#109
Radical Self-inquiry with Jerry Colonna
Former American venture capitalist and once named a “Prince of New York” by New York Magazine, Jerry Colonna faced a profound depression that compelled him to confront his inner demons through what he calls “radical self-inquiry.” This transformative process led him to Buddhism and leadership coaching. Now a certified professional coach and author, Jerry leverages his diverse experiences to help clients design more conscious lives and make meaningful changes to their careers, enhancing both performance and satisfaction.
He has been recognised on Upside magazine’s list of the 100 Most Influential People of the New Economy and Forbes’ list of the best VCs in the U.S. Jerry is the co-founder and CEO of Reboot, an executive coaching and leadership development company, and hosts the Reboot Podcast. His best-selling books, 2019’s Reboot and last year’s Reunion, delve into the process of radical self-inquiry and how we can become better leaders by becoming better people.
Summary
04:24 What personal challenges pushed Jerry towards this transformation journey that he is on today?
- Compares transformative experiences to being struck by an asteroid, which catalyses change.
- A college professor offered him an unexpected scholarship, leading to a career turning point.
- Life doesn’t unfold in a straight line and transitions should be embraced.
- Realising life’s non-linear nature is key, and being open to unexpected changes (like asteroid strikes) creates opportunities for growth.
10:47 How much free will do we have?
- Jerry reflects on his Catholic upbringing and its complex relationship with free will and preordination.
- In his Buddhist practice, the focus isn’t on free will but on karma and reincarnation.
- He doesn’t dwell on free will; instead, he prioritises being kind, thoughtful, and good in daily life.
- He values self-awareness and doing good at the moment rather than striving for a specific outcome.
13:13 How deep examination helps leaders overcome challenges and improve their decisions
- Better humans make better leaders, highlighting the importance of self-awareness and confronting difficult truths.
- “Radical self-inquiry” involves examining how one’s behaviour perpetuates limiting beliefs.
- Benefits include recognising one’s role in creating undesirable situations.
- This process requires questioning deeply ingrained habits and beliefs, often inherited from family.
- Radical self-inquiry helps leaders grow in consciousness and better direct their lives and organisations.
26:12 Is it always worthwhile to engage in radical self-inquiry, given the pain and difficulty of examining deep-seated issues?
- The balance between handling pain and the necessity of facing difficult truths.
- He advises against unpacking everything at once; instead, approach it like gradually organising a messy closet.
- Practical steps include identifying impactful issues, understanding their benefits, and assessing whether those benefits are still necessary.
33:11 How can someone recognise their own limiting beliefs or social conditioning that may hinder personal growth and freedom, and what early steps can they take to free themselves from these “collars”?
- Jerry uses the metaphor of a dog tied to a stick to illustrate limiting beliefs.
- Recognising the “collar” involves bringing awareness to unconscious behaviours.
- Practical steps include journaling, which externalises and examines thoughts and feelings.
- Working with a coach or therapist helps process and reframe thoughts, empowering individuals to gain agency over their reactions.
38:30 The components of the formula ‘practical skills + radical self-inquiry + peer experiences’ and how they interact to create effective leaders
- Autocratic leadership persists due to fear and the desire for a powerful figure.
- To counter this, leaders must build resilience and well-being through self-awareness and peer support.
- The formula includes practical skills to manage fear, radical self-inquiry to recognise internal capacities, and peer experiences to share vulnerabilities.
- These elements reinforce healthier, more humane organisations by reducing fear-based leadership and empowering individuals.
43:34 Advice for leaders trying to balance vulnerability with maintaining authority?
- Jerry challenges the dichotomy between empathy and authority.
- He stresses that being clear, direct, and speaking with agency is both empathetic and kind.
- Research by experts like Brené Brown shows that clear, direct communication fosters authenticity and kindness.
- Leaders should embrace discomfort while maintaining clarity and kindness simultaneously.
Links mentioned:
‘Leadership and the Art of Growing Up’ by Jerry Colonna
‘Reunion: Leadership and the Longing to Belong’ by Jerry Colonna
Connect with Jerry Colana on LinkedIn
