You’re lying in bed at 2:00 AM. Suddenly, that one thing you said to your boss five years ago pops into your head. Or maybe it’s the girl you didn't ask out. The business you didn't start because you were scared of losing your steady paycheck. Your stomach does a little somersault. It’s uncomfortable. It’s heavy. Most people will tell you to just "let it go" or live with "no regrets."
They're wrong. Honestly, that "no regrets" philosophy is kind of a disaster for human growth.
When we talk about the power of regret, we aren't talking about wallowing in a pit of self-pity forever. We’re talking about using that sting—that specific, sharp emotional pain—as a data point. It’s a signal. If you didn't care, it wouldn't hurt. Because it hurts, it means you actually value something deeply. Regret is basically your internal GPS telling you that you took a wrong turn and, more importantly, showing you how to get back on the right track.
What Daniel Pink Discovered About Our Rearview Mirror
If you want to understand why we feel this way, you have to look at the World Regret Survey. Author Daniel Pink collected regrets from over 16,000 people in 105 countries. That’s a massive amount of human "coulda-shoulda-woulda." What he found wasn't a random mess of complaints. Instead, human regret mostly falls into four very specific buckets.
First, you’ve got Foundation Regrets. These are the "if only I’d done the work" moments. It’s the health issues from not exercising or the financial stress from overspending in your twenties. It’s about stability. Then there are Boldness Regrets. This is the big one for most people. We regret the chances we didn't take way more than the ones we did. If you started the business and it failed, it hurts for a bit. But if you never started it? That ghost haunts you for decades.
The third category is Moral Regrets. These are the ones where we feel like we compromised our integrity. Bullying someone in school, cheating on a partner, or being dishonest in a deal. These linger because they attack our sense of who we are as a "good person." Finally, we have Connection Regrets. These are the "if only I’d reached out" stories. A friendship that drifted away. A parent you haven't spoken to in years.
Understanding these categories changes the game. It stops being a vague cloud of "I suck" and becomes a map of what you actually value: stability, growth, goodness, and love.
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The Science of Counterfactual Thinking
Psychologists call this "counterfactual thinking." It sounds fancy, but it’s just our brains imagining a version of the world that doesn't exist. "If I had done X, then Y would have happened."
There are two types: downward and upward. Downward counterfactuals make us feel better. "At least I didn't lose my whole house in the fire." Upward counterfactuals make us feel worse. "If only I’d checked the stove, the fire wouldn't have happened." While downward thinking makes us feel happy in the moment, upward thinking—the regretful kind—is actually the one that helps us perform better next time. It’s a survival mechanism. It sharpens our decision-making skills.
Studies by researchers like Neal Roese have shown that people who lean into their regrets (moderately) often become more effective at problem-solving. They don't make the same mistake twice.
Why "No Regrets" Is Actually Toxic
The "No Regrets" tattoo is basically a badge of stagnation. If you never regret anything, you’re either a sociopath or you aren't learning.
Think about it. Regret is an essential cognitive function. Children don't actually start feeling regret until around age six or seven because it requires a complex level of brain development to imagine a different reality. It's a high-level skill. When we try to "positive vibe" our way out of regret, we’re essentially lobotomizing our ability to self-correct.
The trick is not to let it become "rumination." Rumination is when you spin the same negative thought around and around like a broken record without any intent to change. That’s toxic. But the power of regret lies in "action-oriented reflection." You look at the mess, you acknowledge it was your fault (or partially your fault), and you decide how to prevent it in the future.
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Breaking Down the Big Career Regrets
In the professional world, regret looks a little different. A huge study by Bronnie Ware, a palliative care nurse, found that one of the top regrets of the dying was "I wish I hadn't worked so hard." But that’s a bit of a misnomer. People don't regret working hard on things they love; they regret grinding away at things that didn't matter to them for people who didn't care about them.
In business, boldness regrets dominate. Most people don't regret the failed startup. They regret the "safe" job they stayed in for fifteen years while their soul slowly withered. They regret not asking for the raise. They regret staying silent in meetings when they had the winning idea but were afraid of looking stupid.
If you’re sitting there wondering if you should take a leap, remember that the "regret of inaction" grows over time, while the "regret of action" (failure) tends to diminish. We have psychological immune systems that help us justify failures, but we have no defense against the "what ifs."
How to Actually Use This Power
So, how do you turn this around? You can't change the past. That’s a fact. But you can change what the past means to you right now.
Self-Compassion over Self-Criticism. This isn't just fluffy talk. Dr. Kristin Neff’s research shows that people who treat themselves with kindness after a mistake are more likely to take responsibility for it than those who beat themselves up. If you're busy hating yourself, you're too defensive to learn. Treat yourself like a friend who messed up.
The "At Least" Tactic. If you're stuck in an upward counterfactual ("If only I'd..."), force yourself to find a downward one. "If only I hadn't crashed the car... but at least I wasn't hurt." This breaks the spiral and lets you move into the learning phase.
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Disclose It. Write it down. Talk to someone. When we keep regrets in our heads, they're abstract and terrifying. When we put them into words, they become concrete. They become manageable.
The Failure Resume. Write a list of your biggest mistakes and regrets. Next to each one, write down the one thing you learned or the one way you changed because of it. If you can't find a lesson yet, that's your homework.
The Social Aspect: Amending What’s Broken
Connection regrets are the most painful for many. We lose touch. We say something cruel. We let pride get in the way of an apology.
The beautiful thing about the power of regret is that it's often a catalyst for restoration. Most people are terrified of reaching out after years of silence. They think it'll be awkward. But the data shows that the recipients of these "reach outs" are almost always more grateful than we expect. The awkwardness lasts five minutes; the regret of a lost connection lasts a lifetime.
If you're regretting a moral lapse, the path forward is restitution. You can't undo the harm, but you can do something now that balances the scales. This is how you reclaim your identity. You aren't just "the person who did X"; you are "the person who did X, regretted it, and became Y."
Actionable Next Steps to Harness Regret
Stop trying to bury it. It’s like trying to hold a beach ball underwater; it’s eventually going to pop up and hit you in the face. Instead, try this:
- Identify your "Boldness Gap." What is the one thing you’re currently avoiding because you're afraid of failing? Realize that in ten years, you’ll regret the avoidance more than the failure.
- Send the "Thinking of You" text. If you have a connection regret, resolve it today. It takes 30 seconds. Don't overthink the wording. Just say, "Hey, I was thinking about you and realized it's been too long. Hope you're well."
- Conduct a "Pre-Mortem." Before making a big decision, project yourself six months into the future. Imagine the project failed. Now, ask yourself: "What do I regret not doing that led to this?" Then, do those things now.
- Reframe your narrative. Stop saying "I shouldn't have done that." Start saying "I did that, it sucked, and now I know never to do it again."
Regret isn't a sign that you're a failure. It’s a sign that you're a human being with the capacity for growth. It’s the ultimate teacher, provided you’re willing to sit in the front row and listen to the lecture, even when it’s uncomfortable. Use that sting to build a life you won't have to look back on with "what ifs."