Chapter 4: Living in Yesterday

Amara was scrolling through the news on a Sunday morning when she saw the name of her old friend’s design studio, and beneath it, a headline about an award.

Six years earlier, that studio had been three people and a borrowed office. Her friend Iris had invited her to join as the fourth. Amara had spent a week agonizing over it, made lists, asked her parents, and finally said no. She had a stable job at a reputable firm, a lease she could afford, and a nagging voice that said start-ups fail. It had been a sensible decision. Everyone told her so.

Now she stared at the photograph of Iris holding a trophy, and something heavy settled in her chest.

That night, the old week returned to her in full. If only I had said yes. If only I had trusted myself. What if I had known? She reconstructed the conversation with Iris, the evening she’d decided, the exact moment she could have chosen otherwise. She imagined the life she might have had: a different city, different friends, a different version of herself, perhaps braver, perhaps more fulfilled.

And then, somewhere around midnight, the mind did what minds do. It reached into a different drawer entirely and pulled out something small and unrelated: the time, seven years ago, when Amara mispronounced the CEO’s name during a company meeting. Nobody had made a fuss about it.

It had been over in two seconds. But her face went hot in the dark, as though it had happened that afternoon.

By two in the morning, Amara was not living in the present at all. She was living in several different yesterdays at once.

Why the past will not stay put

It can seem strange that a moment lasting two seconds, years ago, can still make us wince. But there are reasons the past is so sticky.

Emotionally charged moments are encoded more strongly in memory than neutral ones. That is why you can vividly recall the humiliating mispronunciation but not a single ordinary Tuesday from that same year. The mind has a built-in tendency to keep what felt important or threatening on hand, in case it should matter again. This is useful for survival and tiring for sleep.

Beneath that, there is a quieter motive that many of us share, though we rarely notice it: the hope that if we understand the past well enough, we can be safe from it. If we can just identify the exact mistake, the precise turning point, the thing we should have seen, then perhaps we will never be caught off guard again. Looking backward becomes a way of trying to protect the future.

There is something moving about this. It is an effort at care. But there is a catch, and it is the central problem of this chapter: the past is the one thing we cannot change by thinking about it.

The mind that edits history

Psychologists call the mental habit of imagining how things might have turned out differently counterfactual thinking. The psychologist Neal Roese has spent years studying it. We say if only I had left earlier, if only I had said yes, if only I had spoken up. When we imagine a better alternative, researchers refer to it as an upward counterfactual.

These thoughts are not inherently bad, and Roese’s research suggests they can serve a real function: they help us extract lessons and prepare for next time. If you missed a train because you left five minutes late, if only I had left earlier is both painful and instructive. The sting carries a lesson.

But counterfactuals can also fail. When the situation is over, when the lesson has already been learned, or when the imagined alternative depends on information we could not possibly have had at the time, the thought stops teaching and only hurts. It becomes a kind of mental editing of a document that has already been printed.

Judging then with what we know now

The cruelest trick of regret is that it judges a decision using information the decision-maker did not have.

When Amara said no to Iris, she did not know the studio would win awards. She knew she had a steady job, an uncertain start-up, a modest savings account, and a fear of financial instability. She knew that most young companies struggle. Given what she knew, her choice was reasonable.

But now she knows how the story ended, and that knowledge pours backward over the past like dye through water, coloring every detail. The decision that was sensible then now looks like a failure of nerve. This pattern echoes the hindsight effect we met in the last chapter, and it has a close cousin that researchers Jonathan Baron and John Hershey studied in the 1980s: outcome bias, the tendency to judge a decision by how it turned out rather than by how well it was made.

The writer and former professional poker player Annie Duke calls this habit “resulting”: grading a decision by its result. In poker, a skilled player can make an excellent bet and lose to a lucky card. A weak player can make a terrible bet and win. If you judged every hand only by its outcome, you would learn all the wrong lessons.

This doesn’t mean every past decision was wise. Some were not. It means that the fair way to examine a decision is to put yourself back in the room, with the information, the resources, and the emotional state you had then, and ask what a reasonable person might have done. Often that person looks a lot more like you than the one in the replay does.

Accountability and self-punishment

There is an important difference between two things that can look alike from the outside.

Accountability asks: What did I do? What did it affect? What can I do now? It looks at behavior, it is specific, and it leads somewhere: an apology, a repair, a changed habit.

Self-punishment asks: What kind of person does that? It looks at the self, it is global, and it leads nowhere. It often disguises itself as moral seriousness, as if suffering were the price we owe for what we did, and as if easing off would mean we didn’t care. But suffering is not a repair. It does not return what was lost, mend the person we hurt, or change what happened.

A natural fear is that without self-punishment we would stop trying to be better. Research suggests the opposite may be true. In a series of studies, the psychologists Juliana Breines and Serena Chen found that people who were encouraged to respond to a personal failure with self-compassion tended to be more motivated to improve, not less. Kindness and standards are not opposites. We will return to this in Chapter 6, and again in Chapter 9, where we look at guilt and shame in more depth. For now, let this be the main point: we can take the past seriously without punishing ourselves for it.

Three kinds of yesterday

Not every piece of the past asks for the same kind of response. It helps to sort what keeps returning.

Choices that did not work out. These are decisions made in good faith whose outcomes disappointed us: the job not taken, the move not made, the relationship that ended. They call for fairness (I chose with what I knew), perhaps a lesson, and eventually acceptance.

Actions that harmed someone. Here something real was damaged, and the regret is pointing at something that matters. These call for responsibility and, where possible, repair.

Moments that were merely embarrassing. Amara’s mispronunciation falls here. No one was hurt. It simply carries a sting. These don’t need analysis so much as time, perspective, and the knowledge that, as we saw in Chapter 3, everyone else has most likely forgotten.

Sorting is itself a relief. Much of the weight of a regret comes from treating all of it as the same kind of problem.

Try this: One regret, three exits

Choose one regret that tends to return. Not the most painful thing in your life, just a regular visitor. Then ask whether it can leave through one of three exits: a lesson, a repair, or a release. You may use more than one.

1. Lesson. Complete this sentence: Next time I am in a situation like that, I will… If you honestly cannot find a lesson, that is also information. Some outcomes are the result of luck or circumstances, and there is nothing to learn from them except that life is uncertain.

1. Repair. Ask: Is there anything I can still do, however small, for someone affected by this or for myself? An old wrong can often be addressed with a short honest message. An old missed chance can sometimes be revived by a different door.

1. Release. Make a deliberate decision to stop revisiting it. Write one sentence: I understand what happened. I’ve taken what I can from it. I’m retiring this file. When the memory returns, as it probably will, don’t argue. Just tell it: That one is closed.

Here is how it went for Amara.

For the studio decision, her lesson was real and specific: When I’m scared, I tend to choose whatever feels safest, and I want to notice when fear is making the decision for me. Her repair turned out to be unexpectedly warm. Reading the news article, she realized she had quietly stopped contacting Iris out of a mixture of envy and embarrassment. She sent a message congratulating her. They talked for an hour. And her release was a sentence she wrote on a sticky note: I chose with what I knew and who I was then.

For the mispronounced name, she used only the third exit. There was nothing to learn and no one to repair it with. When the memory next arrived, she silently said, That one is closed, and made tea.

In short: a regret that holds a lesson gets a lesson; a regret that points to someone you affected gets a repair; and a regret with nothing left to learn or mend gets a deliberate release. Regrets about harm done to another person are treated more fully in Chapter 9.

A caution: this tool is built for the ordinary regrets that most of us carry. If a memory involves serious loss, trauma, or harm that continues to overwhelm you, it deserves more support than a single exercise, and reaching out to a professional is a strong and sensible step.

How long it takes. A regret that has circled for years rarely closes in one sitting. If a memory returns after you have released it, that is normal; minds do not delete files. What changes is how long it stays and how hard it lands. Return to the same regret, with the same three exits, over several weeks. The sting often softens before the memory fades.

A THOUGHT TO CARRY

The past can be understood, learned from, and, where possible, repaired. It cannot be revised. And you do not have to reread it every night to prove that you care.