#767: Jerry Colonna — 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! 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 Android Eight 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-sponsors Sign up for Tim’s email newsletter ( 5-Bullet Friday ) at tim.blog/friday . For transcripts of episodes, go to tim.blog/transcripts . Discover Tim’s books: tim.blog/books . Follow Tim: Twitter : twitter.com/tferriss Instagram : instagram.com/timferriss YouTube : youtube.com/timferriss Facebook : facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss 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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .