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But how long do you spend setting up the time-tracking process that ensures you don't exceed you 20% time frame in a given day/week/month/year? And don't you also have to track that time as tool-time? How do you even do that without your time-tracking system up and running?!

Facetious, i know - but this is a confessional, the OP is basically saying he isn't capable of separating his time out like that - he would get drawn into the optimization process - like an addiction and blow past he's 20% allotment.

If a person is able to maintain the don't go over 20% of your time on optimization then by definition they aren't dealing with the same issue as the OP.

But how long do you spend setting up the time-tracking process that ensures you don't exceed you 20% time frame in a given day/week/month/year

Well, lots of devs have 10 sided dice...

But seriously, this could be determined stochastically per hour or pomodoro.

And for that matter, doesn't 1/5 of your time spent like this sound like you went down the rabbit-hole already?

That depends on what your expected payoff is.

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