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Dear Tech Editorial

Opinion & Commentary

3 editorials published
What this section is

Most of Dear Tech explains things: how a tool works, what a scam looks like, which settings to change tonight. Those articles try hard to stay neutral. This section doesn't.

Editorials are arguments. They're where I say what I actually think about where AI is heading, who's profiting from the noise, and which parts of the story the industry would rather you skipped. They're still sourced and still checkable — the difference is that a conclusion is being drawn, and it's signed.

If you disagree with one, that's a reasonable outcome. Tell me why — the good arguments end up shaping the next piece.

All Editorials
The privacy tax is paid in evenings
Opinion Privacy Self-Hosting
The Privacy Tax Is Paid in Evenings

I lost a night to a single backtick in a config file. The out-of-the-box version would have taken four minutes and asked for one small payment I wasn't willing to make. On blast radius, the oopsie economy, and why self-hosting isn't safe — it's small.

S
Sheldon · Jul 25, 2026
11 min read
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Citizen 11574 — the assistant paradox
Opinion AI Privacy
Citizen 11574: I Want a Real AI Assistant — And That's Exactly the Problem

An assistant that doesn't know your life isn't an assistant — it's a timer with a personality. But knowing your life means holding it, and we've spent twenty years proving we do anonymization theater instead of security. On day runners, Citizen 11574, and what would have to be true.

S
Sheldon · Jul 25, 2026
10 min read
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The Data Tsunami and the Noise Machine
Opinion AI Future Privacy
The Data Tsunami and the Noise Machine: Where AI Is Really Heading

The data trade we quietly normalized is about to scale beyond anything we agreed to — and the loudest voices explaining it to us are salesmen. On car-lease letters, glorified search bars, and why the fragments assemble themselves.

S
Sheldon · Jul 12, 2026
9 min read
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More commentary in the works

Editorials publish when there's something worth arguing, not on a schedule. In the meantime, the reported side of Dear Tech — guides, safety alerts, and the AI Watch series — updates far more often.

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