One night many years ago, I was driving my Chrysler LeBaron convertible with the duct-taped top to a Target store near the Pennsylvania-Delaware border. I was in the area for a regional academic conference, and I needed, well, who knows what. I came to an intersection and saw the familiar red, illuminated letters through my driver’s-side window. There was little traffic. I got in the left lane and turned into the store’s parking lot.
Immediately, I was stuck. In mud. The intersection was a T, not a cross, as I had thought, and I had been looking at the back of the Target. There was no parking lot, just a grassy expanse between the road and the shopping center. After spinning the LeBaron’s wheels without effect and swearing just as unprofitably for several minutes, I called for a tow. When the truck came, the driver parked it on the road and unspooled a long cable from the winch. I asked him why he wasn’t going to hook the wheel lift up to the front of my car. “Just because you decided to get yourself stuck,” he replied, “doesn’t mean I have to.”
The kind of confident motion in the wrong direction that got me stuck is a long-standing feature of my romantic, professional, and online lives—of romantic, professional, and online lives generally. That night by the Target, for the better part of an hour, I wanted nothing more than to undo the decision, to yank it back from beyond the brink and do things differently. Of course, I couldn’t take the turn back, any more than you can take back an insult, a bullet, an affair, or a vote. You can’t make it so those things never happened. All you can do is regret them.
But you’re not supposed to. At least, not according to our collective store of cultural wisdom. Life is short. What’s done is done, and there’s no use worrying over it. Meanwhile, an infinitude of possible experience awaits you out in the world. Life happens now, and regret keeps you mired in the past. People get the words “no regrets” tattooed on their flesh, but we needn’t be so literal about this common truth. Every one of your actions is just as indelible. So if you’re going to regret your past behavior, you may as well regret the sunrise, or the tides. Instead of ruing our past, we should own it—our wins, losses, truths, lies, loves, cruelties, scars, jail terms, adolescent poems, tweets, everything—and enter the future with abandon. According to digital-age folklore, the only regrets that truly sting are over actions not taken: jobs not applied for, alluring beauties not dated, trips untaken, fears unfaced.
To test your commitment to the philosophy of no regrets, imagine, as Friedrich Nietzsche suggests, that a demon comes to find you “in your loneliest loneliness” to tell you that you will repeat all your actions, past and future, in exact sequence, an infinite number of times. Even the demon’s visit, and your response to it, will recur forever. “Would you not throw yourself down and gnash your teeth and curse the demon who spoke thus?” Nietzsche asks. “Or how well disposed would you have to become to yourself and to life to crave nothing more fervently than this ultimate eternal confirmation and seal?”11xFriedrich Nietzsche, The Gay Science, trans. Walter Kaufmann (New York, NY: Vintage, 1974), 273–74. First published 1882.
How well disposed, exactly? How well disposed is someone who refers to himself in the third person or says, to a reality show’s camera, that he has no regrets, none at all? How well disposed is a typical Kardashian? Or a Trump? During the 2016 presidential campaign, Megyn Kelly asked then-candidate Donald Trump whether he regretted any of his false and offensive comments about her, about Heidi Cruz, about John McCain. Trump cinched up his face, bobbed his head, and said, very quickly, “Yeah, I guess so.” Then he immediately steadied himself and continued, more directly, chopping the air with one hand, “but you have to go forward. You make a mistake, you go forward. And, you know, you can correct the mistake, but to look back and say: ‘Gee whiz, I wish I didn’t do this or that,’ I don't think that’s good.... In a certain way, I don’t even think that’s healthy.”22xQuoted in Jenna Johnson, “Donald Trump Does Not Apologize for Anything—Even Things He Seems to Regret,” Washington Post, May 17, 2016, https://www.washingtonpost.com/news/post-politics/wp/2016/05/17/donald-trump-does-not-apologize-for-anything-even-things-he-seems-to-regret/.
“No regrets” sounds great on TV and shares well on social media because we equate decisiveness with importance and control. But to live proudly without regret is to ratify your own idiocy, to take unjustified self-satisfaction in your existence. Your past actions made you who you are, sure, but maybe who you are isn’t so great. Without regret, you have no way to reckon with that. Knowing that dating that person blew up several friendships and netted you an STD (its own eternal recurrence), do you relish the thought of repeating the affair over and over, forever?
To be fair, there are more sophisticated versions of the “no regrets” ethos than the ones tagged #yolo (“you only live once”) on Instagram. Because the past is unchangeable, a Stoic might say, it’s irrational to attach any psychological interest to it at all. “Remove aversion, then, from all things that are not in our control,” wrote the Stoic philosopher Epictetus, “and transfer it to things contrary to the nature of what is in our control.”33xEpictetus, The Enchiridion, trans. Elizabeth Carter (Internet Classics Archive, n.d.), chap. 2, http://classics.mit.edu/Epictetus/epicench.html. There’s no point in crying over spilled oil or wine, Epictetus adds. Such losses are “the price paid for equanimity, for tranquility, and nothing is to be had for nothing.”44xIbid., chap. 12.
Today’s Stoics are economists and psychologists who espouse rational decision-making. We should take an unsentimental view toward sunk costs, they counsel, and make our decisions based on the future we wish to live, not the past we’ve already lived. One prominent cognitive therapist writes, “You can bemoan the loss in your stock portfolio, or stare at the [ugly] tie in your closet, or review all the terrible things in the relationship that is over. Or you can focus on making your life better now. The great thing about making your life better now is that you actually have control over what happens now. You can actually do something. Unless you have a time machine, you can’t go back and change the past.”55xRobert Leahy, “Reversing Regrets: 7 Steps to Moving On,” HuffPost, July 19, 2012, https://www.huffpost.com/entry/no-regrets_b_1676117. We might think of ourselves at every moment as a new manager who arrives at the company and has to survey things as they currently are and forge an optimal way forward. Handwringing over our predecessors’ choices won’t help us maximize the next quarter’s profits.
But ethics is about more than rationality. It’s also about relationships with strangers, including the strangers we each are to ourselves. Regret allows us to enter into an ethical relationship with who we have been in the past. The self-as-eternally-new-manager model is right about one thing: Even the person you were a moment ago can seem alien to who you are now, given a sufficiently consequential decision separating the one from the other. What kind of nitwit drives straight into a muddy field, thinking it’s a parking lot? I would never do that. But that guy? What was wrong with him?
Moral growth doesn’t just mean looking to the future but reconciling past and present selfhood. It demands regret. The person who regrets nothing becomes a conduit for experience without being enlarged or deepened by it. It passes right through her uninterrupted, never bending back on itself, never pooling, never overflowing her banks.
The Value of Not Forgetting
I used to teach religion at a small Catholic college in Pennsylvania. Once I was grading papers in my office and came across yet another intro paragraph that began something like “Since the beginning of time, mankind has wondered how the bible was compatible with modern science.” I groaned audibly. My door was open, and two of my colleagues happened to be walking by at that moment. I read the atrociously reasoned opening paragraph of the essay to them, seeking sympathy. They said something noncommittal and went back to their offices. I kept grading.
A day or two later, a student came up to me after class to say she had overheard me making fun of that paper. She was sitting at a desk in the hallway outside my office taking an exam for another class, and my rant interrupted her train of thought. It was her paper. They were her words I was reading back and mocking in front of my colleagues—and in her hearing.
I was shocked and mortified—though surely not as much as she had been. I apologized profusely but knew that the harm I had done was deep. She lectured me about my arrogance and my disdain for students. I deserved to feel as small as I did at that moment. In confronting me, she didn’t just call out my sin; she showed a moral courage I rarely display in my own life.
The next time I ran into my dean, a kind, gregarious priest, he said the student had approached him too, and he had promised her he’d talk to me about it. He didn’t need to say much more than that. I knew what I’d done was wrong, and he knew it came from frustration.
What would a “no regrets” approach to this episode look like? What could have been more callous than to brush off the hurt I caused this student because I believed in living without regret? I couldn’t move past the incident. I kept coming back to the moment when the student confronted me, when I felt so morally inferior to someone whose intellect and effort I had derided. I owed her my regret. I owed all my students, really. I learned to grade in silence, to suppress the desire to laugh out loud at an unintentionally hilarious sentence. But as I was learning, I needed the memory of my past failure and all its consequences to keep me from relapsing. I could forgive myself, but to forget and to move on—staples of conventional wisdom—would be unjust.
I recoil at the suggestion that I am reliving my past, but my regret really is an attenuated way of doing just that. It’s a way of using my imagination to inoculate me against actually reliving it. If I didn’t regret making stupid left turns into the muck, I might just keep making them, spinning my tires and calling a sturdier, more sensible person to winch me out.
Listening to Our Better Self
In the lonely loneliness of midlife, I sometimes regret more than just one incident of thoughtless cruelty in my career. I regret the career itself, and the two solid decades I spent pursuing it. I’m poorly disposed toward myself.
I wanted to be a religion professor from the time I took my first undergraduate religion classes and spent hours at a time in the on-campus apartment of one of my professors, talking over cups of coffee about Big Questions. This man seemed to live the good life. I wanted to do the same. So I did the things you need to do, to live in an on-campus apartment and host students for coffee and chats about St. Augustine’s theory of the will. I went to graduate school and eventually got the job teaching at the college in Pennsylvania. My identity melded with the work. I wore wool blazers everywhere. I took students’ intro paragraphs personally.
My outburst over that one student’s paper was an early and fleeting symptom of a slow-developing illness I contracted in the course of pursuing this dream. Like many jobs people do for the sake of love, mine became thankless. Too much teaching, too little student interest in the subject I loved, too many escalating administrative demands. I glimpsed the good life here and there. For a while, years after I had shamed that student in front of my colleagues, I even got myself thinking it was an honor to read students’ papers. They were sharing their best ideas with me—the best they could come up with under the circumstances, anyway—just because I asked them to.
But that sense of fulfillment didn’t last. I had very few wide-ranging discussions of Augustine. My wife and I lived apart while we both chased academic jobs. Because I had pinned my vision of the good life to my job, when the work soured, so did my entire sense of myself. I burned out. I quit.
Would I wish to repeat, indefinitely, the unappreciated labor, the years of my marriage lost to academia’s two-body problem, the disappointment of repeated failures to get a job elsewhere? Absolutely not. Not that my preference matters. Nietzsche’s option isn’t between the eternal recurrence of the same and a nice, linear life of freely chosen happiness. It’s between celebrating the fact of eternal recurrence and crying over it. And I’ve made my choice.
The essayist Meghan Daum proposes her own version of Nietzsche’s thought experiment. She imagines being her own demon, picturing her current, middle-aged self appearing to her younger self—“out of nowhere, like a goon sent in to settle a debt”—and telling her to change, to undo some decision Daum now regrets, such as staying with a guy she didn’t really care about or coasting through her college classes. The experiment ultimately goes nowhere; Daum’s older self has no real advice for her younger self, since her older self is “the cumulative effect of all those failures.”66xMeghan Daum, The Unspeakable: And Other Subjects of Discussion (New York, NY: Picador, 2014), 76–77
When I perform the same experiment, I tell my mid-twenties, grad-school self to ignore the older, more worldly-wise friends who claim to be coaching him on school and life. Don’t mistake their confidence for wisdom, I say. I also tell him he doesn’t need a complete Banana Republic wardrobe, that someone making $12,000 a year shouldn’t be going out five nights a week, and that the debt he’s ringing up will trouble his future self. I tell him what he’ll regret.
To get to the root of my regrets, though, I need to go further back, to meet the version of myself that had just graduated from college, the guy who was animated by a fresh vision of the good life. I buy him a Pete’s Wicked Ale. I tell him he doesn’t need to rush off to graduate school. I tell him he already has a good job at a nonprofit, an easy commute, and plenty of friends. I tell him it’s possible to have an intellectual life without being in academia. After all, he’s reading Annie Dillard and Michael Ondaatje on the train to work and meeting up with friends to argue about philosophy in cozy bars. He’s already doing the thing he wants to do, and he doesn’t have to live in a cinder-block dorm apartment to do it. I tell him grad school can wait. He won’t lose his identity if he pursues something else. I remind him he loves writing—he even loves writing poetry—and should work on that, find a mentor in journalism, and start pitching stories. I teach him how to pitch. I tell him to be more confident in his ability to find a pathway outside academia, which, if he’s honest, is the only version of the good life he’s ever seen.
I tell him that if he takes the turn he’s planning, he’ll get everything he wants, and it will still nearly ruin him. He’ll eventually dread going to work every morning—because it’s still work. He needs to realize it’s work. He’ll want nothing more than to run from the reality he now dreams of. His career will be short. He’ll wish he’d listened to me.
I tell this to my twenty-one-year old self, and because he’s polite, he hears me out and thanks his older self for the beer and the talk. And then he plows straight into the academic mire anyway, leaving me alone again.
In rooting around my past for regrettable memories, I also stumble upon things that mitigate my regret. I did talk to students about Augustine. One came up to me after a class on the Confessions and said, “This book makes me think about everything!” Another student told me, after a field trip to the art museum, that he had never previously thought of what paintings could communicate theologically. “They always just seemed like a bunch of pictures,” he said. There are countless belly laughs over coffee with my colleagues. There are memorial services for colleagues who frustrated me, but whom I also loved.
Regret is built on memory, which means it’s always built on a bit of a lie. There’s no question that our memory editor cuts the footage to flatter us, but it can just as easily create a blooper reel, if that’s what the client seems to want. The past self I engage with when I’m feeling regret made me who I am through his decisions, but I’m also selective in recreating him. I imagine him in a way that suits my current psychological needs. I picture my younger self as someone who can still change. That’s because I worry if I can still change. I’m the one who needs the advice I dispense in the thought experiment. I’m the one who, at forty-four, is anxious about creating an identity outside the academy. I’m the one who, as much as he regrets having gone into academia, regrets having left it, too.
Our cultural fear of regret is a sharp spur to action. It’s also, no surprise, big business. The trillion-dollar insurance industry turns anticipated regret into revenue. My dentist convinced me to buy a $200 plastic mouthguard by getting me to think about the inevitable day my persistent teeth-gnashing would mean I needed a new coat of enamel. Parents, pastors, and guidance counselors all play on future regret, even absent the profit motive. We resent their power over us. What they recognize is that regret is a great teacher. The versions of me who drove into the mud or blew up over a bad intro paragraph or went without hesitation into academia all acted without regret’s counsel.
But there’s a real limit to anticipatory regret’s usefulness. Our future selves are even more a mystery than our past selves. We can’t know what our future selves will wish they had done, because we can’t anticipate what they’ll wish at all. Desires come to us spontaneously, often prompted by new acquaintances and envies. Your younger self couldn’t have guessed how important living in a dry climate would become to you. Or that you’d fall in love with someone with deep religious commitments. What this present self regrets would be as opaque to the humidity-loving, avowedly secular younger you as the desires of the person who just moved in across the street. Yet both our neighbors and our younger selves make ethical demands on us.
Paradoxically, the way to live confidently isn’t to banish regret and look only to the future. The challenge is to act, informed by reflection on past mistakes and ready to regret the decision later. It’s to realize that there are worse things than regret. Learning to regret well makes you humble in the face of the consequences your actions will have for a person—your future self—who remains something of a stranger. So act with circumspection and humility, and be ready to earn reproach. If you know how to regret, then you’ll accept the consequences and learn to forgive the self you were.
I recently started teaching college classes again, just part-time, to get me out of the house and earn a steady, if small, paycheck. I sent my CV to the first-year composition program at a nearby university, and it turned out they needed a class covered right away.
I threw together a syllabus, a crude map of the intellectual terrain I hoped to cover. On the first day, I rode my bike to campus and met the students in a dimly lit classroom in a dorm basement. A massive, unwanted fake ficus tree crowded anyone who sat in the corner. We talked about the meaning of work, and how ideas become essays. In the first few weeks of the semester, the class approached the ideal of what I had dreamed university education ought to be. Not yet doing work that would be graded, my students were experiencing learning for its own sake.
Then they had a paper due, and the next day, I knew they wouldn’t do the assigned reading—the longest of the semester so far—but I decided to pretend they had anyway, forcing them to talk about it in small groups. I asked what they thought about the reading, and they looked at each other and giggled. As the laughter spread, I grew more angry and embarrassed. I flashed back to the days of my burnout, when every class put my ego on the line. I felt stuck again, and I couldn’t back out. I had lost the students already, and there were still three months of the semester to go. I hadn’t learned anything from my career regrets, and here I was, repeating the same mistakes—taking my teaching too personally, relying on undergrads to read a long magazine article so I could feel fulfilled in my work. I spent several days in a deep funk. I didn’t want to go back.
But I did. And I talked with the students about my frustration. I adjusted my expectations of them and myself. I redrew the map. I put less time into planning the class sessions and reminded myself that the students’ learning depended more on them than on me. I recast myself as their writing mentor and relied on the fact that I knew how to teach students, even if I wasn’t sure how to teach composition. I gave the students my full attention in our meetings and didn’t worry about class much when I was home. I focused on my own writing.
Things turned out fine. I decided I would do it again.