You Are Not Ruthless Enough
Every time you throw in a quick fix for something because it’s Getting Late(tm), stop and see if you can fix it correctly right then. Pragmatism says it might not be possible in the time remaining, and that’s ok; “Real artists ship” and all that but a ruthless artist will fix the problem first thing in the next release so they can keep shipping again and again and again.
In other words, don’t accumulate technical debt.
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[...] we burn development and support time without having much to show for it. It also makes it harder to be ruthless. So I question the wisdom of having yearly updates to both OS X and [...]
Exactly.