You are the one who says yes before the whole plan exists. Not because you are careless — because you have noticed that waiting for certainty usually means waiting forever, and you would rather be moving while you work it out.
That has cost you a few times. You know which ones. But it has also given you a life with more in it than a more careful version of you would have collected, and you would not trade the shape of it.
What you are still learning is that beginning again is not the same as running. The Fool who keeps starting over is different from the one who starts because something genuinely new is in front of him. You usually know which is which. Trust that.