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

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Dec 14, 2021

Guest

Jerry Colonna

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

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INSIGHT

Origin of Sabbaticals

Jerry Colonna models his sabbaticals after his therapist's vacation schedule.
He realized he needed extended time off to avoid depletion from his work.

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ADVICE

Sabbatical Mistakes

Avoid creating rigid rules for sabbaticals, which can lead to self-criticism.
Set expectations with an away message that encourages others to consider similar breaks.

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ANECDOTE

Email Management

Jerry Colonna checks emails during sabbatical, despite initially aiming to disconnect completely.
He prioritizes responding to genuine crises from clients.

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Exploring Leadership and Personal Growth with an Expert Coach

04:09 • 3min

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The Power of Sabbaticals

07:01 • 23min

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The Art of a Meaningful Sabbatical: Emphasizing Rest and Balance

30:00 • 4min

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The Transformative Power of Rest

34:16 • 14min

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Navigating Boredom and Anxiety

47:54 • 8min

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Unplugging for Clarity

55:41 • 24min

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Reflections on Self-Care and Growth

01:19:43 • 7min

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#2054

• Mentioned in 21 episodes

Reboot

Leadership and the Art of Growing Up

Jerry Colonna

In 'Reboot,' Jerry Colonna shares his approach to leadership development through radical self-inquiry. The book helps leaders identify and address the emotional baggage and psychological habits that have both driven their success and hindered their relationships and well-being. Colonna draws on his experiences as a venture capitalist and executive coach, blending Buddhism, Jungian therapy, and entrepreneurial insights to guide leaders in finding meaning, building healthy interpersonal bonds, and becoming more compassionate and bold leaders. The book emphasizes the importance of self-awareness, mindfulness, honesty, and self-critique in transforming both personal and professional lives.

#1817

• Mentioned in 24 episodes

Vagabonding

An Uncommon Guide to the Art of Long-Term World Travel

Rolf Potts

In 'Vagabonding', Rolf Potts provides a comprehensive handbook for long-term world travel. The book is not just about travel but an outlook on life, encouraging readers to use the prosperity and possibilities of the information age to increase personal options rather than possessions. It covers practical advice on financing travel, determining destinations, adjusting to life on the road, handling travel adversity, and re-assimilating back into ordinary life. Potts emphasizes the importance of an independent spirit, simplicity, and a friendly interest in people, places, and things, making the reader an explorer in the truest sense of the word.

#33900

• Mentioned in 2 episodes

To Bless the Space Between Us

A Book of Blessings

John O'Donohue

This book by John O'Donohue provides a series of blessings that address different aspects of life, from birth and coming of age to love, marriage, and death. The blessings are meant to offer spiritual comfort, guidance, and reflection, helping readers navigate the complexities and joys of life.

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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