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Sam Okafor
Sam Okafor
Men's Mental Health & Modern Masculinity Writer

The Top 5 Regrets of the Dying Were Published in 2009. We Have Fixed Exactly Zero of Them.

4 min read

In 2009, a palliative care nurse published the five things dying people regret most. Fifteen years later, the world has gotten worse at all five. Bronnie Ware spent years sitting with people in the final weeks of their lives. She wasn't a researcher with a grant and a methodology. She was just someone present enough to ask, and quiet enough to listen. What she heard became a list that spread across the internet, got shared millions of times, inspired keynote speeches and TED talks and self-help books. The five regrets. You've probably seen them. You probably nodded reading them. You probably forgot them by Thursday. Here they are again, because forgetting is the point: I wish I'd had the courage to live a life true to myself, not the life others expected of me. I wish I hadn't worked so hard. I wish I'd had the courage to express my feelings. I wish I had stayed in touch with my friends. I wish I had let myself be happier. Five sentences. Fifteen years. Zero progress.

We Optimized Our Lives in the Exact Wrong Direction

The average American works more hours today than in 2009. Remote work didn't give us time back — it dissolved the boundary that used to protect evenings, weekends, the thirty-minute commute that was actually the only time you had to think. Productivity tools have multiplied. Rest has not. We built apps that let us work from anywhere, and then we worked from everywhere, including the dinner table, including the hospital waiting room, including the two minutes between waking up and getting out of bed. The second regret — I wish I hadn't worked so hard — is not about laziness. Ware's dying patients were not people who failed to hustle. They were people who hustled past everything they loved, and then, with no time left to correct the course, understood what they had traded. A 2023 Gallup study found that 59% of workers globally are "quiet quitting" — disengaged but present — which sounds like a solution until you realize that disengagement is not rest. It is suffering that has learned to perform. You can be hollowed out at a desk just as efficiently as you can be hollowed out in a boardroom at midnight.

The Feelings Nobody Said Out Loud

The third regret is the one that lands differently when you sit with it. I wish I'd had the courage to express my feelings. Not: I wish I'd been angrier. Not: I wish I'd made more demands. The regret is about love that went unnamed, gratitude that was assumed, apologies that were drafted and deleted. A 2019 study published in Psychological Science found that people consistently underestimate how much a message of appreciation means to the recipient — by a factor they called "surprisingly large." We withhold because we assume people already know. They don't. Or they do, and it still would have mattered to hear it. Here is a tangent that seems unrelated but isn't: there is research on deathbed conversations that shows people will often wait until a loved one is unconscious before saying the things they needed to say. As if the act of saying it was too vulnerable to survive eye contact. The dying person may or may not hear. But the living person needed the release. We have built entire emotional vocabularies around avoiding the moment of nakedness that honesty requires.

Friendships Nobody Has Time to Keep

I wish I had stayed in touch with my friends. This one is quiet. It doesn't announce itself like regret over career choices or uncourageous living. It arrives as a slow accumulation of unanswered texts, of birthdays that passed with a social media reaction instead of a phone call, of people who were once essential and became peripheral without any single decision being made. A 2023 meta-analysis in PLOS ONE found that friendship quality — not quantity — is the strongest social predictor of wellbeing past age fifty. Quality requires time. Time requires priority. Priority requires choice. The average adult in the United States reports having fewer close friends than in any previous decade measured. The number of people who say they have no close friends at all has tripled since 1990. This is not a pandemic artifact. The trend predates COVID by at least fifteen years. We had already been drifting before we were forced apart. Here is the second tangent: some people have found that a standing recurring moment — a weekly call, a monthly dinner with no agenda — is the only infrastructure that keeps closeness alive. Not because the connection isn't real, but because adult life produces friction that passive relationships cannot survive. The people who maintain friendships tend to make the maintaining explicit, almost formal, in a way that feels strange until you realize that the alternative is the regret.

The Happiness We Refused

I wish I had let myself be happier. That word — let. Not: I wish I had been happier. Not: I wish circumstances had allowed. The regret is about permission. About the voice that said things aren't good enough yet to enjoy, about the habit of treating the present as infrastructure for a future that kept not arriving. Ware noted that many of her patients held onto bitterness long past the point it served any purpose. Not because they were hard people, but because releasing it required believing they deserved something better — and that belief had never quite formed. A 2021 study in the Journal of Positive Psychology found that actively practicing gratitude does not change circumstances; it changes the threshold at which circumstances register as sufficient. The people who let themselves be happier were not people with better lives. They were people who decided that their lives, as they were, contained enough.

What Is Actually in Your Control

The uncomfortable truth is that most of the five regrets are structural. They emerge from cultures that reward overwork, from economies that make financial precarity a permanent backdrop, from communication norms that treat emotional directness as weakness. You cannot individually opt out of the material conditions that produce regret. But the word at the center of regret number one is courage. Not circumstance. The people who died wishing they'd lived more truthfully weren't people who had no other option. They had options they didn't take. So do you. So do I. The question that doesn't resolve cleanly is whether knowing this, reading a list that has been in circulation for fifteen years, is enough to change the calculus. Or whether we nod and scroll and return to building exactly the life we'll eventually regret. The list hasn't changed. What you do with it still might.

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