It's a shame he doesn't give the origin of this expression in programming. It comes from Ward Cunningham (inventor of the wiki) in his work with Kent Beck. In an interview a few years back on Dr. Dobb's, he stated that as the two of them were coding together in the late 80s, they would regularly remind each other of the principle. Eventually, it became a staple of their talks and writing.
They were cognizant of the limitations that are touched on in this article. The example they gave was of coming to a closed door. The simplest thing might be to turn the handle. But if the door is locked, then the simplest thing might be to find the key. But if you know the key is lost, the simplest thing might be to break down the door, and so on. Finding the simplest thing is not always simple, as the article states
IIRC, they were aware that this approach would leave a patchwork of technical debt (a term coined by Cunningham), but the priority on getting code working overrode that concern at least in the short term. This article would have done well to at least touch on the technical debt aspect, IMHO.
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