#554: Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year

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Hello, boys and girls, ladies and germs. This is Tim Ferris. Welcome to another episode of the Tim Ferris Show. I'm gonna keep my preamble short. My guest today is Jerry Colonna, C-O-L-O. N N A on Twitter at Jerry Colonna. He is the CEO and co-founder of reboot.io, 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 has already been on the show. It was an excellent episode. And it was Named.

The coach with the spider tattoo. We're not gonna 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 twenty years, he has used the knowledge gained as an investor, one hell of an investor, an executive and a board member for more than one hundred organizations to help entrepreneurs and others 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 twenty five.

A youngin', 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.

You can find that at Tim.blog slash Jerry Kelona. Again, one more time, C O L O N N A. You can find him on Twitter as mentioned at Jerry Kelona on LinkedIn, of course. Reboot's Twitter is at reboot HQ, and the website for all things Jerry and Reboot is Reboot.io. Jerry, welcome back to the show. Thanks for having me, Tim. You know, it's a bizarre experience hearing your life play back at you like that. I'm I'm sitting there listening and I'm going.

Damn, I'm old. Referencing something nineteen ninety six. 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. I'm like, wow, well that's the highlight reel. It's all downhill from here. So that 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. I'm in Austin. And I remember it very, very clearly. And We reconnected. I wanna say a month, six weeks ago, maybe something like that.

And we were covering a number of different things. But It quickly Finished. A two month sabbatical.

And then you've you've sort of casually mentioned that you'd done that for How long, roughly? Would you say? I interrupted it last year because of the disruption that was twenty twenty. But previously it was nine straight years, so that was my tenth.

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 launch pad 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 T V show, you know, the image would get all wavery as he flashes back in time.

I think that so I've been a coach now for about Seventeen years. And I came to coaching on the one hand, very much having been trained in 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 Yor who was 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, but It's also when all of our therapists are Gone. Right. Home alone in New York City. Exactly. For more on this, watch the movie What About Bob? Which is which is a very good anybody who watches the movie will get the reference. Is this corn hand shucked? Sorry, continue Excellent. Indeed. Excellent. Excellent movie. Continue, please. Excellent movie. Bill Murray uh in search of his therapist. 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. And emotionally present then.

Most folks are in a 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 gonna sound really indulgent. But I also wanted to take a vacation during the middle of sabbatical. I know that's a bit of that's a bit of a controversial statement.

But I would do things like Go to Tibet for two weeks and help build a An orphanage. Or I would

take these monumental trips. I rafted the Grand Canyon for the third time in twenty Fourteen with my son. 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, right? 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 slip there. More waves than one. A much better coach. A much better coach because I was rested. And I could be there more fully for my clients.

What did the very first internal conflict or pushback. Oh yeah. It doesn't have to be the very first. It could be one of the first, but one that comes to mind.

The first one that comes to mind is Can I afford this? Right. Which is crazy, but it's it's the thing that we're programmed to think about.

The second is if I go away, will everybody leave me? 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 ya, buddy. There were those feelings, and and those feelings can still arise for me. Which is why I think when we were talking on email

I was like, Yeah. Course Tim is kind of interested in this. So We can get to that. What 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 hear from clients.

even just about taking a long weekend or a vacation. There's the Hot and cold boredom. That can set in. You know

We often live with a forward momentum. inertia. If you will, this pushing forward, pushing forward. And when you suddenly Stop.

Here's a mixed metaphor. It can feel like musical chairs and the music has just stopped and you're standing there and you don't have a chair. And that's really disconcerting. Because Pardon. 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, you know, like a good Buddhist, there's a piece in me that goes, Oh, very good. That's perfect. That's exactly what we want to have happen. But it's challenging. I wanna touch upon something that you mentioned briefly for folks. And that is can I Afford it.

And this question. Depending on your expenses, one could argue that a sabbatical is a very Indulge. one percent 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 people. I later became friends with the author Rolf Potts, but

Vagabonding was one of the books I took with me when I When I took my uh sabbatical of sorts in two thousand four, I wanna say. Two thousand four, two thousand five, about eighteen 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 size. Cellular phone walking on the beach, you know. Iconic film, Greed is good, et cetera. And The Charlie Sheen character at one point

is asked by I I want to say his girlfriend or his love interest, you know, 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 travelling, 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. But it doesn't have to be. It can also be something that's very, very

Achievable. And I just wanted to Yeah, I I I think that's a really, really important conversation. we are two relatively Well off white men.

you know, yaking 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 month sabbatical or an eighteen month sabbatical or a two month sabbatical every year for ten 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 this To spend. Less money.

But I think what we're also talking about, Tim, is is something really important, which is behind all of that. Which is a mindset. In the mindset, I think Not to do

Work. The mindset is the mindset behind rebooting and resetting. Let's go back and think about that word sabbatical for a moment. In 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 the term think week. It's the same. Impulse.

Which is I'm not 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 effects 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 in this way is is this notion of can I afford myself A moment to pause, and 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. 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 we I mean Tim Ferris has a rare opportunity to King Tim King Tim who has uh Deep pockets and short arms. So he gets his 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 wanna front load.

Some tactical stuff. to People in the year. as a honeypot. So 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. 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 twenty fourteen. 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 modelled 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. We have to do something else.

Right. 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. You know, we we have this funny notion, especially in the tech community, of unlimited pay 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. 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 lines. If we build that into our model

We start Two Change the perspective about E beta.

About profitability. And if we start thinking about this as a simply a cost of doing business. Yeah. builds into the structure of the business.

A humane work environment. 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 and we say, Okay, let's build in some Mental health time.

But It's always after some sort of Horrible event. 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

Backslid. Two. Default behaviors. And how you perhaps Counteracted those.

When you were kicking the tires and first taking Sabbaticals. 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 gonna 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.

was The first thing I did, which kinda didn't work, was create All sorts of rules. I'm only gonna answer email this time or this time. You know, you're smiling'cause Because you know your rules. Right. And you create all these structures around the rules and I'm gonna do this and

And for me that just doesn't work. All it did was engender a sense of Self criticism. Because I would quote unquote backslide. I remember I always do in a way message and I always try to do in a way message that in some way or another inspires other people to think about these things. So I remember

one away message I did on Sabatical where I 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 have failed. And that tends to make people laugh, but it what it does is it also helped me in managing expectations. So A mistake, a 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 uh 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 I if I remember correctly, in our first conversation, you also asked me about email. Like, how do you d handle email, Jerry? Or some point in our life.

You asked me this question. And I s gave you the perplexing answer of Just don't respond. You're like, No, that's We'll come back to that. It's it's I have a slightly like Rashimon Perhaps d slightly different remembrance. But we can we can we can dig into that.

To go back to your question for a moment, I think the way I handle email on that is I will scan it. Yeah. And I feel super liberated if I decide not to respond. Because I've already given them a response that says I'm not gonna respond. 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.

When you say sessions, what do you mean? A session is a coaching conversation. And there was Genuine crises. That my clients needed some help with.

And I consciously said Yes, I can do that. you know, two o'clock on 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. And I don't ha have anybody answering my notes and stuff like that. I 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. I think you know that I have a a a fairly uh 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 uh I'm a really early riser.

Pretty much regardless of time zone, I'm up between five and six AM every day. My morning consists of a little caffeine. And a lot of journaling. And A 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, then 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, you know, my partner Allie or My children. They always get responded to, even if officially I'm off the grid. Yeah. But the other thing I will do is I will say to people I'll be unavailable next week.

And then I'm really unavailable. When you look back at the sabbaticals you've taken. So Nine or ten two month 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. This past sabbatical was incredibly recharging.

It came after the Year that time forgot. twenty twenty. And in twenty twenty, 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 I'm working on a new book. And working on my new book. And I slept. Well I eat.

Well And I rested. Well And I exercise my mind. With a new book.

And I traveled, I saw a family that I hadn't seen in Eighteen months. I spent Two weeks on the coast of California and uh Lovely beach house.

And my kids. Each came to visit and cycled through. Which was lovely. And If I would say there's a pattern of 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 gonna finish a book. Or I'm gonna read this. These ten books. Or

I'm gonna write a new business plan. Or I'm gonna travel to Europe and see all these friends and then travel back. I mean, these are all examples that my clients have given me. And The number one rule In sabbatical is Sabbath.

Rest. Rest. The body. Need. Rest.

The mind and heart Need. Rest. That's the simplest way I can put it for you.

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Tim. I Do you have or could you tell us if if there are any examples? Any Examples of

Epiphanies or breakthroughs. Ahas of any type that resulted from being fully rested. When you came back to quote unquote normal life. The epiphany could have happened during the Sabbath, but let's just say something. And what I'm trying to do here

is you 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. And If that at 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 two thousand and one when I was lying on the Ground.

at 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 laying next to me says, Oh, shooting star. And I began 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 ca start catching the motion.

And that's an image I would give you for sabbatical. People who go into sabbatical with the plan to A, I'm gonna lose ten pounds. B, I'm gonna get into really sh good shape. C, I'm gonna finish that book. Typically after Farting around for a week, not getting anything done, start to feel terrible.

And then it becomes this like voice of you're 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, you know, in the Jewish tradition disavow or disconnect from anything that is electrical, right?

Put your keys down. Put your money down. Rest. There's something very, very profoundly holy. And rest. Now I know I'm swimming upstream. Everybody wants to be productive.

I could also just If 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 gonna 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 Uh За production goals.

Some writers like to say, you know, thousand words a day. Five hundred words a morning. Something like that. And I went into this past sabbatical with a little bit of that mindset. I'm gonna get part one. It's all mapped out. I'm gonna get part one done this summer. And

I did hand in fifteen thousand words. Of what will eventually be a seventy thousand word manuscript due next summer. And they're kind of a mess. As Annie Lamott would say, 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 stop trying to be productive.

I mean I hate to sound Zen like here. But 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. Well let's If I may. We can make this personal on my side and we can we can explore those muddy waters for a minute. So I have been able

Over the years to take Many trips and disconnect. Typically for Particularly since I'm in an intimate relationship with my

lovely long term girlfriend. We don't like to be apart for long periods of time. She has a job. that doesn't totally disallow, but largely disallows her to take the type of time off that I might want to take off. For a sabbatical, let's say. None the less 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 electronic for a period of time. I do that generally at least once or twice a year.

None the less what I have found for myself and some people may resonate with this. Actually I'm gonna Give a few examples of friends and then I'll give my personal example. So there are friends who have been in Zero sum games for so long that that lens has become their default. Right, 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. Like I I do think there are certain scenarios in which that's the case. However. Let's say you ride that hundred 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. Or I have a friend I w I shan't name, but very good friend. And we've known each other a very long time. And I've watched as his magical number, 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, Yep, 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.

So And uh I Identified with that quite a bit. I said, You're right. I mean you 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. So I'm gonna Park that for a second. 'Cause 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, ten or fifteen years, there has a been a creep of complexity.

So when you have Dozens of different entities. Like LLCs and so on. When you have Hundreds of or at least a hundred 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. 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 like a tax authority or some registered agent or an employee. that I do feel like I Shoep 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 complexity so that it has less of a Fearful impact. Anem? Or

And 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 frame that question. And There are tips and tricks and hacks that you can do to reduce the complexity. But The complexity will creep.

Back. Right. 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. Right. 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 is The third person. Hulk my Hulk smash Jerry Ask Jerry ask question that caused tear How am I complicit in creating the conditions I say I don't want?

Right. And so I'm gonna 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 autoresponders. Tax person go here kind of thing. Mm-hmm. So If you want to alter that behavior.

You have to understand what the benefit is to you. The payoff or the secondary payoff. That's it. The 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? I 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.

Yeah. And I would say that for much of my life I had competitive athletics and other things. That's 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, yeah, you know what, maybe I don't need to get heel hooked 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 Lou 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 I've substituted in Investing. And I've substituted in

different types of projects. that often have some creative component. Almost always they do. Whether it's deal structuring or A podcast episode. Or a pre-loading podcasts 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 in the systems. That makes sense to me. What's the opposite of excitement? 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 am sure fundamentally it comes down to not wanting to be alone with my own thoughts and certain feelings that might come up. So the question of, you know, what is it that you're unwilling to feel? I think it was Tara Barack 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'm I've looked at my family and I went to a 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 gonna make you feel really uncomfortable because I'm really fucking proud of you. Thank you Jerry. You go there. So we're gonna go there.

Yeah. Proclivity towards 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 afraid, be alone with my own thoughts. Or to phase 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 wanna 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.

Yep. And let's Make sure That were 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 Terra Brock. Family systems. Can reject.

Feelings. Mm. Not just individuals. Yeah. It reminds me of a I I remember sitting with a group of uh 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 any time 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.

Yeah. And Sometimes We get really complicated and busy because we don't actually want to feel. What those thoughts.

Bring up. And there again is a reason why Sabbatical can feel really challenging. If I pause I'm gonna feel really uncomfortable. I'm gonna feel

Hot porn. Can you expand on hot boredom and then I'm gonna 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.

Hot boredom and cold boredom is really great. Framing to think about it. We don't really do this so much anymore, but imagine you're online at the post office or online at the DM V. And it's just an interminably long line, and you gotta be someplace else. And there's nothing to distract you.

And that discomfort, that's hot boredom. That's like it's 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. What the hell am I doing here? I gotta I can't even sleep. It's in a But by the day four, day five, day seven, day ten.

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. That's called boredom. And I would argue that the mind Need called boredom. It needs

Does it. Days of Simple You know, my therapist calls it just simple stir in the oatmeal kind of morning. Here I am, do just stirring the oatmeal.

Mm. 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. Let's start with Hypothetical situation. And 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 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. Ha ha And still haven't prematurely committed to something huge just commit.

But I got to a point where sitting with that void. felt unhealthy. So my question to you, and I'm not at the point of total burnout, but if you're talking to a client. Cool.

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 he or she decides they're gonna take a sabbatical. So they have yet to become

Sort of comfortable stirring the oatmeal. But they're gonna take a sabbatical. What advice do you give to that person? Start small. Start with tiny steps. Baby steps out of the office. Baby steps, yes. How about starting with a weekend.

How about starting with one evening, you know? I mean, literally, you were asked me before about the When I started Sabbaticalizing. 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. For the ten years previous to me taking Two months sabbatical. 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. 'Cause if you go to as I did, you know, cross the polar ice cap and Greenland. For some reason you don't get a good sell signal. It's like it's amazing. You are forced or you know, I went rafting the Foodala Fo River in in the Chilean Patagonian area and there really isn't a good Wi Fi signal.

And It's beautiful. And so those small little steps. I I have a client I just started with in September. And he's taking his first vacation. Two weeks.

In Namibia. First vacation in ten years. First vacation in ten years. And it was only because his life partner recently sold Her business.

And that they have they feel like they have the time. That's not healthy. So practical advice. Start small. Start where you are. Start with

A day. Our mutual friend Brad Fell was the first person I know. who use the notion of digital sabbath. I'm gonna 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 just start there. Just start there. 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 say a city. Like Austin. Here's what happens.

To me. Let's just say so I'm sitting downtown. In Austin right now. I decide I'm gonna take a couple couple of weeks away from my normal routines, but I'm gonna stay here.

In So called civilization. My girlfriend mean. while is going to continue with her normal routines.

Most of my friends At least here. Coincidentally taking

Sabbath a sabbatical the same time that I do. And so I I go about my day. And ultimately A it's very lonely. B. I end up feeling unemployed slash 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 sort of unemployed And or crazy people.

I realized this in San Francisco actually. When I was like I'm gonna take a break and I'm gonna 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 like 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. Uh it's not so m I mean, there is that

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, right? Like if somebody were Yeah, this is an extreme example, but just to kind of Play out the point.

If somebody actually Where sitting inside an insane asylum. I know that's probably not the the politically correct term these days, but like one flu over a cuckoo's necks and you weren't like working behind the desk. You're actually sitting in there like playing chess with these people all day. Uh 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. And that's not limited to Austin. I mean, if you want it times ten, go to San Francisco. So I don't automatically assume I'm one of those people, but uh my instrumentation is very sensitive, so I do get I do feel

Impacted. by being in those settings. And I I think we could treat these two things almost separately. There's being in those settings and being affected by The settings genuine sense of loneliness. And I and I know a lot of people who are quote unquote free, right? Who can work

Wherever they want, 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 if you have any thoughts. 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 out that I'm uh insane. I mean, leave that on the table. But I I think the lonely is is really important and and You know What you're helping me see is that my lens is very much affected by the fact that

On the spectrum I tilt toward it. Introversion. So I don't quite have the same reaction to the word lonely. Uh 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, Jerry?

So 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. Right. 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 and w when 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, you know, as we've talked about before, I too

I actually attempted suicide at eighteen. And You know, in an odd way. I make my bed every day. And I make my better 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 a bet 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 ізнt about being alone. So much. It's about feeling lonely. Because that's the association back to the depression. That's right.

And the suicidal impulses. And that 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 gonna stay out of a bar.

You're gonna 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 Yeah. 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 there could be some overlap.

But for instance, if I go on A I'll tell you one of my happy places, and maybe that'll 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 hot liquid is in the world. And then hiking at altitude and feeling like I'm just getting punched in the lungs for like twelve hours, taking a nap on a mountaintop 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.

That's great for me. And you're not lonely. I'm also not hyperactive. 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 that would seem to me to be a form of Of cold boredom. That is definitely a form of culture. 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. Just a side note. Sleeping on a rock. Side note. I can I tell a funny story just for just for a diversion. So I I went on one of these first outings with a couple of Couple of guys who were very experienced. outdoorsmen. Also a number of them. Former

professional level sponsored athletes. So I was already intimidated and I was a C level. 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. I said, Shouldn't we be concerned about bears? And they said, Ah no And one of them said, They're just black bears. 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 uh 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 10 four inches from my fucking face. And it's this j gigantic Bear. I'm kidding. First night. First night. And I don't know. Any of these guys except for like 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 Pray mode. Like every every single

corner of my psyche just lit up on fire. Can't sleep, not surprisingly. It comes back a few hours later. And then uh in the morning we're having our coffee. And uh I mentioned this and the same guy who told me it would lick me to death is like Jesus fucking Christ, man, you gotta love stuff that kinda shit. None the less.

After that trip felt like I had taken a six month vacation. You just said it. The experience of resetting for you. Wasn't something that's time delimited. There were 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 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. Yeah. 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 rebel. I can't wait to be able to climb into that. And I live in a forty acre farm. With A woman I love and three horses and an eighteen year old cat. Coyote's running across my

the pastures and Hawks and birt and eagles and stuff. But sometimes you m you need to change the venue, sometimes you need to change it up. And I g I get that. I paused and hesitated. Tim,'cause you said should I?

And you know me well enough to say I'm not so sure I can answer I should. Should you, yes, should you, no. I think you have to go You have to design it for yourself. You have to sort of tune into what you know and

Collect the information as you have been doing and design your own. Retreat. I find it enormously helpful. to be able to periodically even within

The envelope of my m normal days. to be able to Cut. The chatter. I often say that

I sit on the meditation cushion 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 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. I think ultimately take the sabbatical with you. Take that mindset with you. And live it into your days. Are there any resources? Thank you, Jerry.

Uh that that resonates with me. And I meditated this morning. twenty minutes. Nothing fancy. Mm. Just T M repeating repeating some sound in my head so that my monkey mind has something to do. Climb up and down the pole for twenty minutes. That's it.

Mm-hmm. 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 red. I wanna say this was around two thousand four, two thousand five.

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. Doesn't matter. Are there any resources that you might

Recommend. One of my little mental tricks that I do when I when I do a public talk as 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. Excited, scared. And almost always I land on the word exhausted.

And everybody just resonates with that. Like your your b your shoulders just dropped as soon as I said the word exhausted. Because you c you you know what I'm talking about. It's just this constant sense. And You know, there is a blessing, and I'm not gonna re recall the fullness of it, but John O'Donneu, 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. And

In that blessing. Among the things he says is Steer clears. Of those vexed in spirit. So think about those folks in the Starbucks. They're vexed in spirit.

And Become 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. I mean whether you follow

Judaism or Christianity In the story. From the Old Testament. And on the seventh day even God Himself rested. Easy.

Shento. There's another line from that poem in which Hanius says Be excessively gentle. With yourself. So I don't have a

Ten tips and tricks to make your sabbatical Has productive as possible. You know me. That's not the way my brain is working. We saw the draft of my next blog post. Damn you Tools for Titans for Semanicals. Semanical edition. Volume one. Yeah. But I think that there's there is a really profound wisdom.

And O'Danius 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 in in the land with your friends. That's what you're doing. Rest is not You know, zonking out on the couch. to Netflix 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 uh Pure Exhaustion. It's not a paper cut exhaustion. It is a pure Focus.

Holistic Deliberate exhaustion. And That's a straightening through fire of sorts. Yeah, listen, I I'm all for

The physical exhaustin As long as the mental turn off Is happening. As long as the mental The chatter, you called it the monkey mine, as long as the chatter is quieted. Yeah. Because I'll bet you when you guys are

hiking and you know, you're you're going from one camping spot to another. Your minds are quiet it, Oh yeah, yeah, yeah. Even as your body is physically taxed. Yeah.

Yeah, it's a different experience. Well, Jerry We're coming up on time for both of us for different reasons. Mm-hmm. And uh

I Would like to read a name and you can tell me the pronunciation. 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 E O N E R And I'm happy to read, but if you have it Since you sent it to me. I feel like May make 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. Conversation one on Sabbaticals, but moreover. All of the Questions and queries and

Introspection that can surround The idea of a sabbatical. I can read it. I'm just bringing it up right now. 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. Or the same to Ren. If what a tree

Or a bush. does is lost on you. You are surely lost. Before the tree Or a bush.

Does Is lost on you, you are surely lost. Stand still. The forest knows where you are. Yeah. Must let it find you.

So good. So so good. I'm so glad you sent this to me. This 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 Spent time.

Recognizing it again. Well, I appreciate your 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 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. 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 Tim.blog slash Jerry Kalona on Twitter at Jerry Kalona C O L O N N A. Reboot.

at reboot hq on Twitter and the website reboot. I owe. Cherry, is there anything else you would like to say before we Hit pause on this conversation. Just that I hope that folks take a little bit of time off.

Yeah. And take a little bit of rest and to remember the words from John O'Donnell, you 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. And to everybody listening, we'll have show notes, links to everything at Tim.blog slash podcast. And until next time.

Be gentle. with yourself. Hey guys, this is Tim again, just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kinda like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests, and these strange esoteric things end up in my field, and then

I test them and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to Tim.blog slash Friday. Type that into your browser, Tim.blog slash. Friday, drop in your email, and you'll get the very next one. Thanks for listening. This episode is brought to you by 8 Sleep. My god, am I in love with 8 Sleep. Good sleep is the ultimate game changer. More than 30% of Americans struggle sleep. And I'm a member of that sad group. Temperature is one of the main causes of poor sleep and heat has always been my nemesis. I've suffered for decades, tossing and turning, throwing blankets off, putting them back on, and repeating ad nauseum, but now I am fall asleep in record time, faster than ever. Why?

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Headspace is one of the only meditation apps advancing the field of mindfulness and meditation through clinically validated research. Headspace is backed by 25 published studies on its benefits, 600,000 five-star reviews, and more than 60 million downloads. So if people keep telling you to try meditation and you're like, when would I do that? When would I possibly have time? You should check out Headspace. If you have 10 minutes, Headspace can change your life. Headspace offers a really light lift and a lot of features to keep you going, which is part of the reason that I've used Headspace for years now. So whatever the situation, Headspace can really help you feel better. Overwhelmed, Headspace has a three-minute SOS meditation for you. Need some help falling asleep, Headspace has wind down sessions their members swear by, and for parents, Headspace even has morning meditations you can do with your kids. Headspace's approach to mindfulness can reduce stress, improve sleep, Just focus and increase your overall sense of well-being. And it really starts with very, very simple practices and if you look at my case for instance I just went through one of the basics

today with the co-founder, Andy. It's Putticum. Could be putticom, I'm not sure, but former monk. turned into co-founder of Headspace has the most soothing hypnotic voice imaginable, and I did a three minute meditation, something like that. It's easy it's fundamental, and it always puts me in a better space. So I'm going through the basics, even though I've meditated for years, I'm going through the basics once again. and I would suggest to anyone that they consider starting there. Headspace makes it easy for you to build a life-changing meditation practice with mindfulness that works for you on your schedule anytime, anywhere. We all want to feel happier. We all want more peace. And Headspace is meditation made simple. Go to Headspace.com slash Tim. That's Headspace.com slash Tim for a free one month trial with access to Headspace's full library of meditations for every conceivable possible situation. You can break glass in case of emergency in almost any situation and find something on Headspace. This is the best deal offered right now for Headspace?

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