Once you’ve become really good at doing something, then what? I mean really good.
For the purposes of this musing, I’ll define “really good” as ‘when the thing you are doing becomes so natural, so effortless that you stop thinking about the thing that you’re doing.’
When that happens, then what?
Do you keep doing it ad infinitum?
Do you keep doing it until it behooves you not to?
Do you stop, and look for something new to do that might accomplish the same goal?
Do you stop, and move on to something entirely new?
Do you not even ask yourself this question?
I’m wondering about this both in a general sense, but also with specific reference to Jewish life.
When we can identify Jewish things we do that become rote, effortless, mindless, and entirely on the keva side of things, what should we make of this?
Rabbi Jesse Paikin 
I’d open (maybe unhelpfully) by saying that it’s hard to generalize. “Rote,” “Effortless” and “mindless” are all pretty different, right? I mean, those who believe in “prayer as mantra” would say that mindless is exactly what we’re going for, but that that’s different from rote. So, mindless prayer MIGHT be a good thing, but mindless teaching probably never is.
So – did you have a specific example in mind?
Jesse,
If you can answer your own question, I’d be interested in publishing it in my upcoming philosophy zine on moral relativism. (Not necessarily “for” or “against,” just “on”.) I don’t know how else to contact you. Love your photos, too.
Tucker