There is probably something in your past that you still go back to. Something you said or did not say, or a person you kept meaning to call while there was still time. I have mine, and I would be surprised if you did not have yours. Regret is a kind of pain that is often made almost entirely out of our own thinking, which is also the reason it can be worked on.
The Stoics taught that a wise person never regrets anything, and it is one of the claims that has made people dislike them for two thousand years. Cicero once used it in a courtroom against Cato the Younger, who was the best-known Stoic in Rome and was prosecuting Cicero’s client. He read out the Stoic rules one after another so that the court would laugh at them, and among them was that the wise man “never repents of anything, is never deceived in anything, and never alters his opinion.” You can hear why it worked. A person who regrets nothing sounds either like someone who has never done anything wrong or like someone who has done plenty and feels fine about it.
What makes the claim strange is that the Stoics were harder on their own mistakes than almost anyone. Seneca told his friend Lucilius to “prove yourself guilty, hunt up charges against yourself,” and Epictetus has a whole lecture addressed to a student who had let himself go downhill. These were people who looked at what they had done wrong, in detail and often. So when they called regret a mistake, they meant something narrower than looking back and admitting a fault. They meant the thing regret turns into for the rest of us, and I think it is worth describing exactly, because we tend to mistake it for conscience.
What separates regret from grief or disappointment is one extra thought, which is that it could have gone differently and that we were the ones who could have made it so. That thought is what keeps it running. We replay the conversation and give ourselves the better line. We work out where we would be living now if we had taken the other job or stayed with the other person. We go back to the hour before the mistake, when it could still have been avoided, as though there were something left to do there. And it does not fade the way other pain fades. Something said fifteen years ago can arrive in the shower as sharp as it was on the day.
We hold on to it for a reason, and the reason is a decent one. Regret feels like taking responsibility. To stop regretting something seems to mean deciding that it did not matter, or that we have let ourselves off, and nobody with a conscience wants to do that. So we go on suffering over it, on the quiet assumption that the suffering is the punishment we deserve. The trouble is that the suffering reaches nobody. The person we hurt is not helped by it, the chance we missed does not come back, and after ten years of regretting we are usually no better at the thing we got wrong.
Seneca’s instruction to Lucilius is longer than the part I quoted, and the rest of it is what we skip. “Play the part,” he wrote, “first of accuser, then of judge, last of intercessor.” An intercessor is someone who pleads for mercy on another person’s behalf. Think of regret like a trial in which only the accuser ever gets to speak. He reads out the charge night after night with great conviction, and there is no judge to weigh it, nobody to speak for the defense and no sentence handed down, which means the case can never be closed. A trial like that can run for forty years. The Stoics had no objection to putting yourself on trial. Their objection was to a trial that never reaches a verdict, and the rest of what Seneca told Lucilius is how you get it to one.
Continue reading with a paid subscription to learn how the Stoics handled regret, including the three questions a fair judge asks, why Epictetus held that your past self could not have chosen differently, what Seneca said punishment is for, and how to close a case you have been trying for years.