How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)
Jerry Colonna, co-founder & CEO of Reboot, discusses radical self-inquiry, the dangers of a fixed "growth mindset," and how leaders' unresolved personal issues often cause team failures. He shares an equation for cultivating great leaders and resilience.
Deep Dive Analysis
16 Topic Outline
Introduction to Jerry Colonna's Core Question
The Equation for Great Leadership and Resilience
The 'Big Lie' of Success and Happiness
Consciousness as a Hack for Self-Delusion
Overcoming Fear of Self-Inquiry's Consequences
The Price of Unsorted Childhood Baggage
Key Questions for Radical Self-Inquiry
The Power of Shared Experiences and Community
Understanding the Trap of Busyness and Attachment
The Importance of Intentions and Unconditional Self-Worth
Legacy, Meaning, and Purpose in Life
Using Writing for Self-Discovery
Navigating the Unsettling Impact of AI
The Pitfalls of a Fixed 'Growth Mindset'
How Leaders' Unresolved Issues Affect Teams
The Moral Responsibility of Leaders for Self-Examination
8 Key Concepts
Complicit vs. Responsible
Being 'complicit' means being involved in something negative, like driving a getaway car, but not necessarily being directly 'responsible' for the primary action, like sticking up a bank. This distinction helps individuals acknowledge their role in creating unwanted conditions without immediately assigning full blame.
Radical Self-Inquiry
This is a process of asking tough, often unsettling questions about oneself to cut through delusions and uncover deeper motivations. It aims to raise one's level of consciousness, allowing individuals to be in the driver's seat of their lives rather than being driven by learned behaviors or unconscious patterns.
The Equation for Great Leadership
Jerry Colonna's equation is: practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resiliency. The ultimate purpose of this framework is to help individuals grow up and become effective leaders and adults without succumbing to misery or self-destruction in the process.
Spiritual Bypassing
This refers to the act of using spiritual or self-help practices (like meditation, psychedelics, or positive affirmations) to avoid confronting unresolved emotional issues or discomfort. It's a way of 'blasting over Band-Aids' rather than tending to the parts of oneself that need genuine attention.
Unsorted Baggage of Childhood
This concept refers to the unresolved emotional issues, anxieties, and learned behaviors developed during childhood. If this 'baggage' is not sorted out, individuals will eventually 'pay the price,' often manifesting as depression, self-sabotage, or repeating dysfunctional patterns in adulthood.
Attachment (Buddhist concept)
In a Buddhist context, attachment means becoming overly invested in outcomes, material possessions, or external validation. This attachment inadvertently fuels suffering because when desired outcomes are not met or possessions are threatened, it creates anxiety and discomfort, eroding one's sense of 'okayness.'
Growth Mindset (problematic aspect)
While generally helpful, a 'growth mindset' can become problematic if held too rigidly, turning into a 'fixed mindset.' This happens when individuals become attached to the 'proper' way of doing things or to the idea of continuous growth, leading to suffering when life inevitably brings change or challenges those assumptions.
Unconscious Patterns in Groups
Teams, like families, often unconsciously repeat dysfunctional patterns stemming from the unresolved issues of individual members, particularly those in positions of power. These patterns can lead to blame, lack of decision-making, and overall team dysfunction if not brought to conscious awareness through self-inquiry.
9 Questions Answered
Jerry Colonna's key question is: 'How have I been complicit in creating the conditions I say I don't want?' This question aims to evoke personal agency and reveal self-delusion, rather than assigning blame for life's difficulties.
The equation for great leadership is: practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resiliency. Its purpose is to help individuals grow up and lead effectively without feeling miserable in the process.
Teams most often fail not due to a lack of talent or strategy, but because of the unresolved emotional 'baggage' or unconscious patterns from individual members' childhoods, which manifest as group dysfunction.
Constant busyness and the pursuit of growth can be a coping mechanism to quiet an internal voice that questions one's self-worth. This creates an attachment to external achievements, rather than valuing oneself intrinsically.
While a growth mindset is beneficial, it can become problematic if held too rigidly, transforming into a fixed mindset. This leads to attachment to specific ways of doing things, causing suffering when circumstances change or challenges arise.
Considering one's legacy helps define purpose, eases personal suffering, and enables individuals to be more present and contribute to creating the kind of world they wish to see for future generations.
AI tools with memory, like ChatGPT or Claude, can act as writing and thinking partners. They can analyze personal data like journal entries or meeting transcripts to reflect back patterns, highlight blind spots, and generate further powerful questions for self-inquiry.
Key questions include: 'What am I not saying that I need to say?', 'What am I saying that's not being heard?', and 'What's being said that I'm not hearing?' These questions are designed to be startling and reveal deeper truths about oneself.
If childhood baggage remains unsorted, individuals will eventually 'pay the price' later in life, often through depression, self-sabotaging success, or repeating dysfunctional patterns, as these unresolved issues do not simply disappear.
12 Actionable Insights
1. Embrace Radical Self-Inquiry
Regularly ask, “How have I been complicit in creating the conditions I say I don’t want?” to evoke your own agency and cut through self-delusion, rather than blaming external factors.
2. Cultivate Leadership & Resilience
Develop enhanced leadership and greater resilience by combining practical skills, radical self-inquiry, and shared experiences, which helps you grow without feeling overwhelmed or miserable.
3. Ask Powerful Self-Inquiry Questions
Regularly ask yourself: “What am I not saying that I need to say?”, “What am I saying that’s not being heard?”, and “What’s being said that I’m not hearing?” to uncover hidden truths and foster personal growth.
4. Confront Your Unsorted Baggage
Address discomfort and unresolved personal issues now, as ignoring your “unsorted baggage” will inevitably lead to a higher price in future suffering, depression, or self-sabotage.
5. Detatch Self-Worth from Outcomes
Recognize that your value as a human being is unshakable, independent of success or failure, to reduce suffering caused by attachment to external achievements and the need to quiet self-doubt.
6. Hold Mindsets Loosely
Approach concepts like a “growth mindset” with flexibility, avoiding the trap of rigid adherence, as fixing on one “proper” way can lead to attachment and therefore suffering.
7. Leaders: Do Your Internal Work
If you hold power in a team, commit to radical self-inquiry and resolve personal issues, as your unresolved “demons” will otherwise manifest as dysfunction within the group.
8. Focus on Intrinsic Purpose
Engage in work and projects for the enjoyment of the challenge and the intrinsic satisfaction of creation, rather than solely to quiet self-doubt or achieve external validation.
9. Create Shared Experience Spaces
Seek or create environments (like circles or trusted groups) where you can authentically share truths and vulnerabilities without judgment or the need for “fixing,” fostering connection and reducing self-delusion.
10. Leverage AI for Self-Reflection
Utilize AI tools (like ChatGPT or Claude with memory) as a “writing and thinking partner” by uploading journal entries or meeting transcripts to gain new perspectives and generate further self-inquiry questions.
11. Examine Your Life
Embrace the responsibility to examine your own life and “shit” through self-inquiry, particularly if your role involves leading or impacting other people, to avoid unconsciously repeating dysfunctional patterns.
12. Identify Benefits of Dysfunction
If you’re on a dysfunctional team with less power, ask yourself how you might be complicit or benefiting from the dysfunction to understand your role and learn from the experience.
7 Key Quotes
How have I been complicit in creating the conditions I say I don't want?
Jerry Colonna
You don't have to be an asshole to be successful.
19-year-old kid (recounted by Jerry Colonna)
The unsorted baggage of our childhood... at some point, we're going to pay the price of not sorting that baggage. And the price, more often than not, is in tears.
Bruce Springsteen (recounted by Jerry Colonna)
You know you're in the radical self-inquiry zone when the questions take your breath away.
Jerry Colonna
When we become attached to the outcome, we inadvertently fuel our own suffering.
Jerry Colonna
Until you make the unconscious conscious, it will direct your life and you will call it fate.
Carl Jung (recounted by Jerry Colonna)
If you choose to live an unexamined life, please don't take a job that involves other people.
Parker Palmer (recounted by Jerry Colonna)