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The easiest bug in the tax code to explain to programmers has got to be the backdoor Roth IRA.
I've been helping my siblings with some personal finance decisions over the last few years and they asked me how I knew so many random things about taxes and the different investment account options and retirement math.
There are many problems to which "If it's silly and it works, it isn't silly" might apply. These sorts of problems come up surprisingly often in software engineering. It's tempting to reach for complex solutions and we need to constantly remind ourselves to keep it simple.
Web performance is unique compared to other types of performance work, largely due to the fact that we need to serve Javascript code to browsers on nearly every request to make sites interactive.