Breath-Taking Questions (Radical Self-Inquiry Prompts)
Journal on questions that scare you — that's where the gold is
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 92%
A concrete set of prompts for the 'radical self-inquiry' component. Most people journal but don't know what to journal on. Colonna supplies four questions designed to startle you; the litmus test is that a real radical-self-inquiry question 'takes your breath away.' You answer them for yourself first, optionally sharing later with a trusted group, coach, or therapist.
Origin
Jerry Colonna's coaching practice; the questions appear after every chapter of his book Reboot and in Reboot's published journal.
Core principles
- 01You know you're in the radical self-inquiry zone when the questions take your breath away
- 02The most important person to share the answers with is yourself
- 03Fear-inducing questions point precisely at what needs tending
- 04Pause first — via meditation, journaling, or time away — then ask
How to run it
- 1
Create a pause
Sit in meditation, journal, or take time away — deliberately stop so you can ask yourself questions instead of reacting.
- 2
Ask the four questions
Work through: (1) How have I been complicit in creating the conditions I say I don't want? (2) What am I not saying that I need to say? (3) What am I saying that's not being heard? (4) What's being said that I'm not hearing?
Pro tip These apply equally to a struggling relationship and to leading a team.
- 3
Use the breath test to find the real ones
Notice which questions make you a little afraid of the answer. The startling ones — the ones that take your breath away — are where the gold is; follow those.
Pro tip Add deeper prompts like 'Who would you be without the story of who you are?' and 'What do you wish the people in your life knew about you but you're too afraid to tell them?'
Watch out Bypassing the scary questions to keep things comfortable defeats the purpose.
- 4
Answer for yourself first, share selectively
Write honest answers for yourself. Optionally share them later with a group of friends, colleagues, a coach, or a therapist — but you are the primary audience.
In the wild
Colonna models the second question against a relationship that isn't working: 'What am I not saying in that relationship that I need to say?' — a question he notes is terrifying and applies equally to leading people.
→ Surfaces the withheld truth that, unspoken, keeps the relationship or team stuck.
Colonna observes that over his 27 years journaling has become popular, but people 'journal but they don't know what they should be journaling on.' He supplies the four questions as the missing prompts.
→ Gives journalers a concrete, high-leverage focus instead of aimless writing.
Common mistakes
Asking only safe questions
Sticking to comfortable prompts keeps you out of the radical-self-inquiry zone. If a question doesn't startle you, it isn't doing the work — the fear is the signal you're near something real.
Answering to perform for others
Treating the answers as material to impress a group misses that the most important person to share them with is yourself; performance reintroduces the self-delusion the exercise is meant to cut through.
Is it for you?
Best for
Anyone starting a journaling or self-inquiry practice who wants high-signal prompts, especially leaders navigating a hard relationship or team dynamic
Not ideal for
People in acute crisis who need clinical support rather than solo confrontation with destabilizing questions
From the transcript
“what am I not saying that I need to say?”
“what am I saying that's not being heard and then of course uh 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.”
“the most important person with whom you should share the answers is oneself.”
“questions that may cause us to be a little afraid of the answer. That's where the gold is.”
From the episode
How have I been complicit in creating the conditions I say I don’t want?
Jerry Colonna (CEO of Reboot, executive coach, former VC)