I agree with you that personality plays a role. But regardless of which way your personality pushes you:
You can never think enough up front to know all you need to know, or even 95%. You're not omniscient enough, and you never will be. Big Design Up Front fails because of this - you have to be able to iterate.
You also have to know what you're trying to build, and at least roughly how you're going to build it. If you don't, no amount of iteration and experimentation will enable you to converge on a solution. You need to experiment and iterate and explore within at least a sketch of a larger picture, not on a blank canvas.
You can never think enough up front to know all you need to know, or even 95%. You're not omniscient enough, and you never will be. Big Design Up Front fails because of this - you have to be able to iterate.
You also have to know what you're trying to build, and at least roughly how you're going to build it. If you don't, no amount of iteration and experimentation will enable you to converge on a solution. You need to experiment and iterate and explore within at least a sketch of a larger picture, not on a blank canvas.