pole for 20 minutes, that's it. And it's so that I can remember for the rest of the day, ideally what it feels like not to rush. That's it for me, largely. Are there any resources that you might suggest to folks who are considering the possibility of a sabbatical? I remember there is a book that I read.

Jerry recommends these resources on the topic of sabbaticals (01:10:03)

I want to say this was around 2004, 2005, called Six Months Off. And I'm sure a lot of it is dated, but it was focused on different approaches to taking sabbatical. So are there any other resources? And these could be non-obvious resources, could be a story, a poem, a book, a movie. It doesn't matter. Are there any resources that you might recommend? Well, one of my little mental tricks that I do when I do a public talk is I often open up the talk simply by asking people, "How are you?" And that's the question, by the way, that typically gets people crying. And then I throw up a couple of different words, you know, excited, scared, and almost always I land on the word "exhausted." And everybody just resonates with that. Like your shoulders just dropped as soon as I said the word "exhausted." Because you know what I'm talking about. It's just this constant sense. And you know, there is a blessing, and I'm not going to recall the fullness of it, but John O'Donne, the great Irish poet, the late Irish poet, has a book of blessing called "To Bless the Space Between Us." And in it, he has a blessing for those who are exhausted.

Inspirational Readings And Closing Remarks

A blessing for the exhausted (01:11:26)

And in that blessing, among the things he says is steer clear of those vexed in spirit. So think about those folks in the Starbucks, they're vexed in spirit. And becoming inclined to watch the rain. And it's kind of a guidepost. You know, if we think about sabbatical as a Sabbath time, as a holy time, it's a holy time for those of us who are exhausted. And that's the time to rest. Right? I mean, whether you follow Judaism or Christianity in the stories from the Old Testament, and on the seventh day, even God Himself rested. Right? Easy, gentle. Now, there's another line from that poem in which O'Donne says, "Be excessively gentle with yourself." So I don't have 10 tips and tricks to make your sabbatical as productive as possible. You know me, that's not the way my brain is organized. You saw the draft of my next blog post to him. Tools for Titans for sabbatical. Yes, sabbatical edition. Volume one. Yeah. But I think that there is a really profound wisdom in O'Donne's poem, which is easy, easy. This is a better time to take a breath. And I love the image of you hiking and camping and being out in the land with your friends. That's what you're doing. Right? Rest is not zonking out on the couch to Netflix's latest binge watching stream, Squid Game something, right? Rest is turning the brain off. It's getting the heart rate down. It's taking care of yourself. And to me, that's what sabbatical is all about. Yeah, I suppose it could take different forms, right? Like in my case, at high elevation, I'm actually really physically taxing myself, but it's a, for me, it's a pure exhaustion. Yes. It's not a paper cut exhaustion. It is a pure focused, holistic, deliberate exhaustion. And that's a straightening through fire of sorts. Yeah. Listen, I'm all for the physical exhaustion as long as the mental turn off is happening. As long as the mental, the chatter, you called it the monkey mind. As long as the chatter is quieted, because I'll bet you when you guys are hiking and you're going from one camping spot to another, your mind's quieted. Oh, yeah. Yeah. Yeah. Even as your body is physically taxed. Yeah, that's a different experience. Well, Jerry, we're coming up on time for both of us for different reasons. And I would like to read a name and you can tell me the pronunciation.

Lost by David Wagoner (01:15:21)

And if you have this in front of you, I would love for you to read this. But if not, I can read it. And that is lost by David Wagner. Is that correct? That is correct. W-A-G-O-N-E-R. And I'm happy to read. But if you have it, since you sent it to me, I feel like it makes sense for you to read this because I think it encapsulates a lot of what we're talking about and could be a good place to bookmark us for this conversation. Sure. So, I'm going to read it. I'm just bringing it up right now. Yeah, please. Here we go. Lost by David Wagner. Stand still. The trees ahead and bushes beside you are not lost. Wherever you are is called here. And you must treat it as a powerful stranger. Must ask permission to know it and be known. The forest breathes. Listen. It answers. I have made this place around you. If you leave it, you may come back again, saying here. No two trees are the same to Raven. No two branches are the same to Ren. If what a tree or a bush does is lost on you, you are surely lost. Stand still. The forest knows where you are. You must let it find you.

Final thoughts (01:17:34)

So good. So, so good. I'm so glad you sent this to me. This is basically the North Star for me. Something along these lines for the last few years. And it's funny how easy it is for me anyway, to lose sight of that North Star, but how corrective it is as soon as I realign and spend time recognizing it again. Yeah. Well, I appreciate you giving me the opportunity to read it and I would not have missed that opportunity because I think as you can tell, reading poetry is one of the ways that I reach a Sabbath state. So many things to talk about, Jerry, but great to see you, my friend.

Contact Information For Jerry

Where to find Jerry online (01:18:28)

You too. And we will catch up again, separate from the recording. And I will just let everybody know for people listening. You can find Jerry's book, reboot subtitle leadership and the art of growing up wherever books are sold. He's been on this podcast before. You can find more of Jerry at on Twitter at Jerry Colona C O L O N N A reboot at reboot HQ on Twitter and the website Jerry, is there anything else you would like to say before we hit pause on this conversation? It's that I hope that folks take a little bit of time off and take a little bit of rest and to remember the words from John O'Donnaue. Be excessively gentle on yourself. Good advice for me also to hear and remember. So thank you, Jerry. I really appreciate you. Thanks for having me on, Tim. It's always a delight to hang out with you. Be well. You too. Everybody listening will have show notes, links to everything at And until next time, be gentle with yourself.

Great! You’ve successfully signed up.

Welcome back! You've successfully signed in.

You've successfully subscribed to Wisdom In a Nutshell.

Success! Check your email for magic link to sign-in.

Success! Your billing info has been updated.

Your billing was not updated.