Technical Debt. Whys, hows and whens.
I prefer to be in control of a situation over acting in a reactive fashion. This leads me to make decisions in another way. Way earlier. In terms of how to produce good software, I would choose a way which allows me to deliver often, scope out or change my mind equally often and use that feedback [data] to guide my future decisions.
Here is another article from Martin Fowler on Technical Debt.