Reflections on Legacy and Connection

Here is my brand-new conversation with Jerry Colonna, CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. Enjoy!

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[00:00] Start 

[08:40] “How have I been complicit in creating the conditions I say I don’t want?” and its misinterpretations.

[21:55] Recharging off the grid on sabbatical.

[24:41] Is a tired dog a happy dog?

[29:21] What are you hearing that’s not being said?

[33:14] Closing transgenerational, transpersonal, and intergenerational wounds.

[44:05] Focusing on the future when the past keeps pulling us back.

[52:18] Changes in challenges Reboot’s clients have faced over the past decade.

[55:34] Guilt vs. remorse and how to move from one to the other.

[1:01:40] Interpretations of legacy.

[1:13:17] Jerry’s parenting experience and advice.

[1:19:02] My thoughts on having children and grandchildren.

[1:24:54] “This Be the Verse” by Philip Larkin.

[1:26:08] Book recommendations and their impact on Jerry and his children.

[1:28:46] Novel truths.

[1:32:40] The importance of laughter and human connection in difficult times.

[1:35:45] Parting thoughts.

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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, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.

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