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

Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year| Brought to you by Wealthfront http://wealthfront.com/tim automated investing, Headspace http://headspace.com/tim easy-to-use app with guided meditations, and Eight Sleep’s Pod Pro Cover http://eightsleep.com/Tim sleeping solution for dynamic cooling and heating. More on all three below. “What benefit do I get from the conditions I say I don’t want?” — Jerry Colonna Jerry Colonna (@jerrycolonna https://twitter.com/jerrycolonna) is the CEO and co-founder of Reboot.io https://www.reboot.io/, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, and equanimity. Prior to his career as a coach, he was a partner with JPMorgan Partners (JPMP), the private equity arm of JPMorgan Chase. Previously, he led New York City-based Flatiron Partners, which he 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, was editor-in-chief of InformationWeek magazine. He is the author of Reboot: Leadership and the Art of Growing Up https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536/?tag=offsitoftimfe-20. Jerry lives in Boulder, Colorado. This is his second appearance on the podcast. His first can be found at tim.blog/jerrycolonna https://tim.blog/2019/06/11/jerry-colonna/. Please enjoy! This episode is brought to you by Eight Sleep http://eightsleep.com/Tim! Eight Sleep’s Pod Pro Cover http://eightsleep.com/Tim is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Pro Cover http://eightsleep.com/Tim to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature. And now, my dear listeners—that’s you—can get $250 off the Pod Pro Cover http://eightsleep.com/Tim. Simply go to EightSleep.com/Tim http://eightsleep.com/Tim or use code TIM at checkout. This episode is also brought to you by Headspace https://www.headspace.com/tim! Headspace is your daily dose of mindfulness in the form of guided meditations https://www.headspace.com/tim in an easy-to-use app. Whatever the situation, Headspace https://www.headspace.com/tim can help you feel better. Overwhelmed? Headspace has a 3-minute SOS meditation for you. Need some help falling asleep? Headspace https://www.headspace.com/tim has wind-down sessions their members swear by. And for parents, Headspace https://www.headspace.com/tim even has morning meditations you can do with your kids. Headspace’s approach to mindfulness can reduce stress, improve sleep, boost focus, and increase your overall sense of well-being. Go to Headspace.com/Tim https://www.headspace.com/tim for a FREE one-month trial with access to Headspace https://www.headspace.com/tim’s full library of meditations for every situation. This episode is also brought to you by Wealthfront http://wealthfront.com/Tim! Wealthfront http://wealthfront.com/Tim pioneered the automated investing movement, sometimes referred to as ‘robo-advising,’ and they currently oversee $20 billion of assets for their clients. It takes about three minutes to sign up, and then Wealthfront will build you a globally diversified portfolio of ETFs based on your risk appetite http://wealthfront.com/Tim and manage it for you at an incredibly low cost. Smart investing should not feel like a rollercoaster ride. Let the professionals do the work for you. Go to Wealthfront.com/Tim http://wealthfront.com/Tim and open a Wealthfront account today, and you’ll get your first $5,000 managed for free, for life http://wealthfront.com/Tim. Wealthfront http://wealthfront.com/Tim will automate your investments for the long term. Get started today at Wealthfront.com/Tim http://wealthfront.com/Tim. For show notes and past guests, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts http://tim.blog/transcripts. Discover Tim’s books: tim.blog/books http://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ YouTube: youtube.com/timferriss https://www.youtube.com/timferriss Past guests on The Tim Ferriss Show http://tim.blog/podcast include Jerry Seinfeld https://tim.blog/2020/12/08/jerry-seinfeld/, Hugh Jackman https://tim.blog/2020/06/26/hugh-jackman/, Dr. Jane Goodall https://tim.blog/2020/04/16/jane-goodall/, LeBron James https://tim.blog/2018/11/27/lebron-james-mike-mancias/, Kevin Hart https://tim.blog/2020/05/20/kevin-hart/, Doris Kearns Goodwin https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/, Jamie Foxx https://tim.blog/2015/12/06/jamie-foxx/, Matthew McConaughey https://tim.blog/2020/10/19/matthew-mcconaughey/, Esther Perel https://tim.blog/2017/05/21/esther-perel/, Elizabeth Gilbert https://tim.blog/2020/05/08/elizabeth-gilbert/, Terry Crews https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/, Sia https://tim.blog/2020/08/12/sia/, Yuval Noah Harari https://tim.blog/2020/10/27/yuval-noah-harari/, Malcolm Gladwell https://tim.blog/2016/06/21/malcolm-gladwell/, Madeleine Albright https://tim.blog/2020/05/27/secretary-madeleine-albright/, Cheryl Strayed https://tim.blog/2017/03/30/cheryl-strayed/, Jim Collins https://tim.blog/2019/02/18/jim-collins/, Mary Karr, https://tim.blog/2020/11/11/mary-karr/ Maria Popova https://tim.blog/2014/10/21/brain-pickings/, Sam Harris https://tim.blog/2020/05/15/sam-harris-2/, Michael Phelps https://tim.blog/2021/01/21/michael-phelps-grant-hackett/, Bob Iger https://tim.blog/2020/01/16/bob-iger/, Edward Norton https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/, Arnold Schwarzenegger https://tim.blog/2015/02/02/arnold-schwarzenegger/, Neil Strauss https://tim.blog/2014/06/24/neil-strauss/, Ken Burns https://tim.blog/2019/09/12/ken-burns/, Maria Sharapova https://tim.blog/2017/08/26/maria-sharapova/, Marc Andreessen https://tim.blog/2016/05/29/marc-andreessen/, Neil Gaiman https://tim.blog/2019/03/28/neil-gaiman/, Neil de Grasse Tyson https://tim.blog/2019/10/03/neil-degrasse-tyson/, Jocko Willink https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/, Daniel Ek https://tim.blog/2020/12/03/daniel-ek/, Kelly Slater https://tim.blog/2020/09/08/kelly-slater/, Dr. Peter Attia https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/, Seth Godin https://tim.blog/2016/02/10/seth-godin/, Howard Marks https://tim.blog/2018/09/25/howard-marks/, Dr. Brené Brown https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/, Eric Schmidt https://tim.blog/2019/04/09/eric-schmidt/, Michael Lewis https://tim.blog/2020/05/01/michael-lewis/, Joe Gebbia https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/, Michael Pollan https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/, Dr. Jordan Peterson https://tim.blog/2021/03/01/jordan-peterson/, Vince Vaughn https://tim.blog/2017/05/31/vince-vaughn/, Brian Koppelman https://tim.blog/2020/04/23/brian-koppelman/, Ramit Sethi https://tim.blog/2019/05/07/ramit-sethi/, Dax Shepard https://tim.blog/2020/11/18/dax-shepard/, Tony Robbins https://tim.blog/2014/10/15/money-master-the-game/, Jim Dethmer https://tim.blog/2020/05/18/jim-dethmer/, Dan Harris https://tim.blog/2020/11/19/dan-harris/, Ray Dalio https://tim.blog/2017/09/13/ray-dalio/, Naval Ravikant https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/, Vitalik Buterin https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/, Elizabeth Lesser https://tim.blog/2021/03/16/elizabeth-lesser/, Amanda Palmer https://tim.blog/2019/04/18/amanda-palmer-2/, Katie Haun https://tim.blog/2021/02/18/katie-haun/, Sir Richard Branson https://tim.blog/2017/10/09/richard-branson/, Chuck Palahniuk https://tim.blog/2020/09/02/chuck-palahniuk/, Arianna Huffington https://tim.blog/2017/10/18/arianna-huffington/, Reid Hoffman https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/, Bill Burr https://tim.blog/2017/09/17/bill-burr/, Whitney Cummings https://tim.blog/2015/06/26/whitney-cummings/, Rick Rubin https://tim.blog/2015/05/15/rick-rubin/, Dr. Vivek Murthy https://tim.blog/2020/03/26/vivek-murthy/, Darren Aronofsky https://tim.blog/2017/09/09/darren-aronofsky/, and many more. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  This episode is brought to you by Headspace. Headspace is your daily dose of mindfulness in the form of guided meditations in an easy to use app. Now, you might ask yourself, very reasonably, there are 2,000 plus apps for meditation. Why would I use Headspace? 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.

• 0:39Tim Ferriss?

  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, boost 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.

• 1:24Tim Ferriss?

  I think it's Puttacom, could be Puttycomb, 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/Tim. That's Headspace.com/Tim for a free one-month trial.

• 2:10Tim Ferriss?

  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. So check it out. Go to headspace.com/tim today.

• 2:32Tim Ferriss?

  This episode is brought to you by Eight Sleep. My God, am I in love with Eight Sleep. Good sleep is the ultimate game changer. More than 30% of Americans struggle with 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 nauseam. But now I am falling asleep in record time, faster than ever. Why? Because I'm using a simple device called the Pod Pro Cover by Eight Sleep. It's the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced,

• 3:13Tim Ferriss?

  but most user-friendly solution on the market. I polled all of you guys on social media about the best tools for sleep, enhancing sleep, and Eight Sleep was by far and away the crowd favorite. I mean, people were just raving fans of this. So I used it, and here we are. Add the Pod Pro Cover to your current mattress and start sleeping as cool as 55 degrees Fahrenheit or as hot as 110 degrees Fahrenheit. It also splits your bed in half, so your partner can choose a totally different temperature. My girlfriend runs hot all the time. She doesn't need cooling. She loves the heat, and we can have our own bespoke temperatures on either side, which is exactly what we're doing. Now, for me, and for many people, the result:

• 3:57Tim Ferriss?

  Eight Sleep users fall asleep up to 32% faster, reduce sleep interruptions by up to 40%, and get more restful sleep overall. I can personally attest to this because I track it in all sorts of ways. It's the total solution for enhanced recovery, so you can take on the next day feeling refreshed. And now, my dear listeners, that's you guys, you can get $250 off of the Pod Pro Cover. That's a lot. Simply go to eightsleep.com/tim or use code TIM. That's eight, all spelled out, E-I-G-H-T, sleep.com/tim, or use coupon code TIM, T-I-M. eightsleep.com/tim for $250 off your Pod Pro cover.

• 4:42Speaker 01

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 4:46Speaker 02

  Can I ask you a personal question?

• 4:48Speaker 03

  No, I would just say that I'm pretty tired.

• 4:52Speaker 02

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 5:05Tim Ferriss?

  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 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 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

• 5:46Tim Ferriss?

  on for reasons that will be clear shortly. For nearly 20 years, he has used the knowledge gained as an investor, one hell of an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, and equanimity. Prior to his career as a coach, he was a partner with JP Morgan Partners, the private equity arm of JP Morgan Chase. Previously, he led New York-based Flatiron Partners, which he co-founded in 1996 with partner Fred Wilson. Flatiron became one of the nation's most successful early-stage investment programs. Jerry's first leadership position at age 25, a young'un, a young whippersnapper, was editor-in-chief of Information Week

• 6:26Tim Ferriss?

  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/jerricolonna.

• 6:45Tim Ferriss?

  Again, one more time, C O L O N N A. You can find him on Twitter, as mentioned, at Jerry Colonna 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.

• 7:01Jerry Colonna?

  Thanks for having me, Tim. You know, it's a bizarre experience hearing your life played back at you like that. I'm sitting there listening and I'm going, damn, I'm old.

• 7:12Jerry Colonna?

  You're referencing something from 1996, and I know that's in my bio, so.

• 7:19Tim Ferriss?

  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 want to say, a month, six weeks ago, maybe, something like that. And we were covering a number of different things. But it quickly

• 8:04Tim Ferriss?

  came up that you had just finished a two month sabbatical. And then you've casually mentioned that you'd done that for how long roughly, would you say?

• 8:17Jerry Colonna?

  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.

• 8:27Tim Ferriss?

  Okay, so 10th two month sabbatical. And I wanted to hear all about this. I wanted to dig into this and thought it might be a great bridge and launchpad for discussing all sorts of things. So since we covered so much of your bio and background and trajectory, the ups and the downs, let's just jump right into it. Can you perhaps begin at the beginning with the first sabbatical that you took and how that came about?

• 9:01Jerry Colonna?

  It's like, and if we were a TV 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 17 years. And I came to coaching, on the one hand, very much having been trained and gone through methodologies that are known as coaching. But it would be dishonest, or not completely honest, if I didn't also say that I modeled myself after my psychoanalyst. And as every good New Yorker who was in therapy knows, August is when all the therapists go on vacation. And so

• 9:42Jerry Colonna?

  you don't want to be in New York in August, because not only does it stink to high heaven, it's also when all of our therapists are gone, right?

• 9:51Tim Ferriss?

  Home alone in New York City.

• 9:53Jerry Colonna?

  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.

• 10:08Tim Ferriss?

  Is, is this corn hand shucked? Sorry, continue.

• 10:12Jerry Colonna?

  Indeed.

• 10:16Tim Ferriss?

  Excellent, excellent movie. Continue, please.

• 10:19Jerry Colonna?

  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 emotionally present, more fully and emotionally present than most folks are in a given conversation. And I also found myself terribly depleted, terribly exhausted on a regular basis. And I remember talking to my therapist with the idea of at first taking four weeks off. And what I started to do, though, was I started to

• 11:01Jerry Colonna?

  realize that I needed longer than that. 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, it's a bit of a controversial statement, but.

• 11:17Jerry Colonna?

  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 2014 with my 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, 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.

• 12:01Jerry Colonna?

  I found myself being a better therapist. Oh, did I say that out loud? A better.

• 12:07Tim Ferriss?

  Brilliant slip there. More ways than one.

• 12:11Jerry Colonna?

  A much better coach, a much better coach because I was rested and I could be there more fully for my clients.

• 12:18Tim Ferriss?

  What did the very first sabbatical look like? Did you have any internal conflict or pushback?

• 12:28Jerry Colonna?

  Oh, yes.

• 12:29Tim Ferriss?

  It doesn't have to be the very first. It could be one of the first, but one that comes to mind.

• 12:33Jerry Colonna?

  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 you, 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, of course, Tim is kind of interested in this. So we can get to that. What, what, what prompted you?

• 13:17Jerry Colonna?

  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, just pushing forward, pushing forward.

• 13:42Jerry Colonna?

  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 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 of me that goes, oh, very good. That's perfect. That's exactly what we want to have happen. But it's challenging.

• 14:24Tim Ferriss?

  I want to touch upon something that you mentioned briefly for folks, and that is can I afford it in this question? Because on one hand, depending on your expenses, one could argue that a sabbatical is a very indulgent 1% activity, but you can also take a different perspective. And it makes me think of a book called Vagabonding by a now friend. After I read the book and gave it to many, many, many, many, many, many people, I later became friends with the author, Rolf Potts.

• 15:01Tim Ferriss?

  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 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. Iconic film, greed is good, etc. And the Charlie Sheen character at one point is asked by, I want to say his girlfriend or his

• 15:46Tim Ferriss?

  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 traveling, said, you could work as a toilet cleaner for six months and save enough to ride across China on a motorcycle for a year. Particularly if you put a pause on some of your other expenses. And I think about a lot of people over the pandemic, including family members of mine, who packed everything up or put it into storage, canceled their leases and ended up traveling around the country, trying different cities. And it cost a lot less than their previous fixed expenses.

• 16:31Tim Ferriss?

  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 mention.

• 16:50Jerry Colonna?

  Yeah, I think that's a really, really important conversation. We are two relatively 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 it's a two month sabbatical every year for 10 years, those are choices that are afforded us, sometimes by external forces, sometimes a combination of what we ourselves, the choices that we make, we choose to spend less money.

• 17:33Jerry Colonna?

  But I think what we're also talking about, Tim, is something really important, which is behind all of that, which is a mindset. And the mindset, I think, not to be too playful with my own work, the mindset is the mindset behind rebooting and resetting. Let's go back and think about that word sabbatical for a moment. 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.

• 18:15Jerry Colonna?

  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.

• 18:45Jerry Colonna?

  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. And that's a problem that not only affects them physically, it's a problem that affects them mentally. It's a problem that actually, I would argue, undermines their leadership capabilities and creates toxic environments. And so what we're really talking about in this way is this notion of, can I afford

• 19:24Jerry Colonna?

  myself a moment to pause, stand still, and think a little bit differently and see the world a little bit differently?

• 19:34Tim Ferriss?

  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...

• 19:45Tim Ferriss?

  We have a rare opportunity. We, I'm using the royal we. I mean, Tim Ferriss. It's a rare opportunity.

• 19:52Jerry Colonna?

  King Tim.

• 19:53Tim Ferriss?

  King Tim, who has deep pockets and short arms, so he gets his therapy for free on the podcast.

• 20:02Tim Ferriss?

  Would like to ask you tactically and practically, what you have learned about making sabbaticals work? What do you set up in advance? What are some of the mistakes you made early on? What are some of the things you've learned? Because we're going to get into much more of the deeper first principles philosophies, but I want to front load some tactical stuff to kind of lure people in as a honeypot. So, 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.

• 20:47Jerry Colonna?

  You raise a really good point, which is to think about it in advance. And I would argue that a corollary to that is to set expectations. And so a good example of this from my own life was that when my three co-founders and I set up Reboot in 2014, two of my co-founders had previously been clients of mine, so they were aware of this. But I said to them, whatever budget we model for this enterprise, if it cannot afford to have me not working, not bringing in revenue for two months a year, then I don't want to do it.

• 21:27Jerry Colonna?

  And so if you think about it, you think about me not as a coach, but as a CEO, stepping into the launch of a business. And from the beginning, we modeled in the notion of taking time off. Now, as soon as I said that, my co-founders were like, hey, I like that idea. I'd like to take December off. I'd like to take this time off. And so we built a financial model, presuming not two weeks vacation, but sabbatical time.

• 21:59Jerry Colonna?

  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 have this funny notion, especially in the tech community of unlimited paid time off, unlimited PTL. And studies have shown that the more unlimited is, the less time people take because there's

• 22:41Jerry Colonna?

  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, 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

• 23:22Jerry Colonna?

  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.

• 23:47Tim Ferriss?

  Jerry, may I double click and zoom in a little bit?

• 23:50Jerry Colonna?

  Sure.

• 23:51Tim Ferriss?

  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 to default behaviors and how you perhaps counteracted those when you were kicking the tires and first taking sabbaticals?

• 24:20Jerry Colonna?

  I wouldn't say that there was a mistake that I encountered as much, but there was a heck of a lot of backsliding. And there still can be a heck of a lot of backsliding. So I guess one mistake is I said to myself, I was going to be completely off the grid and not answer any email. And that's just not possible. I just don't do that. And so what I did early on 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 your rules, right? And you create all these structures around the rules and I'm

• 25:00Jerry Colonna?

  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 an away message, and I always try to do an away message that in some way or another inspires other people to think about these things. So I remember one away message I did on sabbatical where I talked about my plan to go to Italy for a couple of weeks. And I did that. And I said, you know, my plan is to eat more gelato than to read email. And so if you're actually getting an email from me, I have failed. And that tends to make people laugh. But what it does is it also helped me in managing expectations.

• 25:44Jerry Colonna?

  So a mistake, a lesson I learned was to not turn the sabbatical into another source of self criticism.

• 25:55Tim Ferriss?

  How did you decide to then handle, say, email? Because it's easy to get pulled into the vortex and time dilates and you realize four hours later, holy shit, I've been looking at my inbox for four hours and I'm supposed to be eating gelato.

• 26:12Jerry Colonna?

  Yeah, you know, it's so funny. When I was thinking about our conversation today, I was thinking about it yesterday. And if I remember correctly, in our first conversation, you also asked me about email. Like, how do you handle email, Jerry? Or some point in our life, you asked me this question. And I gave you the perplexing answer of, just don't respond. And you're like, no, that's in there.

• 26:36Tim Ferriss?

  We'll come back to that. It's, I have a slightly like Rashomon, perhaps slightly different remembrance, but we can, we can, we can dig into that.

• 26:46Jerry Colonna?

  To go back to your question for a moment, I think the way I handle email and that is I will scan it.

• 26:52Tim Ferriss?

  Yeah.

• 26:53Jerry Colonna?

  And I feel super liberated if I decide not to respond. Because I've already given them a response that says, I'm not going to respond. And yet there are times where it could be really important to respond. And so, for example, this, this past summer, I think I did probably six or seven sessions while I was on sabbatical.

• 27:18Tim Ferriss?

  When you say sessions, what do you mean?

• 27:20Jerry Colonna?

  A session is a coaching conversation.

• 27:24Jerry Colonna?

  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 and such and such afternoon kind of thing.

• 27:38Tim Ferriss?

  Boring process question. How did news get to you that that was a crisis and important to handle?

• 27:46Jerry Colonna?

  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 have anybody answering my notes and stuff like that. I need to have a direct relationship with people.

• 28:00Tim Ferriss?

  So does that mean that you're scanning each day?

• 28:03Jerry Colonna?

  Yeah.

• 28:03Tim Ferriss?

  As the spirit moves you?

• 28:06Jerry Colonna?

  I think you know that I have a fairly healthy morning ritual where I don't really, for the most part, check email.

• 28:14Tim Ferriss?

  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?

• 28:21Jerry Colonna?

  Yeah. So 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 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

• 29:05Jerry Colonna?

  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, Ally, or my children, they always get responded to, even if officially I'm off the grid.

• 29:25Tim Ferriss?

  Got it.

• 29:25Jerry Colonna?

  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.

• 29:34Tim Ferriss?

  When you look back at the sabbaticals you've taken, right, so nine or 10 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?

• 30:00Jerry Colonna?

  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 smores. 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

• 30:35Jerry Colonna?

  book. And I slept well. I ate well. And I rested well. And I exercised my mind with the new book. And I traveled. I saw a family that I hadn't seen in 18 months. I spent two weeks on the coast of California in a lovely beach house. And my kids each came to visit and cycled 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 it's resting both and taking care of both.

• 31:18Jerry Colonna?

  For sabbaticals that did not go so well, I would say the pattern is to load it up with expectations, like I'm going to finish a book, or I'm going to read 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. Rest.

• 31:53Jerry Colonna?

  Rest. The body needs rest. The mind and heart need rest. That's the simplest way I can put it for you.

• 32:07Tim Ferriss?

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• 32:50Tim Ferriss?

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• 33:38Tim Ferriss?

  Do you have, or could you tell us 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 sabbatical, but let's just say something, and what I'm trying to do here is to 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?

• 34:15Jerry Colonna?

  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 2001, when I was lying on the ground, the bottom of the Grand Canyon, which by the way,

• 34:56Jerry Colonna?

  if you really want to disconnect, go to the bottom of the Grand Canyon. You're four billion years into the past. It's an extraordinary experience. And I'm lying on the beach. There may or may not have been some alcohol involved. And I'm staring up at the sky. And someone lying next to me says, "Oh, shooting star." And I begin trying to stare at the shooting stars. And I'm looking, and I'm looking, and I'm looking, and it's driving me crazy because I can't see them. And then finally, someone says, "Stop looking for them." And I rest my eyes. And with peripheral vision, this is true fact, all of a sudden I can start catching the motion.

• 35:40Jerry Colonna?

  And that's an image I would give you for sabbatical. People who go into sabbatical with the plan to, A, I'm going to lose 10 pounds, B, I'm going to get into really good shape, C, I'm going to finish that book, typically after

• 35:59Jerry Colonna?

  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 in rest. Now, I know I'm swimming upstream. Everybody wants to be productive.

• 36:41Tim Ferriss?

  I could also just, if you don't mind me playing stand-in for the listener, I could also say, well, you spoke about this hot, cold boredom, and even if you don't say, I'm going to finish the book, the fact of the matter is you were writing, working on a book, and likely on some level, feeling productive. So if we removed that, would you have needed an alternate activity, which I don't make wrong, by the way, but one could say, hey, you're a writer, you're working on books, you're saying we don't need to be productive, but I bet you feel productive after a good day of writing. What if I'm not a writer? There may be people who would say something like that.

• 37:20Jerry Colonna?

  Sure. And I get that. When I felt good working on the new book this summer, it was when I let go of the production goals. Some writers like to say, you know, 1,000 words a day, 500 words a 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 due next summer.

• 38:06Jerry Colonna?

  And they were kind of a mess, as Andy 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 stopped 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.

• 38:44Tim Ferriss?

  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. Nonetheless, we're able to take trips.

• 39:25Tim Ferriss?

  We took our first trip post-COVID just a few months ago, and I was effectively offline for three weeks, which was wonderful. And I will take shorter trips and be typically completely in the wilderness or the jungle or somewhere with nothing, no electronics for a period of time. I do that generally at least once or twice a year. Nonetheless, what I have found for myself, and some people may resonate with this. Actually, I'm going to give a few examples of friends, and then I'll give my personal example. So there are friends who have been in zero-sum games for so long that that lenses become their default, right?

• 40:07Tim Ferriss?

  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 do think there are certain scenarios in which that's the case. However, let's say you ride that 100-foot wave. You have some wonderful exit, in the case of a founder. They think they will just be able to turn off that script. And I have seen close to zero examples of them being able to, right? It's very common. Or I have a friend, I shan't name, but very good friend. And we've known each other a very long time.

• 40:48Tim Ferriss?

  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 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. Or 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. Yes.

• 41:33Tim Ferriss?

  And I identified with that quite a bit. I said, you're right. I mean, it's a lot, it's reassuring in some perverse way to have an external object or circumstance you can point at and say, that explains why I have this really uncomfortable feeling inside. So I'm gonna park that for a second, because this is all a way of me sort of backing into my own personal experience. So when we last spoke, and I thought, hot damn, this is something we should talk about on the podcast. What I had realized for myself is not that I can't take time off, or that I can't ignore the inbox, or refuse to reply on the vast majority of things that come in.

• 42:20Tim Ferriss?

  What I simultaneously have realized is that over the last, say, 10 or 15 years, there has been a creep of complexity. So when you have dozens of different entities, LLCs and so on, when you have hundreds, or at least 100 different investments and funds and capital calls and this, that, and the other thing, and you've added people to your organization so you have more headcount, there is a certain amount of complexity that comes with that. So while there are a million emails I feel like I can safely ignore, there are certain

• 42:58Tim Ferriss?

  others from, whether it's a tax authority, or some registered agent, or an employee, that I do feel like I should keep track of, or there will ultimately be some consequences to ignoring those things. And so this is a very roundabout way of asking how you have seen people either reframe the complexities so that it has less of a fearful impact on them, or, and/or, reduce complexity

• 43:40Tim Ferriss?

  in a way that lessens this sort of internal drama that they experience going along with it.

• 43:48Jerry Colonna?

  I love the way you framed that question. And there are tips and tricks and hacks that you can do to reduce the complexity, but the complexity will creep back.

• 44:02Tim Ferriss?

  Right.

• 44:03Jerry Colonna?

  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 two.

• 44:15Tim Ferriss?

  Right.

• 44:16Jerry Colonna?

  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?"

• 44:31Tim Ferriss?

  I like that you just referred to yourself like the Hulk is the third person.

• 44:36Jerry Colonna?

  Hulk mod.

• 44:37Tim Ferriss?

  Yeah.

• 44:38Jerry Colonna?

  Hulk smash Jerry ask. Jerry ask question that caused tear.

• 44:46Tim Ferriss?

  How am I complicit in creating the conditions I say I don't want?

• 44:50Jerry Colonna?

  Right. And so I'm going to alter that just slightly. What benefit do I get from the conditions I say I don't want? What benefit do I get from the conditions I say I don't want? And so let's turn it back to the question. So you create these really complex structures and you probably spend an enormous amount of energy sorting them out, responding them, maybe even use auto responders, tax person go here kind of thing. So if you want to alter that behavior, you have to understand what the benefit is to you.

• 45:26Tim Ferriss?

  The payoff or the secondary payoff.

• 45:29Jerry Colonna?

  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 in multiple pies and doing all sorts of things. What does it do for you?

• 45:47Tim Ferriss?

  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.

• 46:03Tim Ferriss?

  And I would say that for much of my life, I had competitive athletics and other things that consumed in a very good way, I think, a lot of my focus and provided a lot of excitement. Just as important, excitement. And I haven't had that in a very long time after a shoulder reconstruction and then elbow surgery and twisted SI joint and all these things. I'm like, 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.

• 46:42Tim Ferriss?

  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. 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

• 47:24Tim Ferriss?

  or a preloading podcast that I can do A, B, and C elsewhere. But very often I would say the investing side in particular is related to excitement. I would say that's what I get from it. And the side effect of having lots of investments and lots of

• 47:48Tim Ferriss?

  things that come along with that is this complication, the complexity and the systems.

• 47:54Jerry Colonna?

  That makes sense to me. What's the opposite of excitement?

• 47:59Tim Ferriss?

  Opposite of excitement would be boredom, which is why I wrote down this hot and cold boredom for you that you mentioned earlier. I think it's boredom. I think it's, and I'm not, you know, I used to be more maybe optimistic about this. I 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're unwilling to feel? I think it was Tara Brach 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.

• 48:41Tim Ferriss?

  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.

• 49:15Jerry Colonna?

  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.

• 49:26Tim Ferriss?

  Thank you, Jerry.

• 49:27Jerry Colonna?

  You go there. So, we're gonna 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 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 face those things.

• 50:10Jerry Colonna?

  And God bless you, you've done a fantastic job of learning to deal with your own thoughts. So let's imagine, if you will, that the learned behavior was boredom, bad. Hulk, boredom, bad. Well, the learned behavior may just as equally have been the family saying, we don't want to actually be with these questions. We don't want to be alone with our thoughts collectively. Because when we're alone with our thoughts, bad things happen. So let's get busy.

• 50:45Tim Ferriss?

  Yep.

• 50:46Jerry Colonna?

  And let's make sure that we're competitive, and complicated, and busy with lots and lots of different things, so that we don't have to feel those things over here. To go back to Tara Brock, family systems can reject feelings, not just individuals.

• 51:09Tim Ferriss?

  Yeah.

• 51:11Jerry Colonna?

  It reminds me of, I remember sitting with a group of executives at a company and they asked me to just observe their executive team and I was watching and something came up, it happened once, it happened twice, it happened a 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. And sometimes we get really complicated and busy because we don't actually want to feel what those thoughts bring up. And there again

• 51:52Jerry Colonna?

  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 boredom.

• 52:03Tim Ferriss?

  Can you expand on hot boredom? And then I'm going to come back to what we're talking about. But could you just explain the difference between hot boredom and cold boredom, or the spectrum of boredom?

• 52:15Jerry Colonna?

  Hot boredom and cold boredom is really great framing to think about. We don't really do this so much anymore, but imagine you're online at the post office, or online at the DMV, and it's just an interminably long line, and you got to be someplace else. And there's nothing to distract you. And that discomfort, that's hot boredom. That's like, literally, my body starts to feel achy and all that stuff. But contrast it to cold boredom. And I know you've done meditation retreats. Imagine, not the first three or four days of meditation retreat, which often provokes hot boredom. What the hell am I doing here? I can't even

• 53:00Jerry Colonna?

  sleep, it's, but by the day four, day five, day seven, day 10, you're sitting there and literally, there's nothing dramatic going on in your mind. There's no drama.

• 53:16Jerry Colonna?

  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 needs cold boredom. It needs those days of simple, you know, my therapist calls it just simple stir in the oatmeal kind of morning. Here I am, do, do, just stir in the oatmeal. Ah, because that's a moment of rest from which we can then go about the rest of our time, the rest of our day.

• 53:59Tim Ferriss?

  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 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, in the wilderness. I threw everything I had at it and ultimately decided, sitting with this void for this

• 54:44Tim Ferriss?

  long is actually not good for my mental health. And still haven't prematurely committed to something huge just to 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 who, like it or not, is not going to

• 55:14Tim Ferriss?

  Get to a place of comfortable cold boredom before they burn out and you jointly decide or he or she decides they're going to take a sabbatical. So they have yet to become sort of comfortable stirring the oatmeal, but they're going to take a sabbatical. What advice do you give to that person?

• 55:33Jerry Colonna?

  Start small. Start with tiny steps.

• 55:37Tim Ferriss?

  Baby steps out of the office.

• 55:38Jerry Colonna?

  Baby steps, yeah. How about starting with a weekend? How about starting with one evening? You know, I mean, literally, you 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 10 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.

• 56:19Jerry Colonna?

  Because if you go to, as I did, you know, across the polar ice cap in Greenland, for some reason, you don't get a good cell signal. It's like, it's amazing. You are forced, or, you know, I went rafting the Fudalafu River in the Chilean Patagonian area, and there really isn't a good Wi-Fi signal. And it's beautiful. And so those small little steps, I have a client I just started with in September, and he's taking his first vacation, two weeks in Namibia. First vacation in 10 years. First vacation in 10 years. And it was only because his life partner recently sold her

• 57:02Jerry Colonna?

  business and that they have, they feel like they have the time. That's not healthy.

• 57:09Jerry Colonna?

  So, practical advice, start small. Start where you are. Start with a day. Our mutual friend Brad Feld was the first person I know who used the notion of digital Sabbath. 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.

• 57:39Tim Ferriss?

  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, a couple of weeks away from my normal routines, but I'm gonna stay here in so-called civilization. My girlfriend, meanwhile, is going to continue with her normal routines. Most of my friends, at least here, are not gonna be

• 58:24Tim Ferriss?

  coincidentally taking a 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.

• 59:08Tim Ferriss?

  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 not good for me.

• 59:21Jerry Colonna?

  Well, what I also hear you doing was then deciding that you were one of those people.

• 59:27Tim Ferriss?

  Ah, it's not so, I mean, there is that.

• 59:31Jerry Colonna?

  I mean, you know, you're not unemployed if you're not working.

• 59:33Tim Ferriss?

  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, this is an extreme example, but just to kind of play out the point, if somebody actually were sitting inside an insane asylum, I know that's probably not the politically correct term these days, but like one flew over, Cuckoo's next, 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 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 it's not limited to Austin.

• 1:00:18Tim Ferriss?

  I mean, if you want it times 10, go to San Francisco. So I don't automatically assume I'm one of those people, but my 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 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

• 1:00:58Tim Ferriss?

  laptop somewhere without people around them who are in a similar situation, that it can be agonizing how lonesome that feels. So that's a big mouthful. I don't know if you have any thoughts?

• 1:01:13Jerry Colonna?

  I'm glad you circled back to the word lonely, because you went lonely, unemployed, insane, and I zipped in on insane. But I think the lonely is-

• 1:01:24Tim Ferriss?

  We don't have to rule out that I'm insane. I mean, leave that on the table.

• 1:01:29Jerry Colonna?

  But I think the lonely is really important, and, you know.

• 1:01:35Jerry Colonna?

  What you're helping me see is that my lens is very much affected by the fact that on the spectrum, I tilt toward its introversion. So I don't quite have the same reaction to the word lonely or alone as say, my daughter, who is very much an extrovert. And during the lockdowns, she would really yearn to be outside with other folks.

• 1:02:05Tim Ferriss?

  May I interject for one second, Jerry? 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

• 1:02:47Tim Ferriss?

  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.

• 1:03:09Jerry Colonna?

  I appreciate that distinction. I think that that's really helpful. And what I'm feeling my way to, and I can relate to this, is there are certain mental states that are reminiscent of the past states, you know, as we've talked about before, I actually attempted suicide at 18.

• 1:03:30Jerry Colonna?

  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 bed still to this day. Because if I don't, it starts to bring up those feelings that I might end up back emotionally in that place. And so what I'm hearing you say is, the fear isn't about being alone so much, it's about feeling lonely.

• 1:04:06Tim Ferriss?

  Yeah.

• 1:04:06Jerry Colonna?

  Because that's the association back to the depression.

• 1:04:08Tim Ferriss?

  That's right.

• 1:04:09Jerry Colonna?

  And the suicidal impulses. And that's a really good observation about yourself. And so I applaud you being able to say to yourself, okay, as an alcoholic might say, I'm going to stay out of a bar. You're going to stay out of those situations that can be triggering for you and bring you back to some of those states.

• 1:04:32Jerry Colonna?

  And I like where we are right now, because what we're seeing is that perhaps there's a little fear of cold boredom, because it might remind one of feeling lonely.

• 1:04:47Tim Ferriss?

  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 in the world. And then hiking at altitude and feeling like I'm just getting punched in the lungs for like 12 hours, taking a nap on a mountain top and.

• 1:05:34Tim Ferriss?

  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 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 cold. 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 side note. Sleeping on a rock.

• 1:06:18Tim Ferriss?

  Side note, I, can I tell a funny story just for, just for 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, a San Francisco resident at that point, going up to high elevation. And I asked about bears because they were all eating candy bars and all this garbage inside the tent. And I said, shouldn't we be concerned about bears? And they said, ah, no. And one of them said, they're just black bears. They're more likely to lick you to death than hurt you. Relax. And I was like, okay. And sort of shamed into silence.

• 1:07:01Tim Ferriss?

  So we go to bed and we're sleeping all around the perimeter of this large tent. And I wake up and it's close to a full moon. I wake up and the tent's about four inches from the side of my face. And there's literally a huge nose pressed to the tent. Four inches from my fucking face. And it's this gigantic bear. I'm not kidding, first night, first night. And I don't know any of these guys, except for like one, one and a half, let's call it. And so I think to myself, more likely to lick me to death. If I wake these guys up on the first night, I will just be, I will be shamed to death for the rest of this trip. And so I don't say anything.

• 1:07:46Tim Ferriss?

  I'm in full. Pray mode, every, every single corner of my psyche is 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 and the same guy who told me it would look me to death is like, Jesus fucking Christ, man, you gotta let us know that kind of shit.

• 1:08:13Tim Ferriss?

  And nonetheless, after that trip felt like I had taken a six month vacation.

• 1:08:18Jerry Colonna?

  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.

• 1:08:43Tim Ferriss?

  Yeah.

• 1:08:44Jerry Colonna?

  You know, being in the land nourishes you. Being physically in your body nourishes you. That is a sabbatical, dude.

• 1:08:52Tim Ferriss?

  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.

• 1:09:17Jerry Colonna?

  I totally get that. And, you know, changing physical location is really important. I just put a reservation down on a Sprinter van, you know, from Winnebago, the Revel. I can't wait to be able to climb into that. And I live in a 40 acre farm with a woman I love and three horses and an 18 year old cat, coyotes running across my, the pastures and hawks and eagles and stuff.

• 1:09:48Jerry Colonna?

  But sometimes you you need to change the venue. Sometimes you need to change it up. And I get that. I paused 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? 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 retreats. I find it enormously helpful to be able to periodically, even within the envelope of my normal days, to be able to cut the chatter.

• 1:10:32Jerry Colonna?

  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.

• 1:11:16Jerry Colonna?

  I think ultimately, take the sabbatical with you. Take that mindset with you and live it into your days.

• 1:11:23Tim Ferriss?

  Are there any resources? Thank you, Jerry, that resonates with me. And I meditated this morning, 20 minutes, nothing fancy, just TM, repeating some sound in my head so that my monkey mind has something to do, climb up and down the pole for 20 minutes, that's it. And it's so that I can remember for the rest of the day, ideally, what it feels like not to rush. That's it for me, largely. Are there any resources that you might suggest to folks who are? Considering the possibility of a sabbatical, I remember there was a book that I read, I want

• 1:12:04Tim Ferriss?

  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 a story, a poem, a book, a movie, doesn't matter. Are there any resources that you might recommend?

• 1:12:31Jerry Colonna?

  One of my little mental tricks that I do when I, when I do a public talk is I often open up the talk simply by asking people, how are you? And that's the question, by the way, that typically gets people crying. And then I throw up a couple of different words, excited, scared, and almost always I land on the word exhausted. And everybody just resonates with that. Like, your, your, your shoulders just dropped as soon as I said the word exhausted. Because 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 going to recall the

• 1:13:13Jerry Colonna?

  fullness of it, but John O'Donoghue, 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 clear 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

• 1:13:53Jerry Colonna?

  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 stories from the Old Testament, and on the seventh day, even God himself rested. Easy, gentle. There's another line from that poem in which O'Donoghue says, "Be excessively gentle with yourself." So I don't have 10 tips and tricks to make your sabbatical as productive as possible.

• 1:14:38Jerry Colonna?

  You know me, that's not the way my brain is working.

• 1:14:40Tim Ferriss?

  You saw the draft of my next blog post, damn you.

• 1:14:47Jerry Colonna?

  Tools for Titans for Sabbatical.

• 1:14:49Tim Ferriss?

  Sabbatical Edition, Volume One.

• 1:14:53Jerry Colonna?

  But I think that there is a really profound wisdom in O'Donoghue's poem, which is, "Easy, easy. This is about a time to take a breath." And I love the image of you hiking and camping and being out in the land with your friends. That's what you're doing. Rest is not, you know, zonking out on the couch to Netflix's latest binge-watching stream, Squid Game, something, right? Rest is turning the brain off. It's getting the heart rate down. It's taking care of yourself. And to me, that's what Sabbatical is all about.

• 1:15:38Tim Ferriss?

  Yeah, I suppose it could take different forms, right? Like, in my case, at high elevation, I'm actually really physically taxing myself, but it's a, for me, it's a pure exhaustion. It's not a paper-cut exhaustion. It is a pure focus,

• 1:15:59Jerry Colonna?

  Yes.

• 1:16:01Tim Ferriss?

  holistic, deliberate exhaustion. And that's a straightening through fire of sorts.

• 1:16:12Jerry Colonna?

  Yeah, listen, I'm all for the physical exhaustion, as long as the mental turn-off is happening, as long as the mental, the chatter, you called it the monkey mind, as long as the chatter is quieted.

• 1:16:25Tim Ferriss?

  Yeah.

• 1:16:25Jerry Colonna?

  Because I'll bet you, when you guys are hiking and, you know, you're going from one camping spot to another.

• 1:16:34Jerry Colonna?

  Your minds are quieted.

• 1:16:36Tim Ferriss?

  Oh, yeah, yeah.

• 1:16:37Jerry Colonna?

  Even as your body is physically taxed.

• 1:16:40Tim Ferriss?

  Yeah, yeah, it's a different experience. Well, Jerry, we're coming up on time for both of us for different reasons.

• 1:16:52Tim Ferriss?

  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 is Lost by David Wagner. Is that correct?

• 1:17:11Jerry Colonna?

  That is correct.

• 1:17:12Tim Ferriss?

  W A G O N E R. And I'm happy to read, but if you have it, since you sent it to me, I feel like it makes sense for you to read this because I think it encapsulates a lot of what we're talking about and could be a good place to bookmark us for this conversation.

• 1:17:37Jerry Colonna?

  Sure.

• 1:17:38Tim Ferriss?

  Conversation one on sabbaticals, but moreover, all of the questions and queries and introspection that can surround the idea of a sabbatical.

• 1:17:50Jerry Colonna?

  I can read it. I'm just bringing it up right now. Here we go. Lost by David Wagner.

• 1:18:02Jerry Colonna?

  Stand still.

• 1:18:05Jerry Colonna?

  The trees ahead and bushes beside you are not lost. Wherever you are is called here.

• 1:18:13Jerry Colonna?

  And you must treat it as a powerful stranger.

• 1:18:17Jerry Colonna?

  Must ask permission to know it and be known.

• 1:18:23Jerry Colonna?

  The forest breathes. Listen. It answers. I have made this place around you. If you leave it, you may come back again saying here.

• 1:18:41Jerry Colonna?

  No two trees are the same to raven. No two branches are the same to wren. If what a tree or a bush does is lost on you, you are surely lost. If what a tree or a bush does is lost on you, you are surely lost. Stand still. The forest knows where you are. You must let it find you.

• 1:19:12Tim Ferriss?

  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 spend time recognizing it again.

• 1:19:42Jerry Colonna?

  Well, I appreciate you giving me the opportunity to read it, and I would not have missed that opportunity because I think, as you can tell, reading poetry is one of the ways that I reach a Sabbath state.

• 1:19:56Tim Ferriss?

  So many things to talk about, Jerry, but great to see you, my friend.

• 1:20:02Jerry Colonna?

  You too.

• 1:20:04Tim Ferriss?

  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/jerricolonna, on Twitter, at Jerry Colonna, C-O-L-O-N-N-A, Reboot, at Reboot HQ on Twitter, and the website, reboot.io. Jerry, is there anything else you would like to say before we hit pause on this conversation?

• 1:20:39Jerry Colonna?

  Just that I hope that folks take a little bit of time off.

• 1:20:44Tim Ferriss?

  Yeah.

• 1:20:44Jerry Colonna?

  And take a little bit of rest and to remember the words from John O'Donoghue.

• 1:20:50Jerry Colonna?

  Be excessively gentle on yourself.

• 1:20:53Tim Ferriss?

  Good advice for me also to hear and remember. So, thank you, Jerry. I really appreciate you.

• 1:20:59Jerry Colonna?

  Thanks for having me on, Tim. It's always a delight to hang out with you. Be well.

• 1:21:03Tim Ferriss?

  You too. And to everybody listening, we'll have show notes, links to everything at tim.blog/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 kind of like my diary of cool things.

• 1:21:45Tim Ferriss?

  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/friday, type that into your browser, tim.blog/friday, drop in your email, and you'll get the very next one. Thanks for listening. This episode is brought to you by Eight Sleep. My God, am I in love with Eight Sleep.

• 1:22:28Tim Ferriss?

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• 1:23:09Tim Ferriss?

  social media about best tools for sleep, enhancing sleep, and Eight Sleep was by far and away the crowd favorite. And people were just raving fans of this. So, I used it, and here we are. Add the Pod Pro cover to your current mattress and start sleeping as cool as 55 degrees Fahrenheit or as hot as 110 degrees Fahrenheit. It also splits your bed in half, so your partner can choose a totally different temperature. My girlfriend runs hot all the time. She doesn't need cooling. She loves the heat. And we can have our own bespoke temperatures on either side, which is exactly what we're doing. Now, for me, and for many people, the result: Eight Sleep users fall asleep up to 32% faster, reduce

• 1:23:51Tim Ferriss?

  sleep interruptions by up to 40%, and get more restful sleep overall. I can personally attest to this because I track it in all sorts of ways. It's the total solution for enhanced recovery, so you can take on the next day feeling refreshed. And now, my dear listeners, that's you guys, you can get $250 off of the Pod Pro cover. That's a lot. Simply go to eightsleep.com/tim or use code TIM. That's eight all spelled out, E-I-G-H-T, sleep.com/tim, or use coupon code TIM, T-I-M. eightsleep.com/tim for $250 off your Pod Pro cover.

• 1:24:32Tim Ferriss?

  This episode is brought to you by Headspace. Headspace is your daily dose of mindfulness in the form of guided meditations in an easy-to-use app. Now, you might ask yourself, very reasonably, there are 2,000-plus apps for meditation. Why would I use Headspace? 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. Headspace can change your life.

• 1:25:11Tim Ferriss?

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• 1:25:50Tim Ferriss?

  I just went through one of the basics today with the co-founder, Andy. It's put a come, could be putty come, I'm not sure. But a 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.

• 1:26:35Tim Ferriss?

  Go to Headspace.com/Tim. That's Headspace.com/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. So check it out. Go to Headspace.com/Tim today.