Personal Histories

A Lifetime’s One Regret

Does hindsight improve with age? People, ages five to 60, name their life’s biggest mistake and what they learned.

Anthony Blunt, 2003, Dexter Dalwood. Courtesy the artist.

We learn from our mistakes, or so we’re told. But what do we learn, exactly? I’ve made a few myself, some more educational than others. Hindsight would have so much more going for it if we could relive those painful moments and get them right the second time round.

Sharing mistakes, and sharing the lessons learned from them, has a good feeling about it. It’s not just sharing knowledge, but sharing experience, and though additional knowledge is easy to acquire if you put the hours in, additional experience is a different challenge. You need to find a way to get people to open up about their most painful moments.

I wondered how the perception of mistakes, and the understanding of what was learned from them, changes with age. Do we really get wiser as we get older? Do we just get better at seeing where we went wrong? Does hindsight always increase, like entropy?

I went searching for people of all different ages who might confess their greatest mistakes. Some volunteered on social networks, others volunteered their loved ones, or friends of friends. Still more were colleagues, neighbors, and vague acquaintances. We spoke on the phone, by email, or over instant-messaging apps. I asked everyone the same thing: What was your greatest mistake? And what did you learn from it?

Some names have been changed to protect the regretful.


When you’re in your twenties you think you’ve learned all there is to know.

Charlie H., 62, London, UK

I got married far too young.

I met her in a pub, she was out with some friends and we got talking. Bought her a drink, then another. We had a laugh that night, so we went out again.

Ten months later we were married and she was pregnant. I was 26, she was only 23. Of course having children changes you, it changes your life and your relationship. I had to get the first job I could find to raise the money to afford a bigger flat. I didn’t enjoy the work—I was in the technical drawing trade, which sounds glamorous but it wasn’t, especially not if you started at the bottom like I did.

We had two kids, a girl and a boy, but we didn’t get on. We had almighty rows. I behaved very badly towards her and I regret that now. I was so young and impatient.

We split up soon after the kids had left home. There just wasn’t any point staying together, and I think by then we’d both realized that. Actually we’ve got on better since then. We’ve both found new people to fall in love with, but we can share a joke and have a laugh now. We stay in touch on Facebook. I think the children like it that we do that. Or perhaps they’re embarrassed by it, I can’t tell.

I learned that you always think you know everything, but you don’t. When you’re in your twenties you think you’ve learned all there is to know, because you’ve done your education and you’re out in the big wide world. But you’re still a kid in your twenties. I’ve given the same advice to my own kids: take your time. Use your brain. Think on things—it really helps.


I spent years daydreaming about what path my life might have taken if I had said yes.

Patrick G., 53, Kent, UK

I said no to a girl who asked me out when I was a young man. I’ve regretted it ever since.

In those days it was quite unusual for a girl to ask a boy out, but I was shy and never very confident with ladies. She actually wrote me a note and handed it to me in front of a crowd of friends—I suspect her closest friends knew what was on it, but I had no idea until the moment I opened it. I didn’t know what to do, so I turned it into a joke and tried to change the subject. It’s funny, how vivid your memory can be of something so brief and so long ago.

Anyway we moved on. We grew up and lost touch. I met someone and got married and settled down and everything was mostly fine, except there were times when I argued with my wife and afterward my thoughts would drift back to that moment when I turned down someone whom I think, with hindsight, would have been a better fit.

I say that, but it’s just a fantasy. I spent years daydreaming about what path my life might have taken if I had said yes. I would have made different choices. I might have not gone to college. I might have chosen a totally different career. I see that other version of me, like someone in a parallel universe, and I think he’s happy. No, wait, he’s happier than me. Looking back, I can see I turned down something special. She was a fantastic girl, absolutely gorgeous. I was such an idiot to say no.

I learned that you’ve got to make the most of life. I said no to that girl all those years ago because I was so terrified of saying yes. You can’t live your life like that, or you’ll end up full of regrets. Even one big regret, even if it’s about something trivial, is enough to haunt you.


If I had held on to that Bitcoin until today, I could have sold it for £550,000.

Stephen A., 41, Shropshire, UK

I bought 800 Bitcoin. Then I sold them.

This was all about a year or so ago. No one had heard of Bitcoin. They cost me about £2,000. At the time I had money in all sorts of places, even gold. I thought it was a good idea to spread my money about, it would be safer that way. We sold a house in London and got crazy money for it, six figures.

Then we bought another house and we had no cash. All this money in different places, different investments, but no actual cash anywhere. So I looked at my Bitcoin wallet and the value was still there, it hadn’t actually gone up. In fact I think I made a small loss, about £100 or so. At the time, I was just pleased to get my hands on the cash, it was useful.

If I had held on to that Bitcoin until today, I could have sold it for £550,000. I could have paid off my mortgage in full, and probably stopped working. Our lives would have changed.

I learned that I should trust my instinct, because my instinct was to keep the Bitcoin. But it was politically more sensible, and marketable to my wife, to sell them. You don’t invest money you can’t afford to lose.

I’m not upset about it. There’s no point. That’s life isn’t it?


Nobody really makes an effort to stay in touch even as I neglect staying in touch with them myself.

Ralph M., 40, Sydney, Australia

I moved to the other side of the world.

Travel may broaden the mind but emigration ended up splitting my world in two.

I shouldn’t complain, because mostly it’s been the single most successful decision of my life. I have a wife, two lovely kids, a nice house, two passports. None of these things would have seemed likely to me 13 years ago, before this whole adventure started.

But I find it horrible now that wherever I live, one set of grandparents will always be hopelessly distant. Expense, distance, and the awfulness of air travel sometimes making the journey seem impossible.

I miss my friends and family in the UK. I have a brother and sisters back home whom I never see now. It’s the tyranny of time zones.

I lament the fact that nobody really makes an effort to stay in touch even as I neglect staying in touch with them myself. I remember when I was at university in the ’90s, everyone still wrote letters to each other. I miss that. It’s hard to even buy writing paper here now.

I’ve learned to be realistic about how much time people can invest in staying in touch over long distances. And it’s taught me that decisions aren’t single-faceted. Lots of things about moving have been good.


I had never cheated on my spouse or prior girlfriends. It wasn’t the kind of person I was.

Robert M., 38, Arizona

I got a blowjob from a receptionist at work.

My marriage hadn’t been going too well for just over a year. I was in a really shitty sales job at the time, it was all about dealing with negatives the whole time.

Having a young, busty woman giving me blowjobs seemed like a great way to just enjoy life, even if it was just for 15 minutes on a Friday afternoon when everyone else had left.

I switched jobs—my conscience was starting to bother me about it—but I got busted.

My wife kicked me out and I lived at a friend’s place for a week. Reality came back to me and I was remembering all the things I enjoyed about my marriage and family. Namely, my three young sons.

My ex and I are in a better place now. We only spent a short time apart. As soon as we got back together, there were big swings in emotion. We would go from her being upset with me, to me feeling defensive and insecure from guilt, to a fierce bout of lovemaking. All of those emotions have cooled, but we want to stay together. 

We’ve been through a lot together. A few years before, she was diagnosed with cancer, I’d lost a job right afterward, we moved into a new house, and we had a new baby. All in the space of two weeks. It was a lot of strain on our relationship because we didn’t handle things as well as we could have. The affair was a wake-up call for both of us. We still have ups and downs, but we’re working hard to love each other and give what the other needs.

The lesson I learned was not what I expected if someone would have asked me about it. It wasn’t that I should be faithful in all regards to my wife. It wasn’t that I should keep my sons at the forefront of my decisions.

It was that I should be true to who I want to be. I had never cheated on my spouse or prior girlfriends. It wasn’t the kind of person I was. And I learned it wasn’t the kind of person I wanted to be. It wasn’t even about being honest with others, but being honest with myself.

As it immediately relates to marriage, I would have been far better off to muster up the courage to tell her I’m out of the relationship and that we should separate, than to run around like a coward.


My dad and I got along well. He asked me all sorts of stuff about my life. He seemed OK, a normal sort of guy.

Jennifer W., 28, Washington, DC

I went looking for my estranged father.

He left home when I was three years old, and my mother never wanted to talk about him. As I got older she gave me a few details, so I had a name and address. I waited longer, though, because I wanted to be sure that finding him was the right thing to do. I made such a terrible misjudgment.

Finding him wasn’t hard, but it wasn’t that easy either. He had moved, and started another family. I found him on LinkedIn, of all places. I took a friend with me and we sort of stalked him a little, well we tried to. We sat in a coffee shop near where I thought he worked, but didn’t see him. Then we went and parked outside his apartment block, but I was getting freaked out by then so we drove home.

Eventually I got a phone number via another distant relative, and I think she must have tipped him off because he didn’t sound that surprised when I called. We arranged to meet, and actually that first meeting was great. We met in another coffee shop. My friend came too and hung out at a different table, incognito. It felt like something from an action movie. My dad and I got along well. He asked me all sorts of stuff about my life. He seemed OK, a normal sort of guy.

Things turned bad pretty fast after that. I can see now that he struggles with relationships. He would be nice one minute, then turn on me the next. He shouted at me on the phone. He sent me horrible texts. It was like he felt he owned me. Eventually I had to cut him out. I got a new phone number and blocked him online. He has my address but I think he got the message, I’ve not heard anything from him for two or three years.

I learned—I’m not sure what I learned. Some wisdom you should trust, like the wisdom of my mom who warned me to stay away from him. And that thing about the grass being greener. It usually isn’t, and there’s a usually a reason for that.


I’m not allowed to watch YouTube when I’m supposed to be going to sleep.

Luke D., 12, Bath, UK

I got caught watching YouTube videos on my iPhone in bed.

Basically, I’m not supposed to do that. It’s my dad’s old phone and it’s my favorite thing. When he gave it to me he said there were rules, although I can’t remember what all of them were. Don’t tell him that.

One of them is definitely that I’m not allowed to watch YouTube when I’m supposed to be going to sleep. Especially on a school night. I’m not even allowed to be using the phone at all after 9 p.m.

Anyway dad found out and said that was my last chance, and if he catches me doing that again he’ll take the phone away for a week, and I know he actually will ‘cause he’s done that sort of thing before. And that would be, like, a nightmare.


William L., 5, New York

I pushed my little sister.

Mommy put me in a timeout. I learned that if I don’t want to get timeout again I shouldn’t push my little sister.