Listen to this Deep Dive, 13 min, read by Simon
Personal Development Series
Regret has a bad reputation. We speak about it as though it is something to avoid at all costs, a sign of weakness, a failure of perspective, proof that we are living in the past instead of moving forward. We tell people not to dwell. We say everything happens for a reason. We encourage them to let go, move on, focus on the future, and stop looking backward.
There is wisdom in that, but only up to a point.
Regret is not always unhealthy. Sometimes regret is the mind’s way of telling the truth after the ego has run out of excuses. It is the emotional residue of seeing clearly what we did, what we allowed, what we ignored, what we protected, what we postponed, or what we failed to become when a better version of ourselves was available.
That kind of regret is not the enemy. It may be one of the more useful forms of pain.
The enemy is repetition. The enemy is taking the same wound, the same mistake, the same avoidance, the same self betrayal, the same relational pattern, the same leadership failure, the same private compromise, and carrying it into the next chapter as though nothing has been learned.
Regret hurts. Repetition harms.
Regret Is Information
A mature relationship with regret begins by refusing to treat it as merely negative. Regret is not pleasant, but many important signals are unpleasant. Hunger is unpleasant. Exhaustion is unpleasant. Pain is unpleasant. Guilt, embarrassment, sadness, and anxiety can all be unpleasant. But unpleasant does not mean useless.
Regret can reveal the gap between who we were in a moment and who we believe ourselves capable of being. It can show us the values we violated before we had the language to name them. It can point to the truth we avoided because comfort, fear, pride, loyalty, ambition, or insecurity felt more urgent at the time. Cornell psychologist Thomas Gilovich’s research, covered in Woulda, coulda, shoulda: the haunting regret of failing our ideal selves, finds that our most lasting regrets concern the people we hoped to become.
A person who regrets being harsh with a child may be discovering how deeply they value gentleness. A leader who regrets staying silent in a meeting may be discovering that courage matters more than approval. A person who regrets remaining in the wrong relationship may be discovering that peace is not selfish. A founder who regrets tolerating a toxic high performer may be discovering that culture is not built by what we say, but by what we permit.
Regret becomes destructive only when we turn it into identity rather than instruction. “I made a bad choice” is painful, but workable. “I am a bad person” is heavy, vague, and often paralyzing. One invites repair. The other invites shame.
Shame Freezes What Regret Could Teach
The great danger of regret is that it can slide into shame if we do not handle it honestly. Regret says, “That mattered.” Shame says, “You are beyond repair.” Regret asks us to pay attention. Shame asks us to hide.
This difference matters because shame often prevents the very change regret is trying to create. When people feel ashamed, they become defensive, evasive, self punishing, or performatively remorseful. They either collapse under the weight of what happened or rush to explain why it was not really their fault. Neither response produces growth. A study described by the Association for Psychological Science in After Committing a Crime, Guilt and Shame Predict Re-Offense found that guilt pushed people toward repair, while shame made repeating the behavior more likely.
The more useful posture is harder and quieter. It says, “Yes, this happened. Yes, I played a part. Yes, I wish I had chosen differently. And now I need to understand what this is asking me to change.”
That is not self hatred. It is accountability with oxygen.
Healthy regret requires enough courage to look directly at what happened and enough compassion not to turn that truth into a life sentence. Without courage, regret becomes avoidance. Without compassion, regret becomes punishment. With both, regret becomes a teacher.
Repetition Is the Real Failure
There is a strange arrogance in repeating the same mistake while claiming to understand it. We say we learned the lesson, but then we recreate the conditions that made the lesson necessary. We apologize, but do not change the pattern. We name the wound, but keep choosing the same kind of person. We admit the cost, but keep paying it.
At some point, repetition becomes more revealing than regret.
Everyone makes poor decisions. Everyone acts from fear at times. Everyone misses signals they should have noticed earlier. Everyone has chapters they would rewrite if life allowed clean revisions. But when the pattern repeats, the question changes. It is no longer only, “Why did this happen?” It becomes, “Why do I keep participating in the conditions that make this likely?”
That question is uncomfortable because it removes some of the drama. It moves the focus from the event to the architecture. What am I rewarding? What am I avoiding? What am I afraid would happen if I finally chose differently? What payoff does this pattern still give me, even if the cost is high?
Repetition is rarely random. It usually serves something. It protects an old identity, preserves a familiar story, avoids conflict, secures approval, maintains control, delays grief, or keeps us from stepping into a version of life that would require more responsibility.
The Pattern Is the Message
When the same kind of pain keeps returning, it is tempting to blame circumstance. Another bad boss. Another selfish partner. Another unreliable friend. Another failed initiative. Another exhausting team dynamic. Another season of overcommitment. Another situation where we were misunderstood, underappreciated, betrayed, or disappointed.
Sometimes circumstance really is unfair. People can be harmful. Markets can be brutal. Families can be complicated. Organizations can be political. We should not use personal responsibility as a way to deny reality.
But we should also be honest enough to ask why certain realities keep finding us.
Patterns are not always our fault, but once we see them, they become our responsibility. That is the line many people do not want to cross. They want the relief of insight without the burden of change. They want to understand themselves without inconveniencing the habits, relationships, environments, and emotional arrangements that keep producing the same outcome.
But insight without interruption is just commentary.
The pattern is the message. If you keep overgiving and resenting people afterward, the issue is not generosity. It is dishonest generosity, giving more than you can freely offer while quietly expecting recognition, reciprocity, or rescue. If you keep choosing emotionally unavailable people, the issue may not be bad luck. It may be that availability feels unfamiliar, vulnerability feels risky, or longing has become confused with love. If you keep burning out, the issue may not be your workload alone. It may be your attachment to being needed, impressive, indispensable, or unable to disappoint anyone.
Regret points backward. Patterns point inward.
Apologies Are Not Change
Many people mistake remorse for transformation. They feel badly, say the right words, express regret, ask for forgiveness, promise to do better, and genuinely mean it in the moment. But remorse has a short shelf life unless it is converted into structure. Daniel Pink’s research on regret, discussed by strategy+business in To err is human, to regret, divine, treats regret as a guide for making better choices the next time.
If you regret how you speak when you are angry, what will you do before anger takes the microphone again? If you regret neglecting your health, what changes in your calendar, environment, sleep, habits, and standards? If you regret avoiding hard conversations, what rhythm of honesty will you install before avoidance becomes comfortable again? If you regret poor financial decisions, what guardrails will prevent the next emotional purchase, impulsive commitment, or delayed reckoning?
Change needs architecture.
This is especially true in leadership. A leader can regret the damage caused by unclear expectations, inconsistent accountability, or emotional reactivity. That regret may be sincere. But unless the leader changes meeting rhythms, decision rights, scorecards, communication habits, hiring standards, and consequences, the same regret will reappear in better language six months later.
Organizations do not change because leaders feel bad. They change because leaders build different conditions.
The Mercy of a Different Choice
The hopeful truth is that repetition can be interrupted. Not always instantly. Not always cleanly. But more often than we tell ourselves.
A different choice may begin quietly. A pause before sending the message. A boundary stated before resentment hardens. A difficult conversation held before the story becomes distorted. A sober look at the numbers before denial becomes crisis. A decision to stop calling chaos chemistry, overwork commitment, silence peace, or avoidance patience.
These moments can look small from the outside, but they are not small. They are the places where a person begins refusing to let yesterday become tomorrow.
There is mercy in that. We cannot undo every choice, repair every wound, restore every relationship, recover every year, or return to every fork in the road where we wish we had chosen differently. But we can refuse to keep reenacting what hurt us. We can let regret become the place where the pattern ends.
That is one of the great dignities of being human. We are shaped by the past, but not required to keep obeying it.
The Work After Regret
The right question after regret is not, “How do I stop feeling this?” The better question is, “What is this feeling asking me to see?”
Maybe it is asking you to apologize. Maybe it is asking you to set a boundary. Maybe it is asking you to finally tell the truth. Maybe it is asking you to stop negotiating with a pattern that has already shown you its cost. Maybe it is asking you to grieve the fact that you cannot become who you needed to be back then, but you can become someone more honest now.
Regret becomes wise when it produces repentance in the original sense of the word: a turning. A change in direction. Not merely sadness about what happened, but a refusal to keep walking the same road with more sophisticated explanations.
The goal is not to live without regret. That is unrealistic, and perhaps not even desirable. A life without regret may simply be a life that has not been examined closely enough. The goal is to live without needing the same regret to keep teaching the same lesson.
Regret is not the enemy. Repetition is. Regret is the hand on the shoulder saying, “Look again.” Repetition is what happens when we look, understand, agree, apologize, explain, and then continue as before.
Growth begins when the lesson finally changes the pattern.
