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Not necessarily, Not always, and Not in every situation
Some work needs to be studied and planned well in advance.
Other types of work could tolerate the "trial and error" approach ... or simply shoot up in the air, and hope it wil hit !!
Another example, is to to get your feet wet which I agree with, but not to ask someone to jump from12 yards into a swimming pool to find out if it has water in it or not !!
I come from IBM school of thought where time/money/effor invested in proper planning will pay back in smooth, trouble-free and minimal cost/effort/risk implementation work later on
But as I said in the begining ... it all depends
So, what is your situation so that I can give a targeted answer specifically to your situation !