Thought I was just trying to understand why I’m terrified of public speaking.

Three hours later, I’d uncovered a whole web of fears I didn’t even know existed and somehow ended up doing the exact thing I was most afraid of.

These prompts don’t just help you identify fears, they turn ChatGPT into your personal courage archaeologist, digging up the roots of your anxiety and showing you exactly what’s waiting on the other side of your terror.

The crazy part?

The fears that feel the most overwhelming are usually guarding the exact things you need most.

Warning: You might end up surprising yourself with what you’re actually capable of when you stop running from what scares you.


1. The Fear Timeline

“Help me trace one of my biggest fears back to its origin. When did I first remember feeling this fear? What was happening in my life? Keep asking me to go deeper—what was the story I told myself about what this fear meant about me or the world? Don’t let me stay surface-level. What is this fear actually protecting me from?”

This completely blew my mind. ChatGPT helped me realize my fear of “looking stupid” wasn’t about intelligence—it traced back to being laughed at in third grade when I mispronounced a word. The fear was protecting me from feeling that specific shame again. But it was also preventing me from trying anything new for the past 20 years.

2. The Courage Inventory

“I want you to help me identify a time when I acted courageously, even if I didn’t feel brave at the time. What was I afraid of in that moment? What made me do it anyway? What did I learn about myself from pushing through that fear? Now help me figure out what other areas of my life need that same kind of courage.”

This prompt made me realize I’ve been way braver than I give myself credit for. ChatGPT helped me see that leaving my toxic job two years ago was actually an act of massive courage, even though I felt like I was just running away. The conversation helped me identify the pattern of courage I already have and how to apply it to my current fears.

3. The Fear Shadow

“Help me explore what I think I would become if I wasn’t held back by my biggest fear. Be specific—what would I do differently? How would I show up in the world? What opportunities would I pursue? Now let’s examine what this tells me about what I actually want. What is my fear preventing me from becoming?”

Absolutely devastating. ChatGPT walked me through imagining myself without my fear of rejection, and I realized I’d be an artist sharing my work publicly. The fear wasn’t just stopping me from dating or making friends—it was preventing me from becoming the person I actually am inside. The conversation made me post my first piece of art online that same day.

4. The Worst-Case Scenario

“I want you to help me walk through the absolute worst-case scenario of my biggest fear coming true. What exactly would happen? How would I handle each step? What resources do I have? What would I do to recover? Keep pushing me to be specific until I realize that even the worst case is survivable.”

This exercise was terrifying but incredibly freeing. ChatGPT helped me map out exactly what would happen if I got fired for speaking up about workplace issues. When we actually walked through the practical steps of job hunting, updating my resume, and using my network, I realized the “worst case” was actually just… inconvenient. Not life-ending. I had that difficult conversation with my boss the next week.

5. The Fear Flip

“Help me identify a fear that might actually be excitement in disguise. What am I avoiding that also makes me feel energized when I think about it? What would change if I reframed this fear as anticipation instead of anxiety? Walk me through the physical sensations—are they actually that different from excitement?”

Mind-blowing reframe. ChatGPT helped me realize that my “fear” of starting my own business was actually excitement that I’d been interpreting as anxiety. The physical sensations were almost identical—increased heart rate, butterflies, heightened alertness. When I started thinking of it as excitement instead of fear, everything changed. I registered my LLC two days later.


The Results

I’m not going to lie—these conversations forced me to confront some uncomfortable truths about how much I’ve been shrinking my life to avoid discomfort. But the weird part? Once I understood the specific anatomy of my fears, they lost most of their power over me.

ChatGPT doesn’t give you courage—it helps you see that you already have it. It just asks the right questions to help you trace your fears back to their source and realize that most of them are based on outdated information about what you can handle.

Four of these prompts led to me actually doing things I’d been avoiding for years. One of them made me realize that my “fear of failure” was actually a fear of success and what that would mean for my identity.

Try these and let me know what fears you end up conquering—I’m genuinely curious if mapping your fears makes them less scary for other people too. Sometimes the most courageous thing is just understanding what you’re actually afraid of.


Pro tip: Don’t try to be brave during these conversations. The goal is to understand your fears completely before you try to overcome them. ChatGPT is incredibly good at helping you see patterns in your avoidance that you can’t see on your own.