Regret Essays Free

I regret everything. Decades-old decisions, things I said, things I didn’t say, opportunities I missed, opportunities I took, recent purchases, non-purchases, returns. I turn all of these things over in my mind and examine them for clues — to what, I’m not sure. All I know is that very little of what I do or fail to do escapes the constant churn of revision. It’s just the way I process experience: sceptically, and in retrospect. It’s like being a time-traveller, only instead of going back to Ancient Rome or the French Revolution, I return again and again to the traumatic sites of my own fateful (or not so fateful) forks in the road. Some people see this as self‑flagellation; I tend to think of it as a lifelong effort to reconcile the possible with the actual — a getting to know the real me. After all, as they say, we’re defined by our choices.

When I was six years old, I pulverised a friend’s brand-new Etch A Sketch. Actually, he wasn’t my friend — our mothers were friends, I didn’t know him all. He was a little bit older than me — maybe seven or eight — and I found him aloof and intimidating. He lived in an enormous modern house made of glass and concrete, with an exterior staircase that led to a balcony overlooking a terrace and pool. We were visiting Lima, where my Peruvian parents were from, from suburban New Jersey, and I felt like a fish out of water — shy, awkward, foreign, weird. At some point, I broke away from the other kids and went up to the balcony to be alone with the Etch A Sketch, which the boy had received for Christmas a few days earlier. Alone, I was gripped by the sudden urge to balance the Etch A Sketch on the balcony railing. Even as the idea was forming in my mind, I knew that its risks far outweighed its dubious rewards, and that I’d live to regret it. I was still thinking these thoughts as I watched the Etch A Sketch fall through the air and land in one piece with a sickening crunch. When I picked it up, it made a sound like a maraca. The knobs moved but no lines appeared on the screen. I then placed the Etch A Sketch carefully on a nearby chair, went to find my mother, and told her I had a headache and wanted to go home.

Remorse, it seems to me, would have been the more appropriate response to having destroyed my young host’s shiny new present from Santa, but that would have involved a degree of empathy that I’m ashamed to admit I didn’t feel for him. Somewhere deep down, I interpreted his cool self-possession as contemptuous indifference or outright disdain, and in enacting my tiny rebellion, I succeeded only in manifesting my worst fears about myself. In my fit of alienation and insecurity, I’d turned myself into the person I thought he thought I was: The weirdo who broke his new toy. And I’d made sure he’d remember me that way forever.

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There’s a particular disdain for regret in US culture. It’s regarded as self-indulgent and irrational — a ‘useless’ feeling. We prefer utilitarian emotions, those we can use as vehicles for transformation, and closure. ‘Dwelling’, we tend to agree, gets you nowhere. It just leads you around in circles.

Regret is so counter to the pioneer spirit — with its belief in blinkered perseverance, and dogged forward motion — it’s practically un-American. In the US, you keep your squint firmly planted on the horizon and put one foot in front of the other. There’s something suspiciously female, possibly French, about any morbid interiority.

Best, then, to treat the past like an overflowing closet: just shut the door and walk away. ‘What’s done is done,’ we say. ‘It is what it is.’ ‘There’s no use crying over spilt milk.’

Sometimes, the prevalence of this point of view makes me feel regret toward my tendency toward regret. It’s hard not to feel bad when your way of processing experience is routinely pathologised, or dismissed offhand as whiny, weak, and useless. As I write this, I regret writing it because I fear it makes me sound more neurotic than I really am. At the same time, I worry that it makes me sound exactly as neurotic as I actually am, and I regret not having done a better job of keeping this under wraps. I regret regretting things all the time, because surely I could be putting my imagination to better use. What’s more, I regret that I’m compelled to talk about my regrets, not just in therapy, but at dinner, at the playground, on the phone, and in print. I regret these things in part because I’m acutely aware of how my regrets are perceived when I express them. What I want are deep explorations of parallel universes and alternative outcomes. But what I get in return are sad-eyed smiles, gentle pats on the arm, and the occasional rousing pep talk, which is never what I’m after.

The assumption is that these ruminations stem from a flaw in my character, or an unresolved trauma, or some questionable behaviourist conditioning. It’s a neurobiological glitch, maybe, or a bad habit. And all of these might apply, but I also think I’m driven by a combination of pragmatism and curiosity. Whenever I come up against a problem, or find myself plagued by questions I can’t answer, my impulse is to lift up the hood of my day-to-day denial and complacency and dive into the intricate circuitry of my past in search of whatever minor gasket malfunction sparked the powder train that eventually blew up the spacecraft. I guess in some way, I’ve come to think of regret as a deductive game that, although it’s almost never fun, will eventually unlock all of life’s mysteries. Is this what I intended to do? Could I have predicted this outcome? How did I get here?

The idea that maybe nothing happens for a reason is deeply unsettling to many

In the fall of my senior year of high school, my dad and I flew from Madrid, where we lived, to Boston for college interviews. My dad’s career was going off the rails at the time, but he was feeling hopeful and expansive, so when the airline misplaced his luggage, we headed straight for Brooks Brothers and then went out for lobster. My first college interview, which also happened to be my first interview of any kind, ever, was at Harvard. It hadn’t occurred to me to do anything to prepare for it, much less to try to get a sense of what to expect.

As it happened, the person who interviewed me had been a teacher at my high school in Madrid 20 years earlier. He knew my principal as well as several veteran teachers. We talked about Spain’s transition to democracy after Franco, about the way the country seemed to wake up after a deep 40-year sleep. We talked about dress codes in restaurants and porn on TV. As the interview was ending, I was suddenly struck by the feeling that I’d messed up. I’d frittered away the interview making clever observations about the politics of shorts. And even though the interviewer seemed encouraging, I decided, when it came time to work on the application form, to save my dad the $50 application fee. And neither one of my parents had anything to say about it. Yes, I could have applied and gotten rejected like everyone else. But if I had, I probably wouldn’t have blown my interview 20 years later, when I was a finalist for a fellowship. But I guess I’ll never know that, either.

Pop psychology books on the subject of regret offer easy-to-follow plans on how to eradicate it, like a virus or a muffin top. They dismiss it with titles such as Woulda, Coulda, Shoulda: Overcoming Regrets, Mistakes, and Missed Opportunities (1989), No Regrets: A 10-Step Program for Living in the Present and Leaving the Past Behind (2004), and One Month to Live: 30 Days to a No-Regrets Life (2008). Regret isn’t just seen as antithetical to reason, it’s spiritually transgressive as well. Sayings such as ‘Everything happens for a reason’ inherently condemn the sort of nihilist relativism that might experience regret as proof of the random meaninglessness of life. Regret is sinful, a direct rebuke to the existence of a God that knows what he’s doing, and cares.

What these two world views, pop psychology and religion, have in common is a deep-seated need for meaning and order, for a system or a narrative that makes sense of the world. The idea that maybe nothing happens for a reason is deeply unsettling to many people. For the rationalist, regretting past events or actions is tantamount to admitting to the terrifying possibility that failing is as easy as knocking over a glass. Goal-based decision-making gives structure to what would otherwise be a series of random events, and accomplishing those goals gives the illusion of meaning. The idea that it’s always preferable to keep your eyes trained on the future, to look on the bright side, and to let go and let God take over is deeply ingrained in both rational and religious world views.

And yet something about these attitudes toward regret rankles me. They strike me not just as inhumanly opposed to emotion, but also as anti-intellectual.

In her book Regret: The Persistence of the Possible (1993), the poet and psychologist Janet Landman argues that our views on regret are shaped in large part by decision theory as it relates to the theory of economic choice. In this framework, the past must be repudiated in rational decision-making because decision theory assumes that the person making the decision is rational, informed, and able to make accurate calculations. ‘If conflicting values and demands are resolvable by the astute application of cost-benefit analysis,’ Landman writes, describing this economic idea in a nutshell, ‘then regret’ — which is both counterfactual (it dwells on what might have been, but wasn’t) and emotional (these imagined alternative scenarios spark feelings) — ‘is simply uncalled for.’

People feel they need to deny regret — deny failure — in order to stay in the game

Our discomfort with regret, she writes, reflects an ‘existential discomfort with the limits of our personal control’. The idea that human experience and behaviour can best be understood and optimised by reducing it to data has become only more entrenched since Landman wrote her book. It gets easier every day to project a future without regret; to be the best, most optimal people we can be today, so that we can look back without ambivalence. Life is not mysterious, it’s mathematics. All we have to do is track our productivity, our spending, our steps, our calorie intake. All we have to do is count our friends and likes and follows. The illusion of control that these tools grant us over every aspect of our lives is powerful. There is always something we can do today to avoid regret tomorrow. To admit regret is to admit to a previous failure of self-control. ‘In the reigning economic models of decision, human beings are “calculating machines” who decide their preferences based on calculations of utilities and probabilities,’ Landman writes. ‘We deny regret in part to deny that we are now or have ever been losers.’

In a culture that believes winning is everything, that sees success as a totalising, absolute system, happiness and even basic worth are determined by winning. It’s not surprising, then, that people feel they need to deny regret — deny failure — in order to stay in the game. Though we each have a personal framework for looking at regret, Landman argues, the culture privileges a pragmatic, rationalist attitude toward regret that doesn’t allow for emotion or counterfactual ideation, and then combines with it a heroic framework which equates anything that lands short of the platonic ideal with failure. In such an environment, the denial of failure takes on magical powers. It becomes inoculation against failure itself. To express regret is nothing short of dangerous. It threatens to collapse the whole system.

In starting to lay out the possible uses of regret, Landman quotes William Faulkner. ‘The past,’ he wrote in 1950, ‘is never dead. It’s not even past.’ Great novels, Landman points out, are often about regret: about the life-changing consequences of a single bad decision (say, marrying the wrong person, not marrying the right one, or having let love pass you by altogether) over a long period of time. Sigmund Freud believed that thoughts, feelings, wishes, etc, are never entirely eradicated, but if repressed ‘[ramify] like a fungus in the dark and [take] on extreme forms of expression’. The denial of regret, in other words, will not block the fall of the dominoes. It will just allow you to close your eyes and clap your hands over your ears as they fall, down to the very last one.

Not surprisingly, it turns out that people’s greatest regrets revolve around education, work, and marriage, because the decisions we make around these issues have long-term, ever-expanding repercussions. The point of regret is not to try to change the past, but to shed light on the present. This is traditionally the realm of the humanities. What novels tell us is that regret is instructive. And the first thing regret tells us (much like its physical counterpart — pain) is that something in the present is wrong.

Some years ago, I was working at a job I liked when I was approached about another, higher-paying job. In fact, it paid so much more that I was convinced my current job would never match it. I don’t know what I based this knowledge on, having never had a similar experience, but I did. The process of interviewing for the new job was secretive and stressful, and it made it hard to get advice from people who might have helped. When I got the offer, I did get advice from someone I knew in finance. ‘Don’t base your decision on the money,’ she said. ‘Decide where you’d rather be and don’t try to start a bidding war. In the end, you’ll be resented for it.’ This advice came from someone who made more money than I ever would, for whom the money — beyond a certain a level — became theoretical. But it didn’t apply to my situation. While the money wasn’t entirely the point, it was unignorable.

I took the job, declined to listen (embarrassingly) to counteroffers from my employer, which caused hard feelings, and immediately regretted it. At the end of my first day, feeling as if I’d entered the Twilight Zone, I called my friend from the car, very upset. ‘I made a huge mistake!’ I said. She took command. ‘It’s too late now,’ she said. ‘You made your decision. What’s done is done.’ It took a couple of years for me to realise that this was the second bit of bad advice I’d received in relation to this decision. Both stemmed from a total rejection of things that are hard to quantify, and a slavish belief in the primacy of quick, decisive action over ambivalence, ambiguity, and mixed feelings.

It’s in this privileging of reason unfettered by emotion, this thinking of people as ‘calculating machines’ that Landman suggests we’ve gone all wrong. The problem lies in clinging to absolutes and falling for false dichotomies. Sometimes, our assessment of reality is faulty, or obsolete, or weirdly ideological, or based on false dichotomies such as reason vs emotion, or the past vs the present.

Mixed feelings are not only what make us human, they’re what make us truly rational. They help us arrive at complicated truths by way of a dialectic process. Rather than deny regret, we should embrace ambivalence. We should strive for an ideal — that is, behave as if it’s possible for an absolute ideal to exist — while remembering that it doesn’t, that in fact outcomes are random, and that all possibilities exist simultaneously.

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Meaning & the Good LifeMemoirMood & EmotionAll topics →

Carina Chocano

is a freelance writer whose work has appeared in The New Yorker, The New York Times Magazine and Wired, among others. She is the author of Do You Love Me or Am I Just Paranoid? (2003).

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I wish I had spent more time with my sister


1st place $50

By Bellen Avelar,Clark Magnet HS (La Crescenta)

Bellen wears a jacket and pins that belonged to her sister Quira, who died almost three years ago.
Photo by Jean Park, 16,
Harvard-Westlake School (North Hollywood)


I have always heard people say, “Don’t have any regrets.” For some reason I believed it was true. Why regret something if there is nothing you can do to change the past? On January 14, 2007 I realized that I did have one regret—not spending more time with Quira, my sister. Quira was a loving and caring person, someone who could make you smile. She had cerebral palsy and on January 14, 2007 she passed away.

I remember the day as if it were yesterday. The day before, my mom, Quira and I went to a birthday party. We got home late and woke up late the next morning. I had to run an errand and my mom went to the kitchen to make breakfast. I was with my sister Elsy’s husband when he got a phone call. He told me to run to his car. I was scared not knowing what was going on. It felt like the longest car ride of my life. When we were about five minutes away from my house he told me that maybe my sister had passed away. I could not move. I could not cry. My body went cold. When I got home I saw the ambulance and my family around my house. I ran and saw my mom and Elsy crying and I knew it was true, Quira was dead. I have never felt so much pain in my life. I started to cry and hugged Elsy.

For the next few days my life was a blur. I would go to school and forget Quira was dead and feel that she was still alive, but when I would get home, the day of her death replayed. It was a recurring nightmare.

As time went by I started to think of all the things Quira and I had not done together, all the things she missed in life. I regret not doing more for her. I regret not telling her thank you for all the things she did for me. I regret not saying sorry for making her feel bad or for upsetting her. I regret not making an effort to help her when she needed my help. I regret not being there to defend her when people made fun of her. I regret not accompanying her when she had doctor appointments. I have many regrets when it comes to all of the things I could’ve done and did not do.

Now that she is dead I realize how much I didn’t do for her. If I could go back in time and be a better sister I would do it without thinking. I would change my attitude and help much more. I would stop being so selfish. I know death is a part of life, but that doesn’t stop death from hurting.

It has been almost three years since Quira passed away and I still feel terrible. When I heard about this contest I knew it was the perfect opportunity for me to let go of all the pain I feel. I want people to know to never go to sleep mad at someone or without telling the person “I love you” because you never know if they will wake up.

I want people to learn from my mistake and appreciate their loved ones. Now that I have written this I feel a lot better and hopefully I will no longer hold on to all these regrets. My sister passed away and holding on to regrets will not bring her back to life. Instead of thinking of all my regrets, I should focus on the beautiful moments we had together.



My father is in prison


2nd place $30

By J.S., Washington Prep HS

When I was 11, I didn’t make a good choice. One night  I was watching TV with my cousins while my dad was drinking with his friends in the other room. A few moments later I heard a lot of commotion and arguing. I went to check on my dad and he was ready to fight. I pulled him out of the room to talk but he wasn’t willing to listen to me. I then told him to take me home.

We were walking down the street because we lived just down the block. He seemed pretty mad about what had happened, but I had no idea how he felt. As we walked up the steps he kissed me on my forehead and said “I love you.” At that point I knew something was wrong. He then walked away as I went in the house.

The next day I received some bad news. Two of my neighbors had been reported dead. Then it hit me—the reason my dad didn’t stay the night and the reason he didn’t tuck me into bed and the reason he didn’t eat dinner with me. I regret not pushing him to stay the night with me and my mother, sister and brother. Maybe I would still have my father to look up to and count on instead of him being in prison. He was my everything, my other half, my best friend and a loving father. I didn’t get why this would happen to me at such a young age. I figured I was cursed or just had bad luck with the things that were most important to me.

As the years went by I cried a lot, but as I got older I realized I had to live with it. I never forgave my dad for leaving me. He would write me letters but I would never reply. I didn’t know what to say. When I was mature enough to understand everything I wrote him back and expressed all my feelings. I was just so angry because he said he would never leave me again. Maybe if I would have had a clue or was old enough to change his mind that night, I would still have my father.



A sketchy Internet relationship


3rd place $20

Author’s name withheld

Not too long ago, I was in a “relationship” with someone I met on MySpace. We had never met and I had never even been in a relationship. The fact that we were both gay and had to keep it secret from our friends made the situation more awkward. We first had to come out to each other and our “relationship” grew from there. Soon after we started our conversations, we decided that it was time to hear each other’s voices, so we started to talk on the phone. Now, keep in mind that I still had never met this person. For all I knew, he could’ve been a 50-year-old man pretending to be a young adult, yet I stupidly continued to talk to him.

We talked on the phone nightly until the wee hours of the morning. This left me grumpy in the morning, and my schoolwork became sloppy. This relationship with a person that I really didn’t know was affecting every aspect of my life. My friends didn’t know why I was mad, my teachers didn’t know why my work kept getting worse and worse, and my parents didn’t know what was happening to their son.
Things felt OK for a while, but the guy slowly began to show his true colors. Every conversation we had, online or on the phone, kept getting more and more sexual. All that mattered to him was sex. What’s worse is that I played along with everything that was happening.

Eventually, we decided that it was time to meet. Deciding on the place was difficult. I wanted a public place like the mall, but all of his suggestions were private places. He invited me to his house, or a little cove with plenty of deserted areas where anything could happen. It was clear that he was either an online pedophile or a guy my age who was looking only for sex. Whichever it was, I refused to go along with it. I finally made the decision not to go.

After I missed the first meeting, we stopped writing. We essentially broke up. However, this could barely be labeled a breakup because it wasn’t much of a healthy relationship to start with.

The decisions I made while talking to him were stupid, and I still feel unbelievably angry with myself for doing it. I am constantly asking myself, “Why did you play along with what he was saying?” I knew that I wasn’t ready for what was going on, yet I pushed myself to do it anyway, thinking that somehow it was what I needed.

I regret trying to force myself to find someone, and I regret doing the things I did to try and keep a boyfriend. I regret feeling that I needed someone because I felt like everyone else had someone. I regret every decision I made during the entire ordeal, and am glad that I had the power to say no. Although I said no after so many things had gone by, I am proud that I didn’t go through with meeting him. I learned valuable lessons that I will never forget. I learned about the strength I possess. And I know now that drawing the line, and saying no to something you don’t believe in, is not a bad thing to do. Stand up  for yourself and say no when you know something isn’t right.



I’m sorry I bullied my brother


Honorable mention

By Kevin Melendez, Birmingham Community Charter HS

Bullying my brother is my biggest regret. It’s something I should’ve never done.

I know what you’re probably thinking, that I’m a cruel brother. I don’t hit my brother anymore. One reason is because I got in trouble too much. The second reason is he got hurt badly. My brother rarely got bruises. Then there were times that I made him cry. Not really a good feeling when you think about it.

For a while my brother wouldn’t want to be around me, not even when we were at a party where we had no one to talk to and didn’t know anyone. He avoided me at home and anywhere else he could. I don’t blame him for what he did. I mean getting hit in the arm just because your brother is angry or jealous isn’t something you want. It probably made him fear me. I should never have let my anger get the best of me.

I wonder how my relationship with my brother would be if I hadn’t been so cruel and evil. I see my friend’s strong and healthy relationships with his siblings, knowing that could have been my brother and I. We have an “OK” relationship now, but I can’t raise my hand without him flinching. It’s not as bad as it used to be because he rarely does that anymore. Still it makes me feel like a monster when he does.

I wish I could go back in time and take it all back, make sure that my anger didn’t get the best of me. No one should let their anger get the best of themselves or pick on someone just because you’re angry, no matter what. Trust me, it’s not a great feeling when you pick on someone. It makes you feel like a monster. You should have a relationship that has trust and a strong bond. Don’t have a relationship that’s based on fear.



Next essay contest—What don’t your parents understand about you?

Your parents were once teenagers and they probably think they get you and know what it’s like to be a teen. But do you think they do? Do they get on you about the way you dress, the music you listen to or the friends you hang out with? Do they question your interests or think you don’t spend enough time studying? Do they expect you to follow in their footsteps? Tell us what you wish your parents understood about you. MAIL YOUR ESSAYS TO:

L.A. Youth
5967 W. 3rd St. Ste. 301
Los Angeles CA 90036

OR E-MAIL THEM TO:

editor(at)layouth(dot)com.



DEADLINE: Friday, Dec. 11, 2009

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