“I was feeling bad about not meeting my deadline, but then I asked myself, ‘What have I been doing instead?’ And realized that, really, I’ve been on the right track. I just need to tell myself a more encouraging story.”

People ask each other how things are going. The polite and motivational response is some variation on “Great” – polite, because maybe the person asking doesn’t want a long answer, and motivational, because hearing ourselves declare that things are going great can improve the chances that they will.

However, taking the question literally raises another question: How well do any of us know how things are going? In a day, the news comes in. Expectations get met (the meeting felt good); expectations get dashed (the computer crashed again). Do the day’s ups and downs reveal how things are really going? The answer depends on time scale. They reveal how things are going today but not how they’re going this month, this year, this lifetime, or this millennium.

Mind Readers Dictionary: The Podfast : Play in Popup

Mind Readers Dictionary : Play in Popup

Some of today’s news — events we count as significant — prove to be tomorrow’s insignificances. Some of today’s insignificances turn out to be tomorrow’s big news. What with some aspects of the future being irreducibly uncertain, and us not being able to tell which aspects those are, today’s news is a weak and even distracting clue to how things are going. Tomorrow, one could discover cancer or win the lottery.

Assuming the questioner means to ask how things are going in general, a literal response might be a cheerful “Haven’t a clue!” or an annoyed “How would I know?”

The annoyance would be understandable. It really is a bummer that we don’t know how things are going. If we knew, we could prepare for the successes and failures in store for us. We could manage our expectations with greater precision and efficiency. We could stop expecting what won’t happen and start expecting what will. Instead, we cling to some expectations that will be frustrated, and we let go of expectations that could be met.

Some say that, short of knowing what the future will hold, we’re best off not clinging to any expectations at all – when an expectation isn’t met, we should just let it fall from our grasp like a cigarette butt and move on. But most people are lousy at not clinging, and for good reason: Expectations motivate us. Clinging to our expectations is how we stand our ground and ground our standards. We’re glad Gandhi clung to his expectations.

Ideally, we would cling to the expectations that motivate us to do possible and good things and treat like cigarette butts the expectations that motivate us to do impossible and bad things. But we can’t tell with exactitude what’s possible or impossible, nor can we know with certainty what will turn out good or bad. We all struggle with the future’s irreducible uncertainty – some of us more acutely than others. Cancer patients face both cure and death. Should they fight not only the disease but also the temptation to cling? Who among us would not cling to a cure?

To match reality’s multiple possible futures, others counsel that we should cling to multiple alternative expectations. Rather than have no expectations, we would collect many. Rather than committing to a single “official future,” we would invest in several. We would go on fork-finding missions into the future, embracing what’s out along the many branches of possibility. The more expectations we have about how things are going, the less likely we are to cling to any one of them, and the more prepared we’ll be to make good use of whatever our circumstance deal us.

Quakers say, “Build to last one hundred years; be ready to leave tomorrow.” F. Scott Fitzgerald said, “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to act.” Note that intelligence, by this standard, is not just being able to hold opposed ideas, which can lead to paralysis or diluted focus. It’s also being able to act on them, to invest in multiple scenarios – in a word, to hedge. How can we cultivate this kind of intelligence?

As Aristotle noted in his “Ethics,” the difficulty with cultivating wisdom that doesn’t come naturally is getting started – taking the first uncomfortable steps out of the comfort zone in order to get to a more profound comfort zone. Typically, motivating a move out of any comfort zone is done with some kind of compensatory introductory offer or premium, the equivalent of the toasters banks used to give to people when they opened a new account. What toasters do the wise offer to those clinging to one expectation so as to entice them to invest instead in a diversified portfolio of expectations?

A common approach is to encourage the easiest and most immediately rewarding hedges – positive expectations as hedges on negative ones. Think your boss hates you? Expect your boss to tell you you’re fired next week? Tell a different, happier story. What if your boss really likes you? Imagine and assume she does. There’s more than one way to interpret the future, so turn that frown upside down.

This is a wonderful introductory offer, a great promotional exercise to help one begin to limber up one’s expectations. Naturally, many people stop there and assume that the solution is merely to hold optimistic expectations instead of pessimistic ones. That’s not being limber, though; that’s swapping one cling for another. Both optimism and pessimism are forms of possumism – playing possum to avoid having to think about alternative futures. Maybe the best sequence is from pessimism to optimism, but then to abandon both possumisms for a life on the hedge, imagining what could happen from many angles.