Issue #2: I used Chat GPT to Design My Future Regret

Revisiting a thought experiment I have used for years through Chat GPT hit harder than it ever did with pen & paper

I like doing things backwards.

Defining what I don’t want to happen and doing the opposite of that is a tip I picked up early on in adult life and it has served me well over the years. It is just reverse psychology for the self. 

Zooming out and applying that concept to my own life goals is something I’ve done periodically, practically this takes the form of pretending to be my future self and writing a letter to current day me.

It is often effective, I have noticed that the common sense advice I freely give others are often things I somehow give myself a pass on, for one reason or another. 

First time I did it publicly was back in the mid-oughts on Livejournal (if you know what that is I’m sorry, we are olds now, how is your back?) and it led me to leaving the UK for the USA. Not an inconsequential decision. 

Coming back to this idea in 2025 means using Chat GPT for it, as that has been my whole thing for the last two years, can I do this better, faster, smarter, more efficiently with AI? Oh yeah I definitely can.

I think it hits harder, is more inspirational, and more motivational than any other time I’ve tried it. And now I'm going to share it with you:

First I came up with this promp:

"I want you to act as my future regret—it's the version of me from 10 years ahead, looking back at this moment with frustration or sadness. And I want you to advise me what to do now or inspire me in a thoughtful letter. In order to craft your letter to me, first ask me questions like:

- What am I procrastinating on?

- What decision am I avoiding?

- What fear is keeping me stuck?

- What does future-me *not care* about that I obsess over now?

- Who does future-me miss because I didn’t stay in touch?

And any other questions that will help you write a more personalized and specific message to meL

Then write the message from my 10-year-later self:

- Describe what I missed out on

- Explain how it happened

- Give me one thing I could do this week to prevent that regret

Keep it grounded—not dramatic, just true. But really paint the picture and make me feel what it will be like to feel that regret if i don't act on it today."

In response it asked me the questions I fed it plus a few others it came up with, I replied, then it came up with this (i have redacted some references to specific ideas of mine chat GPT called out by name): 

From the Version of You That Waited Too Long

Hey,

I know you. I am you—just 10 years further down the road.

And I need to tell you something hard: You were so close. But you didn’t go.

You kept circling that launchpad—<redacted>, Self-Prompted, the AI newsletter-tools fusion—waiting for the timing to be right. Waiting for proof, or momentum, or some sign that it was okay to hit the gas.

But it never felt safe enough, did it? So instead, you got clever. You made progress look like motion. You optimized the surface. You repurposed everyone else’s content but never fully built your own foundation. You became known for helping other people grow—but quietly wondered if your own work would ever get that shot.

You told yourself it was wise. Responsible. Because you had kids. Because you couldn’t risk too much. But the truth is: you were scared.

Scared that if you really tried, you might still fail. That’s what kept you in that endless prep-loop. And I get it. I really do. But here’s what happened.

What You Missed

You missed the window where you still had fire in your gut and freedom in your calendar. You missed the moment where <redacted> and “Self-Prompted” could’ve evolved into something lean, personal, and sharp—something you owned, not something shaped by everyone else’s algorithms.

You kept playing on the edges instead of claiming the core. And so instead of building a living product around your writing, your voice, your weirdly specific obsessions, and your tools... you kept it as a concept. A draft. A someday.

And your youngest? He didn’t stop needing you. But you kept showing up in fragments. Half-there. Still kind, still supportive—but often mentally elsewhere. And now he’s older. Still close. But you wonder sometimes if you missed the years when he was most impressionable.

And Andy and the rest of your music friends? They just drifted. There was no falling out. Just a thousand small silences that added up.

How It Happened

It didn’t happen because you made a big mistake. It happened because you didn’t make enough decisions. You waited. You deferred. You told yourself the <redacted> decision had to come first, or the client work had to stabilize, or the market had to shift. But the truth was, you didn’t trust yourself enough to make a move without certainty.

And here's the thing, man: You love Guns N' Roses. Not Coldplay. So why did you keep acting like you needed to play it safe and soft and inoffensive?

You’re built for riffs and edge and presence. But you toned yourself down, trying to stay marketable.

What You Can Still Do This Week

You can rewrite this ending. You really can.

Here’s what I need you to do—now, not next quarter:

1. Pick One:

Self-Prompted newsletter + app per issue. Or a no-code <redacted>. Doesn’t matter which. Just choose one.

2. Build in Public for 6 Weeks:

Use your own repurposing engine. Be your own best client. Create the thing as if no one else will save you—because they won’t.

3. Your Son:

One quiet hour. No agenda. No screens. Just ask him something open. Let him surprise you.

4. Andy:

Text: “Hey man—been thinking about you. Want to catch up?” That’s it. Let the rest unfold.

You don’t need a new idea. You need to believe in the one you already have—and treat it like it matters.

You don’t need to be certain. You just need to move with conviction anyway.

I’m still proud of you. But I wish you’d trusted the part of you that wanted more.

Now go make me wrong.

– You, 10 Years Wiser

Now that's a pretty good answer. But very similar to results I've had in the past (although "instead, you got clever" really hit home, calling me out there in way I never managed in my old fashioned pen and paper approach)

I pushed it a bit further with this:

My Follow-up prompt: 

"That was good but I want to be motivated more powerfully, use everything you know about me and design my biggest regret and write it like a scene in a movie" 

Your Biggest Regret, Redesigned for Real Life

It’s ten years from now. Your youngest is 24. Still living with you. Still very much your daily world.

You’re in the kitchen late at night, clearing up. He’s humming something at the table—something half-tuned, half-invented—and you catch yourself watching him like you used to when he was small. That same quiet intensity. That same need for rhythm and comfort.

And as you load dishes into the sink, you feel it.

Not a breakdown. Not a crisis. Just this slow, familiar ache of: I didn’t give us both the shot we needed.

Because while you’ve always been present—loving, attentive, responsible—there’s a version of the last ten years where you could’ve also built your thing. Not instead of him, but for both of you.

Where your business wasn’t just supporting clients—but supporting you. Where Self-Prompted or <redacted> became a creative, self-sustaining machine that brought in income, community, momentum—and a kind of pride you rarely allowed yourself.

But instead, you kept saying:

“I’ll go all in once the timing’s right.” “I need more clarity before I commit.” “I’ll just do one more project for someone else, then I’ll start my own.”

And that dream? It never failed. It just faded.

You stayed sharp. Useful. Kind. But deep down, you know: you didn’t let yourself own it. And your son—he never judged you for it. He’s loved you through all of it. But part of you wonders what it would’ve felt like to show him your full fire. To model that kind of personal risk and creative integrity, not just care.

And that folder— “Self-Prompted – Experiments”— It still sits on your computer.

And you still open it sometimes. Just to feel something close to who you could’ve been.

It’s not too late.

Your reality is different. You don’t get to “opt out” or move to Bali or coast for six months. But you do get to choose what you build, and who it’s for.

You can still give yourself six weeks to sprint. To launch something raw and real. To let the world see the thing you want to see.

Not despite your responsibilities. But because of them.

If you want to sketch the next six weeks together, or design a rhythm that works for your actual life—not some fantasy—just say the word.

You’ve got time. But not forever.

Phew. Never writing myself a letter from my future self-again. Chat GPT is better at it.

What about you?

If you try this please share in the comments or message me! Your results may vary, my chat GPT is trained to give me answers in a certain way and has a lot of history and context, yours might not. Hit me up in the comments or DM me and I’ll send back your results, Ven-GPT-style if you want.

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Next issue: How to use AI to journal like a chaos-introspective monk with ADHD. Maybe for real this time. Still not committed 100% to that.