In a conversation with one of my department chairs this week, addressing a move we're considering making to respond to a state mandate, he asked a variation on "how do we know this will work?"

I responded that we didn't, but that we knew that doing nothing would surely fail, and that the move we're considering seemed the most reasonable choice available. If he had a better idea, I was happy to hear it, but in the past year that this has been on the table (and we've been discussing it and our possible responses), nothing better has come along.

He didn't want to involve his people without a guarantee.

I walked him through several contingencies, outlining the likely (though not guaranteed) consequences of each of several possible courses of action. He agreed, but it was pretty clearly one of those "you're not wrong, but I'm still not buying it" agreements that inevitably leads to foot-dragging and high-minded blowing off. It was the educated-grownup version of "(sigh) whatever."

I've seen this move before as a simple deflection. It's a staple of the passive-aggressive playbook. "I can't possibly act until conditions are utterly perfect in every way. You failed to perfect them. Therefore, my inaction is your fault." But this wasn't that. He wasn't angling for an excuse not to act. He seemed to actually mean it. He needed a guarantee.

So much of managing involves contingencies, shades of gray, and best guesses that I sort of get used to it. Although the blogosphere lends itself to moralistic posturing – as does academic life generally, for that matter – actual situations in all their messy thickness usually don't lend themselves to simple morality plays. It's true that invoking complexity can be a way to evade guilt, but it's also true that things can actually be complex. And when you're used to that, calls for certainty come across as naïve, if not stupid.

They aren't stupid, necessarily (though I'll stand by 'naïve'). They can reflect a history of broken trust and misunderstanding. Or they can reflect a personality type. Or a wildly exaggerated estimate of the cost of failure. Or a susceptibility to hype, or Manichean thinking, or probably a hundred other things.

But whatever their source, they're debilitating, and they make actual progress much harder.

Somewhere between 'optimism' and 'pessimism,' there's something much more useful. I'll ask my more articulate readers for a good word for it, but it's something like 'a willingness to risk hope.' It's forward-looking, yet tinged with the awareness of the inevitability of failures. If you've ever asked someone out, you know what I mean. There's that willingness to take a leap without a guarantee, knowing full well that there's a very real possibility of rejection. If you've auditioned, or gone on multiple unsuccessful job interviews, you've seen it.

One of my pet obsessions is behavioral economics. (I have some pretty pedestrian obsessions.) From what I've read of it, it's apparently pretty well established that most people overestimate the cost of future failure or losses. Accordingly, they'll forego opportunities for fear of failure, or stay with failing enterprises because they're 'safe.' They'll take slow, sure decline over the risk of abrupt failure, even if that risk also carries with it the real possibility of a better life.

Yes, there's wisdom in prudence. But prudence isn't stasis. Sometimes you have to take a deep breath, walk over to the hottie, and hope for the best. If you do it enough, you'll discover that rejection isn't the end of the world. And that the thicker skin and additional perspective you've gained actually makes future successes more likely.

If you want certainty, don't ask her out. She certainly won't say yes. But I don't see the success in that certainty.