Digest

This episode of the Tim Ferriss Show features Jerry Colona, CEO and co-founder of reboot.io, an executive coaching and leadership development firm. The conversation delves into various aspects of personal growth and leadership, including the concept of complicity, the difference between guilt and remorse, and the importance of finding a balance between past and future focus. Tim and Jerry explore the question of how we might be complicit in creating the conditions we say we don't want, emphasizing the distinction between complicity and responsibility. They discuss the struggle with creating space and taking breaks, highlighting the restorative power of physical movement and hardship. The conversation also touches upon the importance of self-reflection and asking powerful questions to prevent self-deception. Tim and Jerry share their personal experiences with navigating trauma and forgiveness, emphasizing the role of humor, acceptance, and genuine care in this process. Jerry discusses his company, reboot.io, and the unique challenges clients are facing in the current world, including global tensions and the after-effects of the pandemic. They explore the difference between guilt and remorse, highlighting how remorse can lead to learning and growth, while guilt can keep us stuck in a loop of negative self-talk. The episode concludes with a discussion about legacy and parenting, with Jerry emphasizing the importance of being real and honest in order to leave a positive impact. He shares his parenting experiences and the books that have impacted him and his children.

Outlines

00:00:00

Introduction and Guest Introduction

Tim Ferriss introduces the podcast and his guest, Jerry Colona, a CEO and co-founder of reboot.io, an executive coaching and leadership development firm. Jerry is also a former operator with experience in private equity and early-stage investments.

00:00:29

Jerry Colona's Background and Expertise

Tim highlights Jerry's diverse background, including his roles as a partner at JP Morgan Partners, founder of Flatiron Partners, and editor-in-chief of Information Week magazine. Jerry has also authored several books, including \"Reboot\" and \"Reunion.\"

00:01:12

Podcast Recap and Conversation Overview

Tim mentions that Jerry has been on the podcast twice before and recaps some of his favorite aspects of those conversations. He also previews the topics they will cover in this episode, including Jerry's toolkit and the questions he uses with himself and clients.

00:01:39

Recording Location and Encouragement to Move

Tim shares that he is recording the podcast outdoors in nature and encourages listeners to move while listening. He emphasizes that audio is a secondary activity and suggests walking or listening while moving.

00:02:49

Advertisement: The League Dating App

This segment is an advertisement for The League dating app. Tim shares his personal experience using the app and highlights its features, including its focus on smart and verified users, multi-city dating, and interest-based search.

00:06:34

Advertisement: Eight Sleep Pod Cover

This segment is an advertisement for Eight Sleep's Pod Cover, a sleep technology that automatically cools or warms each side of the bed. Tim discusses the features of the Pod Pro Ultra, including its cooling, heating, and elevation capabilities.

00:08:22

Complicity and Misinterpretations

Tim asks Jerry about a question he often revisits, \"How have I been complicit in creating the conditions I say I don't want?\" He explores the misinterpretations of this question, particularly the confusion between complicity and responsibility.

00:14:56

Exploring Complicity in Personal Life

Tim and Jerry delve into the concept of complicity by examining Tim's own desire for less busyness and how he might be complicit in creating the conditions that lead to it. They discuss the fear of empty space and the potential for negative narratives to dominate thoughts.

00:18:39

The Struggle with Creating Space and Taking Breaks

Tim shares his personal struggle with taking breaks and creating space in his life, despite the advice from friends and his own desire for it. He acknowledges the risk of returning to negative narratives and seeks Jerry's guidance on finding a balance.

00:24:41

Physical Movement and Restorative Experiences

Tim and Jerry discuss the restorative power of physical movement and hardship, particularly for Tim who finds it helpful in reminding him of his simple needs. Jerry shares his belief that 95% of the time, physical fixes are more effective than mental ones.

00:29:21

Powerful Questions for Self-Reflection

Tim and Jerry revisit the powerful questions Jerry's therapist taught him: \"What am I not saying that needs to be said?\" \"What am I saying that's not being heard?\" \"What's being said that I'm not hearing?\" They discuss the importance of these questions in preventing self-deception and bypassing difficult truths.

00:33:10

Additional Questions for Self-Reflection and Circumventing Bullshitting

Tim shares additional questions he has found helpful in circumventing self-deception, including \"No, really, how are you doing?\" and asking people if they want their kids to feel the same way they do. He also discusses the importance of distinguishing between \"doing the work\" and \"picking on yourself.\""

00:36:27

Navigating Trauma and Forgiveness

Tim and Jerry discuss the importance of humor, forgiveness, and genuine care in navigating trauma. Jerry shares his personal journey of reuniting with his father and forgiving him and his ancestors, highlighting the role of laughter and acceptance in this process.

00:44:05

Past Focus vs. Future Focus: Finding the Right Blend

Tim explores the different approaches to dealing with the past, from a forward-focused perspective that emphasizes moving on to a more introspective approach that involves metabolizing past experiences. He asks Jerry how to help someone find the right balance.

00:46:42

Acknowledging the Past and Moving Forward

Jerry emphasizes the importance of acknowledging the past and addressing ignored trauma, but also highlights the need to move forward. He uses Carl Jung's quote, \"I am not what has happened to me. I am what I choose to become,\" to illustrate this point.

00:52:13

Reboot.io: Executive Coaching and Leadership Development

Tim transitions to discussing Jerry's company, reboot.io, and asks about the types of challenges clients are facing in the current world. Jerry acknowledges the unique expressions of these challenges, including global tensions and the after-effects of the pandemic.

00:55:50

Guilt vs. Remorse: The Importance of Learning and Growth

Tim and Jerry discuss the difference between guilt and remorse, with guilt being self-focused and remorse being about the other person. They explore how remorse can lead to learning and growth, while guilt can keep us stuck in a loop of negative self-talk.

01:01:19

Legacy and Circles of Impact

Tim and Jerry discuss the concept of legacy and how Jerry is thinking about it. Jerry identifies three circles of impact: himself, his children and descendants, and the world. He emphasizes the importance of being real and honest in order to leave a positive impact.

01:13:13

Parenting: What Did Jerry Get Right?

Tim asks Jerry about his parenting experiences and what he believes he did right, particularly in light of his son's desire to spend time with him. Jerry attributes this to his focus on giving his children words and listening to them.

01:22:33

The Next Big Chapter: Family and Kids

Tim shares his own thoughts about starting a family and the potential challenges and joys it brings. He acknowledges the importance of being conscious of the games we play in life and the stakes involved.

01:26:09

Books That Have Impacted Jerry and His Children

Tim asks Jerry about books that have impacted him and his children. Jerry mentions \"The Wisdom of Insecurity\" by Alan Watts, \"Call It Sleep\" by Henry Roth, and the \"Library of America\" series by Wendell Berry.

01:32:41

Closing Thoughts and Encouragement to Laugh

Jerry emphasizes the importance of laughter in a challenging world and encourages listeners to find joy and connection. He also reminds listeners to be kind to themselves and others.

01:36:51

Advertisement: Five Bullet Friday Newsletter

This segment is an advertisement for Tim's free newsletter, Five Bullet Friday. Tim describes the newsletter as a short and fun email that shares cool things he has found or discovered each week.

01:37:55

Advertisement: Eight Sleep Pod Cover

This segment is a repeat of the advertisement for Eight Sleep's Pod Cover.

01:39:44

Advertisement: The League Dating App

This segment is a repeat of the advertisement for The League dating app.

Keywords

Q&A

• What is the difference between complicity and responsibility, and why is it important to understand this distinction?

  Complicity implies being involved in a wrongdoing, even if not directly responsible, while responsibility focuses on being the cause of an action. Understanding this distinction helps us avoid taking on unnecessary guilt and focus on our actual role in creating situations.

• How can we move from guilt to remorse, and what are the benefits of doing so?

  By shifting our focus from self-blame to the impact of our actions on others, we can move from guilt to remorse. This allows us to learn from our mistakes, make amends, and grow as individuals.

• What are some ways to distinguish between \"doing the work\" and \"picking on yourself\"?

  \"Doing the work\" involves confronting and addressing negative patterns with a focus on growth and healing, while \"picking on yourself\" involves dwelling on past mistakes and self-criticism without a clear path forward. Humor, forgiveness, and genuine care can help us navigate this distinction.

• How can we find the right balance between past focus and future focus?

  Acknowledging the past and addressing unresolved issues is crucial, but it's equally important to move forward. We can use the past as a source of learning and growth to shape our future, rather than being trapped by it.

• What are some of the unique challenges people are facing in the current world, and how are these challenges impacting leadership and executive coaching?

  Global tensions, the after-effects of the pandemic, and the constant barrage of negative news are creating unique challenges for individuals and organizations. Executive coaching is becoming increasingly important in helping leaders navigate these complexities and develop resilience.

• What are some practical ways to help someone who is stuck in a loop of negative self-talk and guilt?

  By asking questions that challenge their self-perception and help them decouple their sense of worthiness from their actions, we can help them move towards a more balanced perspective. Encouraging them to learn from their mistakes and focus on growth can also be beneficial.

• What are some key principles for effective parenting, and how can we create a positive and supportive environment for our children?

  Giving children words, modeling healthy communication, and listening to them are essential for building strong relationships. It's also important to forgive ourselves for mistakes and learn from them, creating a space for growth and connection.

Show Notes