Radical Self-Inquiry and the Real Equation for Great Leadership: Lessons from Jerry Colonna¶

What does it really take to be a great leader—and a fulfilled human being? In a world obsessed with success, productivity, and constant growth, executive coach Jerry Colonna offers a radically different equation: practical skills plus radical self-inquiry plus shared experiences equals enhanced leadership and greater resilience. In a deeply honest and wide-ranging conversation, Jerry shares his insights on leadership, happiness, the myths of success, and the transformative power of asking ourselves the toughest questions.

Introduction: Beyond the Bullshit of Success¶

From the outside, leaders often look like they’re “crushing it.” But as Jerry Colonna, CEO of Reboot and author of Reboot and Reunion, reminds us, appearances can be deceiving:

“We're socialized to bullshit not only ourselves, but everybody else, especially in the entrepreneurial community. All our companies are moving up into the right. Every product is working. We don't really have any problems because we're crushing it, and that's just a lie.”

The real work, Jerry argues, is not just about acquiring more skills or strategies. It’s about radical self-inquiry—facing our own stories, fears, and motivations head-on.

The Key Question: How Have I Been Complicit?¶

At the heart of Jerry’s coaching is a deceptively simple, yet profound question:

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

This isn’t about blaming yourself for your problems. Instead, it’s about agency—recognizing where we have power and responsibility to change our own lives. As Jerry explains:

“The purpose of this question is actually to evoke your own agency, is to look at the ways in which you may have been diluting yourself.”

Whether it’s chronic busyness, relationship issues, or dissatisfaction at work, Jerry encourages us to examine how our own choices, beliefs, and behaviors contribute to the situations we find ourselves in.

The Equation for Great Leadership¶

Jerry’s approach to leadership development boils down to a simple equation:

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership and Greater Resilience

• Practical Skills: The “how” of leadership—communication, decision-making, execution.
• Radical Self-Inquiry: The courage to ask hard questions about our motivations, fears, and patterns.
• Shared Experiences: Building community and vulnerability with others, breaking the isolation of leadership.

“People will come and ask me how, and I will drive them crazy because I will say something like, tell me about your father, or tell me why you chose to be in the job you're in the first place, or tell me about your relationship to money, or tell me about your relationship to self-worth.”

The goal? Not just to create better leaders, but to help people “not kill themselves in the process.”

The Big Lie: Success Doesn’t Guarantee Happiness¶

One of the most persistent myths in our culture is that success leads to happiness. Jerry calls this out as “the big lie”:

“A lot of people think that when they reach a certain point, become successful, make a certain amount of money, get a beautiful house, [they’ll] be happy. And essentially what you're saying here is that's very often not the case. Maybe in most cases, not the case.”

He shares a personal story from his own life—reaching outward success as a venture capitalist, only to find himself deeply depressed and unfulfilled. The lesson? Outward achievements don’t resolve our inner struggles.

Consciousness as the Ultimate Hack¶

So, what’s the “hack” for a more meaningful life and leadership? Jerry points to consciousness—raising our awareness of why we do what we do.

He encourages us to ask:

• What do I believe success will give me?
• Where did my definitions of success come from?
• What am I not saying that I need to say?
• How have my childhood experiences shaped my adult choices?

“The hack, if you will, is consciousness. Part of what makes radical self-inquiry radical is we're socialized not to ask certain kinds of questions.”

Facing the Fear of Consequences¶

Many people avoid self-inquiry because they fear what they’ll find—or what changes it might demand. Jerry acknowledges this fear:

“The fear is if I go there, I don't know what's going to happen as a consequence of that... And the good news bad news is that's true. That is absolutely true.”

But avoiding our “unsorted baggage” only makes the pain worse over time. Jerry quotes Bruce Springsteen, who spent 25 years in psychoanalysis, warning that the price of not sorting out our childhood baggage “more often than not is in tears.”

Radical Self-Inquiry in Practice: The Power of Questions¶

Jerry offers a set of powerful questions for radical self-inquiry, whether through journaling, meditation, or conversation:

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

“You know you're in the radical self-inquiry zone when the questions take your breath away, when the questions... may cause us to be a little afraid of the answer, that's where the gold is.”

The Power of Community and Shared Experiences¶

Leadership—and life—can be lonely. That’s why Jerry emphasizes the importance of shared experiences and supportive communities, whether in the form of circles, bootcamps, or simply honest conversations.

“Imagine sitting in a circle of people who just have your back, who really care about you as a person. And imagine then discussing some of the answers to those questions... Imagine having the capacity to be in relationship with people where you can just tell the truth. That's what shared experiences are about.”

Even listening to authentic podcasts, Jerry suggests, can create space for realness and connection.

The Trap of Busyness and Attachment¶

Why do so many of us stay perpetually busy? Often, it’s to quiet the inner voice of self-doubt or to chase validation. But this “attachment” to outcomes—whether it’s success, money, or recognition—only fuels suffering.

“When we become attached to the outcome, we inadvertently fuel our own suffering... But really the deeper attachment is see, I'm not nothing. See, I'm not a nobody, I'm a somebody, and that's the source of the suffering.”

The antidote? Learning to separate our self-worth from our achievements and embracing unconditional self-compassion.

Legacy, Purpose, and the Art of Growing Up¶

As we reflect on our lives and leadership, questions of legacy and purpose inevitably arise. Jerry shares his own guiding question:

“With my children being fully fledged adults, I am really focused on what kind of ancestor to my descendants would I like to be?... At the end of my days, what would I like the people who come after me to say about me?”

He finds meaning in striving to be kind, caring, and purposeful—a “giving tree” for others.

The Impact of AI and the Future of Humanity¶

The conversation also touches on the anxiety and excitement surrounding AI. Jerry is cautiously optimistic:

“What I am hopeful about is that that which does not matter in the experience of being human gets burned away and is taken care of, call it by AI, but that that which matters, which is presence and connection, human-to-human contact... that gets elevated and our skills get better at doing that.”

He encourages using AI as a tool for reflection and growth, but reminds us that the deepest answers still come from within.

Growth Mindset: A Double-Edged Sword¶

While the concept of a “growth mindset” is popular, Jerry warns against turning it into another fixed rule:

“When we get too fixed on the proper way to do things, we're setting ourselves up for attachment and therefore suffering. So if you can hold something like a mindset loosely without attachment, go for it. Have a blast. Enjoy it. But the minute you start to nail it down to the floor and say this is the way it ought to be, I ought to always have a growth mindset, you've become fixed.”

Radical Self-Inquiry in Teams and Organizations¶

The issues that break teams and organizations, Jerry argues, are rarely about talent or strategy—they’re about unresolved personal and group dynamics, often rooted in childhood patterns.

“Teams are groups, and there are group dynamics that always happen... Without the individual's radical self-inquiry skills, groups tend to be condemned to repeating patterns oftentimes of their family of origin.”

Leaders, especially, have a moral responsibility to do their own internal work. As Parker Palmer says:

“If you choose to live an unexamined life, please don't take a job that involves other people.”

Conclusion: You Are Not Alone¶

Ultimately, Jerry’s message is one of hope and solidarity:

“What I always hope from all of these intimate conversations that I try to do in podcasts is that people walk away going, ‘Geez, I'm not alone.’... What makes it hardest is to feel like. I'm the only one who's going through this.”

The path to great leadership—and a meaningful life—starts with radical honesty, deep self-inquiry, and the courage to connect with others. The questions may be hard, but the rewards are resilience, authenticity, and a sense of true belonging.

Books Mentioned and Recommended¶

• Reboot: Leadership and the Art of Growing Up by Jerry Colonna
  Jerry’s first book, foundational for radical self-inquiry and leadership.

• Reunion by Jerry Colonna
  Jerry’s second book, exploring connection and self-discovery.

• Soldiers and Kings by Jason De León
  Recommended by Jerry for its exploration of human smuggling and the realities of Central America.

• The Giving Tree by Shel Silverstein
  Referenced as a metaphor for legacy and purposeful living.

• Bruce Springsteen’s Autobiography (Born to Run)
  Cited for its honest discussion of the “unsorted baggage” of childhood and the importance of self-work.

Ready to start your own journey of radical self-inquiry? Try journaling with Jerry’s four questions, or gather a circle of friends for an honest conversation. Remember: better humans make better leaders—and you are not alone.

Podcast: How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna

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