When People Look Back on Their Lives, What Are Some Common Regrets They Have?

Save your regrets for when you're older.
Save your regrets for when you’re older.

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This question originally appeared on Quora.

Answer by Gary Teal:
You ask what people in their 30s, 40s, and older regret when they look back at their lives. I suppose it’s wise of you as a teenager to think about how you might avoid a future regret. But I’d counsel you to take any good path open to you, do the best you can, and be happy. Save regrets for your 50s and sixties. And you will have them. This may sound a little melodramatic, but no matter how happy you are, at my age, your regrets are countless. You have made decades’ worth of little miscalculations you can’t completely erase from your memory, as well as a number of big mistakes that made life permanently harder. Divide regrets into three groups:

The things you did that you wish you hadn’t.
At your young age, you most likely exaggerate the impact of your previous errors. If you’ve done something truly and dreadfully wrong, you are the reason we have a system that protects the identity of juveniles. Either way, you have a lot of time to recover. By age 50, you laugh (if uneasily) about the mistakes you made when you were younger. After all, you see young people making those same mistakes, even when you have drawn them a picture of how to avoid them. Your sins of commission somehow seem not so disturbing, because in all but the worst cases, they’re part of your story now, even if they left scars. You can joke about them with your oldest friends and your family. They played a part in making you who you are. Forgive yourself.
The things you wish you had done but didn’t.
At your age, you may be sorry that you didn’t try to kiss Janie on your first date with her last Friday, but you have the boundless and justifiable optimism that you will kiss her soon. When you’re old like me, you’ll torture yourself over the risks you didn’t take, and the opportunities you missed by failing to act. There is the haunting question of whether, even if you actually made the best decision at the time by not doing what you might have, those actions could, in retrospect, have been good mistakes to make at that point in your life. Maybe it would have been a good time to learn a painful lesson. On the other hand, maybe you really did miss your main chance. You could be living in a nicer house with a bigger car and more attractive children. Or you’d have a Nobel or an Oscar or a young trophy spouse: whatever you thought you wanted. You just can’t ever know what would have happened, good or bad. You can go over it repeatedly, and you can construct the parallel universe where you made your move. And you do, if you don’t train yourself to let it go.

The heavy cost of the time you’ve wasted.
By far, for me, the most significant regrets I have now are about lost time. I have the real sense that it is getting increasingly likely that I will die without having ever seen Machu Picchu, or learning to speak French fluently, or having built my own house. This shocks and disturbs me. As I grow older, the opportunity cost of truly pointless hours piles up. What could I have accomplished instead of playing [redacted] games of freecell? In some cases, what were once very realistic possibilities are just completely out of the question. There isn’t time for me to become a billionaire, much less be elected president. In fact, I may never be a millionaire, or even run for a seat on the school board. At my age, though some given limited subset of your original dreams may be still in reach, you have to start setting priorities. You have that heart-stopping moment when you realize that if you are fortunate enough to have some significant savings (you regret not having saved more, of course), you can only hope to take one or two truly exciting vacations a year to some wondrous place: the Hagia Sophia or the Grand Canyon. So if you don’t draw the wrong card and get prostate cancer at 63, you might make it to 20 or 30 more of the “1,000 places to see before you die.” Even that assumes that you won’t take refuge in the perfectly reasonable, natural, and comforting desire to repeat things you’ve done before and enjoyed, maybe just once, long ago. Or maybe one place becomes your regular hangout, where everybody knows your name. Very tempting.

Have a glass of cognac, look up the lyrics to Pink Floyd’s “Time,” and then have another glass of cognac. How on earth did Roger Waters write these lyrics in his late 20s? Nobody should confront those thoughts until they’re my age.

I myself am a very happy guy. I’m always aware that I have done better than most people, even in the U.S. I have never suffered, much less caused, a premature death or other tragedy in my family, and I’ve never been challenged by some significant handicap or misfortune, nor any big injustice committed by or against me. I don’t want a “do-over.” But I really can’t take seriously those people who say they wouldn’t change anything. Maybe they mean that they are quite content with how it’s going, as I am. But I could have done a lot better. There’s no question. If others say they can’t think of something they’d change, they have a very limited imagination. Don’t they wish they’d spent more time listening and talking to their grandparents? Avoided alienating some dear friend? Even if they have the soul of Mr. Burns, they might be thinking of how they could have bought RIMM at $4 and sold it at $140.

This September is my 25th anniversary, so I’m looking forward to celebrating the only important decision I ever made, and I really nailed it. That decision has defined my life, and it’s been great. Still, I wouldn’t mind being 18 again for a few hours, the one and only time I ever went out with Janie. I took her to a steakhouse, we went to see a movie, and then I walked her up to her front door and just said good night.

Answer by Caroline Zelonka:

 I saw this cartoon in college and thought it was funny. Twenty years later, I can relate. For as long as I can remember, I have wanted to have kids. But in my younger years, I foolishly assumed that unlike certain accomplishments like a career, the marriage and kids thing would just happen.

Well, they didn’t. I dated plenty of people but never even thought about making family a priority. Then, in my late 30s, a bout with ovarian cancer left me permanently infertile.

I think about the kids I never had every day, several times a day. I have a great relationship with my nieces and nephews, and I volunteer at a children’s hospital on a regular basis, but it’s just not the same to be around other people’s kids. I would love to adopt or be a foster mother, and hopefully be in a financial and domestic situation that would make this feasible one day.

But again, not the same. And it pisses me off when people say, “you’re lucky you don’t have kids, they’re so much work, blah blah blah.” Yes, but a lot of things in life that are worthwhile are also so much work.

I think the mothering instinct is so strong in some women that the knowledge that one will never get a chance to give birth and raise their own child goes beyond regret. One that a bar chart cannot capture. I can deal with most of my other regrets in life but am having a hard time dealing with this one.
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