The regret fallacy

This was republished on Lifehacker.

Even though I’m in college I still take a class with my old high school history teacher. No grades are given, and class takes place sporadically on the weeks when I’m back home in Princeton.

Many teachers dislike when students bring food to their classrooms and eat while they lecture. In this class, food is a requirement and lectures are held at the Panera by my house. Most classes become unbearable to sit through after about an hour and a half. Students start wriggling around in their seats, and coughing loudly. The clock starts to move more slowly and the view outside the window suddenly becomes captivating. In this class, though, the hours seem to melt away almost imperceptibly.

This is a class I hope I never graduate from.

Mr. Figueroa is probably the smartest person in any room he walks into. He’s also the type of person that doesn’t seem to know it. Or if he does, he doesn’t let it on.

He’s 40ish and married with two kids. He grew up in Puerto Rico, and moved to the US after he was accepted to Princeton for college. Eventually he ended up staying at Princeton as a professor.

Back in those days, his students probably called him Professor Figueroa. These days he teaches high school history. Everyone calls him Fig. And that’s the way he likes it.

Most of his classes center around religion, or philosophy, politics or history. Today’s class, however, is on regret.

.  .  .

“The older I get the more consequences each decision seems to have. It feels like everything has more weight. Like staying in school. What if by staying in school instead of dropping out I missed my opportunity to build a big company?” I begin. Fig is listening intently, hands folded in his lap. “How do I live with myself if that’s what happens?”

“Do you feel like you regret staying in school?” The thing about Fig is that no question is innocent. One question leads to another, which leads to another, until he’s asked you so many questions that the answer becomes clear to you. Very rarely does he need to do any explaining himself.

“Most days I don’t. But at least for me it’s sometimes easy get stuck on ‘what ifs’. And sometimes it’s difficult to get rid of. I read somewhere that you end regretting the things that you don’t do, rather than the things that you do. That kind of stuck with me.”

“Let’s think about that. You end up regretting the things that you don’t do, rather than the things that you do. Explain that to me a little more.” Fig replies leaning back in his chair.

“Well the idea is if you go and ask senior citizens what they regret, most of the regrets start with ‘I wish had pursued my music career’ or ‘Or I really missed out on hanging out with my kids’. So most of their regrets come from times when they decided not do to do something.”

“But isn’t every decision not to do something, also a decision to do something else in disguise? So when the senior citizen said ‘I wish I had pursued my music career’ couldn’t that just as easily have been rephrased as ‘I wish I hadn’t become an accountant’?”

“I guess,” I say thinking hard.

“So ‘You regret the decisions you don’t make’ seems like a pretty vacuous distinction doesn’t it?”

“Well when you put it that way it does, I guess. But if it is a meaningless distinction then there’s no easy way to figure out which decision to make when you’re faced with one.”

“Sounds about right,” he replies with a wry smile.

“This is not helpful,” I say shaking me head and laughing to myself.

“Every single person that has regrets, has them with the benefit of hindsight. But you don’t have the benefit of hindsight when you’re making your decision do you?”

I shake my head, no.

“So it makes no sense to judge a decision you made without the benefit of hindsight and let it affect your emotional state. When you make these types of decisions, and you make them carefully, sometimes you’ll choose right and sometimes you’ll choose wrong. All you can do is always make the best decision given the facts at hand. If you’re lucky you’ll learn your lesson from the wrong decisions and correct them. But other than that you can’t beat yourself up about these kinds of things. It’s just not useful.” Fig takes a bite of his sandwich. “The other thing is, regretting a pivotal decision basically means you want an entirely new life.”

“What do you mean?” I say.

“Well let’s say you regret going to Penn instead of Princeton,” he starts.

“That’s one thing I definitely don’t regret.”

“Alright, well for the sake of argument let’s say you do. In your imagination you’re thinking, if I went to Princeton my life would be exactly the same except that at the top of all my resumes I could write ‘Princeton Class of 2014’ and I could go to Princeton reunions and hang out with all of the high fliers.” Another pause for a bite of his sandwich.

“But what you’re not thinking about is that if you went to Princeton instead of Penn, by doing so you’d have to give up every single moment from the time you decided to go to Penn until now. Everything. Every friend you’ve made, every class you’ve taken, every website you’ve worked on, every lesson you’ve learned. You’re a completely different person if you choose differently on a decision like that.”

“Ok, I see that.”

“And so the only time you ever regret a decision, is if you’d rather give up every single part of your life from then until now. Now, thinking about it that way, do you regret not leaving school?


“And that, my friend, is the regret fallacy.”


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19 Sep 2012, 5:58pm | 12 comments

  • AriannaSimpson
  • Stever Robbins

    Damn. Now I regret having used “will I regret this later?” as a criterion for making some of the major decisions in my life…I’m not sure I agree with Fig. I’m not one to regret, in general, but there are definitely times when I’ve elected to stay within my comfort zone and not do something outside it. When I later ended up doing those outside things, they turned out to be pretty awesome and life transforming. Over the years, it’s become clear that it’s more accurate to say that my regrets are often around staying in my comfort zone when given a chance to move outside it. I could have gone to Fabulous Event X. (“I’m not the kind of person who goes to Fabulous Events.”)Instead, I elected to stay home and watch TV.Ten years later, someone dragged me to Fabulous Event X: Year 10.It was AWESOME! And staying home to watch TV wasn’t. In the future, attending Extraordinary Event Z might be a good idea, even if it’s outside my comfort zone.

  • Dan Shipper

    Very astute comment. I'll have to think about how this plays into my thoughts on parsing out what you will and will not regret beforehand. There is something to be said for making decisions that get you out of your comfort zone. Thanks for posting that.

  • Karl Kranich

    Good stuff to think about. Thanks for taking the time to post it! And Go Quakers!

  • Franklin Chen
  • Franklin Chen

    Great explanation by your teacher. The point is that we tend to frame hypotheticals in terms of one thing being different while everything remaining somehow the same, but in reality, every decision we make creates potentially an entire alternate reality. So although there is sense in listening to the elderly expressing their regrets, we need to be aware that if they had lived differently, they could now be expressing different regrets. I think the best we can learn from these expressions of regrets is simply the knowledge that there really was a choice, and one was made, and possibly without taking the long view. In particular, the young often think “I could always do X later”, and then have regrets later, and therefore we should think more about the present and not a vague future, when making tradeoffs while considering important decisions.

  • David Figueroa

    Dan, you are too kind and generous. Your willingness to continually interrogate reality keeps me accountable to do the same, so thank you. Stever raises a powerful point regarding decision-making. If decisions are based not on an open, clear-headed, and honest processes, but instead on fear, prejudice, and unexamined premises, then we will make decisions that will hinder rather than promote our flourishing and that of others. Once one begins to experience the impact of a decision (I loved Event X) one may be tempted to second-guess a decision to have gone or not have gone to Event X. At that moment of second-guessing, regret may begin, a negative disposition toward a previous decision may take over. What follows may be an endless fretting about missed opportunities, alternative and imagined outcomes, and roads not traveled. It is this circular, negative feeling about the past that I reject not merely as unproductive, but also as deceitful. It is unproductive because by itself it changes nothing. And it is deceitful because regret suggests that one could have known then what one knows now, when what one knows now is a result, in part, of having made the decision one now wants to undo. Regret for missed opportunities is asking one to judge the past by the standards of today, and anyone who has studied history knows this to be a fool’s errand. Now, and directly to Stever’s point, revisiting not the outcome or perceived wrong outcomes, but the factors that led one down a certain path is not regret at all, but mindful reflection. I cannot change the past, but hopefully I can impact the present. (I did not say the future, because nobody really knows the impact of his or her actions, so I may be seeking one outcome and bring about an unexpected one. Therefore, the outcomes are out of our control, but the input is within our reach.) So rather than regretting, we should strive to reflect on what moved us to act. Understanding better what moved us holds the hope that we might be moved by different forces next time, and thus make decisions mindfully. Again, a “good” or “bad” decision is an after-the-fact comparison between an outcome and an imagined one. But reflecting on whether a decision was made mindfully, well, that we can know with greater clarity, and use that insight as we move along.

  • Joyce Bishop

    I rarely comment online but I wanted you to know how much I appreciate that you took the time to share this. This perspective finally cleared up some confusion about an old regret, since in fact I am very happy with how things turned out over the years. What I have gone on record calling a “bad decision” was a pivotal, although not direct, means to my current success. Although I would never recommend anyone take the same path (it shouldn’t have worked), I can no longer call this a regret!. Thank you again – I hope I am one of many people who found this (via LifeHacker) to be forehead-slapping good news.

  • Rob Weddle

    I’m glad I came across this today because I’m recently going through a similar paradigm shift myself.It seems to me that the eradication of regret is dependent upon a couple key things:1) Emotional honesty. Prof. Figueroa mentioned that you can only hope to make the best decisions based on the facts you have–and I agree with that completely–but if you aren’t truly in touch with your perception of the world and of your place in it, then you will always be able to talk yourself out of the best decision. Back to Stever Robbins example in his comment: You had to know at the time you made the decision to not attend Fabulous Event X that watching TV would be a relatively safe if not mundane experience. But are you overlooking any other factors that influenced your decision? Was there perhaps a level of anxiety–such that you wouldn’t be able to overcome until some 10 years later–that would have precluded you from enjoying yourself? Consider that (for example, not to presume it is true): you act on an impulse against your own biological cues only to regress any progress you may have been making at emerging from your social cocoon. The glitter that comes with a later positive similar experience should not mask the motivations behind the original decision. If you ever say “I should have done this years ago,” be prepared to say it over and over again in the future because you’re simply repeating a habit of retrogressively ignoring the emotional forces that drive you to make decisions in the first place.2) Emotions don’t exist in a vacuum. In addition to “things I never did,” I find that another major source of regret is “Things I did that made me feel bad.” People are all too eager to wash over painful past experiences without recognizing their value as true learning experiences. Joy does not exist without grief, nor calm without tension. As you experience grief, remind yourself that it is not only impermanent, but that the decisions you made to cause yourself grief can surely be learned from. 3) The acceptance of chaos, and the illusion of choices. The universe is vast, and you are tiny. Events are set into motion now that will bear results later. If you choose to hurtle yourself in front of any one of these trajectories, you will get one set of results. If you choose not to, you will get another set. Sometimes the differences between theses outcomes is infinitesimal (I didn’t attend the popular concert, and as a result, attendance was 24,999 instead of 25,000), or they can be dramatic (The decision to go/not go to Starbucks that day was the difference between meeting/not meeting the person who would become my spouse). But either way, understand that the results WILL happen, with or without your participation. Living is as easy as drawing breaths. You can go through your existence like a pinball, bouncing about from place to place, not making a single decision. Or you can manipulate every last detail of your life that is conceivably in your power. And there are as many degrees in between as there are people alive right now. But eventually, everyone will be killed by something outside of his/her control.4) Ownership of decisions. Point #3 isn’t meant to be fatalist. I think the answer lies somewhere in the middle of serendipity and full-bore life-planning. I personally happen to find value in the notion of having a say in events that happen to me; not because I think my decisions will have universe-altering effects, but because I find value in the concept of human legacy, of a society which maintains records of significant people and achievements. I want to be such a person who attained such achievements. I believe that the only way to do that is to make daring but informed decisions. But I also find value in being able to recognize situations in which my efforts, talents, and energy won’t make much difference. If my daring is ever too strong or my calculations ever too inaccurate, I will fail. But when I do, that’s for me to learn from and try again–if I even find value at all in a second effort–not to lament that I didn’t get it right. To put it simply: I simply have no time for regret.

  • Stever Robbins

    David, I like your distinction between regret (which I rarely feel) and reflective learning.I’m still not sure I agree with Dan’s teacher, however. While the road not taken is always pure speculation, the road taken is NOT speculation. I don’t believe it’s a fallacy to take a road, decide you don’t like it, and regret not having taken a different road. In my example above, I’m noting that spending a lifetime vegging in front of a TV is sufficiently uninteresting to me that I think it’s highly probable that any of a large number of different lives would be superior. Thus if I’d spent most of my life in front of TV, I may well “legitimately” regret it.We compare and contrast what is with what-is-speculated all the time. Heck, when I get a flu shot, I’m doing it even though I have no proof that I would otherwise have gotten the flu. And if I don’t get the flu shot and come down with the flu, I may regret not having taken the flu shot. To me, neither of those are fallacious positions.But either way, anticipation of future regret can spur me into taking action that I quite enjoy.Thanks to the logic “If I don’t do this, I’ll regret not taking a shot when I’m 80,” I’m learning to sight-sing and act, and have co-written a one-man show I’ll be performing about personal productivity based on my podcast. All with no prior experience in theater or performing. I think it’s one of the coolest things I’ve ever undertaken, and the final decision was driven by fear of regret not giving it a shot.

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  • Carson Chan

    thank you counsellor; this was well written


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