Help me out with something: In considering the outcome of a project, we usually have a pretty firm idea of what success means. The question is integrated directly into GTD, in fact, and it makes sense. After all, why are you doing it, and how will you know you're done.
But there's a trap. If your metric is binary, then you've set yourself up for suffering during the entire thing. You'll be forced to ask yourself at each step, "Will I be successful?". If it doesn't look to be so, you'll be unhappy. But the point is that continual questioning along the way spoils the fun a little bit. (This is what I was getting at in in Coffee, Booze, And Sex: Is It The Journey Or The Destination? - life is in the process.)
What about if things are looking good? Well, you're still attached to the outcome, so the satisfaction of being on target is short-lived. Unless you're certain, you'll keep coming back and questioning. As I understand it, this is built into Buddhism (details, anyone?) See, for example, The origin of suffering is attachment, which identifies craving and clinging in particular.
So here's my question: How do we balance a clear craving (wanting a project to work out in a certain way) with desire to enjoy the life of the thing (being in the moment)? Let's be honest, if I'm putting together a proposal, I want it to succeed, and I'll be disappointed if it doesn't. Is it weakening our effort to even consider not reaching the goal? how do we handle this case? One thing I've been experimenting with is spinning it at the end. "It didn't work out the way I wanted/envisioned, but what I learned/enjoyed/experienced was..."
I'm curious: What do you think? How do you enjoy the ride while simultaneously managing your binary desire?