How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

Overview

This episode features Jerry Colonna, a renowned executive coach and CEO of Reboot, who shares profound insights on leadership, self-inquiry, and the emotional complexities of success. The conversation explores how radical self-inquiry can transform leaders, the hidden costs of busyness, the pitfalls of a growth mindset, and the importance of legacy. Jerry also delves into how unresolved personal patterns impact teams and offers practical tools for self-awareness and resilience.

Notable Quotes

- How have I been complicit in creating the conditions I say I don’t want? – Jerry Colonna, on the power of self-inquiry to unlock personal agency.

- "You don’t have to be an a***** to be successful. And you don’t have to feel miserable just because you’re trying to create a career.* – **Jerry Colonna**, on redefining success.
- *When we become attached to the outcome, we inadvertently fuel our own suffering."* – Jerry Colonna, on the dangers of attachment in leadership and life.

🧠 Radical Self-Inquiry: The Key to Leadership

- Jerry’s foundational question, “How have I been complicit in creating the conditions I say I don’t want?”, is designed to evoke personal agency and uncover self-delusion.

- Radical self-inquiry involves asking unsettling questions like:

- What am I not saying that I need to say?

- What am I saying that’s not being heard?

- What’s being said that I’m not hearing?

- Journaling and meditation are tools to explore these questions, with the goal of cutting through self-deception and fostering conscious leadership.

📊 The Leadership Equation

- Jerry’s formula for leadership success: Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resilience.

- Practical skills address the how, but radical self-inquiry digs into the why, such as understanding one’s relationship with money, self-worth, or ambition.

- Shared experiences, like CEO bootcamps or peer circles, create safe spaces for leaders to share vulnerabilities and learn from others.

🚩 The Hidden Costs of Busyness and Attachment

- Busyness often masks deeper issues of self-worth. Leaders may feel validated only when they’re crushing it, perpetuating cycles of exhaustion.

- Jerry challenges leaders to detach their self-esteem from outcomes, suggesting they approach work as an art project driven by curiosity and joy rather than fear of failure.

- Attachment to success, material comforts, or external validation fuels suffering. Leaders are encouraged to focus on intrinsic motivations and values.

👥 Why Teams Fail: Unresolved Personal Patterns

- Dysfunctional teams often mirror unresolved personal issues of their leaders. For example, avoidance of conflict or over-control can stem from childhood dynamics.

- Leaders must do their own internal work to avoid projecting their insecurities onto their teams.

- Jerry emphasizes that high-functioning teams require leaders to tolerate mistakes and empower others to make decisions, even if they disagree.

🌱 Rethinking Growth Mindset and Legacy

- Jerry critiques the rigid application of growth mindset, warning against turning it into a fixed ideology. Instead, he advocates holding mindsets loosely and staying present to change.

- On legacy, Jerry reflects on living a meaningful life by contributing to a kinder, more empathetic world. He encourages leaders to ask, “What kind of ancestor do I want to be?”

- Legacy is less about ego and more about aligning actions with values, creating a ripple effect of positive impact.