How could I have been so stupid? A simple scheduling oversight costs me hundreds. A project I worked on for months didn't win. A momentary lapse leaves me handicaped for life. Somehow the world failed me, or I failed it. What could I have done differently?

A few months back I covered false positives and false negatives, the two ways we can bet wrong. A false positive is guessing ‘yes' when the answer turns out to be ‘no.' A false negative is guessing ‘no' when the answer turns out to be ‘yes.'

Regret focuses our atteniton on our false positives and negatives. Should I have double-checked my schedule? Damn, I said no when I should have said yes. Should I have run through that yellow light? Damn, I said yes when I should have said no.

Regret also opens a second line of questioning: ‘Could I have done otherwise? ‘Is there something to learn from my error?' Being yes no questions, these too are subject to false positives and negatives.

A false positive on these questions would be thinking that there's something to learn when in fact there isn't, not granting ourselves the forgiveness we deserve, regretting in excess what, in fact couldn't have been helped.

A false negative on these quesitons would be thinking that there's nothing to learn when in fact there is, granting ourselves undeserved absolution, forgiving in excess, letting ourselves off too easy. Since these special breeds of false positive and negative come up so often, they deserve their own names: Call them over-regret and under-regret.

Why do we wonder (sometimes in excess) whether we could have done otherwise? Because sometimes bad outcomes are a sign that we should update something. Belaboring our mistakes is how we summon ourselves to the task of changing our expectations and strategies: Damn, I'm being too careless. I expected things to work out better than they do. From now on I'll double check everything.

And why do we forgive ourselves (sometimes in excess) for past mistakes? Because not every bad outcome means we should update anything. Outcomes are imperfect indicators of decision- quality. Given that nothing we do is 100% certain of success, all of our decisions are bets. This is a surprisingly elusive fact, especially when we're in the throes of regret.

When you bet on the 80% odds and the 20% likely event results, did you bet wrong? Should you update your strategy, from now on betting on the 20% odds? Of course not. You shouldn't change your plans every time they yield disappointing results. Sometimes you should forgive and forget; just move on without updating.

There's a time to say yes and a time to say no; a time to regret and a time to forgive yourself. Remembering this, we nod compassionately, embracing life's balancing acts.

But that ain't the half of it. Knowing that we must find the middle ground isn't the same as finding it. Knowing that there's a time isn't the same as knowing when that time is. Remembering that our choices are just bets makes us even more appropriately compassionate. We spend our lives betting when to say yes or no, when to regret or forgive. We try really hard to guess right. We change strategies when we think we should. And we still guess wrong sometimes.

From the 7 wonderings of the world

Should I be ashamed here?

Grant me regret when there are lessons to learn that will prove helpful with future choices, no regrets when there are no lessons to learn and the wisdom to know the difference.

The wisdom here is the ability to minimize both regretted yes's and regretted no's on the question "Should I regret?" because the last thing I want is regret when there are no lessons to learn that will prove helpful with future choices or no regrets when there are lesson to learn.

Of course, the challenge is that whether there are lessons to learn that will prove helpful with future choices can't be known for sure until tomorrow, and I have to decide today.

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