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#554: Jerry Colonna How to Take a Two-Month Sabbatical Every Year
#554: Jerry Colonna  How to Take a Two-Month Sabbatical Every Year

#554: Jerry Colonna How to Take a Two-Month Sabbatical Every Year

The Tim Ferriss ShowGo to Podcast Page

Jerry Colonna, Tim Ferriss
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31 Clips
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Dec 14, 2021
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0:00
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5:05
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 Kelowna, C 0, L 0 and n a on Twitter at Jerry Colonna. He is the CEO and co-founder of reboot dot IO and Executive coaching and leadership development firm dedicated to the notion that better humans. Make better leaders. Now for those of you don't know, jury's already been on the show. It was an excellent episode and it was named.
5:35
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. It will be clear shortly for nearly 20 years. He has used the knowledge gained as an investor one, hell of an investor, and 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.
6:04
Organ Partners, the private Equity arm of JPMorgan Chase previously. He led new york-based flat iron 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.
6:35
Podcast definitely also check out his first which goes deep into his bio and all sorts of topics. You can find that at Tim dot blog, / Jerry Kelowna, again, one more time, Co Loa nna if I drew them on Twitter as mentioned at your Kelowna on LinkedIn, of course, reboots Twitter is at reboot HQ and the website for all things Jerry and reboot is reboot dot IO. Jerry, welcome back to the
7:01
show. Thanks for having me Tim. You know, it's a bizarre experience.
7:04
He's here in your life, played back at you, like that. I'm sitting there listening and I've gone damn, I'm old processing some in 1996 and I know that's in my bio. So
7:20
yeah. When I ever hear my bio red back which you know, I've usually crafted carefully and third person. 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.
7:34
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 want to say a month six weeks ago, maybe something like that. And we were covering a number of different things, but quickly came.
8:04
Up that you had just finished a two-month sabbatical and then you've casually mentioned that you done that for
8:14
how long roughly would you say? 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-month sabbatical. Okay, so
8:28
10th to on sabbatical and I wanted to hear all about this. I wanted to do.
8:34
Get into this and thought it might be a great bridge in 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
8:59
about? It's like it. And if we were a TV show, you know, the image we get
9:04
All wavery as he flashes back in time. I think that. So I've been a coach now for about 17 years,
9:13
and I
9:15
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.
9:35
And as every good New Yorker 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 stink to high heaven. It's also when all of our therapists are gone, right home alone, in New York
9:53
City. Exactly.
9:58
For more on this, watch the movie, What
10:00
About Bob? Which is
10:04
Which is a very good. Anybody who
10:06
watches the movie will get. The reference, is this corn hand, shucked. Sorry, continue.
10:17
Excellent.
10:17
Excellent movie. Continue, please.
10:19
Excellent movie Bill Murray 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.
10:35
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 it first taking four weeks off. And what I started to do though was I started to realize that I needed longer than that.
11:04
Because I know this is going to sound really indulgent. But I also wanted to take a vacation during the middle of sabbatical. I know that's a bit a bit of 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 drafted the Grand Canyon for the third time in 2014 with
11:34
Son, so what began as well, maybe I'll take a month and then take two weeks of vacation started to morph very, very quickly into modeling myself after my therapist morphed very, very quickly into no. I actually
11:52
need to take a pause. I need to take a
11:54
break and a Funny Thing Happened on the Way to the Forum. Write a funny thing happened on the way back. I found myself being a better therapist. Oh, did I?
12:04
I say that out loud. A better Freudian slip. There
12:09
are ways than one.
12:11
I'm much better Coach, a much better Coach because I was rested and I could be there more fully for my clients. What
12:18
did the very first sabbatical look? Like? Did you have any internal conflict or push back? Oh, yeah. It doesn't have to be the very first, it could be one of the first but one that comes to
12:32
mind. The first one that comes to.
12:34
Minders, can I afford this right? Which is
12:40
Crazy, but it's the thing that were 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. You buddy. 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.
13:10
Is kind of interested in this, so,
13:13
we can get to that what, 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 have heard from clients, even just about taking long week in our 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 just push
13:40
Pushing forward pushing forward and when you suddenly stop here'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 for motion.
14:05
We take meaning from performance.
14:09
And then when I take away the motion, what happens to my meaning?
14:15
So, you know, 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.
14:25
I want to
14:26
touch upon something that you mentioned, briefly for folks, and that is, can I afford it? And 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.
14:56
I can gave it to many many, many, many, many, many people, I later became friends with the author Ralph pots. But vagabonding was one of the books I took with me when I 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
15:25
In his book with a story, is recounting part of the movie Wall Street, with Gordon Gekko, with the brick sized cellular phone walking on the beach. This iconic film greed is good, etcetera and the Charlie Sheen. Character. At one point is asked, by, I want to say his girlfriend, his love interest, you know, what he 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
15:56
All 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.
16:25
He's 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
16:49
mention. Yeah, I think that's a really, really important conversation. We are too well.
16:56
Heavily well off, white men, you know, yakking 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 18 month, sabbatical or to a two-month sabbatical every year for 10 years. Those are choices that are afforded us sometimes by external forces.
17:25
Times 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 do be too playful with my home work. The mindset is the mindset behind rebooting and resetting.
17:53
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 is 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.
18:20
Of thinking differently.
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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
18:46
For many of our friends who are in start-up 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
19:16
Raids toxic environments. And so what we're really talking about in this way is, is this notion of can I afford myself a moment to pause standstill?
19:29
And think a little bit differently and see the world a little bit differently.
19:34
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,
19:45
We have a rare opportunity. We I'm using the Royal we I mean Tim Ferriss, I say this is a rare opportunity to King Tim's Kings him who has 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.
20:09
Making sabbaticals work.
20:12
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 a front load some tactical stuff to kind of lure people in as a honey pot. So, so let's if you don't mind focus on some of the Tactical practical, anything that comes to mind.
20:42
Terms of what you've learned about making, sabbaticals work for yourself.
20:47
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 home 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.
21:12
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.
21:27
And so if you think about it, you think about me not as a coach, but as a CEO.
21:33
Stepping into the launch of a business. And from the beginning we modeled in the notion of taking time off. Now it soon as I said that my co-founders were like, I yeah, 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.
21:59
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.
22:27
You know, we have this funny notion, especially in the tech community of unlimited paid time off unlimited PTO.
22:34
And Studies have shown that the more unlimited 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 models,
23:03
We start to change the perspective about ebitda about profitability. And if we start thinking about this as a simply, a cost of doing business, it 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.
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And then periodically something awful happens. And we say, okay, let's build in some mental health time.
23:42
But it's always after some sort of horrible event
23:47
Jeremy. 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?
24:11
And how you perhaps counteracted those when you were kicking the tires. And first taking
24:19
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.
24:26
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 was 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 know, you're smiling because because, you know, you're wrong.
24:56
Rules, right? And you create all these structures around the rules and I'm going to 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 an away message that in some way or another inspires other people to think about these things. So I remember
25:21
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. So if you're actually getting an email from me I felt and that tends to make people laugh but it what it does is it also helped me in managing expectations. So mistake our lesson I learned was to not
25:51
And the sabbatical into another source of
25:55
self-criticism. 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
26:11
gelato. Yeah, you know, it's so funny when I was thinking about our conversation today was thinking about it yesterday, and if I remember correctly in our first conversation,
26:21
Ocean. You also asked me about email. Like, how do you do handle, email? Jerry or some point in our life. You asked me this question and I gave you the perplexing. Answer of just don't respond. You like no, that's internet.
26:36
Welcome back to that. It's have a slightly complicated rashomon. Perhaps a slightly different remembrance, but we can we can we can dig into that
26:47
to go back to your question for a moment. I think the way I handle email on that.
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Is I will scan it. Yeah, and I feel super liberated. If I decide not to respond.
26:58
Because I've already given them a response that says I'm not going to 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. While I was on,
27:18
sabbatical you say sessions. What do you mean?
27:20
A session is a coaching conversation? And there was genuine crises.
27:28
That my clients needed some help with and I consciously said, yes, I can do that, you know, 2:00 and such and such afternoon kind of
27:38
thing boring process. Question. How did news get to you that? That was a crisis in important to
27:45
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.
27:54
And I don't have anybody answering my notes and stuff like that. I need to have a direct relationship with
28:00
people. So, does that mean that you're scanning each day? Yeah, as the spirit moves
28:05
you, I think, you know that I have a fairly healthy morning ritual where I don't really, for the most part. Check email. Why
28:15
don't you remind people? I do recall us discussing this in episode 1, but just for people who don't have that
28:19
context. Yeah, so I'm really early riser.
28:24
Pretty much regardless of time zone them up between 5:00 and 6:00 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.
28:54
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 are most responsive to our the people. I love. So, you know, my partner Ally or my children, they always get responded to even if officially I'm off the grid.
29:25
Got it. 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.
29:34
When you look back at the sabbaticals. You've taken it. So 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?
29:54
See any characteristics that have some explanatory power
29:58
for you?
30:00
This past sabbatical was incredibly recharging. 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.
30:29
Singing 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 ate well, and I rested well, and I exercise, my mind was 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 or lovely.
30:59
Beach house, and my kids speech came to visit and cycle through which was lovely. And if I would say there's a pattern of sabbaticals that are done, right? It's a focus on mind and body and its resting both and taking care of both for a 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.
31:29
Or I'm going to read this 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. I mean, these are all examples that my clients have given me and the number one rule in sabbatical is Sabbath.
31:50
Rest.
31:53
Rest.
31:55
The body needs rest, the mind and heart need rest. That's the simplest way. I can put it for you.
32:07
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33:38
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, The Epiphany could have happened during the sabbatical, but let's just say something. And what I'm trying to do here is to speak to people who
34:04
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
34:14
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. Hmm.
34:32
And if that all feels resonant, that's the problem.
34:39
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 your 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
35:08
Alcohol involved. And I'm staring up at the sky and someone lying 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.
35:27
And then finally, someone says stop looking for them.
35:31
And I rest my eyes and with peripheral vision. This is true fact. All of a sudden. I can't start catching the motion.
35:40
And that's an image. I would give you four sabbatical people who go into sabbatical with the plan to say I'm going to lose 10 pounds. Be I'm going to get into really good shape. See I'm going to finish that book typically after.
35:59
Farting around for a week, not getting anything done. Start to feel terrible.
36:04
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, and Jewish tradition disavow or disconnect from anything. That is electrical, right? Put your keys down, put your money down, rest.
36:31
There's something very, very profoundly. Holy.
36:35
In rest now. I know I'm swimming Upstream. Everybody wants to
36:39
productive.
36:41
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 are writing working on a book unlikely on some level feeling productive. So if we removed that,
37:01
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
37:19
that. Sure. And I get that when I felt good working on the new book, this summer.
37:28
It was when I let go of the production goals.
37:39
Some writers like to say thousand words a day 500 Words morning, something like that. And I went into this past sabbatical 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.
38:06
And they'll kind of a mass as any lamotte 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 stopped trying to be productive man. 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.
38:36
Master Bates, the stress and tension that causes us. Need to take the rest in the first place.
38:44
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 to over the years to take many trips and disconnect typically for particularly since I'm in an intimate relationship with my lovely.
39:06
Lee 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 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
39:33
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 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
40:03
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.
40:16
Things would blow apart. Like 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 and the case of a Founder? They think they will just be able to turn off that script and I have seen close 20 examples of them, being able to write. It's very common. Or I have a friend, I shan't name but
40:45
Very good friend, and we've known each other very long time. And I've watched as his magical number this number once I hit X, right? Right, then I'm going to build a workshop in my garage and make artisinal 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
41:15
Yep, I've heard that before, and he said something to me, which I thought was interesting. It's not totally Jermaine 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 yes, and I
41:36
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 going to park that for a second. 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.
42:06
Just 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, llc's and so on, when you have
42:35
The hundreds or at least 100 different Investments and funds and capital calls 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 their certain others from whether its tax Authority or some registered agent or
43:05
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
43:31
fearful impact on them or end or reduce complexity.
43:40
in a way that
43:42
lessons this sort of internal drama that they experience going along with it.
43:48
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.
44:13
I hire an assistant and then all of a sudden I need to write 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
44:30
want, I like the you just referred to yourself like the Hulk uses. The third person Hulk mom.
44:42
Question that cause
44:43
tear my complicit in creating the conditions. I say, I don't want, right? And
44:51
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.
45:12
Sorting them out, responding them. Maybe even use autoresponders tax person, go here, kind of thing.
45:21
So if you want to alter that behavior, you have to understand what the benefit,
45:26
isn't it? Pay off or the secondary pay off.
45:29
That's it. The watch 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 Pi's and doing all sorts of things. What does it do for you?
45:46
I
45:47
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 are 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
46:16
a lot of excitement just as important excitement and
46:23
I haven't had that very long time after a shoulder reconstruction and then elbow surgery and twisted SI joint and all these things like, you know what, maybe I don't need to get he'll 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.
46:42
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 I've substituted in investing
47:11
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 podcast that I can do a b and c elsewhere but very often I would say. The investing side in particular is related to
47:34
Excitement, I would say that's what I get from it and the side effect of having lots of Investments.
47:43
and lots of,
47:48
Things that come along with that is this complication the complexity and the systems
47:54
that makes sense to me. What's the opposite of
47:57
excitement?
47:59
Table Civic 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, may be optimistic about this. I am sure fundamentally it comes down to not wanting to be alone with my own thoughts and certain feelings. It might come up. So, the question of, you know, what is it that you are unwilling to feel?
48:28
Mr. Brock, who said, you know, one Sage 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, you know what to 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.
48:57
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
49:14
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.
49:27
You go there. So we're going to go there, the proclivity towards anxiety. Could have a genetic component here, but the proclivity to be uncomfortable with what the Buddhists would call Hot boredom.
49:43
Is not DNA. It's, you know, to use the term from my first book. It's a subroutine its 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 face those things. And God bless you. You've done a fantastic.
50:13
The job of learning to deal with your own thoughts. So let's imagine if you will that does learned behavior was boredom bad, Hulk boredom bad.
50:26
Well, the learn Behavior May Justice 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. Hmm. Because when we're alone with our thoughts bad things happen.
50:44
So let's get busy. Yep, 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.
51:00
To go back to Tara Brach family systems can reject feelings. Hmm. Not just individuals. Yep. It reminds me of a guy. 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 happens a third time and what it was was any time that there was a really moment of tension. Somebody would make it.
51:29
A joke and the whole energy would dissipate.
51:33
And when I called it out, 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.
51:51
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 board. Can you
52:04
expand on Hop 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
52:15
hot boredom in called boredom is really great framing to think about.
52:21
We don't really do this so much anymore. But imagine you're on line at the post office or online at the DMV and it's just an interminably, long line. And you 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 contrasted to cold board and I know you've done meditation retreats.
52:50
Imagine not the first three or four days of Meditation Retreat. Which often provokes hot boredom. What the hell am I doing here? I got to, I can't even sleep. It sooner to. But by the day four day, five day, seven day. 10 years sitting there and literally there's nothing dramatic going on. In your mind. There's no drama.
53:16
You're okay.
53:18
And all of a sudden you catch a glimpse of a bird, that's really interesting.
53:26
That's called boredom.
53:28
And I would argue that the Mind needs cold boredom.
53:34
It needs those days of simple, you know, my therapist calls. It just simple, Stern, oatmeal, kind of morning. Here. I am do do just during the oatmeal.
53:50
Because that's a moment of rest from which we can then go about the rest of our time. The rest of our day
53:59
as many questions as one would expect, if I invited you on the podcast to talk about this. Let's start with
54:09
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 of 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
54:38
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. So my question to you, and I'm not at the point of total burnout, but if you're talking to a client
55:08
Who?
55:10
Like it or not is not going to.
55:14
Get to a place of comfortable cold boredom before they burn out and you jointly decide or 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
55:32
person? Start small, start with Tiny
55:35
Steps. Baby steps out of the office. Baby steps.
55:40
Yeah. How about starting with a weekend? How about starting with
55:44
Evening, you know, I mean literally you asked me before about the when I started sabbatical lysing 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 10 years previous to me taking two-month sabbatical. I would take Monumental Off the Grid trips. Why were they monumental?
56:14
Well, because that was the only way I could really break being attached to the grid. Because if you go to is, I did, you know, cross the polar ice cap and Greenland for some reason you don't get a good cell signal. It's like, it's amazing, you are force or, you know, I went rafting the food of the Foo River and in the Chilean Patagonia 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
56:44
Started with in September and he's taking his first vacation two weeks in Namibia first vacation in 10 years.
56:55
First vacation in 10 years and 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 Feld was the first person I know who use the notion of digital Sabbath.
57:23
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 just start there. Just start there.
57:39
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
57:50
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 going to take a couple couple of weeks away from my normal routines, but I'm going to stay here in so-called civilization. My girlfriend mean, while is going to continue with her normal routines, most of my friends.
58:20
At least here are not going to be.
58:24
Coincidentally taking a Sabbath, a sabbatical, the same time that I do. And so I go about my day and ultimately a, it's very lonely. Be, I end up feeling, unemployed /, insane, because if you go to the Starbucks, or you go to the library, or you go to
58:50
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 going to take a break. 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 pole towards like the River Edge of Chaos.
59:20
It's not good for me. Well, what I also hear
59:23
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 work. I
59:33
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 in, this is an extreme example, but just to kind of play out the point if somebody actually were sitting inside
59:50
with an insane asylum. I know, it's probably not the politically correct term these days. But like One Flew Over the Cuckoo's Nest and you weren't like, working behind the desk. You're actually sitting in there like playing chess with these people all day or whatever. It might be. I think that would affect just about anyone if they're exposed to Troy. 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 10, go to Sea.
1:00:20
And Cisco, so I don't automatically assume am one of those people, but I might instrumentation is very sensitive. So I do get, I do feel impacted by being in the settings. And I think we could treat these two things almost separately. There's being in those settings and being affected by the settings. And there's also just a genuine sense of loneliness and I know a lot of people who are quote unquote, free, right? Who can work wherever
1:00:50
Whoever 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 get agonizing how Lonesome that feels. So, that's a big mouthful. I don't know if you have any thought.
1:01:13
I'm glad you Circle back to the word, lonely. Because you went lonely, unemployed insane. And I
1:01:20
Update and saying that, but but I think the, why don't we don't have to rule
1:01:25
out that. I'm insane. Now, we can leave that on the table,
1:01:29
but I think the lonely is really important. 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 its introversion. So I don't quite have the same reaction to the
1:01:50
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
1:02:05
folks. May I interject for one, secondary? 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.
1:02:19
I think in part as a byproduct of certainly, lots of factors, but one of them being I was all 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 actually consider it a real return to
1:02:48
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.
1:03:09
I appreciate that distinction. I think that that's really helpful and what I'm feeling my way too and I can relate to this is
1:03:18
There are certain mental states that are reminiscent of the past States, you know, as we've talked about before I to, I actually attempted suicide at 18 and, you know, 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
1:03:48
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 recital, impulses, and that a really good observation about yourself. And so, I
1:04:18
I applaud you being able to say to yourself. Okay, there's an alcoholic. Might say I'm going to stay out of a bar.
1:04:24
You're going to stay out of those situations that can be triggering for you and bring you back to some of those States.
1:04:32
And I like where we are right now, because what we're seeing is that perhaps there's a little fear of cold boredom.
1:04:41
Because it might remind one of feeling lonely.
1:04:47
maybe, maybe
1:04:48
I
1:04:51
Maybe, maybe, I think that 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
1:05:20
Just like the best hot liquid that's 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 Mountaintop and
1:05:34
Having a fire night like thaw out your feet, and then going to bed. And the majority of the day. There is no talking. That's great for
1:05:42
me and you're not
1:05:43
lonely. I'm not lonely. I'm also not.
1:05:48
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 cold
1:06:00
boredom, that is definitely a form of
1:06:03
cold. I love that. I find after 45 days of doing that. Even if I'm getting the shittiest, sleep, you might imagine right? Three hours a night. It's just a side note weeping on.
1:06:17
Ross side note, I can I tell a funny story just for this diversion. So I went on one of these first outings with a couple of couple of guys who were very experienced. Outdoorsman. Also number of them, former professional level sponsored athletes. Those already intimidated, and I 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 the candy bars. And
1:06:47
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 close to a Full Moon. I wake up and the tents about 4 inches from the side of my face, and there's literally a huge nose.
1:07:17
Ten four inches from my fucking face and it's this gigantic bear. I'm getting not getting first night first night. And I don't know any of these guys except for like 11 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.
1:07:47
You'll pray mode every every single corner of my psyche just a lit up on fire, can't sleep not surprisingly. It comes back a few hours later. And then in the morning, we're having our coffee and I mentioned this, the same guy who told me it would like me to death. It's like Jesus fucking Christ, man. You gotta let
1:08:09
us know.
1:08:13
And
1:08:13
nonetheless. After that trip felt like I had taken a six-month
1:08:17
vacation. You just said it the experience of resetting for you.
1:08:23
Wasn't something that's time to limit it. 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. Yeah, you know, being in the land nourishes, you being physically in your body nourishes, you that is a sabbatical to
1:08:52
do.
1:08:53
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.
1:09:17
I totally get that. And you know, changing physical location is really important.
1:09:23
Didn't 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 with the woman. I love and three horses and an 18 year old cat coyotes running across my the pastors and Hawks and Burt and Eagles and stuff. But sometimes you need to change the venue. Sometimes you need to change it up and I get that.
1:09:53
I pause and hesitated Tim because you said should I and you know me well enough to say I'm not so sure I can answer a. Should 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 in to 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
1:10:23
Periodically even within the envelope of my 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.
1:10:53
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 day.
1:11:23
These are there any resources? Thank you
1:11:25
Jerry that that resonates with me and I meditated this morning, 20 minutes. Nothing fancy. Hmm just TM repeated, no dropping some sound of 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, right? That's it for me. That's largely. Are there any resources?
1:11:52
has that, you might suggest to folks who are
1:11:56
Considering the possibility of a sabbatical. I remember there is a book that I read. 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. Sabbaticals. Are there any other resources? And these could be non-obvious? Resources could be story, a poem, a book, a movie doesn't
1:12:26
Matter, are there any resources that you might recommend?
1:12:31
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 exhaust.
1:12:58
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'donohue, the great Irish poet, the late Irish poet has a book of blessing called to bless the space between us.
1:13:24
And ended. He has a blessing for those who are exhausted.
1:13:29
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, their vexed in spirit.
1:13:45
And become inclined to watch the rain.
1:13:50
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.
1:14:04
And that's the time to rest. I mean, whether you follow Judaism or Christianity in the story, he's from the Old Testament. And on the seventh day even got himself arrested, easy, gentle. There's another line from that poem in which, oh, Donny is says, be excessively. Gentle with yourself.
1:14:30
So I don't have a 10 tips and tricks to make your sabbatical as productive as possible. You know, me. That's not the way my brain
1:14:39
is, we saw the draft of my next blog post. Damn, you
1:14:47
tools for Titans first sabbatical. Yes,
1:14:50
volume 1,
1:14:53
but I think that there's, there is a really profound wisdom in O'Donoghue's Palm, which is
1:15:01
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.
1:15:12
That's what you're doing.
1:15:15
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.
1:15:29
It's getting the heart rate down.
1:15:33
It's taking care of yourself. And to me, that's what sabbatical is all about.
1:15:38
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.
1:15:52
Exhaustion. It's not a Papercut exhaustion. It is a pure Focus. Yes.
1:16:01
Holistic, deliberate exhaustion and that's a straightening Through Fire of
1:16:10
sorts. Yeah. Listen, I'm all for the physical exhaustion. As long as the mental turn off is having a long as the mental the chatter, you called it. The monkey mind. As long as the chatter is quiet it. Yeah. Because I'll bet you when you guys are hiking and you know, you're going from one.
1:16:31
Camping spot to another.
1:16:34
Your minds are quiet it though. Yeah, even as your body is physically taxed.
1:16:40
Yeah, it'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, 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
1:17:04
Is.
1:17:06
Lost by David
1:17:07
Wagner, is that correct?
1:17:11
That is
1:17:11
correct. Whe, oh, ner. And I'm happy to read. But if you have it, since you sent it to me, I feel like they make sense for you to read this because I think it encapsulates a lot of what we're talking about and
1:17:30
could be a good place to bookmark us for this
1:17:36
conversation. Sure
1:17:38
conversation. One on sabbaticals, but moreover, all of the questions and queries and introspection that can surround the idea of a
1:17:50
sabbatical, I can read it. I'm just bringing it up right now. Here we go.
1:17:57
Lost by David Wagner.
1:18:02
Stand still.
1:18:05
The trees ahead and bushes beside you or not lost, wherever you are, is called here.
1:18:13
And you must treat it as a powerful stranger.
1:18:17
Must ask permission to know it and be known.
1:18:23
The forest breathes.
1:18:25
Listen.
1:18:27
It answers. I have made this place around you if you leave it.
1:18:35
You may come back again, saying here.
1:18:41
No, two trees are the same to Raven.
1:18:45
No, two branches or the same to Ren. If what a tree or a bush does is lost on you. You are surely lost.
1:18:56
If what a tree or a bush does is lost on you. You are surely lost. Stand still.
1:19:06
The forest knows where you are.
1:19:09
You must let it find you.
1:19:12
So good. So so good. I'm so glad you sent this to me. This, this is basically
1:19:19
The North Star.
1:19:23
For me.
1:19:25
Something along these lines for the last few years and it's funny how easy it is.
1:19:33
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.
1:19:43
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 one of the ways that I reach a Sabbath state.
1:19:57
So many things to talk about Jerry but
1:20:01
Great to see you, my friend and two, 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 top. Log / Jerry Kelowna on Twitter at Jerry Kelowna, Co Loa nna reboot at reboot.
1:20:30
Q on Twitter and the website reboot dot IO Cherry. Is there anything else you would like to say before we hit pause on this
1:20:39
conversation just said, 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'donohue, be excessively gentle on
1:20:51
yourself. Good advice for me. Also to hear and remember self. Thank you Jerry. I really appreciate you.
1:20:59
Thanks for having me.
1:21:00
Tim, it's always a delight to hang out with you be
1:21:03
well, you too, and everybody, listening will have show notes, links to everything at Tim top, log / 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 with you. Enjoy getting a short email for 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
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