The Pleasure Project with Dana Skoglund

231. Your Success Playbook


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How I used ChatGPT to uncover my patterns (and turned it into a Success Playbook)

I share a behind-the-scenes experiment that turned into a game-changing self-coaching tool: I uploaded two years of journal entries to ChatGPT and asked it to identify my patterns. What came back was like having an ultra-insightful coach mirror back the exact moments I get dysregulated, slip into fear-based survival mode, and unintentionally self-sabotage… plus the specific non-negotiables that keep me grounded, regulated, and moving forward.

If you’ve ever wondered why you “know what to do” but still fall into the same loops, this episode will help you see the real root: safety. When the body doesn’t feel safe, it defaults to fight/flight/freeze/fawn — and willpower won’t fix that. Awareness + regulation tools + a personalized Success Playbook will.


In this episode, we cover:
  • The real reason self-sabotage happens: your subconscious is designed for survival, not success
  • How fight/flight/freeze/fawn can show up as:
  • People-pleasing and overcommitting (fawn)
  • Overworking and pushing harder (fight)
  • Procrastinating, scrolling, avoiding (flight/freeze)
  • Why “try harder” and “more discipline” often backfire when you’re dysregulated
  • The power of awareness: naming your triggers and patterns so you can interrupt them in real time
  • How I created a Success Playbook (and why certain practices became non-negotiable)
  • Why a simple habit tracker can help reinforce safety, consistency, and momentum
  • How you can create your own Success Playbook in about an hour — even without years of journaling

Get the Success Playbook Prompts (Free)

I created a Google Doc with journal prompts (takes ~1 hour) + the exact ChatGPT prompt to generate your own Success Playbook.

To get it:

  1. Click here to go to the Instagram post
  2. Comment PLAYBOOK
  3. You’ll be automatically sent the Google Doc


If this episode helped you, share it with a friend — and please rate + review the podcast. It helps more people find these tools and use them to create real change.

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The Pleasure Project with Dana SkoglundBy Dana Skoglund

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