March 12

The Benefits of Decisions and Choices We Regret

Have you ever done something you regret?

When I was in college, I left a voicemail on a friend's answering machine. But I forgot to hang up.

I turned to my roommate and said “where is she? She never had a life last year.” A few minutes later she called me back and said, "I'm sorry I was always there for you.".

With one sentence, I destroyed our friendship. She never forgave me, and who could blame her?

We all do things we regret and tell ourselves "If only I knew then what I know now.” But poor choices from the past give us knowledge we can apply to the future. Without regret, we wouldn't learn from our mistakes.

If I didn’t regret saying what I did about my friend, I would never learned that words can cause irreversible damage to a romantic relationship, destroy a friendship, or divide a country.

“We know that positive emotions are enormously important. You want to have positive emotions. There are benefits to optimism. You want to have more positive emotions than negative emotions. But the thing is, we've gone too far in saying that you should only have positive emotions. Negative emotions, particularly our most common negative emotion, regret, is somehow dangerous, that it weakens you” says Dan Pink.

Dan Pink is the author of several influential books on business and motivation, including In his latest work, Pink explores the power that regret has to motivate us both in our personal lives and in our professional ones.

Pink believes that regret can be a powerful motivator because it allows us to reflect on our past decisions and learn from our mistakes. He argues that we should embrace our regrets and use them as a tool to push ourselves to be better in the future.

In this wide-ranging conversation, Dan Pink and I discuss

  • Four Categories of Regret
  • What we can learn from the choices we regret
  • How we can avoid making decisions we regret in the future.
Listen to the Full Interview

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1. Foundational Regrets

Photographer: Jannis Brandt | Source: Unsplash

With foundational regrets, "the full ramifications of our choices don't materialize immediately. But over time, they slow accrue. Soon, the full consequences become too towering to deny-and eventually, too massive to repair," says Dan Pink.

  • Smoking a pack a day won't kill you right away. But if you smoke a pack a day for ten years, there will be long-term health consequences. By the time you decide to quit, it could be too late.
  • The same is true for saving money. Saving 10% of your paycheck doesn't seem like much in one month or year. But the benefits of compound interest slowly accrue just as they do with poor choices.

Sacrificing long-term potential for immediate payoffs and temporary pleasure leads to foundational regrets. As Dan Pink says, "Think ahead. Do The work. Start now."

2. Boldness Regrets

Photographer: Steve Harvey | Source: Unsplash

When my roommate Tim told me that he was moving to Chile, he said, "I feel like if I don't do this now, I never will." Now or never, decisions are often the ones that will cause us to have or avoid boldness regrets.

Boldness regrets cause us to look back and wonder, "what if?"

  • What if I had asked that girl out?
  • What if I had traveled the world for a year after college instead of taking that job?
  • What if I had moved to another city or country when I had the chance?

Avoiding boldness regrets requires us to look years into the future and ask ourselves, "will I regret not having done this ten years from now? It's better to take a chance than spend the rest of your life wondering what might have been.

3.Connection Regrets

Photographer: Melissa Askew | Source: Unsplash

Connection regrets are the largest category in the deep structure of human regret. They arise from relationships that have come undone or that remain incomplete. The types of relationships that produce these regrets vary. Spouses. Partners. Parents. Children. Siblings. Friends. Colleagues. The nature of the rupture also varies. Some relationships fray. Others rip. A few were inadequately stitched from the beginning – Dan Pink

Social connection is vital to our happiness and well-being. If you have everything you ever wanted but nobody to share it with, it's no better than having nothing at all. In every case, these regrets share a common plotline. A relationship that was once intact, or that ought to have been intact, no longer is," says Dan Pink.

Two Types of Connection Regrets

Connection regrets fall into one of two categories: rifts and drifts. Sometimes we have rifts where we feel our relationship with a friend or family member is beyond repair. Other times we drift apart because we're in different chapters of our lives. People move away, start families, etc.

Rifts usually begin with a catalyzing incident-an insult, a disclosure, a betrayal. That incident leads to raised voices, ominous threats, crashed plates, and other mainstays of telenovelas and Edward Albee plays. Rifts leave the parties resentful and antagonistic, even though to outsiders, the underlying_grievance might sound trivial and easy to repair. -Dan Pink, The Power of Regret

Drifts follow a muddier narrative. They often lack a discernible beginning, middle, or end. They happen almost imperceptibly. One day, the connection exists. Another day, we look up, and it's gone. – Dan Pink, The Power of Regret


There are things about me that drive my parents crazy and things about them that drive me crazy. But after 43 years on this planet, I've realized how lucky I am to have a family where the door is always open, with a meal on the table and wine in my glass.

When we have rifts with family members, it's easy to forget reconciliation won't always be an option. The time we have left with the most important people in our lives is limited. We're likely to have connection regrets when we take it for granted.


People say friends are the family members we get to choose. Some of our friendships will end because of rifts. Others will end because of rifts.

Because I grew up worldwide and my parents moved multiple times throughout my childhood, my closest friends are people I've met in the last 10 years. I don't think it's a coincidence that I've designed a career that ensures I'll never stop meeting new people.

To prevent drifts, we have to make an effort to maintain our friendships, but that effort also has to be reciprocal. When it's not, the nature of those friendships changes.

But as Dan said to me in our conversation, "when in doubt, reach out."

4. Moral Regrets

Most of us want to be good people. Yet we often face choices that tempt us to take the low road. When we travel that path, we don't always feel bad immediately – Dan Pink.

Whether we bullied someone, cheated on a significant other, or did nothing to prevent someone from getting hurt, moral regrets force us to see the error in our ways.

Moral regrets also teach us to be empathetic, ethical, and kind. Without them, we wouldn't have a conscience. The world would be full of assholes.

Why It’s Important to Learn from Choices We Regret

Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn't drag us down; it can lift us up. – Dan Pink, The Power of Regret

It's impossible to live without regret. But regret can teach us to make better decisions, take chances, and value our most essential relationships.

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