Unlock The Power of Regret to Scale Up Faster

March 24, 2024 Eric Hinkle

“When feeling is for thinking, and thinking is for doing, regret is for making us better.”
– Daniel Pink

Millions of people have “No Regrets” tattooed on their body. Countless celebrities say they don’t believe in regrets and probably half the self-help books out there champion the philosophy. The Library of Congress even has more than 50 books with the title, “No Regrets.” This positive mindset feels right, but it has one fatal flaw. It’s wrong.

Regret is backward-looking and feels unpleasant. But it’s not dangerous or abnormal. It’s a healthy part of being human. It clarifies and instructs. Done right, regret can lift us up. In fact, the inability to feel regret is a sign of brain damage. The key is to learn how to process the emotion of regret so that we lift ourselves up instead of sinking into a destructive behavior pattern. 

Too much positivity can inhibit learning and limit our potential. Negative emotions are essential to our survival. Regret shows us how to make better decisions, perform better, and bring greater meaning to your life. Regret makes us better humans.How often do you have regrets?

Regret is better understood more as a process than a thing. We are the only species that can visit the past and rewrite the story. Regret happens when we compare our current reality with our story of what might have been. And then assign blame to ourselves.

"At leasts" and "If onlys"

Counterfactual thinking stands at the intersection of thinking and feeling. With downward counterfactuals, we contemplate how it could have been worse. They prompt us to say “At least…”. Bronze medalists think, for example, at least I got a medal. With upward counterfactuals, we imagine how things could have been better. They make us say “If only.” Silver medalists think, if only I tried harder.

  • “At leasts” make us feel better.
  • “If onlys” make us feel worse.

We humans are built to seek pleasure and avoid pain, so we tend to seek out the “at least” moments. But we’re also programmed for survival, so the “if only” moments are even more important. Regret is the ultimate “if only.” By making us feel worse today, regret can help us do better tomorrow. The problem is that we don’t often respond to our regrets properly.

The more you regret a decision, the more time you’ll spend preparing for a similar decision next time. Briefly reflecting on what went wrong can boost your performance next time. But lingering on a regret for too long can have the opposite effect. Ruminating muddies and distracts.

When you know (or think) you’re going to get another shot at something, you are more likely to experience an “if only” regret. If you think it’s a “one and done” however, you're far more likely to treat it as an “at least” regret to make yourself feel better. How do you respond to regret?

Feeling is for thinking. Thinking is for doing. 

How regret affects us depends on our mindset. If we think it’s permanent and debilitating, we’re more likely to make that true. If we think of it as temporary and enhancing however, we will make that our truth instead. Chronic, omnipresent regret is poisonous. But occasional, acute stress and regret are helpful, even essential.

The Four Types of Regret

Compound interest1. Foundation regrets arise from our failures of foresight and conscientiousness. Usually from NOT choosing a short-term sacrifice in the service of a long-term payoff. “If only I did the work.” Eating or drinking too much. Not studying for a test or leveraging the power of compound interest. The best time to start saving is 20 years ago. The second-best time is today.

2. Boldness Regrets. We are much more likely to regret the chances we didn’t take than the ones we did. When we chose to play it safe. The consequences of action are specific, concrete, and limited. The consequences of inaction however are general, abstract, and unbounded so boldness regrets endure because there are so many counterfactual possibilities. At the heart of all boldness regrets is the unrealized possibility of growth. The failure to become the person you could’ve been. “If only I took that risk.”

When I started leading my father's company, one of the first things I did was create "The Most Original Screw Up Award."  Complete with a trophy made from a huge screw pointing up. ☝ Why? I wanted to grow the company, but everyone was afraid to make mistakes. I needed my team to be bold and take more chances. The only requirement to win this monthly award was that the mistakes were made while trying to go the extra mile for our customers.

3. Moral regrets only represent 10% of the total regrets. But they can ache the most and last the longest. Moral regrets are more likely to involve actions than inactions. At the critical moment, we choose the wrong path. We hurt others. It may be exhilarating in the moment, but it eats at us over time. “If only I did the right thing.”

4. Connection Regrets are the most common. They come from relationships that have come undone or remain incomplete. Sometimes, often because of a death, there is nothing more we can do. (“Closed Door”) However, many times, in many roles, we can still fix the relationship. (“Open Door”) But that requires effort, brings emotional uncertainty, and risks rejection. 

The lesson of closed doors is to do better next time. The lesson of open doors is to do something now. If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out. “If only I reached out.”

The Opportunity

The reverse image of our regrets reveals what we value most. A solid foundation. A little boldness. Basic morality. Meaningful connections. The potential negatives reveal a positive path forward.

Social psychologist Tory Higgins proposed we all have an “actual self,” an “ideal self,” and an “ought self.” Our actual self is the bundle of attributes we currently possess. Our ideal self is who we believe we could be. Hopes, wishes, and dreams. And our ought self is who we believe we should be. Duties, commitments, and responsibilities.

Discrepancies between these 3 drives our behavior and the goals we pursue. If your ideal self is healthy and physically fit but your actual self is lethargic and overweight, that gap might motivate you to start exercising. It's when you don’t make the effort that the unpleasant feelings of regret fill the gap.

What To Do

For “action regrets” (regretting what you did), your initial goal should be to change the immediate situation for the better. Make amends, reverse your choices, or erase the consequences. Action regrets typically come from concrete incidents and elicit “hot” emotions you can respond to quickly. 

"Inaction regrets" (regretting what you didn’t do), by contrast, are often more abstract and elicit less immediately intense emotions. Inaction regrets are inherently difficult to undo. Sometimes the best you can do is to “at least” it. For example, “I regret marrying a loser, but at least I’ve got these great kids.” It won’t help you improve in the future, but it can make you feel better now. Like antibiotics. Sometimes we need them to survive an acute trauma. But if we use them too often, they become less effective. 

The optimal response to most regrets, action and inaction alike, is to use the regret to improve the future. If we look backward with the specific intent of moving forward, we can convert our regrets into fuel for progress. They can propel us toward smarter choices, higher performance, and greater meaning. Here’s how...

1. Relive and relieve. We don’t like to share negative information about ourselves. It feels awkward, even shameful, but denying it can devolve into harmful rumination. Writing or talking about your regrets (even with yourself) moves the experience from the realm of emotion into the realm of cognition where you can analyze it. Evidence shows that sharing our regrets builds affinity with others more often than it triggers judgment. 

2. Normalize and neutralize. Self-criticism can project toughness and ambition, but it often leads to rumination and hopelessness instead of productive action. The opposite, self-esteem, can be more effective but it too can have downsides. It can foster narcissism, diminish empathy, and stoke aggression. Criminals, for instance, have higher self-esteem than the general population.

A better alternative is self-compassion. When you make a mistake, extend the same warmth and understanding to yourself that you would offer your friends and family. Self-compassion simply recognizes that making mistakes is part of the human experience. By normalizing negative experiences, we neutralize them. Self-compassion encourages us to take the middle road in handling negative emotions. Not suppressing them, but not exaggerating or overidentifying with them either. 

3. Analyze and strategize. Self-distancing helps you examine your regrets objectively and learn lessons that can guide your future behavior. Distancing regulates our emotions, redirects behavior, strengthens thinking, enhances problem-solving skills, and deepens wisdom. We can distance ourselves from our regrets in 3 ways…

  • View it from a neutral perspective. We’re better at solving other people’s problems than our own. So, instead of saying “I screwed up,” say “Someone screwed up, but all of us make mistakes.” 
  • Time travel to the future. Examine your regret retrospectively as if it was 10 years ago. That will give you a detached, big-picture perspective that can make the problem seem smaller, more temporary, and easier to surmount.
  • Use third-person language to describe the situation. Saying “you” instead of “I” can help strengthen and deepen your commitment to better behavior in the future. 

Looking backward can move us forward, but only if we do it right. The sequence of self-disclosure, self-compassion, and self-distancing offers a simple yet systematic way to transform regret into a powerful force for a better future.

👉 Inspired by Dan Pink's book, The Power of Regret



Share This: