How to Live With Fewer Regrets

There’s a Latin phrase the Stoics used to keep themselves honest. Memento mori. Remember that you will die. It can sound morbid if you hear it for the first time, but the whole idea was to make sure you were actually living while you had the chance.

I’ve been thinking about that phrase lately, because two researchers basically ran the modern version of that experiment. One asked dying patients what they wished they’d done differently. The other collected over 23,000 regrets from people who still had time to change. They came up with almost the same answers, and they’re probably not what you’d guess.

Bronnie Ware spent years as a palliative care worker in Australia, sitting with people in the last weeks of their lives. She started writing down what they told her, and over time, she noticed the same five regrets surfacing again and again. She published them in a book called The Top Five Regrets of the Dying, and the list has been circulating ever since.

Here’s what people said when they were out of time: they wished they’d had the courage to live a life true to themselves, instead of the life others expected. They wished they hadn’t worked so hard. They wished they’d had the courage to express their feelings. They wished they’d stayed in touch with their friends. And they wished they’d let themselves be happier.

Before you read any farther, think about what is NOT on that list. Nobody said they wished they’d played it safer or been more careful. Nobody regretted the time they embarrassed themselves, or the investment that didn’t pan out, or the conversation that got awkward. Most regrets are about something they didn’t do, something they held back or let slide because, at the time, it felt easier to stay comfortable. I would say an area in life where they were playing defense rather than living on offense.

Daniel Pink, the author of Drive and When, approached regret from a different angle. He wanted to understand it while people were still alive and still had time to do something about it. He created the World Regret Survey, collected over 23,000 regrets from people in 109 countries, and ran a separate study of American adults called the American Regret Project. What he found was that 83% of people report wishing they’d done something differently when they look back at their lives. Eighty-three percent! That’s most people.

Pink organized all those regrets into four categories. Foundation regrets, which sound like “if only I’d done the work.” Boldness regrets, which sound like “if only I’d taken that risk.” Moral regrets, which sound like “if only I’d done the right thing.” And connection regrets, which sound like “if only I’d reached out.” Connection regrets were the largest single category, which tracks perfectly with Ware’s findings from the other end of life.

But the finding from Pink’s research that I found the most interesting was that in your twenties, you regret actions and inactions in roughly equal measure. By your thirties, forties, fifties, sixties, and seventies, inaction regrets outnumber action regrets by two to one. The older you get, the more your regret shifts toward the things you didn’t try, the feelings you didn’t express, the people you didn’t call, and the version of yourself you never became.

This connects to something I think about a lot with my work as a Performance Mindset Coach. I call it the 60-80 Dilemma, and it’s the pattern I see most often in coaching, and if I’m being honest, I need to always keep the awareness in my own life.

The 60-80 Dilemma works like this: a person is operating at maybe 60 to 80 percent of what they’re actually capable of. They’re functional, successful by most external standards, with relationships that aren’t bad but feel a little shallow, work that isn’t unfulfilling but isn’t particularly alive either, and health that’s just... fine. Because nothing is broken, there’s no real urgency to change. The gap between where they are and where they could be is filled with comfort, routine, and a vague sense that something is off without any clear evidence of what.

I think this is what Ware and Pink are both pointing towards. The 60-80 zone is where regret gets built. Regret accumulates in the ordinary, and it builds in the years you spent being fine, in the friendships you let fade because scheduling a dinner felt like one more thing, in the risk you didn’t take because the current situation wasn’t bad enough to justify the disruption.

Pink found that people don’t regret the things that went spectacularly wrong. They regret the things that never happened at all. And Ware heard the same thing, just from people who’d run out of time to do anything about it. The convergence is pretty wild. Two totally different approaches, different populations, different decades, and they landed on the same thing: comfort that lasts long enough turns into a lifestyle. And that lifestyle is where regret lives.

I think we have regret backwards. We treat it like a punishment, like evidence that we messed up, and so we try to avoid it. But Pink makes the case that regret is actually one of the most useful emotions we have. It tells you what you value. If you regret not reaching out to an old friend, that tells you connection matters to you more than you’ve been acting like it does. If you regret not signing up for the race or starting the business, that tells you boldness is part of who you are, even if you’ve been living cautiously. Treat regret as information. I’ve found that the people who treat it that way tend to make better personal decisions than the people who push it away.

One thing Pink found in his survey is that 32% of the people who submitted their regrets also voluntarily left their email addresses. He said people deeply want to talk about this, that they’re looking for permission or looking for a role model. I see the same thing in coaching. When a client finally says the honest thing out loud, when they admit they’ve been coasting, that they know they’re capable of more, that they’re scared of what it would mean to actually try... something shifts. The permission to name the gap is almost as important as the work of closing it.

Early in my career I walked away from a strength and conditioning business I’d spent years building. Clients were coming in, the work was good, and by every reasonable metric I should have kept going. We were about to open up new locations and I was looking at houses to buy, but I had this pull toward something I struggled to explain. I loved helping people get bigger, faster, stronger, and more athletic, but what I loved even more was the mental aspect of coaching. I wanted to press pause on that style of coaching life and go off on what Chris Guillebeau, in The Art of Non-Conformity, calls a “One-Year, Alternative Graduate School Program,” where you save up money and travel with a purpose of learning. You don’t get a formal degree but you gain experience and perspective. I packed my bag and set off to study the question: what makes humans happy and healthy? This will be another essay (or future book) but I spent the better part of a year traveling all over, staying with local families and learning as much as I could in places like Costa Rica, Easter Island, Chile, Peru, Austria, Germany, and more.

I didn’t know exactly what I was looking for when I left, or what I was hoping to get, but I was open to the experience and I know that if I hadn’t gone, it would have been haunting me and would be one of my regrets. It would have been so easy to stay. The business was working, I loved my boss and colleagues, and my life was comfortable. I was operating at a solid 80%, and nobody was telling me there was a problem, but the problem was the absence of a problem. I could feel myself settling into a version of my life that I didn’t want to settle into.

Pink would call that a boldness regret in the making. Ware’s patients would call it the first regret on the list: not living a life true to yourself. I didn’t know either of those at the time, but I knew I wanted to live a life true to myself and support others doing that.

Sit down with Ware’s five regrets and Pink’s four categories and ask yourself, honestly, where you’re building regret right now. Ask where you’re comfortable enough that you’ve stopped pushing, where the gap between who you are and who you could be has become harder to see because you’ve lived inside it so long. Write this down.

For most of the people I coach, the answer shows up fast, and it usually has to do with connection or boldness. They’ve let a friendship go quiet, have been sitting on an idea for months, or have been meaning to have a hard conversation with their partner. They often know and have known for a while, but life gets in the way and they can distract themselves. This is where coaching is valuable, because you get the opportunity to look under the hood of your mind.

Pink’s research suggests a simple practice that I’ve started using with clients. He calls it a “regret audit.” Look back at the last year and ask yourself: what do I wish I’d done? Then look forward at the next year and ask: what will I wish I’d done? The gap between those two answers could be your to-do list. Something closer to a values to-do list than a productivity one. The things you’ll wish you’d done aren’t random. They’re usually the things you keep postponing because the current situation is manageable.

Bronnie Ware heard these same priorities from people who couldn’t act on them anymore. Pink is hearing them from people who still can. And the 60-80 Dilemma is the mechanism that keeps people stuck in between, successful enough to ignore the gap, comfortable enough to postpone the work, and one day, if nothing changes, left holding a list of things they meant to get around to.

The Stoics repeated memento mori because they understood something we keep forgetting. The awareness of limited time was always supposed to be clarifying. Ware heard it from people who’d run out of time. Pink is hearing it from people who still have some left. And the 60-80 Dilemma is what fills the space in between, the comfortable middle where you’re doing well enough that nobody, including you, thinks to ask whether you could be doing more.