Jeff Bailey | Think X

Clippy Has No Clothes

Jeff Bailey — Fri, 03 Apr 2026 00:00:00 +0000

I can’t imagine you’ve never used a Microsoft product. Assuming you have, you may have heard of Clippy. Clippy was a feature of Microsoft Office products from 1997 to 2002 and left an indelible mark on the tech industry as one of the biggest software-based personal assistant flops.

Clippy would pop up on the first run of Microsoft Word and Excel, with a friendly intent of helping you use the products. Its most consistent features included being wrong and unhelpful. If the software industry had used user behavior metrics back then, the Clippy disable button would likely have been the most-used feature in Microsoft products.

Things That Are No Longer True With AI

Jeff Bailey — Sun, 01 Mar 2026 00:00:00 +0000

I’m watching Monarch: Legacy of Monsters on Apple TV, and I got to thinking about things that are no longer true with AI. The jury is still out on whether it’s a good show, but I do enjoy Kurt Russell, and his son isn’t a half-bad actor.

Like other technologies, generative AI (GenAI) has displaced the old ways. Doing math by hand or with an abacus was the way until calculators came along, and then computers. Who uses a physical calculator anymore? And, why didn’t they set Monarch in the 1950s? What a missed opportunity.

What Is the Tardigrade Effect?

Jeff Bailey — Tue, 19 Mar 2024 00:00:00 +0000

A random thought emerged today. Is there a cognitive bias, similar to the Dunning—Krueger effect, but for degrees of weirdness?

I couldn’t find any, so I decided to coin one.

Behold, the Tardigrade Effect.

The Tardigrade Effect

A cognitive bias in which the weirdness of a subject is inversely proportional to the observer’s knowledge of the subject. The more one knows about a subject, the weirder it seems. The less one knows about a subject, the less weird it seems.