What should I do with regret?

Judaism has a precise technology for this: teshuvah, the turning. Maimonides laid out the stages clearly — recognize the wrong, feel real regret, make restitution where possible, resolve not to repeat it, and when the same situation arises, choose differently. Regret is not the punishment. Regret is the raw material. A life without regret would be a life incapable of growth, because you would never know which way to turn. But regret that does not convert into action is just a cage you are building for yourself. The tradition does not want you to feel terrible forever. It wants you to use the terror to become a different person.

“In the place where penitents stand, even the wholly righteous cannot stand.”

— Talmud, Berakhot 34b

The Christian answer to regret is grace, and grace is structurally offensive to the kind of person who is serious about their regret. You want to earn your way back. Grace does not let you. The cross — whatever else it is — is an assertion that the bill has already been paid and you do not need to keep writing checks against an account that was closed in your favor. This does not mean the harm you caused was nothing. It means you are not required to do eternal penance for it. You are required to receive the forgiveness and then go live like someone who has been forgiven. That is harder than it sounds.

“For by grace you have been saved through faith — and this is not from yourselves.”

— Ephesians 2:8

The Stoics give regret very short shrift. Epictetus would point out that your past self made the best choice available to your past self with your past self's information and your past self's still-forming character. The fact that your present self would choose differently is not evidence of past failure. It is evidence that you have learned. To despise your past self for not knowing what your present self knows is to despise the entire mechanism of growth. Acknowledge the error. Extract the lesson. Move. A soldier does not sit on the battlefield cursing himself for the last round. He loads the next one.

“Do not look around to discover other men's ruling principles, but look straight to this, to what nature leads you.”

— Marcus Aurelius, Meditations 7.55

In Buddhist psychology, regret — kukkucca — is one of the five hindrances to meditation, and not by accident. It is attachment in reverse: clinging to a past that cannot be rearranged. The past is a thought occurring now. The 'you' who made that choice is not the same aggregate of causes and conditions that is here today. Acknowledge what happened. Make amends if possible. Then notice that continuing to replay it is a second arrow you are firing into yourself, on top of whatever the first arrow was. Put down the bow. The present moment is where the practice actually lives.

“Do not dwell in the past. Do not dream of the future. Concentrate the mind on the present moment.”

— Attributed to the Buddha

Kierkegaard said life can only be understood backwards but must be lived forwards — and regret is the forced confrontation with that asymmetry. The existentialists would reframe your regret this way: you regret because you chose, and the capacity to have chosen otherwise is the only thing that makes you a self in the first place. The version of you who could not have chosen otherwise would have no regret and no dignity. Your suffering over the old decision is the form your freedom takes in memory. Honor it. Then use that same freedom, which is still available to you, to make the next move.

“Life can only be understood backwards; but it must be lived forwards.”

— Søren Kierkegaard, Journals