Second guessing one's decisions

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I find myself torn when reviewing the descisions that I have made as to how to proceed with the next chapter in my life. I used the "dust in the cosmic wind" style of living for most of my teens and twenties. This is when you delay and delay setting a course of action until finally the Universe narrows yuor options down to either two or one and in rare cases the Universe leaves absolutely no choices on the table. As I have started my 30's I find myself agonizing over the choices that have taken me to whatever mental and emotional place I find myself at the time. I twist it this way and that trying to find the alternative path which would lead me to my ultimate goal. Then I can't stop thinking about whther or not I have given the previous choice ample time to clear away all of the smoke and mirrors and to reveal where the path leads, so I can then ascertain if the choices I have made have led me to the solution that I envisioned or some thing totally different. How do you shut your mind down and make it stop playing devils advocate?