Risk Aversion and Prudence

The prudent thing to do is to take your time, evaluate all of your options, build it the right way, and do it once.

The bold thing to do is to make a first pass quickly, pick a path then evaluate, build as many times as necessary improving every time.

Often I am faced with a collision of these ideals- my instinct is to move boldly, experimentally, and progressively. Yet there is a time and place to be prudent, to be safe, and to preserve (and construct) solid ground.

Surely one is no better than the other but how then do two professionals, each entrenched in their own way of thinking, find common ground?