#767: Tim and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck

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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