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Deep, Provocative Success Strategies From the "Yoda of Silicon Valley" | Jerry Colonna

Nov 8, 2023 59m 23s 40 insights
<p><em>New episodes come out every Monday, Wednesday, and Friday for free, with 1-week early access for Wondery+ subscribers.</em></p> <p><em>---</em></p> <p><br /></p> <p>How getting your sh*t together can make you a better leader in your own personal orbit. It can maybe even change the world.</p> <p><br /></p> <p>Jerry Colonna is a leading executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. He is a co-founder and CEO of <a href="https://www.reboot.io/" rel="noopener noreferrer" target="_blank">Reboot</a>, the executive coaching and leadership development company, host of the <a href="https://www.reboot.io/podcast/" rel="noopener noreferrer" target="_blank">Reboot Podcast</a>, and author of <a href="https://www.reboot.io/reunion-leadership-and-the-longing-to-belong/" rel="noopener noreferrer" target="_blank"><em>Reunion</em>: <em>Leadership and the Longing to Belong</em></a>, and <a href="https://www.reboot.io/reboot-leadership-and-the-art-of-growing-up/" rel="noopener noreferrer" target="_blank"><em>Reboot: Leadership and the Art of Growing Up</em></a>.</p> <p><br /></p> <p><strong>In this episode we talk about:</strong></p> <ul> <li>How to avoid the pitfalls of virtue signaling and self-righteousness</li> <li>The term, "reunion" and how it relates to the stories of our ancestors </li> <li>What he means by, "the longing to belong"</li> <li>How we can learn to "do our first works over"</li> <li>The difference between equality and equity </li> <li>And his framing of, "content and container" to help guide good leadership</li> </ul> <p><br /></p> <p><strong>Related Episodes:</strong></p> <ul> <li><a href="https://art19.com/shows/ten-percent-happier/episodes/682888b1-9e27-4d9b-9ab8-15c14b3dde5a" rel="noopener noreferrer" target="_blank"><strong>Jerry Colonna, 'CEO Whisperer' and Reboot.io Founder</strong></a></li> <li><a href="https://art19.com/shows/ten-percent-happier/episodes/fa83ee41-cc2e-4b9f-bf11-095a55a6ce8f" rel="noopener noreferrer" target="_blank"><strong>The Art of Growing Up, Jerry Colonna</strong></a></li> </ul> <p><br /></p> <p><strong>Full Shownotes:</strong> <a href="https://www.tenpercent.com/tph/podcast-episode/jerry-colonna" rel="noopener noreferrer" target="_blank">https://www.tenpercent.com/tph/podcast-episode/jerry-colonna</a></p>
Actionable Insights

1. Radical Self-Inquiry Question

Ask yourself, “How am I complicit in the conditions you say I don’t want?” to examine if you are contributing to the problems you complain about, rather than victim blaming.

2. Honest Self-Assessment

Ask yourself, “How are you, really?” and pause to honestly assess your internal state without pretense, spinning, or telling yourself what you want to hear. This is an emblematic act of self-inquiry.

3. Understand Complicity Nuance

When asking “How am I complicit?”, understand that complicity means being an accomplice, not solely responsible, acknowledging that foundational beliefs and “subroutines” were often given to you, not invented by you. This distinction helps avoid misinterpreting the question as victim-blaming.

4. Examine Benefits of Unwanted Conditions

When using the “conditions I say I don’t want” question, examine the underlying benefits you might be receiving from the very behaviors or conditions you complain about. This helps uncover unconscious motivations.

5. Cultivate Curiosity for Self-Understanding

Cultivate curiosity to understand your internal structures and motivations, which is essential for personal growth and becoming a better human and leader.

6. Meditate & Observe Throughout Day

Practice meditation as an act of inquiry, noticing thoughts and feelings (like shame or guilt) without attachment or looking away. Extend this practice throughout your day to maintain honest self-awareness.

7. Daily Journaling for Self-Understanding

Use journaling for about 20 minutes daily to notice internal states, reflect on past feelings, and understand recurring patterns. This practice helps create self-understanding and curiosity about your experiences.

8. Observe Desires Without Judgment

Acknowledge and observe impulses like greed or desire without judgment, understanding them as natural parts of the human repertoire or the organism’s attempt to protect itself.

9. Avoid Denying Impulses

Avoid denying or pretending that certain impulses (like greed) are not present, as denial gives them power and leads to suffering for yourself and others.

10. Cultivate Compassion from Own Suffering

Cultivate compassion by acknowledging and becoming comfortable with your own suffering and your family’s messy history. This “tenderizing” process allows you to view others with greater empathy.

11. Alleviate Suffering Interdependently

Understand that alleviating your own suffering contributes to alleviating others’ suffering, and vice versa, recognizing the interconnectedness of human experience.

12. Work for Happiness & Contentment

Engage in self-inquiry and reunion work, as it will lead to greater happiness and contentment in your life.

13. Engage in Ancestral Reunion Work

Engage in “reunion” work by exploring the real, often uncomfortable, stories of your ancestors and the dismembered parts of yourself. This pre-work is essential for systemic belonging and self-understanding.

14. Understand Ancestral Influence

Understand your ancestral origins and how they influence your current identity and behaviors, as this self-knowledge is crucial for personal and collective growth.

15. Imagine Ancestral Experiences

If direct ancestral research is not possible, use your imagination to consider the experiences of your ancestors, such as potential queer members or those who experienced “othering” or mental health issues.

16. Acknowledge Painful Family Truths

Engage in reunion work by acknowledging dismembered or painful truths in your family history, even if they are abhorrent, to reunite connections and understand their lasting impact.

17. Reconsider Ancestral Motivations

When examining difficult ancestral actions (e.g., criminal behavior), ask “why?” and consider the conditions they were leaving or the benefits they were seeking (like belonging or safety) to gain clarity and understanding.

18. Remember Ancestral Struggles

Do not forget the ambiguous status or struggles of your ancestors, as there is a moral responsibility to remember your lineage’s journey towards “whiteness” or acceptance.

19. Connect Ancestral & Current Struggles

Use active imagination and research to connect your ancestors’ struggles (e.g., immigration, poverty) with contemporary issues, like the experiences of refugees at the border, to foster deeper understanding and empathy.

20. Empathy Through Future Projection

To cultivate empathy, imagine the future experiences of your children or loved ones if their identity doesn’t fit societal norms, and consider the world you want them to inhabit.

21. Cultivate Empathy from Ancestral Flaws

By understanding your family history includes flawed, conflicted, or marginalized individuals, you can cultivate empathy for others currently struggling, making mistakes, or facing persecution.

22. Empathize with Universal Longings

When encountering someone expressing feelings of unfairness or injustice, recognize that, just like you, they are longing for love, safety, and belonging. This perspective fosters empathy and understanding.

23. Inquire: To Whom Do I Belong?

Ask yourself, “Who’s am I? To whom do I belong?” to reconnect with your true story and lineage, which helps answer the universal longing to belong.

24. Acknowledge Systemic Barriers

Review your family’s “messiness and grit” to understand historical struggles, which helps counter the mindset of “why can’t you do it like we did?” and recognize systemic barriers for others.

25. “Do Your First Works Over”

“Do your first works over” by going back to reconsider foundational beliefs and understandings, especially those related to societal structures, to move forward with greater clarity and avoid being stuck in the past.

26. Global Complicity & Benefit Inquiry

Ask yourself, “How have I been complicit in and benefited from the conditions in the world that I say I don’t want?” to take responsibility for addressing larger world problems beyond personal issues.

27. Identify Sacrifices for World Change

Ask yourself, “What am I willing to give up that I love to see the changes I actually want to see in the world?” to identify personal sacrifices for systemic change.

28. Leverage Credibility to Speak Out

Use your earned credibility and trust to speak up, speak out, and raise difficult questions about societal issues, even if it means leaning into uncomfortable spaces and risking personal comfort or status.

29. Reframe Speaking Responsibility

When questioning your right to speak on difficult social issues, reframe it to “What right do I have not to speak about these issues?” to emphasize your responsibility, especially if you know where the problem lies.

30. Don’t Let Fear Stop Speaking

Do not let the fear of virtue signaling or being perceived as self-righteous prevent you from speaking up about important issues.

31. Be a Co-Conspirator, Not Just Ally

Move beyond being merely an ally to becoming a “co-conspirator” in social justice efforts, implying a deeper, more active, and potentially riskier engagement.

32. Act Genuinely with Power/Privilege

Engage in deep self-inquiry and ancestral work to move beyond virtue signaling, using your power and privilege to genuinely make a difference in the world’s current struggles.

33. Don’t Ignore Necessary Work

Understand that while you are not responsible for completing all the work (e.g., creating a perfectly equitable culture), you are also not at liberty to ignore the work that needs to be done.

34. Strive for Positive Impact

Adopt a mindset of trying to make a positive impact, even if failure is possible, so that future generations can look back and see that you made an effort.

35. Broaden Your Leadership Definition

Recognize that leadership applies to everyone, not just bosses, as it means being able to affect those around you or at least lead yourself. This broadens your sphere of influence and responsibility.

36. Address Disproportionate Power for Equity

When striving for equity, focus on addressing disproportionate power dynamics within organizations and actively work to create equitable opportunities for advancement for all.

37. Create a Healthy Business Container

As a leader, create a “healthy container” by ensuring the business is physically sound and sustainable, and by holding people accountable to high standards and providing conditions for excellent work.

38. Examine Leadership Content & Biases

Reflect on the “content” of your leadership by examining the origins of your behavioral standards and expectations, identifying unconscious biases, and questioning if unresolved personal fears (e.g., about money) are unduly influencing your priorities.

39. Integrate Profit & Ethical Leadership

Recognize that profitability and ethical treatment of people, or being a good leader without being an “asshole,” are mutually supportive objectives, not mutually exclusive.

40. Read Baldwin’s “Price of the Ticket”

Read James Baldwin’s essay “The Price of the Ticket” to reflect on the “price of whiteness” as a disconnection from ancestral memory and the transformation of identity for safety.