Your Inner Critic Just Got Automated

Use AI to weaponize your self-doubt and challenge your resolve

Today’s prompt helps you face your self-doubt, reframe resistance, and build confidence in your creative work. It’s time to fight back.

Meet Leroy, my inner critic

Most of us have a voice in our heads that seems to specialize in bad timing. It doesn’t show up when we need honest feedback or a fresh idea. No, it shows up right when we’re starting to gain momentum. You’re building something new, ready to share something meaningful, and suddenly it slinks in like a mall cop with a clipboard and a god complex:

“Is this really worth putting out there? Hasn’t someone else already done this better?”

It doesn’t yell. It doesn’t insult. It just lobs a few softballs coated in doubt and then quietly steps back, letting you do the rest of the damage.

That’s your inner critic. Not the cartoon villain with the evil laugh, but more like an overconfident intern with tenure. You didn’t hire it, you don’t like its work, and yet somehow it keeps getting invited to the strategy meetings.

Mine has a name… Leroy

Leroy is the part of me that thinks the ship has sailed and I wasn’t on it. He believes I should’ve done more, sooner, with a better haircut and a stronger LinkedIn presence. Leroy believes the internet belongs to the young, the loud, and the algorithm-friendly.

He’s not cruel, but a total vibe killer in sensible shoes—a grumpy realist with a lazy streak and an encyclopedic knowledge of my weak points.

I used to try to block him out by drowning him in productivity podcasts, reorganize my file structure, or tinker with design tweaks no one would ever notice. But I’ve learned that Leroy doesn’t go away, so I gave him a new job.

I’ve turned him into a character in my creative process, and I control when he gets to speak. Here’s what that sounds like:

LEROY:

Oh, this again? Another email course, another funnel idea, another plan to “help brands.” That’s adorable. Maybe this one will finally go viral and earn you… a sandwich.

ME:

I’m not chasing viral. I’m building something steady with real value. It’s not flashy, but it works, and I’m damn good at it.

LEROY:

Sure. And next you’ll be telling me they’ll line up to work with a guy who just figured it out himself.

ME:

That’s the point, I figured it out. I know what doesn’t work because I’ve done it. That makes me dangerous and more helpful than half the so-called experts out there selling recycled nonsense.

LEROY:

Dangerous, huh? Should I be worried? Should I call Mailchimp and warn them?

ME:

You can call whoever you want. I’ll be over here doing the work.

You can do the same

Once you name your inner critic and define how it talks to you, it stops being some mysterious force. It becomes a bit character in your internal sitcom annoying, yes, but manageable. Predictable. You start recognizing its catchphrases.

This week’s prompt shows you how to turn that voice into a fully formed persona that ChatGPT can simulate on demand. You’ll hear it out, talk back, and maybe even get a laugh out of it. Because if it’s going to live rent-free in your head, it might as well pay you in clarity.

The Assignment

This isn’t therapy. You’re not here to journal your way into an emotional breakthrough.

This is creative sparring; one round at a time. You’ll define the critic, let them talk, and then swing back with something true, clear, and sharp.

It won’t fix everything, but it will remind you that you’ve got a voice worth defending.

That might be all you need.

Prompt: Turn Your Inner Critic into a Creative Tool

Copy all the text in the box below, paste it into your AI of choice (I use ChatGPT v4o). You will be prompted to answer questions and then a short discourse with your inner critic.