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Regrets & Lessons Questions

Everyone carries a mistake around. The interesting part is what it did to them afterward, and hardly anyone gets asked about that part. This set goes there without turning the evening into a confession booth.

  1. 1What's a mistake you're grateful you made, in hindsight?
  2. 2What's something you wish you'd said to someone before it was too late?
  3. 3What's a risk you didn't take that still crosses your mind?
  4. 4What's the hardest lesson you've learned about yourself?
  5. 5Is there an apology you still owe someone?
  6. 6What's something you used to be ashamed of that you've made peace with?
  7. 7What would you tell yourself the day before your biggest mistake?
  8. 8What's a failure that ended up redirecting your life for the better?

Want the rest of the regrets & lessons collection?

These are a sample. DeepTalk has over 2,400 questions across 20 categories to explore.

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