Do the simplest thing that could possibly work

I think this works in simple domains. After working in big tech for a while, I am still shocked by the required complexity. Even the simplest business problem may take a year to solve, and constantly break due to the astounding number of edge cases and scale.

Anyone proclaiming simplicity just hasnt worked at scale. Even rewrites that have a decade old code base to be inspired from, often fail due to the sheer amount of things to consider.

A classic, Chesterton's Fence:

"There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road. The more modern type of reformer goes gaily up to it and says, “I don’t see the use of this; let us clear it away.” To which the more intelligent type of reformer will do well to answer: “If you don’t see the use of it, I certainly won’t let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it.”"

At least half the time, the complexity comes from the system itself, echoes of the organizational structure, infrastructure, and not the requirements or problem domain; so this advice will/should be valid more often than not.

> the organizational structure, infrastructure

Those are things that matter and can't be brushed away though.

What Conway's law describes is also optimization of the software to match the shape it can be developped and maintained with fewer frictions.

Same for infra, complexity induced by it shouldn't be simplified unless you also simplify/abatract the infra first.