Brad was telling us yesterday of a management training exercise he attended while at AT&T. They took a bunch of suits rock climbing, and Brad being somewhat atheletic was doing pretty well getting up and down the rock face.
So the instructor told him to try doing it blindfolded.
You would think that would have made it a lot harder, but the reality was, climbing blindfolded made it even easier--because you didn't waste time trying to "overnavigate" your path by sight. You just reached out for sure footing and pulled yourself up. You didn't pick out a rock or a line up the face that "looked ok" which was probably misleading anyway.
Making decisions about your next step is always going to involve some risk. If you think you've calculated all the variables, you've probably overthought it and maybe to your own detriment. Sometimes you just need to take the plunge sometimes, whether its getting creative (and a bit risky) with a marketing strategy, feature development, or your own career.