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Good discussion topic because as you write it's a balance between learning the more powerful tool vs investing time.
One should also consider that when moving up that ladder, one might find fewer colleagues to collaborate. So there is also a balance of better tool vs more lonely ecosystem.
https://en.wikipedia.org/wiki/Paul_Graham_(programmer)#The_Blub_paradox
I wonder what all I'm missing because of this... and when it's OK to settle?
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