33 Topics Women Entrepreneurs in a Success Trap Bring to Coaching (And Why You Don't Need It All Figured Out)

Editor's Note: This post was originally published in May 2023 and updated in December 2025 to reflect my specialisation in coaching women entrepreneurs who feel trapped by their own success.

If you've built a successful business but feel trapped by it, you might be wondering: "What exactly would I even talk about with a coach?"

Here's the truth: You don't need to have it all figured out before you book a session.

My clients are women entrepreneurs who've built thriving businesses — successful on paper, draining in reality. They come to coaching because something needs to change, but they're often not sure exactly what.

That's completely normal. In fact, not knowing what you need is often a sign that you need coaching.

Below are 33 topics that women entrepreneurs in a success trap commonly bring to our sessions. You might see yourself in several of these — or you might bring something entirely different.

The point isn't to have the "right" topic. The point is to start the conversation.

Here are 33 topics you could explore in coaching:

On Feeling Trapped in Your Own Success

1. Why you fantasise about burning your business down (but can’t actually do it)

2. How to know if you're temporarily burnt out or permanently done

3. Why you feel guilty for wanting something different when you're already successful

4. How to stop resenting the business you worked so hard to build

5. Whether you should stay, sell, or completely redesign your role

On Identity & Self-Worth

6. Who you are without the "business owner" identity you've worn for years

7. Why your sense of self-worth is wrapped up in your business performance

8. How to stop defining yourself by what you've built

9. Reconnecting with who you are beneath the entrepreneur persona

10. What happens if you walk away — and whether you'll lose yourself

On Decision-Making When You're Stuck

11. How to make a decision when every option feels terrible

12. Whether this is the "right time" to make a change (spoiler: there isn't one)

13. Why you keep waiting for clarity that never comes

14. How to trust yourself again when you've lost confidence in your judgment

15. Making a big decision without having it all figured out first

On What You Actually Want

16. Figuring out what you want NOW (not what you wanted at 30)

17. Why you don't know what you want anymore after years of building someone else's vision

18. Whether you're allowed to want something different than what you built

19. How to design what "enough" looks like for you

20. What would make you excited to wake up again

On the Practical Realities

21. How to exit or transition without blowing everything up

22. Whether you can redesign your role instead of leaving entirely

23. How to scale back without feeling like you're failing

24. What to do when your business is profitable but you're miserable

25. How to financially prepare for a transition (or whether you even need to)

On Relationships & Other People's Reactions

26. How to tell your partner/family you want to change everything

27. What to say to clients, team, or business partners

28. Dealing with "But you're so successful!" comments

29. Setting boundaries with people who are financially or emotionally invested in your business

30. How to handle the guilt of "letting people down"

On Fear & What Comes Next

31. Whether you're making a huge mistake if you leave

32. What you'll do with your time/identity/income if you walk away

33. How to move forward when you're terrified of both staying AND going

You Don't Need to Pick Just One

Here's what actually happens in coaching: you might come in thinking you need help with one thing (like whether to sell your business), and discover the real issue is something else entirely (like believing your worth is tied to being "the successful entrepreneur").

That's the power of coaching. We don't just tackle the surface problem — we get to the root of what's keeping you stuck.

What Makes Life Redesign Coaching Different

Unlike business coaching (which helps you optimise or scale), life redesign coaching specifically addresses:

• Why you're drained by the business you built

• How to figure out what you actually want NOW (not what you wanted 10 years ago)

• Whether to stay and redesign, exit strategically, or create a third option

• Building confidence in your decision without needing it all figured out

• Reconnecting with yourself beneath the "business owner" identity

If you're a woman entrepreneur who's built something successful but feels trapped by it, this is exactly what we'll work on together.

Not Sure Where to Start?

That's what the free clarity call is for.

In 50 minutes, we'll talk honestly about what's really going on, identify whether this is temporary burnout or something deeper, and explore whether the Redesign Session is right for you.

No pressure. No sales pitch. Just clarity.

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