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!This episode is brought to you by:The League curated dating app for busy, high-performing people: https://click.theleague.com/qmhm/timferriss; available on iOS and AndroidEight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating: https://eightsleep.com/tim (save $350 on the Pod 4 Ultra)LinkedIn Jobs recruitment platform with 1B+ users: https://linkedin.com/tim (post your job for free)*[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.*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at