12 Prompts for when you’re afraid to fail

Journaling to release fear and reconnect with your courage

Sometimes we don’t move forward—not because we’re lazy or lost—but because we’re scared to get it wrong. Scared to disappoint. Scared to shine and still not be enough. If you’ve been stuck in hesitation or perfectionism, you’re not alone.

These prompts are not here to push you—they’re here to hold space for your fear and help you move with it, gently. Through journaling, you can listen to what your fear is trying to protect and reconnect with the part of you that’s ready anyway.

Below you’ll find 12 reflective questions designed to soften your fear of failure and open space for compassion, clarity, and quiet bravery.

  • What would I try if I wasn’t scared to mess up?
  • What old belief about success do I need to let go of?
  • What story am I telling myself about what might go wrong?
  • What part of me deserves a chance, even if things don’t go perfectly?

What would I do today if no one was watching or judging?

What’s the worst that could happen… and how would I handle it?

What past “mistakes” don’t hurt as much now as I thought they would?

  • What did I learn the last time something didn’t go as planned?
  • What could go right if I just try?

What part of me is scared to shine?

  • What might I gain just by giving it a go?
  • What feels heavier: trying or always wondering “what if”?

Even one sentence can begin to shift your inner story. Let your words be a space to feel—not fix. You don’t have to be fearless to take the next step. You just have to be kind to yourself while doing it.

or Explore more intention-based prompts