How to Handle Regrets

Celebrate the miraculous mistakes that led you to this moment.

Shell No. 2 (1928) by Georgia O’Keeffe

One thing you learn from reading advice letters for years is that some people seem to regret every big decision they ever make. “Maybe they didn’t prioritize the things they cared the most about,” you think as you read. But the regrets keep piling up: It was a mistake to waste so much time with this partner but it was also difficult to move on. It was stupid to move from one city to the next repeatedly but it was also impossible to stay in one place. Even though the letter writer makes a convincing case for having messed up their entire life, by the end of a letter you can imagine them making the opposite choices and regretting those, too: I’ve been living in this town my whole life. I should’ve traveled and pursued my dreams but instead I formed roots that keep me stuck here!

Regrets have less to do with a propensity for making bad choices and more to do with a habit of second-guessing every decision and distrusting your instincts. When you see the world through a veil of regrets, you don’t recognize your good decisions. All you can see are your mistakes. Everything smart you’ve ever done looks incidental, and everything foolish you’ve ever done looks like a reflection of your weak character. In this Ask Polly from 2018, I offered art as a remedy for this state of mind. By cultivating a sense that your life is an eccentric creation formed from your particular values, you invest in your interesting impulses and learn to trust your unique compass. And when you turn your back on that self-trust, you buy into the wider culture’s fear of decline and failure.

Some might struggle with the abstract use of shame and art here. People tend to believe that shame means feeling actively embarrassed by yourself, but shame can also be a habit of subconsciously distrusting yourself and questioning everything you do. Likewise, art doesn’t have to mean a work of art created by a trained artist. Viewing your life as a work of art is a way of understanding that if you want to feel happy from day to day, your personal affinities and weird preferences aren’t just selfish quirks that slow you down, they’re the whole point. When you celebrate your odd tastes and desires, you trust yourself and let your instincts guide you toward people, places, and things that will bring you more joy. By celebrating your very peculiar self, you infuse your experiences with value.

One of the saddest dimensions of modern culture is that many of us believe that a life can be objectively measured as a success or a failure. That’s like reducing our rich selves and complicated lives to numbers on a balance sheet: Are you in the red or in the black? Reductive assessments — I made so many mistakes, nothing added up! — hollow out your life experiences instead of capturing the complex rewards and insights you gained from fumbling through life, bewildered and lost, making the series of miraculous mistakes that led you here.

If you have a bad habit of seeing your life as series of unfortunate events brought on by the poor decisions of a hapless protagonist, it’s important to investigate why. Personally, I used to declare myself a complete idiot every few years in order to denounce the bad decisions I made up until that point, but also to feed myself the illusion that I’d radically changed and all of my decisions would be sound from that point forward. By disowning my own complicated interests and impulses and telling a strange narrative about how I was better now because I’d fixed my bad former self, I not only set myself up for more disappointment, but I hollowed out everything I’d valued along the way. I erased and covered up my mistakes instead of learning from them.

So these days, when everything goes haywire and my life feels chaotic — and whose life doesn’t feel a little chaotic right now? — I try to appreciate the small charms of the day, so I can add up the haphazard choices and mishaps that led me to this moment and feel grateful for them instead of questioning them. Sometimes all it takes is to slow down and notice things: the cool breeze floating in the window, the dog asleep next to my feet, the birds singing to each other in the trees, the train whistle fading into the distance over a chorus of cicadas. Even when my overriding sense of myself or my path forward feels shaky, soaking in the sensual experience of the day can feel like a remedy.

Shame subtracts the romance from the day by telling you that you’ve fumbled your way into a state of permanent insignificance. But no one else owns this day more than you do. People who appear successful are often failing to connect in ways you can’t see, and people who appear to be failing are often living lives that are more rewarding and enjoyable than you can understand from a distance. Comparing yourself to another person based on the few details and facts you can gather about their life is as absurd as trying to measure your joy against the joy of a bird singing in a tree. As the artist at the center of your creation, you’re the one who decides what matters the most. But you have to value your role and trust your choices in order to take satisfaction from what you create.

If you treat yourself like a loving parent for long enough — which isn’t easy at first! — you’ll find that you start treating the people around you that way, too. You’ll remind them of who they are, what they’ve already built, what they bring to the table that no one else does.

That’s really what it means to build meaningful connections with people. It’s not just about proximity and permanence. It’s about seeing people clearly and reflecting how interesting and unique they are when they start to feel ashamed of themselves or forget what they own.

Falling into the good habit of grounding yourself in the moment, treasuring the small details of your experience, trusting the strange twists that brought you here, and sharing that gratitude with the people around you: these are the practices that make your life a success. When you’re frustrated with yourself or the wider world or just rattled by the confusion of checking out from the entire world for a full year and then checking back in, it helps to quiet your mind and say to yourself: Nothing is missing. Nothing is lost. My job is to drink in this moment. My job is to see people clearly and love them for exactly who they are. My job is to savor this day exactly as it is.


Thanks for reading! Need advice? Write to askpolly at protonmail.com. Ask Polly publishes twice a week for subscribers, so