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Outsourcing your weaknesses makes sense in the abstract as a comparative advantage play; but think of Coase as a counter. Why are there corporations at all, and not exclusively one-off networks of specialists? The most popular answer is transaction costs, and I think something comparable has bearing on this question.
The benefit of getting better at your speciality could outweigh the transaction costs of outsourcing your non-speciality.
Continuing the earlier example, it may be trivial to solve my math deficiencies by market-contracting whatever the math need is, but that's assuming I'm capable of knowing what needs to be contracted or understanding its proper scope. If I'm an F at math, the prospect of being able to make the requisite contract becomes tenuous.
You probably don't need an A in math to spot a great math person and you could always outsource the hiring to a trusted math friend (assuming one of your talents is finding such friends). You might get as much benefit discussing something with an outsourcee as you do having it all in your own brain.
this territory is moderated