Last week I discussed the relationship between the questions “How can I succeed?” and “Can I succeed?” The two questions form a loop.

In one direction, ambition inspires you to ask, “Can I succeed?” To answer that question, you ask, “Well, how can I succeed?” Then you explore particular plans to do so. If you find a promising plan, you answer “Can I succeed?” in the affirmative, at which point you burrow into the hard work of implementing the plan. In this direction, the loop starts with the question “Can I succeed?”

In the other direction, it starts with an answer to “How can I succeed?” A feasible plan inspires you to answer the question “Can I succeed?” in the affirmative. You then implement the plan and stick with it, at least unless and until that plan proves less promising than you thought it would be. At that point you may be popped back out to the higher-level question, “Can I succeed?”

Mind Readers Dictionary: The Podfast : Play in Popup

Mind Readers Dictionary : Play in Popup

The two questions intertwine in complex ways, like a paradox or a Catch-22. You shouldn’t have hope that you can succeed unless you have a plan for succeeding. You won’t look for a plan to succeed unless you have hope that you can find one.

Which comes first, the hope or the plan? They depend upon each other. Necessity is the mother of invention but invention is also the mother of necessity, in that if you haven’t invented a way of achieving some goal, you’ll try to get over your need of achieving it. Where there’s a will there’s a way, but where there’s a way there’s a will.

So we pursue goals by trial and error, hypothesizing that there’s a way, convincing ourselves there is one (when there only might be) and then seeing how it works. That’s the only way we can deal with the uncertainty. I call it the try/buy dichotomy: You can’t really buy until you try and you can’t really try until you buy.

For example, do you love this date? Do you hope to commit to this person, to really buy in to the partnership? How would you know until you’ve tried out a full partnership? But how can you try a full commitment without having bought in to partnership? You say “I love you” to each other, in part to see if you do, because you can’t really tell whether you do until you’ve seen what it’s like to commit–and even though you can’t actually commit until you’ve seen. You shouldn’t play with people’s emotions. You shouldn’t kiss someone unless you’re really serious. But then how can you tell if you’re really serious until you’ve kissed?

This paradox is at the root of our trial-and-error process. It’s exploratory commitment, even though that’s an oxymoron. We play, literally half-serious, or else the game doesn’t engage us, half-joking or else it goes too far. It’s why so many people get hurt–and not in one way, but two, when someone takes the game too seriously or too lightly. It’s why we can be admonished in two directions when we admit we’re giving up on a plan. Tell a partner that you’re not into it after all and you might hear either or both of these opposite reactions:

Then you shouldn’t have played with my heart by saying you loved me.

And how do you know you don’t love me? You didn’t give yourself all the way over to the exploration.

FDR gave us a great simple description of the trial-and-error process: Do something. If it works, do it some more. If it doesn’t work, do something else. In practice, though, it’s harder than this, because we can’t always tell whether something is working or not. So success seeking isn’t easy. It’s not always clear when you should be asking “How can I succeed?” and when you should be asking “Can I succeed?”

Life involves lots of tough judgment calls–and I take up most of them in these columns. But the overarching tough judgment call is “Is this a tough judgment call?” In other words, when should you stick with a plan, calling it a no-brainer? And when should you wonder whether the plan is working? It’s the tension between decided and deciding, between the first and second level of analysis–between pursuing hope in a particular plan and hope that there is a plan.

When we declare hope as an answer, we try to evade the messy ins and outs between the two levels by simply hovering out at the second level, saying “Can I succeed? Yes, but please don’t ask me how.”