I've thought a lot about optimisation of the last decade, always looking for better tools, productivity systems, and efficient ways of doing many, many, things. Until a few years ago when I started thinking about over-optimisation instead.
I now believe I've been using optimisation as a crutch, to procrastinate from doing the important, but scary, things in life.
Optimising up front is usually a bad idea, it's a worse idea for every day life. Optimising should have a clear outcome of freeing up time. If it doesn't, maybe you shouldn't be spending your time on that?
Maybe that time is better spent on the real work, or life?
(Update: This is a life strategy worthy idea.)