You’ve probably noticed that I’m fascinated by tough judgment calls, which I define as important speculative decisions that can’t be hedged. They’re speculative, because all available options have potential benefits and costs. They can’t be hedged, because the appropriate responses to the different options work at cross-purposes to each other; they are mutually undermining. Examples include that it doesn’t work to both persist and give up at the same time, to announce a problem and at the same time conceal it, to try to change something and simultaneously accept it, to pay attention to something and try to ignore it, to demand perfection and relax your standards, to be realistic and aim high.

The Quakers say, “Build to last a hundred years; be ready to leave tomorrow,” and they’re right, of course. But it’s hard to do both at once. It’s this inability to hedge that makes us yearn for the “wisdom to know the difference” that the serenity prayer evokes — the power to distinguish good bets from bad ones as easily as distinguishing black from white.

Mind Readers Dictionary: The Podfast : Play in Popup

Mind Readers Dictionary : Play in Popup

Of all the tough judgment calls one encounters in a lifetime, which kind is the greatest? It depends on what’s meant by “great.” The oldest is whether to be closed or open. Single-celled organisms were struggling with that one 3.6 billion years ago.

Which tough judgment call stumps us most these days? Maybe deciding what we can and can’t change. We invest a lot of sleepless thought, conversation, gossip, and bickering in deciding whether it’s better to accept or change a particular something about ourselves, other people, or our circumstances.

But the kind of tough judgment call that has the greatest effect on our choices is the superintendent of them all: It’s whether to treat a particular problem as a tough judgment call.

When we face a problem, we have two main options: We can treat it as big so we’re forced to deal with it, or we can treat it as small so we can make an easy decision and put it behind us. It’s hard to do both at once, as you’ve probably noticed if you’ve ever been in a group that’s split between people frustrated because they need more time to make a big decision and people frustrated because it’s no big deal and they’ve already decided.

So, how do you decide whether a problem is big or small, whether to doubt or move on with confidence, whether to evoke your powers of careful decision making or your powers of self-assuredness? That’s a tough one.

Or not, depending on that same choice again. This doubt about whether to doubt was first noted by the philosopher Pyrrho (360-270 BCE), who bested the other Greek Skeptics by noting that the proposition that “nothing is known with certainty” is itself uncertain, and that even its uncertainty is uncertain, as is…you get the point.

When it comes to deciding whether a problem is big or small, I have two rules to suggest: The first is to remember that being a good decision maker is not the same as being decisive. Actually, that’s more of a nonrule, a reminder that deciding whether a problem is big or small is a choice even the great decision makers have to make. Many of us think that to great decision makers, all decisions are small and manageable with swift certainty, but that’s true only in fiction. Fiction is written finale first, whereas life is not.

The other rule isn’t much more definitive. Again, it calls attention to the challenge. Like the rule “Buy low; sell high,” it’s more of a question than an answer. Still, I think it helps. I call it the Spin Doctor’s Hippocratic Oath:

When making a decision, call it a tough judgment call. Treat it as big enough to command your attention, care, and respect, so it compels you to remove the positive and negative bias or spin that distorts decision making. Employ your powers of neutral thinking. Take your thumb off the scale.

But then, once you’ve decided what to do, spin the decision as easy, black and white, and obvious. Use the spin doctor’s instruments to surgically remove your ambivalence. Employ the power of positive thinking to summon enthusiasm for your chosen option, and the power of negative thinking to reject the options not taken.

The Spin Doctor’s Hippocratic Oath pivots on the distinction between deciding and having decided, a distinction not easily drawn. It does point out that the two states call for nearly opposite — which is to say mutually undermining — behavior: The only thing as bad as trivializing a decision while you’re making it is fussing over a decision after you’ve made it. The former makes your decisions sloppy; the latter makes it difficult to act on them with self-assuredness.

Be positive when you’re supportive;
be negative when you’re abortive.
When wisdom is sought
it’s neutralish thought
that helps you become smorgasbord-ive.