Concept

Radical Self-Inquiry

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Radical Self-Inquiry

Radical self-inquiry is Jerry Colonna‘s practice of asking the destabilising questions about one’s own motives, history, and complicity that we are socialised not to ask. It is the middle term of his Leadership Equation and the core of his book Reboot. “Radical” is literal: “you know you’re in the radical self-inquiry zone when the questions take your breath away.”

The premise

We are socialised to develop bypassing skills rather than consciousness skills — to plaster over discomfort with band-aids (overwork, substances, even “spiritual bypassing” via ayahuasca weekends) rather than tend what needs tending. But avoidance doesn’t dissolve the source; the price of “unsorted baggage” (Colonna’s phrase, via Bruce Springsteen’s autobiography) comes due eventually, “more often than not, in tears.” The “hack” is consciousness — raising awareness so you act from choice rather than from a learned childhood behaviour answering your parents’ anxieties. Drawing on Buddhism, Colonna names self-delusion and attachment as the two biggest contributors to suffering; radical self-inquiry is the tool against the first.

The signature question

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

Both halves are deliberate:

  • Complicit, not responsible. Think accomplice: “you are driving the getaway car, you’re not sticking up the bank teller.” The word evokes agency, not blame — the aim is not “how am I to blame for the shit in my life?” but seeing how you have deluded yourself.
  • “I say I don’t want.” The gap between the stated wish and the behaviour. Colonna’s example: “I say I don’t want to feel busy all the time, but the truth is I feel unnerved if my agenda isn’t jam-packed” — so how does feeling exhausted serve me, and is there a more conscious way to get that feeling?

The question applies to both sides of a power dynamic: the person with less power asks “what draws me to this position; how have I benefited from the dysfunction?”; the person with more power carries more moral responsibility to examine their complicity (the CEO furious that no one decides without her — “who hired them?”).

The core questions

  • 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?
  • What do I believe being “successful” will do for me? How do I define success? Where does that come from?

You need share the answers only with yourself, though a circle, coach, or therapist can help (see shared experiences in the Leadership Equation). The questions that startle and slightly frighten you are “where the gold is.” AI can assist — not by answering, but by generating more questions to ask yourself (a colleague uploaded ten years of journals and had Claude reflect them back).

A practice, not a destination

The subtitle of Reboot is “Leadership and the Art of Growing Up,” and growing up is framed as a practice — “not a scientific moment where one day you wake up and you’re done,” but continuous inquiry, “exhausting when you contemplate it, enlivening when you live it.” It connects to Colonna’s reading of growth mindset: hold any frame loosely, because the ego will otherwise nail it to the floor and turn a growth mindset into a fixed one.