The Nine Deep Questions

(see the criteria for choosing which ones to use at the end)

Note: question 2, "what do others say you are?", was added to balance the view of oneself with an outside view of the person.

1. What you went through, and what it taught you

What is the bad thing that happened to you — a hurt, a hardship, a failure — that over time made you able to help other people? Not the story you tell to look good: the one you might avoid telling, but which is the reason you truly understand certain people.

Why this matters: a person’s path often starts not from a talent, but from a bad thing they got through. Someone who has been there becomes, almost without meaning to, a guide for whoever is there now.

2. What do others say you are?

Think of the people who have known you a long time and in different places: family, work, friends. If they had to describe you in a couple of words to someone who doesn’t know you, what would they say you are good at? What do they always ask you to do for them? Is there something everybody recognises in you, even if to you it is nothing special?

Why this matters: about ourselves we are the worst observers. What comes naturally we take for granted, and that is exactly why we don’t see it as a strength. People around us see it from the outside, without the familiarity that makes it invisible to us. This question compares how you see yourself with how others see you: if the two match, the common thread is confirmed; if they differ, that difference is useful data, not something to throw away.

3. Jealousy, and what it hides

Think of someone who makes you jealous for the life they have, the position they hold or the work they do. Not calm admiration: real jealousy, the kind that stings. What is that person doing? And what does it tell you about what you want too, but have never let yourself want?

Why this matters: jealousy looks like a flaw, but it points somewhere. It points straight at what we feel is ours and haven’t yet had the nerve to go after.

4. The time you looked the other way

Tell me about an important choice where, looking back, you already knew what the right thing was, but you took the easier road, the safer one, or the one that kept other people happy. What did you silence in yourself that time?

Why this matters: seeing where we betrayed ourselves once shows where we risk doing it again — and what we have to defend this time.

5. What you’d do if nobody ever knew

If nobody could ever know you had done it — no praise, no "likes", nobody noticing — what would you keep doing anyway, with the same appetite?

Why this matters: it separates what you really want from the need to be approved of by other people. The two are easily confused.

6. The question that keeps coming back

Is there a question you have been asking yourself for years, that keeps coming back even when you thought you had put it away? It can be a big question about life or a practical one. I don’t need the answer: tell me the question.

Why this matters: the questions that won’t leave us matter more than the answers we give. They say where we haven’t understood yet — and that is usually where the work is.

Note: this question can surface on its own, without ever being asked, while the person is answering other questions in Part 4 — for example while working through 5 or 8. If a line like "I always wonder why..." or "it’s something I keep asking myself, year after year" comes up during the process, treat it as an answer to Question 6 and flag it in the final synthesis anyway, even though it was never posed as a question of its own.

7. What you were like before you learned to keep others happy

Think of yourself as a child, before the age of ten, before you had worked out what was expected of you. What made you curious? How did you play? What did you build or invent just because you liked it? Of that child, what is still in you today — hidden, maybe, but not dead?

Why this matters: before we fitted ourselves to what family and everyone else wanted, we already had a character of our own. Recognising it isn’t nostalgia: it is understanding better who we are.

8. How much you’re willing to pay

Imagine having to choose between two lives. One comfortable, safe, respected, but without doing what you feel is yours. The other faithful to what you feel is yours, but uncertain, hard, and maybe not even understood by other people. Which regret frightens you more: never having tried, or having tried and lost?

Why this matters: following your own path always costs something. This question shows how ready a person really is to pay that price — worth knowing before making any plans.

Note: unlike the either/or questions in Parts 2 and 3, this question isn’t given a 0-to-10 number at the outset. Sometimes it produces an answer with no hesitation, other times it stays clearly unresolved. In both cases the data is useful precisely because the question offers no ready-made middle ground.

Note — when the clean-cut choice doesn’t resolve: unlike 3.3, where a concrete question can dissolve a more generic tension, question 8 sometimes stays unresolved even when question 1 has just produced rich and concrete material. The assistant shouldn’t read this as an inconsistency to flag or force through: some clean-cut questions simply don’t "work" for everyone, even when the rest of the material is coherent. The practical rule stands: a clean-cut choice dissolves a tension only if it does so on its own in the person’s answer; if it doesn’t, accept it as open data, without pressing for a definite choice.

9. Who you’d like to thank with your life

Think of someone who gave you something precious without asking anything in return: a teacher, a parent, a friend, even someone you never met or who is no longer here. If you could thank them with the way you live, or by dedicating your work to them, what would you do to say "thank you, it wasn’t wasted"?

Why this matters: many real paths start not from ambition, but from a thank-you someone wants to give back — often to other people, and in a different form from the one they received it in.