Home > NewsRelease > Jerry Colonna — How to Take a Two-Month Sabbatical Every Year (#554)
Jerry Colonna — How to Take a Two-Month Sabbatical Every Year (#554)
Tim Ferriss - Productivity, Digital Lifestyles and Entrepreneurship Tim Ferriss - Productivity, Digital Lifestyles and Entrepreneurship
For Immediate Release:
Dateline: San Francisco, CA
Tuesday, December 14, 2021

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“What benefit do I get from the conditions I say I don’t want?”

— Jerry Colonna

Jerry Colonna (@jerrycolonna) 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. 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.

Jerry lives in Boulder, Colorado. This is his second appearance on the podcast. His first can be found at tim.blog/jerrycolonna.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

Brought to you by Wealthfront automated investingHeadspace easy-to-use app with guided meditations, and Eight Sleep’s Pod Pro Cover sleeping solution for dynamic cooling and heating. More on all three below.

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

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear the last time Jerry was on the show? Listen to our conversation in which we discuss being complicit in creating the conditions in life we don’t really want, nagging self-doubt, finding time for self-discovery, confronting the difficulty most of us have with saying “no,” acknowledging compassion from a distance, journaling, guilt versus remorse, and much more.

#373: Jerry Colonna — The Coach with the Spider Tattoo
  • Connect with Jerry Colonna:

Reboot.io | Twitter


  • When there’s not an unchecked global pandemic going on, Jerry has been taking an annual two-month sabbatical for the past 10 years. He tells us about the first one that kicked off this tradition, how it came about, and the inner thoughts that initially tried to talk him out of it. [07:35]
  • A counter to the “Can I afford it?” question someone of any means might ask themself when considering the form their own sabbatical could take. [14:25]
  • What makes a sabbatical work in preparation and practice? [19:34]
  • What kind of rookie sabbatical mistakes did Jerry make early on, and what did they teach him? [23:47]
  • How does Jerry handle email on a sabbatical? [25:56]
  • What happens if there’s a crisis that requires Jerry’s attention when he’s on sabbatical — and how would someone communicate this to him [27:38]
  • Thinking back on past sabbaticals, what factors contribute to emerging fully charged versus least recharged? [29:33]
  • Shooting stars, terrible first drafts, and sabbatical-related epiphanies about productivity. [33:37]
  • How might we reframe and reduce the complexities that keep us from carving out time for sabbaticals so we don’t suffer consequences for neglecting them? [38:44]
  • Explorations of complex structures, DNA versus subroutines, and hot and cold boredom. [45:46]
  • Advice Jerry would have for someone considering a sabbatical who is unsure how to begin untangling themselves from the complexities that keep them busy. [53:58]
  • Thoughts on feelings of loneliness or alienation that a sabbatical might conjure up, and how changing the surroundings and/or company you keep can make all the difference. [57:39]
  • Resources Jerry might suggest to listeners who are considering the possibility of a sabbatical. [1:11:51]
  • Lost by David Wagner. [1:16:44]
  • Parting thoughts. [1:19:57]


“What benefit do I get from the conditions I say I don’t want?”
— Jerry Colonna

“I was at my most productive when I stopped trying to be productive.”
— Jerry Colonna

“Sabbatical is a time of thinking differently, of considering things differently.”
— Jerry Colonna

“For many of our friends who are in the startup land, the thought of taking a weekend off is as terrifying as my thought of taking two months off. And that’s a problem. That’s a problem that not only affects them physically, it’s a problem that affects them mentally. It’s a problem that actually, I would argue, undermines their leadership capabilities and creates toxic environments.”
— Jerry Colonna

“By law, you have to build into the structure of the business: sick time, vacation time, parental leave, all sorts of policies. And then periodically, something awful happens, and we say, ‘Okay. Let’s build in some mental health time.’ But it’s always after some sort of horrible event.”
— Jerry Colonna

“A lesson I learned was to not turn the sabbatical into another source of self-criticism.”
— Jerry Colonna

“The number one rule in sabbatical is Sabbath. Rest. Rest. The body needs rest; the mind and heart need rest. That’s the simplest way I can put it for you.”
— Jerry Colonna


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 700 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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Name: Tim Ferriss
Title: Author, Princeton University Guest Lecturer
Group: Random House/Crown Publishing
Dateline: San Francisco, CA United States
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