How to be a more confident decision maker

If you’ve ever gone to bed wondering how you flubbed so many of that day’s small choices — How did I possibly think two Shake Shack burgers was a good idea for lunch? — then you might reasonably ask how on earth you could be expected to make the grander, more difficult decisions that determine the course of your life: Which career should I pursue? Who should I marry? Is that house worth buying?

This already unnerving proposition is made even more so when you consider that, according to Ruth Chang, most of us have been approaching hard decisions the wrong way our entire lives.

A philosophy professor at Rutgers — with a Bachelor of Arts degree from Dartmouth, a J.D. from Harvard, and a D.Phil. from Oxford — she has intensively studied the decision-making process, using insights from that research on the TED Talk stage and in lectures to the C.I.A., U.S. Navy, and the World Bank.

It starts with numbers, and our insistence on placing any two things into a quantitative framework. Since any two items with a numerical value can be compared easily — to figure out which is larger and which is smaller (or if they’re the same) — we’re conditioned to believe this applies to qualitative choices, too. When weighing the merits of, say, getting a job out of college or going to graduate school, we believe one alternative is definitely better than the other.

This assumption is a mistake, says Chang. And because it’s a mistake, we think about decisions all wrong. We think that a decision is an information problem. When we can’t decide between two options, it’s because we don’t have the info needed to make the best decision possible. If we could just gather enough information, we could be sure (or surer) we’re making the “right” choice. But so often even after we’ve talked to all the right people, asked all the right questions, and gathered all the necessary info, we still can’t decide.

Luckily, Chang goes offers a new system of decision-making that, she argues, won’t just make your decisions easier, but will keep you from regretting those choices once you make them.

So why are hard choices hard, then, if not for a lack of information?

So if you think of most of your hard choices, they’ll have the following features: One, they’re qualitatively pretty different. You know, [a career in] philosophy versus [a career in] welding. And second, nonetheless, they’re in the same overall neighbourhood of value [meaning one is not clearly better than the other]. But now what?

The best analogy for thinking how this might work is love relationships. There isn’t one person who’s best for you. So whatever criteria you have for what makes a worthwhile, long lasting, loving romantic relationship, it’s just not true that one person is best. Do we say, “Oh, they’re all equally good, so you just flip a coin?” No. There are many people who are on a par, that are gonna be qualitatively different. With one person, you’re gonna have this exciting intellectual life. With another person, you’re gonna have this fun outdoors life. And now the question is: what do you do?

The world hasn’t delivered an answer as to what you should do. Instead, it’s up to you now to put your will behind one of the alternatives, to put your agency behind it. If you can commit to one of these people, then you make it true that you have most reason to be with that person. By committing to someone, you yourself become a source of new reasons that you didn’t have before. So the world didn’t give you the reasons to be with Betty instead of Lolita. You gave yourself those reasons.

But how do you know when you’ve made a mistake? What room is there for mistakes in this thinking?

Maybe we should talk about a concrete case. So many people who have written to me have said, “I have a good nine-to-five job. I have a young family I need to support. But I really, really, really wanna start my own business. But it’s too risky.” So they’re weighing the pros and cons and they don’t know what to do.

Let’s suppose someone commits [to opening the business] in 2007, he starts his business and, in 2008, the world goes haywire [and the financial collapse happens]. Compare the entrepreneur who has committed to his new business with the entrepreneur who hasn’t committed. The one who hasn’t committed is going to say, “Oh my God. What have I done? This was a terrible decision to leave my nine-to-five job. I really screwed up.” And he’ll be filled with regret.

Growth is always accompanied by some sort of pain. How do you distinguish between discomfort that lends itself towards growth, and discomfort that signals that maybe you have committed to something that is not truly who you are?

Well, you can only know from the inside. So people who have committed to something know the signs of it. If you go back to the business entrepreneur, when he started his business, there’s this kind of full engagement. He’s wholehearted. He’s excited about doing things. He’s in a flow [state] often. There’s a kind of great inner-directedness in all of his actions, having to do with starting this business. That can all be accompanied by anxiety. It makes you feel uncomfortable because it’s like you know you’re doing something exciting, but it’s scary. So it’s a bit like going on a roller coaster, but you’re [committed to being] on the roller coaster. There’s no doubt about that.

The other kind of discomfort is one where you’re full of this nagging doubt. You’re not directed by any inner resources. You’re constantly looking outside for validation. Am I on the right path? What does my mother think about this? What do my friends think? Am I getting sufficient returns on my investments? That is the kind of discomfort where you’re taking an action and you’re not committed to it.

One important point is: what do we mean by happiness? What most people mean is a feeling, a mental state of some kind. And that’s a disaster, to think that life is about achieving this feeling.

The person who did the best job of skewering that idea is Robert Nozick, a professor at Harvard. He came up with this thought experiment involving what he called The Experience Machine. Suppose I could offer you the opportunity to be hooked up to a machine — we attach wire and electrodes to your neurons — [and] we make it the case that you experience a life full of happiness.

And he says that that kind of life misses out on all the important values, like genuine human connection, genuine accomplishment, genuine confrontation with beauty and truth, and so on. So you have the [happiness that comes with the] experience of having written the great American novel, but you never actually wrote it. You just have the experience because he’s manipulated your neurons.

That is not a life that we would think was a good life. It’s a kind of fake life. This is why philosophers teach The Matrix, because The Matrix is just an experience machine. And we all think, I think, that even though the red pill leads to a pretty nasty reality, there’s at least one respect in which taking the red pill is better than taking the blue pill: it’s real. We should be trying to get a life that’s real. A good life is not about having a bunch of good experiences. It’s about actually hooking up with reality in good ways. And I think that the best way you can hook up with reality is by being wholehearted and being committed to something.

So an example of someone who was wholehearted, but not terribly happy, is Mother Teresa. She was quite miserable, but she was wholeheartedly committed to doing what she did and so that counts as a good life. A life that’s just full of one happy experience after another is not a life that’s connected with reality. Commitment presupposes some connection with reality. You’re committed to a person, to a project, to doing something. You’re committed to writing the great American novel and goddammit, you’re gonna try to do it. You’re not trying to [just] have the experience of doing it.

How does that then tie back to decision-making?

So when you face a choice between two alternatives that is a genuine hard choice, they’re on a par, you shouldn’t then think, “I’ll just do the job that makes me happiest,” or even, “I’ll just do the option that makes the people I love the happiest.”

That’s a mistake. You have this ability to put your agency, your very self, behind an option and make it true for yourself that you have most reason to do that thing. You can make it true that you should do something, even in a hard choice.

Why do you think people are so scared to exercise their agency?

I think it has to do with the fact that we’re primitive animals. We crawled out of the muck and the world is a very scary place. So it’s natural that we think of agency as nothing other than dodging bullets: “Let’s just try to stay alive. Let’s try to navigate the scary external reality so that we don’t get killed.”

But that’s just animal agency. We humans have rational agency, which is more complex. Our agency is not just a matter of navigating a scary world, but also of creating reasons for ourselves to be one kind of person as opposed to another kind of person. So a lion or a badger or a cockroach, their role really is to navigate an external world. We humans have this further capacity, which philosophers often just call rational capacity, to make it true that we should be this kind of person, not that kind of person.

And it sounds like you make yourself into that person based on the decisions you make.

Yes. So the reasons given to you by the world sometimes make it true that one option is better than another: It’s better not to murder your enemy than to murder him. But I think it’s quite often that the given reasons are on a par and those are the hard choices, and that’s where we can exercise our agency and make yourself into the kind of person who has most reason to be a journalist instead of a lumberjack. Someone else might create reasons to be a lumberjack and then they make themselves into that sort of person.

So what role do regret and responsibility play in this sort of model? It strikes me that it would be easy to say, I changed who I am and so that changes the nature of my commitment, and that would be an easy way to avoid regret or responsibility in a case in which you made a bad decision. Like, say you decided that you could commit to the life of being a lumberjack. Then, five years from now, lumberjacks are replaced by robots.

So it’s a bit like the case we talked about before with the guy who’s opening his own business right before the market crash. So the world may not always cooperate with your plans. But if you’re being clear-headed when you’re thinking journalist or lumberjack, and if we can foresee, “Oh, look: AI is on the horizon and it looks like there’s some probability that the entire field is gonna be wiped out by axe-wielding [robots].” That factors into the initial assessment as to whether or not being a journalist or a lumberjack are on par.

If you factor it in, and they’re on par, and you can commit to a life of a lumberjack, then you become a lumberjack. That’s what you should be. And then in five years, that small probability that the whole field would be wiped out comes to pass, then that’s no big deal. Life is like that. The world doesn’t cooperate.

The question you’re asking is from the point of view of someone who isn’t committed to being a lumberjack. It’s from the point of view of someone who’s still contemplating, “God, should I have been a journalist?” You know if you’re committed to being a lumberjack, you are committed and then you take all of the lumps that the world throws your way in stride.

So take the analogy with the personal relationship: If you really are committed to Betty and in five years, Betty becomes paraplegic in this accident. There’s this terrible car accident, you don’t think, “Oh my God, what did I do? I could’ve married Lolita.” That’s not the state of being committed to something.

So in a way, the question doesn’t take on board what commitment involves. I mean the only kind of regret that makes sense in my picture is the kind of regret that is occasioned by your changing. When you change, when your commitment evolves, and then the new you can regret that you spent so many years as a starving artist, even though while you were a starving artist, if you were committed, you wouldn’t feel any regrets at all.