The Tim Ferriss Show

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

Dec 14, 2021

In this conversation, Jerry Colonna, CEO of Reboot.io and seasoned executive coach, shares his insights on navigating boredom and anxiety, emphasizing the need for stillness in mental health. He discusses the transformative power of sabbaticals and the importance of embracing rest rather than succumbing to productivity pressures. Personal anecdotes highlight how disconnecting and enjoying nature can foster clarity and creativity. Colonna encourages self-reflection and compassion, making a case for leading with humanity and resilience in both personal and professional life.

01:27:06

Episode guests

Jerry Colonna

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Quick takeaways

Start with small steps and gradually build up to longer periods of time off when considering a sabbatical.

Prioritize rest and self-care during sabbaticals to recharge both mind and body.

Engage in activities that nourish the mind and soul during sabbaticals to gain new perspectives and find inspiration.

Deep dives

Start small and set expectations

When considering a sabbatical, it is important to start with small steps and set clear expectations. Begin by taking short breaks, such as weekends or evenings, away from work. Gradually build up to longer periods of time off. Communicate with colleagues and clients about your planned absence, establishing boundaries and managing expectations. By starting small and gradually increasing the length of your breaks, you can ease into the sabbatical mindset and make it more manageable for yourself and others.

How Have I Been Complicit in Creating the Conditions?

01:02

Understanding Hot Boredom and Cold Boredom

01:35

Are You EXhausted?

01:38

You're Four Billion Years Into The Past

01:37

Intro

4min

Exploring Leadership and Personal Growth with an Expert Coach

3min

The Power of Sabbaticals

23min

The Art of a Meaningful Sabbatical: Emphasizing Rest and Balance

4min

The Transformative Power of Rest

14min

Navigating Boredom and Anxiety

8min

Unplugging for Clarity

24min

Reflections on Self-Care and Growth

7min

Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year| Brought to you by Wealthfront automated investing, Headspace 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.

“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!

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.