Regret minimization is a useful thing to consider when thinking about how best to live your life. “Success,” Toni Morrison said, “is when you have fewer and fewer regrets."

But how you go about the minimizing is important. Lots of people have few regrets not because they’ve made few mistakes, but because they don’t spend very much time thinking about them. They close their eyes, refuse to take an honest look, and condemn themselves to repeat the same mistakes over and over again.  

The other path is the reflective one—thoughtfully retracing your steps and attempting to honestly consider where you went wrong and what you could’ve done better, even if you know you were doing your best at the time. In this way, reflecting on our past can help us forge a less disappointing future.

The tricky part is that our memories don’t always serve us well, and the advice we’re given doesn’t always help.

Hindsight, contrary to popular belief, is never 20/20. Our current circumstances—our mood, the things on our mind, the world around us, what someone’s just said—have a way of colouring our past, twisting our perceptions. We must step carefully through our history, hold our past selves gently, never be quick to judge.

I regret, for instance, all sorts of things from the past two years of pandemic life. The time wasted. The junk food consumed. The crippling doubt and dwelling on details I had no ability to influence. I regret not doing a better job of keeping in touch with everyone I love and the times I reached for something to numb the pain, rather than allowing myself to feel it more fully.

Yet I’m still considering what lessons, if any, can be drawn. I want to be more resilient in the future, to be able to respond in more useful ways when times get tough, because I know there will inevitably be more tough times ahead.

It’s not about chastising yourself for falling short, but about recognizing the ways you did, why, and what you would need to do, or how you would need to think, to be able to respond more usefully in the future.

I’ve worked hard to deepen my meditation practice because I know I need to get better at sitting with discomfort, anxiety and fear.

The advice you hear most often is that people end up regretting the things they didn’t do more than the things they did. The chances they didn’t take. The things they left unsaid.

There's some truth to that. It's easy to agonize over the paths not taken in all areas of life. George Saunders, for instance, gave an amazing commencement speech about regretting the times he failed to act kindly when he could have. When I look back at the last three decades, I certainly regret the times I failed to act kindly. I regret not telling people I loved that I loved them. I regret assuming there would always be a next time.

But the idea is often overstated. People regret the things they did all the time. Lying. Cheating on their spouse. Hurting the people they love. If I had to list my greatest regrets, they would all be things I did. Things I never should’ve said. Parties where I drank too much. Times I trusted someone I knew I shouldn't.

Regret cuts both ways. I’m sure to some extent it depends on who you are and where you’ve been. Maybe people who are more reserved are more likely to regret the things they didn’t do, while those who are brash are more likely to regret the things they did.

But I think if you’re honest about it, you’ll find that you have regrets of both kinds, which is one reason they're so hard to minimize, why doing so is a lifelong endeavour. It’s not simply about taking more chances, nor is being thoughtful and deliberate sufficient. Good judgement is required and mistakes, both of omission and commission, will be made anyway.

It’s also why trying to have fewer and fewer regrets is such a good measure of success. Anyone who says they have none at all is almost certainly failing to be reflective or honest about their past.

Success lies, then, not in a life that’s free of regret, which is nothing more than a mirage, but in finding ways to use your past regrets as a source of learning and to behave better in the future.

I never regret the time I spend exercising, meditating, gardening, walking, writing, reading books, thinking deeply, showing gratitude, helping friends, saying I love you, talking with loved ones, playing with my daughter, holding my wife, allowing myself to cry or doing work I believe in.

I still have a lot to learn about regret, but if there’s one thing I know, it’s that it’s easier to be certain of the things you won’t regret than the things you will.

The more time I spend doing those utterly unregrettable things, the better my life seems to go. If I can figure out how to spend more of my life doing those things, I know I'll be successful, by Toni's measure and many others.

It almost sounds too easy. But I'm more and more certain that the simplest way to minimize regret is to spend as much of your time as possible doing things you know you won’t.

Steele