Radical Self-Inquiry and the Path to Better Leadership

Jerry Colonna

CEO, Reboot · Executive Coach

FEATURED EPISODE

The Question

The Complicity Question

"How have I been complicit in creating the conditions I say I don't want?"

Complicit ≠ responsible. You're the accomplice, not the bank robber.
Evokes your own agency and visibility
Example: "I say I don't want to be busy, but I'm unnerved if my agenda isn't jam-packed"
Breaks the delusion between what you claim to want and what you're actually creating

The power moveThis question cuts through self-deception. It's the foundation of radical self-inquiry.

The Equation

How to Cultivate Great Leaders

"The whole point is: how do we grow up and become the leaders we were born to be without feeling like crap?"

Practical skills: How to do the job, live, execute
Radical self-inquiry: Why do you really want this? What serves you about busyness? What's the childhood source?
Shared experiences: Coaching, community, vulnerability with others who get it
The goal: Not just success, but resilience — so you don't sabotage yourself or burn out

The deeper truthSuccess without resilience is fragile. You'll achieve the goal and still feel empty, or sabotage it.

The Questions

Four Questions for Radical Self-Inquiry

What am I not saying that I need to say? The thing you're swallowing, whether in a relationship or as a leader.
What am I saying that's not being heard? Your message, your truth, your feedback — no one's listening.
What's being said that I'm not hearing? The feedback you're defending against, the signal you're ignoring.
How have I been complicit in creating the conditions I say I don't want? The meta-question that reveals your agency.

Journaling Practice

Don't just journal—journal with intention. Use these questions as prompts. Pause. Ask yourself. Write what shows up, even if it's terrifying.

The Unsorted Baggage

Bruce Springsteen spent 25 years in psychoanalysis sorting his childhood baggage. If you don't sort it, you'll pay the price in tears later, not now.

The Root

Why Leaders Fail (The Real Reason)

You're chasing "success" because your childhood taught you that you're not enough
The attachment to outcomes (money, status, couch, house) fuels suffering, not freedom
When we ignore discomfort, we don't make it go away—we band-aid it (work obsession, substance abuse, spiritual bypassing)
The real work: decoupling your self-worth from your achievements

The flipYou are somebody regardless of what you do. Your spouse loves you if the company fails. Your kids need you to be whole, not successful.

Counterintuitive

Jerry's Contrarian Takes on Leadership

✗ Success = happiness INSTEAD → ✓Success without resilience and self-knowledge = sabotage. The big lie we're socialized with since childhood.

✗ Ignore your discomfort and it goes away INSTEAD → ✓Unaddressed suffering increases. You band-aid it (work, substances, ayahuasca) instead of sorting the baggage.

✗ Being busy = being important INSTEAD → ✓Being busy is a learned behavior from childhood anxiety. You can unlearn it and feel OK without jam-packed calendars.

✗ You have to be an asshole to succeed INSTEAD → ✓You don't have to be an asshole. And you don't have to feel miserable to build something great. The 19-year-old got it.