Frank Ramsey was a philosopher at the University of Cambridge who was also a member of the Apostles, an invitation-only group of the intellectual elite at Cambridge – the best of the best. Perhaps the greatest thinker of his generation, Ramsey died at twenty-six. When he was twenty-three, he gave an evening speech that was directed above all at Ludwig Wittgenstein, in some ways his mentor, who contended that on questions that did not involve facts, philosophy did not have a lot to say. Ramsey announced, “Humanity which fills the foreground of my picture I find interesting and on the whole admirable. I find, just now at least, the world a pleasant and exciting place.”Footnote ¹

Squarely addressing Wittgenstein, Ramsey acknowledged, “You may find it depressing; I am sorry for you, and you despise me.” But, Ramsey added, “I have reason and you have none; you would only have a reason for despising me if your feeling corresponded to the fact in a way mine didn’t. But neither can correspond to the fact.” Ramsey’s crescendo: “The fact is not in itself good or bad; it is just that it thrills me but depresses you. On the other hand I pity you with reason because it is pleasanter to be thrilled than to be depressed, and not merely pleasanter but better for all one’s activities.”

A major goal of this book is to pause over Ramsey’s crescendo. It is pleasanter to be thrilled than to be depressed, and that fact should inform our decisions, even when our eye is on some other ball. Before this book was completed, I visited Cambridge University and was fortunate enough to see some of Ramsey’s personal letters, including a number that he wrote to his wife, with whom he was enraptured. His exuberance – his delight about people, ideas, and life – shines through those letters. I hope that a little bit of Ramsey’s spirit has made its way into these pages.

***

A few months ago, I rented a car for a period of two weeks in Ireland. I arrived at Shannon Airport after a five-hour flight from New York, and a nice person at the rental car counter asked me various questions. I was half-asleep, but I knew that some of those questions had to do with insurance. Long ago, a good friend of mine, a distinguished economist, told me always to decline insurance when renting a car, and that is what I did, I thought.

Two days later, I found myself in a rural area in Ireland, driving on the left-hand side of the street on an impossibly compressed road, without room for two-way traffic, even though there was a lot of two-way traffic. It was harrowing. I also got lost.

Amidst the fun, a friend called me. I picked up quickly and said, “I can’t talk! The driving conditions are terrible, and if I talk, I’ll probably get into an accident.” I hung up. The friend immediately called back, and I pulled the car over to talk. You probably know what happened. SCREECH! The left-hand side of the car smashed into a gate, which was much closer than I imagined. No one was hurt, and the gate was fine, but the car suffered real damage.

I had the car for another ten days. On every one of those days, I felt that there was a dark cloud in the sky. How much would I have to pay? Nothing? A lot?

I looked at my rental car agreement. I didn’t quite understand it, and didn’t enjoy trying to figure it out. As best I could tell, I appeared, in my fog, not to have declined insurance altogether, but to have entered into an agreement to pay a maximum of $2,000 for any damage. That was a lot worse than $0 (which, I think, would have been the result if I had obtained insurance), but a lot better than $5,000 or $10,000.

The car didn’t seem that horrifically damaged, and a $2,000 ceiling was not a nightmare. Still, I didn’t know where I stood. That dark cloud was visible in the sky.

When I returned the car to the rental car company, I learned that in my fog, I had indeed arranged for an agreement with a $2,000 ceiling. I don’t know exactly how or why I had done that. And not long after I received the bill for the rental, which included that amount.

Here is what I learned from that little episode: My economist friend might be wrong to advise people to decline car rental insurance. At least he’s not right. True, declining insurance might be the right choice if your goal, over a lifetime, is to save money. But as they say, money isn’t everything. There is also one’s emotional state. For car renters to know that they won’t have to pay anything if they have an accident – or to know that they won’t have to pay more than a specified amount – is worth a lot. My time in Ireland was great, but it would definitely have been greater if I had known, for certain, that I would not have to pay more than $2,000 – and it would have been greater still if I had known that I would not have had to pay anything at all.

At this point, you might be thinking: What else is new? Insurance companies say that they sell “peace of mind.” By promising to do that, they sometimes get a lot more money from consumers than they should. But there is a broader point. When we make decisions, material outcomes matter. Money matters; health matters; safety matters. But people’s emotional experiences also matter, and when we make decisions, we ought to focus on that fact. Our actual and anticipated emotions can steer us right or steer us wrong. You might believe what you believe in part because you really like believing it. You might seek out information because you think it will make you smile; you might hide your head in the sand because you don’t want bad news. You might make a choice because you think it’s fun to make choices. You might refuse to make a choice because making choices makes you miserable.

How do we decide how we decide? We make such decisions all the time, whether or not we think much about them. If you trust your doctor, you might decide to follow a simple rule for medical decisions: Do whatever your doctor suggests. If you are interested in changing occupations but unsure whether you might be being reckless, you might take a small step: Try a new job on a part-time basis. If you like someone a lot, and maybe love them, but are not sure whether you want to marry them, you might do this: Live with them first. If you do not like reading menus at restaurants, and do not enjoy choosing among multiple options, you might do what I do: Decide in favor of the first appealing item you see.

Some of those decisions are rapid and intuitive; we do not formalize them in our minds. It is simply how we proceed. Some of those decisions are a product of experience or reflection. You might learn, over the years, that you cannot handle alcohol, and so you might adopt a firm rule: no alcohol, ever. Or you might have figured out, through long experience, that it rarely helps to get angry with people at work, so you might have decided that, if you are inclined to rage at someone, you will take a deep breath and turn the other cheek. Or you might know that you despise making certain choices, and you might find a way not to make them.

Some of these strategies are wise. They prevent error. They save time. They improve your emotional well-being; they help you to enjoy your minutes, your hours, your days, and your months. Some of these strategies are foolish. They lead you in the direction of terrible mistakes. They prevent you from learning. They might be too flexible. They might be too rigid. They might make you miserable. My main goal here is to understand decisions about decisions – to see what they are, to explore how they go right, and to see where they go wrong. Throughout we shall keep Ramsey’s wisdom in mind: “[I]t is pleasanter to be thrilled than to be depressed, and not merely pleasanter but better for all one’s activities.” That principle applies not only when we are deciding what to do but also when we are deciding what to know and even when we are deciding what to believe.

***

I have been working on these subjects for about thirty years, and this book has emerged from a set of previously published essays, focused not on policy and law (my usual topics) but on practical reason in human life. Not long ago, it occurred to me that I had written something like a book on that topic without knowing it. To turn those essays into a book, I have made substantial revisions – in part because of what I have learned and in part in the interest of unity. If the seams occasionally show (and I know they do), I thank readers for their indulgence.

This book covers a great deal of territory. Most of the focus is on decisions about decisions, but (a confession) the lens will occasionally shift to decisions, period. We will attend, at essentially all points, to the emotional impact of decisions – to how it feels to make them; to whether claiming responsibility is pleasant or joyful or instead a burden or a source of terror; to whether a large-scale change seems like an opportunity and a world of fun, or a threat and a menace; to whether having a certain belief, or seeking new knowledge, induces a sense of security and hope or a sense of fear or despair.

For those who would like a brief overview: Chapter 1 offers general orientation. It explores second-order decisions in general, seeking to identify the specific strategies that we use to make life simpler and less stressful, and to explain when one or another such strategy makes sense.

Chapter 2 turns to decisions about the very largest matters, which might seem to defy ordinary rationality. The reason is that such decisions change who we are and what we value. Even there, I suggest, we can figure out how to decide.

Chapter 3 deals with the decision whether to know. Knowledge is power, as they say, but ignorance is bliss, as they also say. They are right on both counts. The challenge is to know whether we have a knowledge-is-power situation or an ignorance-is-bliss situation. My emphasis is on the fact that information can make us happy or sad; our anticipated emotional reaction to information is often the driver of our decision whether to seek or to avoid information. That is not exactly irrational, but sometimes we neglect our ability to adjust to bad news.

Chapters 4 and 5 deal with a closely related decision: the decision to believe. Chapter 4 explores the case of climate change. It offers evidence that on that question, people decide to believe what they want to believe – which helps explain the polarization we now observe in many nations, and which helps explain how we form beliefs in ordinary life. Broadening the viewscreen, Chapter 5 looks at beliefs in general. It suggests that beliefs are, in a sense, like goods, and we decide whether to “buy” them. We often make a rapid decision: If I believe this, will my life be better? How?

Note well: People might refuse to believe something even if it can help them live a little longer, if believing it will make them live a lot sadder.

Chapter 6 turns to the problem of inconsistency in decisions. With respect to jobs, laptops, cities, and romantic partners, people might decide in favor of A over B, but also decide in favor of B over A. How can that be? I emphasize what seems to me one of the deepest and most intriguing puzzles in all of modern social science: In separate evaluation, A might look a lot better than B, but in joint evaluation, B might look a lot better than A. This is not a simple matter, but very briefly: The comparison set greatly matters, and if you are comparing a very nice house with a much nicer house, the very nice house might not look nice at all. This point matters to daily life, business, and politics.

Chapters 7 and 8 deal with consumption. The unifying claim is that people often decide to consume what others consume. They do so when they are choosing what might be called solidarity goods, as distinguished from exclusivity goods, which people choose because no one else seems to be choosing them. The existence of solidarity goods obviously bears on the success of social media platforms. Chapter 8 turns to those platforms in particular. Among other things, it finds that a lot of people would pay exactly nothing to be able to use them – and also that a lot of people are made less happy by them (but nonetheless keep using them). One lesson is that people do not care only about being made happy. They might want to know useful things, even if the knowledge makes them a little anxious or a little depressed. (There is an evident link here to Chapter 3.)

Chapter 9 explores a pressing current issue, which is when and whether people should rely on algorithms. The discussion tends to answer “yes,” on the ground that algorithms can remove both bias (understood as systematic error) and noise (understood as unwanted variability). But I also emphasize the importance of knowing whether people like or do not like deciding in the particular circumstances. If people like deciding – perhaps because they enjoy it, perhaps because they want to claim responsibility – they will not like deciding by algorithm. It follows that in many cases, people will find deciding by algorithm a blessing, because deciding on one’s own is anything but that. I also have something to say about what algorithms can and cannot do. A preview, potentially with general lessons: They do not seem to be very good at predicting when people will make a romantic connection.

Chapter 10 proposes a right not to be manipulated. It puts a spotlight on, and broadly endorses, a right to decisional autonomy. The Epilogue is called “Get Drunk!” That is more or less what it is about.