A Recovering Worm-Monkey’s Guide to Leaving the Grinder.

I Used AI to Rewire My Life and Reclaim My Time.

May 29, 2025

This started with a comment from Brad on my white-collar work post:

“In this AI phenomenon, I worry that I can't separate hype/marketing from reality.”

He also pointed me to Cal Newport’s latest podcast.
Episode 354: The Workload Fairytale. At around 56:09: “When will AI automate my job?”

Here’s my take: AI started automating my job (advertising) a while ago. So I turned it inward and used it to rewire my life instead. I’m not losing sleep over AGI, superintelligence, or runaway agents—yet.

I Didn’t Use AI to Get Rich

I used it to get clear.

Clear on what I was tolerating.
Clear on what was driving me.
Clear enough to realize I’d been dancing like a worm-monkey—hustling to hold broken systems together, confusing exhaustion for virtue.

AI didn’t hand me a roadmap.
It handed me a mirror.

It reflected what I’d normalized. Surfaced assumptions I’d absorbed. Showed me the split between who I really was—and who I’d become by default.

To the skeptics: this wasn’t magic. Or hype.
It was a faster feedback loop.

I used AI like you’d use a whiteboard, a spreadsheet, or a skeptical friend—to think better, faster, and with fewer lies-to-self.

Rewiring My Work Life

For years, I assumed I’d work forever.
Not out of love. Out of fear. Of collapse. Of irrelevance. Of being the last one holding the bag.

That assumption stayed hidden until I asked:

“What does a fulfilling life actually look like?”

Then the wires started to fray.

I used AI to simulate income models.
To pressure-test exits.
To model trade-offs instead of daydreaming about them.

Brian F., a friend who navigates the financial terrain better than most, helped me reframe my money assumptions. We ran boring-but-beautiful strategies—like dividend aristocrats.

The goal wasn’t retirement. It was rewirement.

I didn’t ask AI what to do. I asked it to challenge what I thought couldn’t change.

Rebuilding on Purpose

Once I stepped off the treadmill, the harder question emerged:

“Now what?”

Turns out, I wasn’t addicted to work.
I was addicted to mattering.

But mattering isn’t a solo sport.

You can’t debug your life in isolation.
You have to understand the life you want with the people who matter—friends, family, partners, kids.
What does alignment look like together?
What do we actually value, and what did we just inherit?

AI helped me audit the mess. Not just projects, but patterns.
Not just my calendar, but my codebase.

It showed me where I was still performing, pleasing, and proving.

So I rebuilt:

More signal. Less noise.
More creation. Less reaction.
More joy. Less armor.
More shared time that actually felt like life, not leftovers.

For the Theoretical Computer Scientist in the Back

Brad—this part’s for you.

You're right to be cautious.
The AI hype cycle is packed with vaporware, TED talk charisma, and theater.

But what I found wasn’t about AI’s capability.
It was about mine.

AI didn’t unlock a superhuman breakthrough.
It let me debug my internal code—faster.

I don’t outsource thinking. I sharpen it.

This isn’t about AI being smart.
It’s about having a tool that doesn’t flinch, doesn’t flatter, and doesn’t care if I’m scared to look.

You don’t have to trust it.
But you can use it—to model, to reflect, to verify before you sink another decade into a workload fairytale that won’t ever resolve.

Want to Try It?

Start with these prompts. Run them through a model—or your own skeptical logic parser. Just run them.

Toleration Audit

What am I tolerating that quietly drains me?
What responsibilities no longer match who I am?
What systems am I carrying that should be carrying me?

System Debug

What beliefs about work and worth am I still running on autopilot?
What would I stop doing if I actually trusted myself?
Where am I still trying to be essential?

Rewire Plan

What would a fulfilling day feel like?
What needs to change—financially, emotionally, practically—to live it?
What can I verify with facts instead of fog?

Final Thought

Newport named the pattern.
But I was already on the other side.

If you’re still stuck in the loop—still trying to “clear the decks,” still chasing rest you feel like you haven’t earned—consider this:

Maybe you don’t need a break.
Maybe you need a system reset.
Cleaner code.

I didn’t kill the organ grinder.
I just stopped dancing like a worm-monkey.

— Ray

P.S. Whether you’re in the loop, breaking it, or already out—drop a note. Let’s compare debug logs.