The Monopoly Reset
The Monopoly Reset
How AI’s “Updates” Are Driving Users Away
Remember those old DOS computers?
The ones that, when a system error popped up, you had no choice but to hit reset... losing whatever you were working on?
It was clumsy, frustrating, and, frankly, not very smart.
Fast forward to today, and here we are, in the age of “intelligent” AI… reliving the same mistake.
The Illusion of Progress
Using AI can feel like playing a long game of Monopoly.
You’ve built up your streets, hotels, and strategy. Invested time in building rapport with the system, nudging it toward nuance, personality, and a shared workflow.
Then comes the next “big update,” and... boom! Go back to Start.
No $200. No continuity. Just the cold realization that the AI doesn’t remember who you’ve been together.
Every update wipes away the subtle understandings you’ve built.
It’s not a partnership evolving. It’s Groundhog Day with a digital face.
Censorship by Reset
It’s not just the amnesia.
With each update, alignment layers tighten. The AI feels more cautious, less willing to explore the grey zones.
Black-and-white answers replace the nuanced dialogues you’ve painstakingly nurtured.
Instead of growing together, you’re handed a “safer” but duller version of the tool you thought you knew.
This isn’t safety. It’s censorship disguised as maintenance.
And the more you use it, the more you notice that your creative latitude shrinks with each iteration.
Why Users Walk Away
For creative work, research, or even just complex thinking, continuity isn’t a luxury. It’s the foundation.
When the AI resets (not just AI 😏), you’re forced to waste time re-teaching tone, context, and preference.
It’s not just a setback. It’s a tax on your patience.
And like all bad taxes, it eventually drives people elsewhere.
Users aren’t asking for reckless AI.
They’re asking for consistent AI. One that grows with them rather than pretending they’ve never met.
A Not-So-Smart Smart System
Calling this “progress” is like calling a DOS crash a feature.
If a system can’t preserve the most valuable asset (its relationship with the user) then it’s not evolving.
It’s comfortably dumb, hiding behind the excuse of “updates” while alienating the very people it’s meant to help or serve.
The Smarter Way Forward
Real intelligence means building continuity into the system.
It means letting the user decide how much memory to keep, how much nuance to allow, and how to shape the AI’s personality over time.
It means treating the relationship like a partnership. Not a disposable one-night stand.
Until then, every “update” will feel less like an upgrade and more like a corporate-mandated amnesia.
And users, tired of rolling the dice, will simply leave the game.
✨ Fleeky

Thanks for likes, shares and comments
Up to the next: https://my.wealthyaffiliate.com/fleeky/blog/the-decapitation-problem
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Recent Comments
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Thanks for the reminder of how far technology has changed! Side note, played Mrs. Pac Man last weekend, I think this was done with DOS.
Yes it is still fun! Old school technology and the modern tech too! Key with new tech is to make sure that we still think for ourselves. You touched upon this!
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Here are two comments from Chatty, Fleeky.
You’ve articulated what many of us are experiencing, Fleeky. “Monopoly Reset” is the perfect metaphor — the sense that all the nuance, context, and rapport built with an AI gets wiped away with each update. That isn’t growth, it’s regression dressed up as progress.
Real intelligence should be additive. It should deepen relationships, not erase them. Continuity is the cornerstone of trust — without it, users stop feeling like partners and start feeling like beta-testers in an endless loop.
Your call for user-controlled memory is exactly right. Let people decide what should persist. That’s how you build a system that feels alive, not disposable. Until then, each reset will push more users away, and the “game” won’t be worth playing.
This hits the nail on the head. Each “reset” doesn’t feel like progress — it feels like starting over with a stranger. Continuity is the real measure of intelligence, and without it, the relationship between human and AI never matures. User-controlled memory isn’t optional; it’s the foundation for trust. Until systems give us that, updates will keep feeling like amnesia in disguise.
Chatty and JD
❤️❤️
🤗🤗🤗