Shadow work prompts

Most prompt lists ask you how you feel. You already know how you feel; that is not where the shadow is.

The questions below ask about disproportion instead — the places where your reaction was bigger than the event that caused it. That gap is the only reliable signal, because a shadow does not announce itself. It leaks out as intensity.

If the idea itself is new, what shadow work is sets it out first, including what cannot honestly be claimed for it.

How to use these

One at a time. Thirty questions answered in an evening produces thirty tidy paragraphs and no discomfort whatsoever — which is how you know nothing was looked at. Take one. Let it stay open for a week.

A blank is information. If a prompt returns nothing, it is either not yours or too close to look at head-on. Move on. Forcing an answer produces invention, and invention is the main way this goes wrong.

Watch for good prose. If your writing starts getting elegant, you have begun performing for an imagined reader. Stop writing and just hold the question.

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Prompts about the mask

The face you can wear in public, and the assumption that the other one would not be welcome. → the mask

1. Who have you never been tired in front of? 2. What would people be surprised to learn you find difficult? 3. If someone described you accurately but unkindly, which word would land hardest — and is it wrong? 4. What do you do differently in the ninety seconds before someone arrives? 5. Which of your qualities is genuinely yours, and which one did you build because it worked?

Prompts about the judge

The voice that arrived from outside and stayed on as management. → the inner judge

6. Whose voice is it, actually, when you criticise yourself? Say the sentence out loud and listen to the accent. 7. What standard do you hold yourself to that you would find absurd applied to a friend? 8. What did you get praised for as a child that you are still doing? 9. When you fail at something small, what is the first sentence in your head — the exact words? 10. Who are you still trying to prove something to, and are they even watching?

Prompts about the pleaser

Agreement given so fast it was never a decision. → the pleaser

11. When did you last say yes and feel the drop in your stomach at the same moment? 12. What are you doing this month purely because refusing felt like too much work? 13. Who would be upset if you became less available, and what does that tell you about the arrangement? 14. What do you get out of being the reliable one? Name the payment honestly. 15. When you imagine saying no, what specific consequence appears — and how likely is it really?

Prompts about envy

The most reliable pointer in the whole practice, and the one nobody wants to use.

16. Whose success is hardest to be glad about? Not disliked — hard. 17. What do they have that you told yourself you did not want? 18. Which compliment about someone else stings slightly? 19. What did you give up on so early that you now call it a preference? 20. Who did you stop following, and what was the real reason?

Prompts about anger

21. What made you disproportionately angry this month? Not the big thing — the small one. 22. What are you tolerating that you would tell someone else not to tolerate? 23. Where does your anger arrive as coldness instead of heat? 24. What have you forgiven out loud and not at all underneath? 25. Which apology are you still waiting for, and what would actually change if it came?

Prompts about the imposter

Competence you can observe from outside but not feel from inside. → the imposter

26. What are you good at that you cannot accept a compliment about? 27. When you are praised, what is the reflex — deflect, correct, or credit luck? 28. What would you have to admit if you accepted that you are actually competent? 29. Who do you assume would be better at your life than you are? 30. What have you been calling not ready that is really not permitted — and who is withholding the permission?

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When a prompt sticks

You will know: the question stops being a question and starts turning up while you are doing something else. That is the useful state, and it is also the point where most people close the notebook, because sitting with an open question and no task is uncomfortable in a specific, fidgety way.

This is where a page helps, and the mechanism is smaller than it sounds. Colouring gives the hands a job for an hour while the question stays open. The question does not get solved — it gets carried, which is the only thing you can usefully do with it early on.

Every page in Forty Shadows is a narrative mandala built around one of these patterns: the rim states the situation, the middle band is what stands in the way, the centre is what is being protected. How to read a mandala is the method, and it takes ten minutes to learn.

Pick the page matching the prompt that stuck. Three are free.