The Secret Power of Big Mistakes

Why regret, when examined honestly, can become one of life’s best teachers.

The Big Idea: Mistakes have a strange power over us. The longer we keep them hidden, the heavier they become—shaping how we see ourselves and the decisions we make next. But when we bring those mistakes into the open, they often transform from sources of shame into sources of insight.

Why it matters: Everyone has made decisions they regret, and the co-authors of this book made world-class mistakes. Yet most of us never fully examine them. By understanding how mistakes unfold—and by talking about them honestly with someone we trust—we can uncover the deeper patterns that led to them and avoid repeating them.

Try this today: Think of one mistake that still lingers in your mind. Instead of pushing it away, try describing it out loud—to a trusted friend, partner, or even in writing. Ask yourself three questions: What led up to the decision? What was happening when you made it? And how have you handled the regret since? Often, clarity begins the moment we start telling the story.

These ideas come from From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You by Joshua Steiner and Michael Lynton. Below, they share five key insights from their new book.

1. Almost everyone has kept a mistake hidden for too long.

Michael and I had both made big mistakes that we buried for years. To write a book about mistakes, we needed to include our own—in all their ugly glory. Michael made a rash decision that caused one of the worst corporate hacks in American history. I kept a diary that embarrassed the White House and landed me on the front page of the New York Times.

But we also wanted to include other stories. So, we called some of the most interesting people we knew and asked them about their biggest mistakes. Everyone had a story they wanted to tell. A story that had stayed with them for too long and that they hadn’t fully explored.

“I kept a diary that embarrassed the White House and landed me on the front page of the New York Times.”

Author Malcolm Gladwell described a passion that he abandoned; Karol Mason, the president of John Jay College of Criminal Justice, recounted a painful interaction with the police; Michael Govan, director of the Los Angeles County Museum of Art, reflected on a career choice that he regretted; and, Irv Gotti, the music impresario, lamented a terrible interview that destroyed a friendship.

As they say on Law & Order, “These are their stories”—raw and often full of regret. Everyone has made a mistake that’s worthy of discussion.

2. Mistakes are different than failures.

Throughout history, we have studied failure. Explorer Ernest Shackleton’s expedition never managed to cross Antarctica, and the journey nearly killed his crew, but his ship—the Endurance—lives on in our imagination. His mission was a terrible failure, but it still inspires us. Failure, in this case, led to success of a very different kind: a celebration of the human capacity for teamwork and survival.

Failures usually follow a similar pattern:

• Painstaking planning with careful risk assessments.

• A series of important accomplishments along the way.

• An unsuccessful outcome.

To fail, one must have strived to fulfill a real achievement—usually with the help of others. Failure requires a level of self-awareness about the ultimate goal, coupled with a determined resolve to reach it.

Those characteristics of failure are quite similar to those of success—up until the outcome. Failure isn’t the opposite of success; it’s a sibling. Success and failure come after planning, commitment, and hard work in pursuit of an ambitious goal.

Mistakes are very different. A mistake is a decision taken without careful consideration or self-awareness, which then causes regret. Compare that to failure, which follows hard work and planning and often leads to learning and growth.

At its simplest, marriages “fail.” Drunken Vegas weddings at 3 am are generally “mistakes.” In the case of marriage, two people come together in the hope of living meaningful lives as a couple—until death do them part. They have an ambitious goal, and sometimes they fail to achieve it. Marrying someone you meet after four cocktails doesn’t take a lot of planning, and the goal is usually not entirely obvious. The impulsive wedding usually leads to regret.

3. Every meaningful mistake follows a three-act structure.

When we started to unpack our mistakes, we couldn’t figure out when they began or ended. We didn’t know why they happened or even how to ask the right questions. We felt a little like detectives before the development of modern policing methods.

For most of history, society focused on solving a crime just the way we focused on our mistakes: Who did what to whom? Authorities used to torture suspects and make assumptions based on stereotypes. They did not employ a systematic approach to understanding why the crime occurred.

In the 19th century, Hans Gross, an Austrian jurist and criminologist, articulated and popularized the now widely adopted investigative technique of considering “motive, opportunity, and means.” He set out a crucial three-part process that worked with almost all cases.

“We felt a little like detectives before the development of modern policing methods.”

Prior to his systematic approach, criminal investigations relied on the intuition and subjective interpretations of the investigators. We, too, needed to stop relying on “intuition and subjective interpretations” when analyzing our own mistakes.

To explore our mistakes productively, we can’t think of them as isolated to the moment the bad decision was made. In the same way, motive provokes a crime, mistakes unfold over a longer period. To figure out what happened and why, you must go back and forth in time. Our most important mistakes almost invariably follow a three-act structure:

• Act I: What happened before the decision

• Act II: What’s happening during the time you make the decision

• Act III: How you handle regret after your decision.

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4. Most big mistakes come from an unexplored aspect of your personality.

In 1981, psychologists William Brewer and James Treyens performed an experiment that showed how much our past shapes our perceptions. They told their volunteers that before the experiment “began,” they had to wait in an office while someone else finished. After this brief stop in the office, the volunteers took a memory test of what they had seen inside it. The subjects hadn’t realized that the experiment would be a test of what they remembered from their wait.

The volunteers were much more likely to remember things that they thought belonged in an office than the objects that didn’t belong in a typical one. And they remembered objects, such as books, that weren’t even in the office. They had a visual “template” for how an office should appear that overrode what they had actually seen. The template came from the volunteers’ memories and experiences of seeing many different offices. Through those experiences, they developed and remembered a prototypical office, which they applied to the real world.

As Henry David Thoreau wrote, “The question is not what you look at, but what you see.”

The technical term for that broader template—the combination of all those memories and experiences—is schema, a concept developed by the Swiss psychologist Jean Piaget. Schemas serve two important purposes:

• They shape our perceptions based on how we’ve interacted with the world in the past. They are abstractions that help us interpret what we see.

• They influence how we react based on our perceptions of what we’re seeing. Schemas help us make sense of what we see and then react to it.

When they work well, they save us a lot of time and energy. For example, when you go into a Starbucks, you know where you are supposed to stand to order your coffee, how to interact with the cashier, and where to wait for your order. If you had to do that afresh each time, life would be exhausting.

However, when we misapply our schemas or they misshape our reactions, they lead to mistakes. Imagine you’re at a family dinner, and an older family member asks a grandchild to help him figure out his phone. Then he asks another grandchild to take out the garbage. Instead of agreeing to help with the garbage, the grandchild barks back, “Why do I have to do it?” The rest of the family gets annoyed with him for shouting at his relative, so he storms out.

“When we misapply our schemas or they misshape our reactions, they lead to mistakes.”

That might just be poor manners. Or maybe that grandchild feels like, at every family gathering, he always gets asked to do the menial labor while others get to help with more interesting assignments. He has a schema about his family that makes him particularly sensitive. If that schema isn’t explored, it may lead to more conflict or make him less eager to attend family events. A small mistake—shouting at his relative—reveals a much bigger issue.

5. Talk your mistakes to death.

The more we talked and then wrote about our mistakes, the better we felt. We basically needed exposure therapy to our own histories. We also knew that storytelling helps make sense of the world. The best narratives reveal cause and effect, and they expose the emotions, schemas, and ideas that drive behavior. We just didn’t know how to do it.

After all our unsuccessful attempts, we have a roadmap—in the form of an acronym—for how to talk about your mistakes: disclose, unpack, empathize, and trust (DUET). This was, after all, a duet between two friends trying to figure out what had happened. DUET is a process for sharing and normalizing mistakes so we make fewer of them and they sting less.

The acronym helped us encourage honesty; it reminded us to uncover hidden layers; it placed empathy at the center of our questioning; and it required trust. These steps destigmatized the unmentionable and surfaced its antecedents.