Learning In Circles
Having a lot of experience in a specific domain only works a little from preventing this repetitive tendency to impart the same set of wisdom, albeit dressed up in different coatings/flavours.
And this is more noticeable when learning from the same person over the years share their insights and frameworks again and again, each time with minor variations, rarely with fundamentally new substance.
Now this repetitive tendency can be perceived as a negative thing but it is not really, at least not to my understanding. It's just boring and doesn't inspire any sort of spark to keep at it if one is on the other side trying to gain knowledge about the said domain.
I think mechanical domains like programming suffer most from this. And I'm assuming when starting out, in terms of deciding whether to keep at it or not, there's a barbell outcome of sorts where most people drop off early, overwhelmed or disenchanted, and the rest who stick around for a while eventually internalize the fundamentals so deeply that the repetition no longer feels repetitive. Just constant reinforcement.
Non-mechanical domains like art are more populated than technical disciplines, both at the surface and higher up levels, given how accessible they appear at first glance.
You can draw badly, write poorly, paint incoherently and still still be embraced by the medium. There is less immediate friction, fewer hard rules, and less obvious failure compared to something like code that refuses to run.
However, the same principle does apply similar to mechanical domains.
The cost of mastery remains high regardless of how approachable a field looks at the beginning.
The early freedom eventually gives way to constraints, technique, and discipline. For me, it's the technical aspect of art that I find the hardest to wrap my head around in terms of mastery. Example here is lacking the ability to actually create the impeccable taste that one has to see what is good. Say admiring a masterpiece like Michelangelo's David yet struggling to sculpt a basic human form without it looking lopsided and amateurish.
Without technical skills, replicating what's perceived up there in one's head to down here in reality takes on a distorted caricature of the original vision and what emerges usually resembles the idea only loosely, stripped of its depth and coherence.
I don't think we appreciate enough how much of skill acquisition is actually just developing the capacity to endure repetition without needing novelty as a reward.
The silver lining, I think, is that repetition paired with time gradually transforms the boring sameness into nuances, having this subtle eye to see the finer details of the invisible decisions shaping the visible result.
At some point, the same advice is also just reference point to dive deeper into unexplored layers of meaning, at least that's how I prefer to interpret it, peeling off the layers of an onion, so to speak, works sometimes.
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