Maybe a nonsequitur but in grad school I was in a study group which naturally split into two. In one group (mine) we'd read a problem and immediately charge in, sometimes have to backtrack, and meander around until the answer revealed itself. In the other they would plan everything out, and figure out what they needed to do, and from that the answer would reveal itself and they would write it all down.

The interesting part is neither group really finished the problem sets faster than the other. Individual problems my group could, if we knew or guessed the right path immediately, be faster. But over the span of a 10 question p-set it would mostly come out in the wash and both groups would finish in roughly the same amount of time.

I often think back on that when reflecting on how I still work that way years later.

I think it can be OK to have a risk if that's the plan of trial and error.

It's when you don't know, or have an inkling of what's wrong but aren't sure where to start probing, that it's better to have a plan or call in experts in an unfamiliar area.