There's a genre of blog posts that frequently get linked on Hacker News, which are basically attempts to explain why problems that seem conceptually simple are very complex when attempted within an organization.

I'm referring to these as Chesterton's fence posts. There's an analogy to the eponymous principle: those not directly involved in the day to day materiality of commercial software production cannot see the looming network of past failures that has led to the current abundance of caution. Of course, one could still make an argument that some of these temporal drags on tasks completion are due to organizational dysfunction rather than prudence.

How many Microsoft employees does it take to change a lightbulb?

I could do that in a weekend!

The unexpected complications of minor features

Simple software things that are actually very complicated

Reality has a surprising amount of detail

A similar, famous example on HN is that of Dropbox, famously dismissed as something trivially accomplishable via rsync -- a fact that's not wrong, but is nonetheless missing the point.