Shadow Work Prompts for Money, Pricing and Visibility

Shadow work prompts are questions that help you notice the parts of yourself you learned to hide, deny or judge. Below are 42 shadow work prompts written for entrepreneurs, grouped into money and pricing, visibility and selling, worth and relationships, and purpose and receiving. Take one prompt at a time, write without editing, and go gently. The point is not to dig up pain. It is to see a hidden pattern clearly enough that it stops running you.

What is shadow work?

The idea of the “shadow” comes from the psychiatrist Carl Jung. He used it to describe the parts of ourselves we push out of sight because they once felt unacceptable. Anger we weren’t allowed to show. Ambition that got us mocked. Needs that went unmet, so we learned not to have them.

Shadow work is the practice of turning toward those parts with curiosity instead of shame. For entrepreneurs, the shadow often shows up around money, visibility and receiving, because those are the places where old rules about safety are tested most. Our complete guide to shadow integration covers the theory in depth.

Before you start: a few gentle rules

• Go slowly. One prompt a day is plenty. Some prompts will open more than you expect.
• Write by hand if you can. It slows you down and makes it easier to notice what you feel.
• Notice your body. If your chest tightens or your mind goes blank, pause. That reaction is information.
• Don’t judge what comes up. The shadow formed because something was judged. Judging it again just pushes it back down.
• Get support if you need it. If a prompt brings up trauma, panic or deep grief, stop and reach out to a qualified therapist. Shadow work is not a replacement for professional care.

If you’re new to this, read how to begin shadow work without making it worse first.

How these prompts are organised

The prompts follow David Cameron Gikandi’s Three Pillars: the Economic Machine (money and business), Mind & Heart (identity, emotions and relationships) and Spirit & Flow (purpose and meaning). The money section is split in two, because that is where most entrepreneurs find their shadow first.

Shadow work prompts for money and pricing

These come from the Economic Machine pillar. They help you see the hidden rules behind how you charge and handle money.

1. When I say my price out loud, what do I feel in my body, and where?
2. What did the adults around me say about people who have a lot of money?
3. What did money mean in my home growing up: safety, conflict, shame, power?
4. When have I lowered my price before anyone asked me to? What was I afraid of?
5. If I charged double, who would I worry about judging me?
6. What part of me feels that wanting more money makes me a bad person?
7. When money comes in, what do I do with it in the first few days, and why?
8. What do I avoid looking at in my finances? What am I afraid I’d find?
9. Whose voice do I hear when I think about getting rich?
10. If I had all the money I needed, what would I stop pretending about?
11. What do I secretly judge in people who charge a lot?

Why these help: most money blocks are old rules, not lack of knowledge. Prompts 2, 3 and 9 point to where a rule was learned. Prompts 1 and 4 show where it lives now. If this section stirs a lot, our article on shadow work for wealth blocks goes further.

Shadow work prompts for visibility and selling

Also from the Economic Machine, these are about being seen and asking for the sale.

12. What is the worst thing someone could say about my work if they saw it?
13. When I was a child, what happened when I showed off, shone or got attention?
14. What part of me would rather stay small and safe than be seen and judged?
15. When I think about selling, what word comes up first? Where did I learn it?
16. What have I kept “almost ready” for months? What does keeping it unfinished protect me from?
17. Whose success makes me feel jealous? What does that jealousy tell me I want?
18. If my work became well known, who in my life would feel uncomfortable?
19. When do I talk too much on a sales call? What am I trying to prove?
20. What would I post if I knew no one I grew up with would ever see it?
21. What am I pretending not to want from my business?

Why these help: jealousy (prompt 17) is one of the clearest windows into the shadow. We tend to envy what we’ve told ourselves we’re not allowed to have.

Shadow work prompts for worth and relationships

These come from the Mind & Heart pillar. They look at identity, the inner critic and the people around you.

22. What do I believe I have to do to deserve rest?
23. When did I first feel I had to earn love or approval?
24. What does my inner critic say most often? Whose voice does it sound like?
25. What trait in other people irritates me most? Where might that trait live in me?
26. Where do I say yes when I mean no? What am I afraid would happen if I said no?
27. What part of myself did I learn to hide to be accepted?
28. What do I need from others that I find hard to ask for?
29. When someone praises my work, what do I do with it?
30. Who would I be if I stopped trying to be “the good one”?
31. What anger have I never let myself feel? What is it trying to protect?
32. Which of my clients do I resent? What does that resentment say about my boundaries?

Why these help: prompt 25 is classic shadow work. What we strongly dislike in others often points to something we’ve disowned in ourselves. Prompts 26 and 32 show how hidden needs leak into business as over-giving.

Shadow work prompts for purpose and receiving

These come from the Spirit & Flow pillar. They look at meaning, wanting and the ability to receive.

33. What do I want so much that I’m scared to admit it?
34. When good things come, what part of me waits for them to be taken away?
35. What dream did I give up on because someone said it wouldn’t work?
36. Where am I using “spiritual” reasons to avoid doing practical things?
37. What would it feel like to receive help without paying it back right away?
38. When do I feel guilty for being happy?
39. What is the story I tell about why my purpose hasn’t fully arrived yet?
40. If I trusted that I was allowed to have what I want, what would I do this week?
41. What part of my old self would I have to let go of to become who I’m becoming?
42. What am I afraid would happen if everything actually worked out?

Why these help: prompt 36 matters for conscious entrepreneurs. Spirituality can become a gentle way to avoid the business side. Prompt 42 often uncovers fear of success, which is easy to miss.

How to use these shadow work prompts

Writing the answer is the start, not the end. Here is a simple way to turn a prompt into change.

1. Write freely for ten minutes. Don’t stop to fix spelling or make it sound wise.
2. Underline one sentence that surprised you. That’s usually where the shadow showed itself.
3. Ask where it came from. Not to blame anyone, but to see it was learned.
4. Notice how it shows up this week. Watch for it in a price, a post or a conversation.
5. Take one small opposite action. If the shadow says “stay small”, share one thing you would normally hide.

If you’d like a guided path, David’s mini-course The 7-Step Shadow Work Sprint helps you find one disowned part and bring it into awareness over seven days. And if you’re unsure how shadow work differs from inner child work, see is inner child work the same as shadow work?

Why shadow work matters for your business

Shadow work isn’t only for personal growth. The parts we hide tend to become the brakes in our business: the undercharging, the hiding, the pulling back just before success. Seeing them is the first step to releasing them.

But seeing isn’t the whole job. At MiraclesFor.me we pair inner work with real business structure every time. In our words:

Because manifesting is as natural as breathing. It is already running, and it is already obeying the conditioning it was handed. So the work is releasing the brakes, rising above that conditioning, and building real structure and flow around abundance — the mindset, the financial plumbing, the entrepreneurial steps.

Questions people ask

What are shadow work prompts?

They are journaling questions designed to help you notice parts of yourself you’ve hidden or judged, so you can understand them and stop being driven by them.

How do I start shadow work as a beginner?

Pick one prompt, write for ten minutes, and notice how your body reacts. Go slowly, and stop if it becomes overwhelming. A qualified therapist can help if deeper pain comes up.

Can shadow work be harmful?

It can stir up strong feelings, especially for people with painful childhoods. That’s why it should be done gently, one step at a time, and with professional support when needed.

How often should I do shadow work?

A few times a week is plenty for most people. Depth matters more than speed. One honest page is worth more than ten rushed ones.

Where to go from here

The Abundance GPS masterclass shows how hidden patterns become brakes in a business, and how to release them while building real structure.

And if you’d like to do this work in good company, the Abundance GPS community on Skool is where it happens. We help conscious entrepreneurs with adverse childhood experiences get out of their own way and release their brakes — so they can multiply their income and magnify their impact. Every tier opens with a 7-day free trial. Join the Abundance GPS community.