
The Deal We Made Before AI
Journey through the bargains we've already struck with technology, and find clarity about the choices AI now asks us to make.
The Brief
This article traces the long history of trading personal data for convenience, from 1998 grocery loyalty cards to modern AI systems. It argues that the privacy-for-convenience bargain predates AI and that understanding these accumulated trades is necessary before negotiating new ones.
- What is the privacy-for-convenience trade described in this article?
- The article describes a pattern of incremental exchanges: giving location data for directions, purchase history for recommendations, social connections for networking, and reading habits for book suggestions. Each individual trade felt reasonable, but the aggregate amounted to a much larger surrender of personal data.
- What did Scott McNealy say about privacy in 2000?
- Sun Microsystems CEO Scott McNealy said 'You have zero privacy anyway. Get over it.' He was mocked at the time, but two decades later the statement reads less like arrogance and more like prophecy, according to a 1999 report in Wired.
- How does AI change the data-for-convenience dynamic?
- AI amplifies the same trade but at a faster pace. What took tech companies years of accumulated data, AI can now infer from a single conversation. The exchange offers more capability for more data, more personalization for more modeling, and more convenience for deeper inference about identity and behavior.
- Can the privacy deals we have made be renegotiated?
- The article argues that these trades were not permanent in the past and are not permanent now. They can be renegotiated, but first people must see them clearly and recognize that terms were often set while they were busy enjoying the benefits of convenience.
I was cleaning out a drawer last year when I found my first loyalty card. A grocery store rewards program from 1998, back when the barcode was the cutting edge of personal data collection. I remember signing up without a second thought. Free groceries for letting them track my purchases? Who wouldn't take that deal?
Each card was a contract we signed without reading
That moment in the checkout line was the first of a thousand invisible handshakes. I gave my location to get directions. My purchases to get recommendations. My social graph to stay connected. My reading habits to find new books. Each individual trade felt reasonable. The aggregate trade was something else entirely.
The Slow Seduction
In 2000, Sun Microsystems CEO Scott McNealy said, "You have zero privacy anyway. Get over it."1 He was mocked at the time. Two decades later, his statement reads less like arrogance and more like prophecy.
The thing about seduction is that it works because the services were genuinely useful. Google Maps really did get me where I needed to go. Amazon really did surface books I wanted to read. The cost was invisible precisely because the benefit was tangible.
The balance was never static
By the time anyone thought to read the fine print, we'd already signed away the library.
The New Deal on the Table
AI amplifies the same dynamic, but the pace has changed. What took tech companies years of accumulated data, AI can now infer from a single conversation. More capability in exchange for more data. More personalization in exchange for more modeling. More convenience in exchange for more inference about who we are and what we'll do next.
The dilemma isn't new. It's just faster.
I still have that loyalty card in my drawer. It reminds me that we've been making these trades for longer than we like to admit. The deals weren't permanent then, and they aren't permanent now. They can be renegotiated. But first, we have to see them clearly.
The question isn't whether we've traded privacy for convenience. We have. The question is whether we did it consciously, or whether we woke up one day and realized the terms had been set while we were busy enjoying the groceries.
References
Footnotes
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He spent two years proving AI needs a contradictory voice. Then he quit to study poetry.

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I told you to find your room. I didn't mention the cost of leaving the one you're already in.

Beware of Frankenstein!
Quit trying to save money with spare parts.
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