As a matter of autobiography, whenever I have had a major life decision to make, I have always been struck by not just the helpfulness, but the apparent significance of thinking about which choices I might come to regret. This paper is an attempt to try to pin down what has seemed to me to be compelling about such cases.
I'll start with some examples, in an attempt to at least try to pin down the kind of thinking that has seemed to me to be probative. I don't claim that what has seemed compelling to me is or should be universally compelling, but the examples are intended to make vivid one way of seeing a major life decision – a way that I claim ought to be at least intelligible. Then we'll take a detour through some puzzles about how expectations about regret could be the right sort of thing to be helpful in decision-making at all, let alone central or probative, especially in the context of decisions of major significance. What I hope to take away from this detour is some insight about what sort of emotion this probative sort of regret might be, and why it might be so important for major life decisions, in particular.
My answer, in a nutshell, will be that though there are many decisions that we make that we can see, in retrospect, to have had large effects on the shapes of our lives, decisions that we know or at least suspect at the time to do so play a special role in our sense of ourselves as the authors of our own lives. These are the choice points through which we can claim authorship over our own lives in the stories that we tell ourselves about who we are, where we have come from, where we are going, and why. Regret over these choice points is therefore a kind of failure to come to peace with our authorship over our own lives. This is what lends expectations of rational regret a special significance in major life decision-making, in particular, for those agents who value this, and this is an intelligible thing to value.
1. Some Stories
We start with some stories whose characters face important life choices:
Last Chance Reginald has recently struck it off well with Adele, who works in the building across the street, and who he has gradually been getting to know. She lives in his neighborhood, is fun to talk to, and last week they had a first date, which went well. But today Clara texts him that she's passing through town, and hints that she is newly single. Reginald and Clara have had chemistry for years, but have also had a series of missed opportunities. When she asked him out in college he already had a hometown girlfriend, and then by the time that soured and he got up the courage to ask her out, she was seeing someone else. And so on – Clara has never stayed single for long. A relationship with Clara would be hard. She lives in another city, and their career paths don't cross regularly. He is somewhat more confident that a relationship with Clara would be fulfilling and meaningful, if it worked, than the same for a relationship with Adele, but he is substantially more confident that a relationship with Adele could work out, than about one with Clara – the logistics are too complicated, and she does seem to go through boyfriends. But Reginald is struck by the following consideration: if he skipped the opportunity to pursue a relationship with Clara and the relationship with Adele did not work out, then he would always regret it. But if he spoiled his budding relationship with Adele to try to avoid missing yet another connection with Clara and nothing came of it, he would not regret it – Adele simply hasn't occupied a large enough role in his life for her to stand out in this way as a possible future source of regret. Reginald isn't trying to reason about what to do – he spends most of the day trying to avoid thinking about either Clara or Adele. But his thoughts keep returning to this consideration about what he would regret, and it strikes him as deeply relevant – indeed, as probative. So Reginald gives up on the more realistic opportunity of a relationship with Adele, and makes plans to see Clara tonight.
Fellowship Match Crystal has just completed her residency in internal medicine, and is applying to do fellowship training in cardiology. She gets interviews for a number of fellowships, but most of the most highly rated fellowship programs decline to interview her, with the exception of the program at University Medical Center, which is directed by Dr. X, the most famous cardiologist whose research overlaps with her own research experience during residency. She is excited for the opportunity, which could lead to far greater job opportunities than the other fellowships that she is a candidate for. But during her interviews, Crystal develops strong misgivings about University Medical Center's treatment of fellows and about Dr. X, including seeing some negative but far from incriminating circumstantial evidence about Dr. X's attitudes toward women. Meanwhile, she has a wonderful time on several of her other interviews at less established programs and feels a strong personal connection with the cardiologists who direct those programs. Overall, as Crystal sorts out her preferences, she decides that University Medical Center is her third-preferred program, behind two of these others. But Crystal doesn't know which programs she will be able to get into. Medical fellowships in the United States are determined by a computer algorithm that takes as inputs ranked lists of programs from each candidate and ranked lists of candidates from each program. The structure of the algorithm guarantees that no candidate ends up with a program that is lower on her ranked list than one that would have preferred to have her. So when the computer tells you your match, you know that you could not have gotten into any program that you had ranked more highly. But in contrast, because of the nature of the match, you can never know whether you would have gotten into a program that you ranked lower, had you ranked them differently. But Crystal is struck by the following thought: even though she is fairly confident that University Medical Center, despite its advantages, is overall a less good fit for her than her other top choices, if she goes somewhere else and it turns out to be a disaster, then she would deeply regret not giving University Medical Center a chance, unless she knew that she couldn't have gone there. Whereas in contrast, if she makes the conventional, safe choice and goes to University Medical Center and it turns out poorly, Crystal doesn't see herself as regretting her choice in the same way – she will simply not be regularly confronted with reminders of those programs, in the way that she will for University Medical Center. In fact, this thought is so compelling to her that she submits a ranked list to the fellowship match with University Medical Center ranked first, followed by her top two choices, and waits anxiously for the computer results, in the hopes that she gets her second-ranked choice.
Corporate Buyout Dwight has worked for eight years to build his small company from scratch. They have a product in which he takes a lot of personal pride, because it's competitive with the products of huge corporate competitors despite being constructed out of kludgy workarounds due to the fact that the corporate competitors own and abuse overbroad patents that make it really difficult to compete. But Dwight and his team have developed a compelling and successful brand for their product that overcomes this difficulty. Now Dwight's largest corporate competitor comes looking to buy Dwight and his company out. They offer to hire everyone in Dwight's company for double their current salaries, and make a large offer for the value of the company as a whole. But they don't plan to use Dwight's company's product – they know, as Dwight does, that it is kludgier than their own product, which doesn't have to evade the overbroad patents. The point of the buyout is just to remove a well-branded competitor to their own product from the market. Once they hire Dwight, they'll set him and his team to work at working around overbroad patents from their other competitors and developing a more compelling brand for their set of products, so the nature and challenges of the work for Dwight and his team would be very similar (and there is a lot of money on the table). But despite this, Dwight doesn't find the decision at all obvious. Oh, part of him grants that it is exhausting having to figure out how to make everything work for his small company, and suspects that he is likely to be quite happy keeping the most stimulating and challenging parts of his work while relieving himself of the responsibility over his other employees and the other attendant stresses of running a small company. But he is also deeply struck by the thought that if things do not turn out well after the buyout, then the buyout will always be something that he could deeply regret – he has so much invested in his current product. Whereas in contrast, despite the large amount of money involved, Dwight doesn't foresee ever regretting staying the course, if things turn out poorly. His team agrees, and they decline the buyout and continue to compete with the larger corporation.
Soured Relationship Sylvia is being courted to move to a new firm, which would require her and her partner to move to a different city. There are many advantages and disadvantages to each option, both for Sylvia and for her partner. But among the disadvantages of leaving, as Sylvia sees it, is that she has a close relationship with her sister, Monica, who lives in the same city. As time progresses, Sylvia's work opportunities at the new firm turn out to be not quite as uniquely promising as had initially seemed to be the case. But at the same time, her relationship with Monica sours. They have a fight from which it has become difficult to recover, and things get bad to such an extent that it is hard to count living near Monica as one of the reasons to stay. Still, Sylvia is struck by the following thought, which seems to be totally compelling, to her: given her current expectation about the value of living near Monica, her expected quality of life is better for the move, than for staying. Yet if she and her partner go through the move and things turn out on the poorer end of what can be reasonably expected, the fact that her soured relationship with Monica might have influenced her decision would lead her to always second-guess that decision and regret the move. And even worse, if things turn out on the poorer end for her partner of what might reasonably be expected, the fact that her soured relationship with Monica might have influenced her decision would lead her partner to resent her for the move. Whereas if she and her partner stay, then even if things never improve with Monica, she would not have the same source for regret. Sylvia and her partner agree to stay.
2. Discussion
In each of these examples, the characters face significant life choices. They are not compelled by the significance of considerations about what they might regret with respect to decisions about whether to order spaghetti or lasagna, or about whether to purchase Dial or Lever handsoap. The decisions that they face have consequences for the future shape of their lives – consequences that they are in a position to anticipate, in advance. What I claim about these cases is that they are realistic, and they are intelligible. In particular, they are not pathological or deeply irrational. I don't claim that no one ever thinks about what they might regret over trivial choices that will recede into the background when they look back at their lives years later, but I am certainly not claiming that it is natural or intelligible to do so. Something about the fact that these are major life decisions has significance.
It is important, of course, for these cases, that considerations about possible regret figure asymmetrically, with regret more easily anticipated in one direction than in the other. But I don't mean to claim that there are no versions of these cases where considerations about regret might take a different shape, and weigh in the opposite direction. For example, one can imagine a different version of Crystal's case, in which she has long been in counseling, struggling to overcome a long history of failing to trust her own judgment. For that version of Crystal, there might be many more opportunities to regret ranking University Medical Center first, if she is unlucky enough to get her top-ranked choice. Or consider an alternative version of Reginald's case, in which Adele works, not just across the street, but on another team at his office with which his team often collaborates, and she is also being avidly courted by Reginald's best friend. One can imagine that if the chances are reasonably good that if Reginald doesn't follow through with Adele, she will end up in a long-term relationship with Reginald's best friend and he will have to see her daily at the office for years, it could be possible that Reginald could have greater regrets about not following through with Adele, if his date with Clara doesn't work out, than about not hooking up with Clara, if his relationship with Adele doesn't work out.
These alternative versions of Crystal's and Reginald's cases highlight yet another important feature of the stories that I have told. The asymmetries that I've described in how each character imagines what they may come to regret in the future do not derive from any particular values for the underlying utilities for non-regret aspects of their situations – indeed, I have not, in most cases, even said what the underlying utilities might be, or what the agents take them to be. Of course, one of the significant factors driving regret is plausibly the difference between how well things turned out and how well they would have (or might have) turned out – you can have greater regrets over things turning out terribly than over things turning out merely poorly. But what the examples illustrate, is that this is not the only factor driving the experience of regret – regret is also driven by attention, and hence by factors that affect what each character expects to attend to at later times. Reginald, Sylvia, and Dwight anticipate regretting their choices because of the significant roles that Clara, Monica, and Dwight's company and product have played in their lives. Crystal anticipates regretting the choice of one of the less established programs because the banal conventionality of choosing University Medical Center makes it unavoidably salient, and Crystal's case also shows that what you know about what could not have happened had you taken another choice can also filter what you are in a position to regret.
Finally, I want to insist on one important feature of all of the cases as I've described them. In every case, the character making the choice feels torn and confused about what to do, until they conceive of the question in terms of what they expect to regret. Each character finds this an illuminating and decisive way of framing their decision, goes from being confused and conflicted to feeling clear and confident about their decision, once they frame it in this light. But none of them approach their decision from the beginning in these terms. Any attempt to explain why it is intelligible to pay attention to expected regrets in decision-making that fails to respect these observations about the examples will therefore fail to do justice to these characters, as I am imagining them.
3. Regret as a Heuristic
In each of the examples, the characters face significant life decisions – choices that are worth putting thought into. Reginald, Crystal, Dwight, and Sylvia all struggle with how to compare the competing values available in their choices, but find it helpful and simplifying to consider their choice through the lens of thinking about what they would come to regret, should they make either decision. As I have said, I myself find this perspective intelligible, and when faced with similar choices myself I have found this way of thinking compelling, even. (I won't get into how autobiographical any of the examples are.) I don't claim that everyone will find it compelling, or even that everyone will find it intelligible. On the contrary, even I find it puzzling what could make the perspective shared by Reginald, Crystal, Dwight, and Sylvia intelligible. My ultimate goal in this paper is to try to say something illuminating about what might make it intelligible. But we must see what makes it puzzling, first.
It isn't puzzling that expectations of regret might be helpful in some way in thinking through what to do. After all, as a first pass, we might think that it is rational to regret a choice just in case you believe that you ought not to have made it. If this is true, then your expectations of what you will rationally regret in the future should line up with your expectations of what you will rationally believe you ought not to have done. But in the future, in general, you will be better-informed about what you ought to have done. So for this reason, it makes sense to defer to the judgment of your future self, in deciding what to do.Footnote 1
This reasoning draws a natural line between expectations of regret and rational choice, but even in the best case, it is only as a heuristic. In the best case, you are sure that you will regret something or believe something only if it is rational to regret or believe it. So in the best case, you are sure that you will regret something only if it is rational to regret it, and hence only if you rationally believe that you ought not to have done it. And in the best case, you are sure that your future self is at least as well-informed as you are now – that you will not forget something important, in the meantime, for example. But then it follows that in the best case, it is already rational for you to believe that you ought not to do it – so reasoning about regret could be helpful as a way of reaching this conclusion, but it cannot be more than just a heuristic – you must have independent evidence that you ought not to do it.
Moreover, we are rarely in the best case. Your future self is not always better-informed, and sometimes you can know this in advance. You can anticipate that you will forget something important, for example, or that you will be distracted. These are all standard counterexamples to the principle of Reflection, which says that your current confidence in some proposition should be consistent with the confidence that you expect to have in the future in that proposition. So these are all ways in which you can be sure that you will rationally believe that you ought not to have done something, but still believe now that you ought to do it. But you could also expect that your future beliefs about what you ought to have done will be irrational – if they are, your regret could rationally correspond to your beliefs, but would still be no guide to what you ought now to believe. Or even if these conditions are satisfied, your expectations about whether you will regret something may not line up with how much you will regret it – so, for example, you could be more confident that you will regret choice A, but expect that if you regret choice B, you will regret it much more. The heuristic role of regret in decision-making cannot accommodate a role for varying expectations about how much you will regret something.
For these reasons, the fact that rational regrets might be tied to the belief that you ought not to have done something seems to fail to do justice to Reginald's, Crystal's, Dwight's, and Sylvia's ways of thinking. In any case, I don't think that it is true that it is rational to believe that you ought not to do something, just because you know that your future self, who is better-informed, will believe that you ought not to do it. Consider, for example, Donald Regan's famous miners case.Footnote 2 There are ten miners trapped in a flooding mine, but you don't know whether they are in shaft A, or shaft B. You could block one of the shafts, so that the flood waters enter only the other shaft, and if you block the shaft that the miners are in, it will save all ten miners, but if you block the wrong shaft, they will all drown. Or you could leave both shafts unblocked, in which case one miner will drown, but the other nine will survive.
You have no way of knowing which shaft the miners are in until it is all over. So you conclude that you ought to block neither shaft. But you know that later, after the flooding is over and the surviving miners leave the mine, you will learn which shaft the miners were in. At that time, you know that you will think to yourself, ‘I should have blocked shaft X’, where X is the shaft that you learn the miners were in. And the claim that you should have blocked X entails that you should not have left both shafts unblocked. So as you are faced with your original choice about what to do, you rationally believe that you should block neither shaft, even though you are rational to be confident that your future, better-informed, self will believe or be committed to believing that you shouldn't do so. This is because ‘ought’ and ‘should’ judgments in natural language – at least, the kind that are practical, and line up with appropriate advice – are information-sensitive in a way that makes them inappropriate objects of Reflection-like respect for the judgments of our future, better-informed, selves.Footnote 3
4. Regret Theory
An alternative source for understanding the role of expectations of regret in life decisions is regret theory, as introduced and developed by Loomes and Sugden, Bell, and Fishburn.Footnote 4 In regret theory, agents are understood as placing some disvalue on regret, which is understood as an increasing function of the difference between the actual value experienced given one choice and some function of the possible values that could have been experienced given an alternative choice.
So, for example, suppose that Aditya is offered a choice between one million dollars and a 9-in-10 chance of ten million dollars. Though his marginal utility for money is declining, let us suppose that the additional $9million is worth more to him than the first $1million, so that a straight expected utility calculation on the basis of the value of money would tell him to take the chance at $10million. But given that he had a choice of getting $1million for certain, if he chooses the chance at $10million but ends up with nothing, Aditya stands to regret his choice. If he would regret it enough, then if we add the disutility of regret to the utility of money, his expected utility calculation may tell him to take the sure $1million.
There is something right about this idea, and something that fits the cases that I have in mind, but it is also an over-simplistic story, and one with many holes. What is right about it, is that regret – and its opposite, positive feeling, whether that is best described as pride or elation – is a real human experience that brings with it pleasures and pains. As a real human experience bringing with it pleasures and pains, it is a candidate to be something that agents care about. And for an agent who cares about it, it would be bizarre for them to make decisions that did not take it into account. So of course minimal regret theory is right, in some sense.
That is not to say that such a minimal regret theory is the correct account of any of the actual human decision behavior which regret theorists have intended to rationalize or explain. For in order to correctly explain behavior in these cases, the disutility of regret must be quite significant, in proportion to the utilities of other things. Take, for example, the case of Aditya. Suppose, for concreteness, that the additional $9million is worth just as much to him as the first $1million. So leaving aside the disutility of regret, the expected utility of taking the chance at $10million is 1.8 times the expected utility of taking the sure $1million. And he has only a 10% chance of experiencing regret, if he takes the chance at $10million. So in order for the disutility of regret to tip the balance toward taking the sure $1million, the disutility of the regret he would experience for not getting anything when he could have had a sure $1million would have to be more than 8 times as large as the utility of $1million – big enough that you would only compensate him for a quarter of it afterwards if you gave him an unrelated $10million a week later. So even with such a steeply declining marginal utility function for money, regret theory can only explain the rationality of Aditya's taking the sure $1million if it assumes that Aditya cares way more about regret than about money – absurdly much, it seems.
The same considerations go if we assume an even more sharply declining marginal utility for money. Suppose, for example, that for Aditya, the extra $9 million would be worth only a 1/5 as much as the first $1million. Then the straight expected values of his utilities from money of taking the chance at $10million would be 1.08 times his utility for the first $1million. In order to overcome the extra .08, his disutility for the regret of missing out on $1million would still have to be .8 times his utility for the first million dollars, since he has only a .1 chance of experiencing this disutility. (In fact, if we allow the plausible assumption that there are positive utilities for the elation that you experience when things turn out better than they could have done, as Loomes and Sugden [1982] and Bell [1982] both assume, then the disutility for regret has to be even greater, in order to rationalize this choice.)
So for these reasons, despite the fact that it is obviously true that expected regret ought to be accounted for in any rational choice, it is highly suspect whether regret theory offers the correct account of any of the things that it is intended to explain. In order to do that, ordinary human beings who consider cases like the Allais paradoxFootnote 5 or are the subjects of Kahneman and Tversky's experimentsFootnote 6 would have to all care about regret to a very high degree – far more, at any rate, than it is at all obvious that anyone does or ought to care about it. Even if people do in fact care so much about regret, it is natural, without a better understanding of why we do, to see it as pathological to care so much more about your own feelings of regret than about anything that can be purchased with $1million – including, for example, saving an expected 352 lives by donating it to the Against Malaria Foundation.Footnote 7
In addition to assuming such a high disvalue on regret without explanation, simple versions of regret theory oversimplify the sources of regret. The original versions developed by Loomes and Sugden and by Bell assume that agents always learn what would have happened, had they taken the other choice, but in all of the major life choices that are described in my examples, agents never learn what would have happened had they made the other choice – the closest to this is Crystal, who hopes to eliminate regret by obtaining counterfactual knowledge of whether she would have gotten the fellowship at University Medical Center, had she ranked it first. They also assume that regret is a function only of the differences between observed and counterfactual values for non-regret utilities. But we have seen that in real life, attention is important for the real lived experience of regret – you are likely to regret more a choice that is rubbed in your face, either by society or your loved ones, or because it is an unavoidable topic of reflection when you tell yourself the story of your life. And for simplicity, regret theorists wisely ignore the recursive possibilities given by the fact that one of the things that we can regret is regret itself. But real human psychology is unfortunately not so simple.
So while regret theory is over-simple, and may not be enough, by itself, to explain everything it is intended by its proponents to explain, its real shortcoming for our purposes is not that its central ideas are wrong, but that it leaves fundamentally unexplained why regret could take the shape that it does in the deliberations of the characters that I have imagined. If regret is just one value among others, it is hard to make sense of why it should have so much disvalue as to loom as large as it does in their decisions, or to be so decisive, just as it is hard to make sense of how it could be disvaluable enough to tip the balance in Aditya's case. Alternatively, if we consider alternative forms of regret-based decision theory, such as the principle of minimizing expected regret or minimax regret, we get a picture of how regret could loom large in the decision problem, but not one about why it would be intelligible to be stuck over the decision problem until framing it through the lens of regret.
Moreover, all forms of regret theory fail to draw an important distinction between minor decisions and major life decisions that could help to explain why it is so much more intelligible for considerations about possible regret to play a role in decisions about romantic partners than about handsoap. So I conclude that what we need is not a better understanding of the nature of decision-making, but rather a better understanding of the nature and significance of major life choices, in order to get better insight into what feature of these choices makes regret as significant as it seems to these agents.
5. Telling Your Own Story
My proposal is that the most promising way to make sense of the role of regret in major life decision-making is to focus not on the nature of regret, as with the idea that regret is a heuristic, or on the nature of decision-making, as with regret theory, but instead on the significance of major life choices more generally. Major life choices, I believe, are the points at which we become the authors of our own lives – the points at which the ways in which our lives develop over time are not merely consequences of our choices, but are what we have chosen, warts and all.
David Velleman's book Practical Reflection begins with a story in which you are walking down fifth avenue, when you forget where you are going.Footnote 8 What do you do, he asks, when you forget where you are going? The answer, obviously, is that you stop. You can't keep going, if you don't understand what you are doing. Of course, you can make a conscious choice to continue to walk in the same direction, hoping that it will come back to you where you are supposed to be going, but that is not what you were doing before you forgot your destination. Velleman takes examples like this one – and many others – to demonstrate that all of us have a deep-seated desire to understand ourselves and our own actions, and to provide suggestive evidence that this motive – the motive of self-understanding – is precisely what makes the difference between genuine action and mere motivated behavior.
In earlier work, Velleman claims that the kind of self-understanding that we require is simply causal understanding – to know our own motives when we act. But in later work, he argues that it is instead narrative understanding of ourselves that we all seek – and indeed, which constitutes us both as agents and in a very important sense, as selves.Footnote 9 And the relationship between Velleman's earlier example and his later appeal to narrative understanding is brought out incredibly forcefully by Susan Brison's Aftermath, which tells the compelling story of how her own life came to a stunning halt in the wake of a personal tragedy that left her without a narrative that gave her the ability to move on.Footnote 10
Velleman's claims about the centrality of narrative understanding in our lives and for the possibility of action itself are extremely strong. His evidence for them, which I will not explore further here, is also extremely suggestive, and what Brison's discussion adds to it, even more so. But what I want to get out of Velleman is not his particular, strong, idea, about the way in which narrative understanding is central to motivation in every action, but simply the much more general observation that most of us do, in fact, care deeply about the stories that we can tell ourselves about our lives. The ways that we make sense of one another when we meet each other is not merely in terms of properties possessed, but of roles occupied – father, sister, teacher, friend.Footnote 11 It is no surprise, moreover, that we naturally understand ourselves in narrative terms – for this is a consequence of the fact that most of our capacity for understanding is narrative in structure. Even our understanding of the arguments in philosophy papers is shaped in narrative terms – we expect stage-setting, an antagonist, a protagonist, conflict, and resolution. When we read academic papers that don't provide this narrative structure for us, we reach for it ourselves, or we struggle to understand what the paper contributes, or why it is interesting.
So of course we all tell ourselves and each other stories about how we became who we are.Footnote 12 And like all good stories, these stories are constructed out of activity as well as passivity. Things don't just happen to the protagonist; she responds to them or provokes them or falls into cycles of provocation and response. These events of activity form the backbone of the narrative – they constitute her character as a person, and not just a set of traits.Footnote 13
But the stories that we tell ourselves about our lives can and rightly do shift over time. Some events, such as our brief flirtation with abandoning philosophy for a career in the law, figure prominently in the stories of our lives earlier, when we are confronted with the difficulties of the academic job market, or briefly while we are dating a lawyer, but fade in significance or drop out over time, as our career in philosophy turns out to be successful and our social network comes to exclude lawyers.Footnote 14 Others, like the student we sit behind in 7th-grade English, may carry little significance in our life stories for decades, but thunder back into central life importance if we meet once more decades later as divorcees, and kindle the relationship that lasts for the rest of our lives. Novelists and clever filmmakers are therefore not the only artists who can include events whose significance only emerges much later – we also do it to ourselves.
With respect to events whose narrative significance emerges only much later, it is impossible to anticipate what role they might play in the stories that we can tell about our lives. (The very impossibility of anticipating this is what makes them play such great roles in these stories.) And we all know that most events will fade in narrative significance over time – that they will either wash out, or recede in importance, in comparison to other events. But some choices – the ones I'm calling major life choices – are choices whose significance seems particularly unlikely to fade over time. These choices are perpetual elephants in the room, which we will always have to come to grips with when we tell ourselves the story of our lives over time, and which we can know in advance are likely to play this role in our future life choices – or at least, where we can know in advance that they will play this role, given some of our options, in some possible outcomes.
Sylvia's choice, I think, is one whose significance is likely to remain no matter what happens. It will always be the case, for Sylvia, either that one of her important life choices involved uprooting her partner to move to a new city for her career, or that it involved giving up an attractive employment opportunity for her partner's sake. Dwight's case is slightly more asymmetric. If Dwight sells his company, he will never be able to tell a story of his life on which this is not a major event. If he doesn't sell, there is a possible but unlikely scenario on which this is just the first of many offers of increasing value for his company – in which case this decision may perhaps pale in comparison to some of the others – but it is still likely to be hard to avoid in telling his life's story. Reginald's case is different. Part of what creates the asymmetry of regret that he anticipates is that it will be much harder to write Clara out of his life story than to write out Adele. And in Crystal's case, if she wins her gamble and ends up at Regional Hospital despite ranking University Medical Center first, that is a way of enabling her to write University Medical Center out of her life's story. Since she will acquire knowledge that she could not have gone to University Medical Center, she makes it possible to write that choice out of her life's story in a way that would not otherwise be possible.
What I've been trying to suggest, in this section, is that major life choices are significant precisely because they are choices for which you know or are in a position to know in advance that you will always have to deal with their narrative significance. This is supported by the general observation that this is precisely what distinguishes major life choices from others and by the particular observations about which features of Reginald's, Crystal's, Dwight's, and Sylvia's cases make them significant in this way – features that also lend themselves to explaining the particular significance of factors like attention, salience, and counterfactual knowledge on the structure of these cases. But it is also supported by the more general observation that our lives’ stories are something that we typically care about – and if Velleman is even close to being right, which we care about in a central way. This puts us on the right track for making sense of how considerations built on these cases could intelligibly play a dominant role in decision-making.
6. The Significance of Anticipated Regret
So far, I've been suggesting that what makes major life decisions distinctive is the way in which we can know in advance that their significance will be ineliminable from future stories that we can tell about our own lives. So the last remaining step is to connect this back to the significance of anticipation of regret in making such decisions. And the basic structure of my answer to this question is simple: regret, or at least one form which regret may take, is a kind of emotional obstacle to coming to grips with the story that we tell ourselves about our own life. It is an emotional obstacle to ownership of the particular story that we are telling ourselves about how we came to be where we are. This kind of regret is the kind of regret experienced by someone who is alienated from their own story about their own life. Call such a form of regret narrative regret.
It is possible, of course, that narrative regret can sometimes be avoided by choosing a different story to tell about one's life. Failures can be re-told as learning experiences or morality tales, or as making possible some greater value, which could not have been anticipated. We have many narrative resources available to us, and with imagination and determination, we can often do pretty well at making the most of it. Indeed, it may even always be possible to tell ourselves some story of what has transpired that we can embrace. So narrative regret isn't a kind of emotion that transcends our storytelling about our own lives; on the contrary, it is deeply embedded within our experience of our lives as aptly described by some particular story – it is an emotion that we experience insofar as that is the story we tell ourselves. But even if narrative regret can often – or even always – be avoided by changing the story that we tell about our lives, the stories that allow us to avoid narrative regret may not always be stories which, in advance, are the ones that we hope to tell.
On this picture, since narrative regret correlates with the stories that we tell ourselves about our lives, and storytelling is something that it is intelligible to find important, narrative regret is likely to be the right kind of thing to make sense to pay attention to, in major life decisions. One might therefore wonder whether this makes it possible to bring back versions of both of our earlier, more naïve, theories about the significance of regret for major life decision-making.
According to regret theory, recall, regret is one feeling among others that it makes sense to want to avoid. So how much regret we experience in each possible outcome of our choice is one of the considerations, among others, which must go in to our overall assessment of how desirable it would be, to end up with that state of affairs as the result of one's choice. My complaints about regret theory included that it fails to account for why regret figures most prominently in major life decision-making, that it does not adequately account for the roles of attention and counterfactual knowledge in our experience of regret, and that it leaves deeply puzzling why it would make sense to care enough about regret, in order for it to make the right kind of difference in major life decisions. But each of these complaints is mitigated by the idea of regret as narrative regret.
Take, first, the objection that regret theory is fully general, rather than specific to major life decision-making. Narrative regret is not fully general – we experience narrative regret only for turning points which, looking back on them, present obstacles for us to feel proper pride of authorship over our own lives. Moreover, only some of these obstacles are cases that we are in a position to anticipate in advance. And these are precisely the cases that constitute major life decisions, in my sense. So even if narrative regret is just one feeling among others, at least it is the sort of feeling that we are in a position to anticipate precisely in those cases in which regret seems to intelligibly play a role in major life decisions.
Next consider the apparent asymmetries in regret – the ways in which attention and counterfactual knowledge shape what and when we regret. These asymmetries are left out of simple ideas from forms of regret theory which measure regret as a kind of disappointment – the distance between what was expected, and what was experienced. But they are central to narrative regret. Events to which our attention is directed are precisely those events that it is hard to leave out of the narrative of our lives, and learning what would or would not have happened had we taken another course of action shapes our understanding of the ways in which our lives are the products of our own authorship, as opposed to our circumstances.
Finally, consider the problem that regret theory left it puzzling why it could possibly make sense to care so much about future regrets. Given the role of narrative regret in our lives, however, it is not just one bad feeling among others. To experience narrative regret is to encounter an obstacle to making sense of oneself as the author of one's own life. This isn't just unpleasant; it is in a very real sense tragic. Indeed, it is disabling in precisely the way described by Velleman and Brison. When people are overcome by narrative regret, they do stop, and it is difficult to move forward with their lives and projects. This is why self-help books tell us to live life without regret, and to move on from the past. So narrative regret is plausibly tragic both intrinsically and for its consequences. So it is at least more intelligible to care significantly about whether one will experience narrative regret than about many other forms of merely bad feelings.
Still, I don't think that placing any value on anticipated regret – no matter how high – can make sense of how thinking about decisions through the lens of regret can have the potential to wash out other considerations – to feel clarifying, rather than merely to tip the balance. So though I think our account of narrative regret helps to see it as something worth caring about more, I still don't think that this can be the right way to think about its role in major life decisions. Fortunately, our other preliminary strategy can do better.
The other preliminary theory that we explored earlier, recall, was the idea that regret is a kind of heuristic. I had many concerns about the specific version of this idea that we explored earlier, on which regret should correspond to hindsight judgments of what you ought to have done. I worried that the argument that regret works as this form of heuristic relied on an over-strong form of the principle of reflection, that reflection in any case does not properly apply to ‘ought’ judgments of the right kind, that it fails to account for the significance of degree of regret, and that if regret does correspond to hindsight, then expectations of regret – even of rational regret – are not the right kind of thing to figure in decision-making. It was also not specific to major life decisions and did little to make sense of the specific asymmetries of regret that are brought out by the choices faced by the characters in our stories.
These objections again turn on the specific form of the theory of regret as a heuristic. They all concern the idea that rational expectations of regret correlate directly with rational expectations of rational belief about what one ought not to have done. But narrative regret does not aspire to correlate in this way – narrative regret is the emotional manifestation of failure to reconcile oneself with authorship over one's own life story. So it is not a heuristic for what one ought to do, but rather, for which life one can – or wants to – reconcile oneself with having authored. Insofar, then, as choosing a life that one can reconcile oneself with having authored is an important value in major life decisions, it is no wonder that expectations of narrative regret will provide an illuminating heuristic.
Indeed, if you care at all about writing the story of your own life, you must care about whether in the future you will be able to live with having authored that story. And that is because you cannot author your whole life at one go, but must cooperate with your future self, giving them good enough material not only to work with, but to be inspired to make a good job of it. Dampening the morale of your co-author is not exactly a promising start at composing your story.
So once we understand the emotion of narrative regret more carefully, and see that what makes major life decisions significant for expectations of narrative regret is precisely that they are the cases in which we can know in advance that we are at a choicepoint that will be ineliminably important in any future story we tell about our lives, we can see how to construct a much stronger and more promising explanation of why considering what you might regret is a helpful heuristic. It is a heuristic not for what you will think you ought to have done, but instead for which choice outcome is regrettable.
7. Consequences
All along I have been treating it as a desideratum to make sense of a certain kind of way of being compelled by considerations about possible regret in major life decision-making. I've tried to make this plausible through consideration of a range of relatively detailed cases in which such decisions makes sense – at least to me. I've considered some simple ideas about the role or significance of regret in decision making that make this particular role for regret puzzling, and have tried to address those sources of puzzlement through invoking the significance of narrative in our understanding of ourselves and the idea of a distinctively narrative form of regret, which does have this role. But what I have not done, is to consider some of the most pressing reasons to be skeptical that it is rational at all to take account of regret in decision making.
Plausibly the most obvious reason to be skeptical about taking serious account of expected regret in major life decision making arises from the case of the decision whether to have children. It is commonly suggested that people who have children generally do not come to regret having had their children, but people who do not have children sometimes come to regret not having had children. Plausible explanations for this phenomenon are not hard to find – regretting having had a child seems to entail wishing that that child had never existed, which is a strong and difficult thing to wish about anyone you care about, even just a little – and an especially difficult feeling to reconcile with the perceived role of being a parent. But if this is right, then if expected regrets can be taken account of in major life decision making, it can seem to follow that everyone – or at least, everyone who takes such regrets seriously – should decide to have children. Indeed, since the same considerations about regret apply to each marginal child, the consequences are even more stark: anyone who takes future regrets seriously, it may seem, must have as many children as possible.Footnote 15
Something must be wrong with this reasoning; either preoccupation with regret is a deeply flawed way of thinking about major life decisions, of which the decision to have a child is certainly one, or else somehow this case must be a perversion of the proper role for expectations of regret. It will come as no surprise that my view is the latter. Fortunately, we now know enough about the proper role of regret in major life decision making, in order to start to see why this might be so.
If narrative regret is a heuristic for something that we really care about – authoring a life that we can live with and take pride in having authored, then it is a heuristic that may fail in some cases to track significant differences in what we will have authored. In particular, we have already seen that one way in which you can avoid regret is to change the story of your life. Since we are good at changing the stories of our lives, anticipation of what you will regret is nearly always anticipation of what you will regret conditional on not changing your story to one that you now hope not to tell. But the only sense in which everyone can expect not to regret having an additional child, is one on which they can be confident that, once they know and love that child, they will seek to tell a story that makes sense of that decision. It does not make that a story that makes sense to you now, or one that you want to tell. So this is precisely the kind of reasoning in which we should expect narrative regret as a heuristic to break down.
In fact, if you choose to have children solely in order to avoid the risk of future regret, and even in spite of not liking children and preferring the childless life, you are placing particularly stringent constraints on what story you can tell later about this life decision. Rather than making you the author of this life, this kind of decision robs you from being the author of such a life except on a version of the story on which the thing you care about most is fear of regret.Footnote 16
