Deep, Provocative Success Strategies From the "Yoda of Silicon Valley" | Jerry Colonna
Dan Harris speaks with executive coach Jerry Colonna (CEO & Co-founder of Reboot) about his "radical self-inquiry" method and the new book "Reunion." They discuss how understanding one's ancestral stories and complicity in global conditions can foster empathy and better leadership.
Deep Dive Analysis
15 Topic Outline
Introduction to Jerry Colonna and Radical Self-Inquiry
Defining Leadership Beyond Traditional Roles
Understanding Radical Self-Inquiry and Its Core Questions
The New Book's Thesis: Systemic Complicity and Global Responsibility
Personal Example of Benefiting from Systemic Conditions
The Moral Responsibility to Address Global Injustice
Navigating Virtue Signaling and Self-Righteousness
Exploring the Meaning of 'Reunion' and Ancestor Work
Connecting Ancestral Stories to Empathy and Compassion
The Universal Experience of the 'Longing to Belong'
The Self-Interested Case for Doing This Work
Understanding 'Do Your First Works Over'
The Impact of This Work on Leadership and Culture
Distinguishing Between Equality and Equity
Balancing Belonging with Accountability: Content and Container
7 Key Concepts
Radical Self-Inquiry
A process of deep psychological understanding combined with insights from dedicated practice like meditation. Its working definition is the compassionate stripping away of masks we wear, leaving no place to hide, because we tend to believe our personas and get into trouble.
Complicity (Personal)
Refers to being an accomplice in the conditions you say you don't want in your personal life. It's about contributing to problems without being solely responsible, often by upholding belief systems or behaviors learned early in life, and benefiting from the unwanted conditions.
Systemic Complicity
An extension of personal complicity, asking how one has benefited from conditions in the larger world that one says they don't want. It acknowledges that individuals are interconnected and have a responsibility to address problems beyond their immediate personal sphere, especially concerning systemic 'othering'.
Reunion
The pre-work of reuniting with the real, often dismembered or unremembered, stories of our ancestors. This process helps individuals understand their origins, how those influences shape who they are, and ultimately move towards reuniting with the 'rest of us' by fostering empathy and compassion.
Longing to Belong
A base, universal human experience. Understanding this fundamental desire in oneself and others allows for greater empathy, recognizing that even those with whom one disagrees share the same core needs for love, safety, and belonging.
Do Your First Works Over
A concept from James Baldwin, urging individuals, particularly those who identify as white, to go back and reconsider the structures and understandings they created to become adults. It means re-examining family stories and societal narratives not to get stuck in the past, but to move forward with greater clarity and integrity.
Content and Container
A framework for leadership where the 'container' refers to the practical, structural aspects of an organization (e.g., profitability, accountability, clear job standards). The 'content' refers to the meaning and purpose within that container, ensuring that the standards and expectations are equitable and foster belonging, rather than being driven by unconscious biases or unresolved fears.
9 Questions Answered
Jerry Colonna defines leadership broadly to include everyone, not just bosses. It means having the possibility of affecting those around you, and at a minimum, leading yourself, thereby challenging standard associations of leadership with power.
Radical self-inquiry is the process of compassionately stripping away the masks we wear to reveal our true selves, often through deep psychological understanding and practices like meditation, to avoid the trouble caused by believing our personas.
Complicit implies being an accomplice or contributing factor, like driving the getaway car, rather than being solely responsible for a situation. This distinction acknowledges that while we may not invent the 'subroutines' that define our character, we are complicit in their ongoing impact.
The new question is, 'How have I been complicit in and benefited from the conditions in the world that I say I don't want?' This expands the focus from personal complicity to a responsibility for systemic problems.
While awareness of these pitfalls is important, the fear of them should not prevent speaking out. Jerry suggests that doing the 'reunion' work and connecting issues to one's own real experiences can undercut performative allyship, making the engagement more genuine.
Reunion is the pre-work of reconnecting with the true, often untold or dismembered, stories of our ancestors. This process helps individuals understand their personal history and how it influences their present, fostering a deeper sense of self and connection to others.
By exploring the struggles, flaws, and marginalized experiences of one's ancestors, individuals can develop empathy for contemporary populations facing similar challenges. This personal connection makes it harder to ignore suffering and encourages a more compassionate view of the world.
Equality often refers to equal opportunity or numbers across demographics, while equity addresses disproportionate power dynamics. Equity focuses on who actually holds power and creating a leveling of opportunity for advancement, ensuring fair outcomes rather than just equal starting points.
Leaders must create a 'healthy container' (a sustainable business with accountability and high standards) and meaningful 'content' (purpose, belonging, and equitable standards). This means holding people to standards for excellent work, but also examining if those standards are influenced by unconscious bias or unresolved fears, ensuring the organization is both effective and humane.
40 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.
5 Key Quotes
How are you complicit in the conditions you say you don't want?
Jerry Colonna
Self-knowledge is always bad news.
Dan Harris
Better humans make better leaders.
Jerry Colonna
It's not enough to be an ally. You have to be a co-conspirator.
Emma Colonna (Jerry's daughter)
It is not your responsibility to complete your work, but neither are you at liberty to ignore the work.
Rabbi Tarfin (quoted by Jerry Colonna)