How Have You Been Complicit in Creating the Conditions You Say You Don’t Want?

This question has a way of landing differently than most. For some people, it arrives like a jolt. For others it settles in slowly, quietly, and refuses to leave. It was coined by Jerry Colonna, co-founder of Reboot, executive coach, and author of Reboot: Leadership and the Art of Growing Up, and has traveled far beyond his coaching practice, cited by other coaches, quoted in boardrooms, passed between leaders, because it does something most leadership frameworks don’t: it assumes you have more agency than you’ve been giving yourself credit for. And that single shift, from helpless to responsible, is where everything begins to change.

THE REAL MEANING OF COMPLICITY

Before you can really sit with this question, it helps to be precise about what complicity means, because the word carries weight that can work against you if it’s misread.

When most people hear complicit, they assume “guilt” or responsibility. They hear the question as, “How have I screwed up my life?” The word often arrives with a verdict attached. Here, it means something more precise and more compassionate than it might first suggest.

Complicit

To enable or to take part in. Jerry often uses the metaphor of a driver in a getaway car — present, involved, but not the one holding up the bank.

Responsible

To be the main cause. The robber who holds up the bank. There is a real difference — and conflating the two leads self-inquiry down the wrong path.

When leaders first encounter this question, the most common reaction is to brace themselves; they expect guilt, shame, or defensiveness. That’s completely natural. But if complicity becomes “this is all my fault,” the question shuts us down to inquiry before it can do anything useful, before it can produce understanding. Understanding and grace.

The question isn’t an accusation. It’s an opening. And what you say to the world, but more importantly to yourself, about what you say you don’t want is where that opening begins. This is where radical curiosity starts. Without that honest inner dialogue and without truly understanding what complicity means in this context, real change stays out of reach. When you begin to recognize that your actions don’t match your expressed wishes, something shifts: in how you trust yourself, and in how you show up for the people around you.

Jerry Colonna

"My own pursuit of moral courage was never about finding blame or evoking shame. It was and remains an invitation to lifelong curiosity. To wonder. To develop your moral courage to look inward with tenderness rather than accusation. It is inquiry, not inquisition."

Jerry Colonna Saved by Hope: Courage, Beauty, and Morality as the Soul of Redemptive Leadership

WHY WE STAY IN THE CONDITIONS WE CREATE

Here’s something that comes up again and again in this work: people who are deeply aware of the conditions they’re living and working in, and who genuinely want something different, are often the ones actively maintaining those conditions.

The executive who says they’re exhausted and overwhelmed keeps scheduling more meetings. The leader who wants a more open culture keeps shutting conversations down. The founder who says they want to step back keeps centralizing every decision. Sound familiar?

Your subconscious is not working against you randomly. It’s working toward something: self-worth, safety, the avoidance of something harder to look at. Being busy can protect you from stillness. Staying in conflict can protect you from accountability. Maintaining control can protect you from the vulnerability inherent in real trust. The conditions you say you don’t want may be serving a function you haven’t named yet, and until you name it, they tend to stick around. As Jerry will often point out, behaviors, even those we deem to be negative, persist because they meet a need, and often that need is unconscious and, perhaps, developed as a child in order to feel loved, safe, and that we belong to our families.

This is where the real work begins. Not in fixing the conditions, but in understanding your relationship to them.

THE IMPORTANCE OF RADICAL SELF-INQUIRY

None of this is easy to do alone, and it isn’t meant to be done through sheer willpower or intellectual rigor. Jerry has a name for the practice that actually makes this kind of honesty possible: radical self-inquiry.

He defines it as “the process by which the masks we wear, concealing ourselves from others but most importantly ourselves, are slowly and compassionately stripped away so there’s no place left to hide.”

The word radical here doesn’t mean harsh or extreme. It means going to the root. And the word that matters just as much, maybe more, is compassionately. Without compassion for yourself, this kind of inquiry collapses into self-punishment, which is just another way of staying stuck. It looks like growth, but it isn’t.

Radical self-inquiry asks something deeper, something more challenging of you. To observe without assigning blame. To notice what’s true without immediately needing to fix or defend it. To hold a question longer than feels comfortable and see what surfaces when you stop trying to answer it.

THIS ISN’T ABOUT SHAME

At its heart, this question is an invitation, not an indictment. A turning toward, not a turning against. It was always meant to be an act of compassion; a gentle nudge to look inward with honesty and curiosity rather than accusation. If shame shows up along the way, and for many people it does, that’s worth naming. Shame, for all its intensity, tends to keep us exactly where we are.

A more useful approach is to become a casual observer of your own actions rather than a judge of them. To ask what you’re not saying that needs to be said. What you’re holding back, and why. You can lightly hold what’s true without assigning blame. That’s the practice. Not self-punishment, but honest noticing.

The goal of asking how you’ve been complicit is not to arrive at a verdict. It’s to restore a sense of authorship. The leaders Jerry works with often come in feeling like their circumstances are happening to them, as if they’re caught in something they didn’t choose and can’t change. This question interrupts that. It says: you have been part of creating this, which means you can be part of creating something different.

Jerry Colonna

"You won't always know what's right. But you will always know when something feels off. That unease? That internal friction? That's not a distraction. That's the beginning of discernment."

Jerry Colonna But How Do I Know What's Right?

THE ILLUSION OF HELPLESSNESS

After decades of this work, here’s what we know: the feeling that you have no control over the conditions you’re living and working in is almost never the full truth. It feels true. It can feel completely, exhaustingly true. But the leaders who arrive most convinced they are stuck, that circumstances are simply happening to them, and there’s nothing to be done, are often the ones with the most authorship they haven’t yet claimed. That’s not a criticism. It’s actually the most hopeful thing we can tell you.

You found this question for a reason. The fact that it’s still with you means something.

FOUR QUESTIONS AT THE CORE OF THIS WORK

In his first book, Reboot, Jerry poses four questions that form the core of this inquiry. They’re not meant to be answered quickly, or in order, or all at once. Think of them less as a checklist and more as a place to keep returning:

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

What am I saying that’s not being heard?

What am I not saying that needs to be said?

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

Each question asks you to step back from the story you’ve been telling and look at it from a little more distance. Not to judge what you find, but to notice it. The shift from judge to observer is smaller than it sounds, and it changes everything.

If these questions are already sitting with you, you might be ready to explore what working with a Reboot coach looks like. Find out more.

LISTEN

These conversations go deeper into the question, radical self-inquiry, and what this work actually looks and feels like in practice.

READ

Three of Jerry’s most essential pieces of writing for anyone who wants to go further with this question.

The One Thing I Tell Entrepreneurs About Great Leadership

Jerry reflects on how his signature question has drifted from its original intent over the years, and what it was always meant to be: an invitation to lifelong curiosity, not a path to shame or guilt.

Speaking Up as Radical Self-Inquiry

On the cost of silence, the courage it takes to name what's true in a room, and why speaking up — however quietly — is itself an act of radical self-inquiry.

When Good Leaders Do Bad Things

The deepest and most unflinching of Jerry's recent writing. On the shadow, the capacity for harm that lives in all of us, and what it means to lead redemptively rather than perfectly.

This is where Reboot begins.

If you’re ready to stop living in the conditions you say you don’t want, we’d love to talk. Coaching exists for exactly these moments — the ones where the questions feel bigger than the answers.

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