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INSIGHTS3 MIN READ

The Monopoly Reset

Fleeky

Published on August 28, 2025

Published on Wealthy Affiliate — a platform for building real online businesses with modern training and AI.

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.

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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

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Up to the next: https://my.wealthyaffiliate.com/fleeky/blog/the-decapitation-problem

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