Why do journaling prompts help with fear of failure?

They encourage honest self-reflection, helping you uncover the beliefs behind your fear and turn hesitation into understanding.

How often should I use these prompts?

Try one prompt a day or revisit the ones that resonate most. Consistency builds awareness and emotional resilience.

Can I use Stoic for these prompts?

Yes. You can journal directly in the Stoic app to track your reflections and notice progress over time.

Journaling Prompts to Overcome Fear of Failure

Licensed therapist Jon Filitti shares journaling prompts to face the fear of failure. Reflect daily, build resilience, and turn hesitation into confident action.

Written by

Jon Filitti, LMHC

Updated on

October 8, 2025

Journal in stoic.

OVERVIEW

Frequently Asked Questions

These journaling prompts were written by licensed therapist Jon Filitti, created as a companion to his essay Upending the Fear of Failure.

Each question helps you confront fear with curiosity — not resistance — and reflect on how much power fear of failure quietly holds over your choices.

Use them when hesitation or self-doubt creeps in, and let journaling become your way to turn fear into forward motion.

Reflect on when you’ve regretted not acting due to fear.

What moments still come to mind, and what held you back?

Think of the last time fear of failure or rejection stopped you.

What would the actual consequences have been if you had tried?

What if instead of asking, “Will I succeed?” you ask, “Can I endure if I don’t succeed?”

How would that change your desire to act?

Reflect if you’re willing to endure the sting of failure or would rather live with the regret of never trying.

Which pain feels lighter to carry?

Small prompts for trying something that causes fear:

What am I afraid will happen? What’s the worst-case scenario? What’s the most likely outcome?

Closing Reflection

Journaling doesn’t need to be dramatic to be transformative. The real power comes from returning to it, not just when life feels heavy, but also when it feels light. Each time you sit down with your thoughts, you’re stretching your awareness and strengthening your connection to self.

Even five quiet minutes can shift your day. Over time, those minutes compound into resilience, clarity, and calm.

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How to Use These Prompts

A short guide to using reflective writing to face fear with courage and build emotional resilience. These prompts were created by licensed therapist Jon Filitti as a companion to his essay Upending the Fear of Failure.

Steps:

Set aside quiet time. Choose a calm moment, like morning coffee or before bed.
Pick one prompt. Read it slowly and reflect on what it brings up.
Write freely. Let your thoughts flow without editing or judgment.
Pause and reflect. Notice any shifts in your emotions or focus after writing.
Repeat often. Consistency is key to turning fear into clarity and calm.