Tim Ferriss

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

Artist's rendering of Jerry Colonna.
Illustration via 99designs

“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-development.mystagingwebsite.com/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.

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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

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. Whatever the situation, Headspace can help you feel better. Overwhelmed? Headspace has a 3-minute SOS meditation for you. Need some help falling asleep? Headspace has wind-down sessions their members swear by. Go to Headspace.com/Tim for a FREE one-month trial with access to Headspace’s full library of meditations.


This episode is brought to you by WealthfrontWealthfront is a financial services platform that offers services to help you save and invest your money. Right now, your cash can earn 3.30% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s 8 times more interest than a typical savings account at a bank, according to FDIC.gov as of 1/22/2026 (Wealthfront’s 3.30% APY vs. 0.39% average savings rate). Right now, for a limited time, Wealthfront is offering new clients that use my sign-up link an additional 0.75% boost over the base rate for three months, meaning you can get up to 4.05% APY, limited to $150,000 in deposits. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started. 

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC (“WFB”), member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.30% Base APY on cash deposits is as of January 30, 2026, is representative, subject to change, and requires no minimum balance. The overall boosted rate is subject to change if the base rate decreases during the three-month promotional period. Tim Ferriss, who’s not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC, which creates an incentive that results in a conflict of interest. Tim expresses his own opinions and Wealthfront does not endorse, sponsor, or promote them. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value. See full disclosures here


This episode is brought to you by Eight Sleep. Temperature is one of the main causes of poor sleep, and heat is my personal nemesis. But a few years ago, I started using the Pod Cover, and it has transformed my sleep. Eight Sleep has launched their newest generation of the Pod: Pod 5 Ultra. It cools, it heats, and now it elevates, automatically. With the best temperature performance to date, Pod 5 Ultra ensures you and your partner stay cool in the heat and cozy warm in the cold. And now, listeners of The Tim Ferriss Show can get $350 off of the Pod 5 Ultra for a limited time! Click here to claim this deal and unlock your full potential through optimal sleep.

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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

Want to hear the last time Jerry was on the show? Listen to our first 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

SHOW NOTES

  • 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]

MORE JERRY COLONNA QUOTES FROM THE INTERVIEW

“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

PEOPLE MENTIONED

Subscribe
Notify of
guest

Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

6 Comments
Oldest
Newest Most Voted

Coyote

A card game by Tim Ferriss and Exploding Kittens

COYOTE is an addictive card game of hilarity, high-fives, and havoc! Learn it in minutes, and each game lasts around 10 minutes.

For ages 10 and up (though I’ve seen six-year olds play) and three or more players, think of it as group rock, paper, scissors with many surprise twists, including the ability to sabotage other players. Viral videos of COYOTE have been watched more than 250 million times, and it’s just getting started.

Unleash your trickster spirit with a game that’s simple to learn, hard to master, and delightfully different every time you play. May the wit and wiles be with you!

Keep exploring.