How to make the hardest choices of your life

Your Mileage May Vary is an advice column offering you a unique framework for thinking through your moral dilemmas. It’s based on value pluralism — the idea that each of us has multiple values that are equally valid but that often conflict with each other. To submit a question, fill out this anonymous form. Here’s this week’s question from a reader, condensed and edited for clarity:

I’m soon to be a part of the legal profession. I went to law school to advocate for marginalized populations who seldom have their voices heard — people who are steamrolled by unethical landlords, employers, corporations, etc. I will clerk after law school, and then I’ll encounter my first major fork in the road: whether I pursue employment in a corporate firm or nonprofit/government. Corporate firms, ultimately, serve profitable clients, sometimes to the detriment of marginalized populations. Corporate firms also pay significantly better. Nonprofit or government work serves the populations I want to work for and alongside, but often pays under the area median income.

I’ll be 32 by the time I reach this fork, and I don’t know what to do. I’m extremely fortunate in that I won’t have law school debt — I was on a full ride. Still, I’m not “flush.” I want to buy a house one day, have some kids with my partner, feel financially secure enough to do so. I also want to have a morally congruent career and not enable (what I consider) systems of oppression. What do I do?

Your question reminds me of another would-be lawyer: a very bright American woman named Ruth Chang. When she was graduating from college, she felt torn between two careers: Should she become a philosopher or should she become a lawyer?

She loved the learning that life in a philosophy department would provide. But she’d grown up in an immigrant family, and she worried about ending up unemployed. Lawyering seemed like the financially safe bet. She got out some notepaper, drew a line down the middle, and tried to make a pro/con list that would reveal which was the better option.

But the pro/con list was powerless to help her, because there was no better option. Each option was better in some ways and worse in others, but neither was better overall.

So Chang did what many of us do when facing a hard choice: She chose the safe bet. She became a lawyer. Soon enough, she realized that lawyering was a poor fit for her personality, so she made a U-turn and became — surprise, surprise — a philosopher. And guess what she ended up devoting several years to studying? Hard choices! Choices like hers. Choices like yours. The kind where the pro/con list doesn’t really help, because neither option is better on balance than the other.

Here’s what Chang came to understand about hard choices: It’s a misconception to think they’re hard because of our own ignorance. We shouldn’t think, “There is a superior option, I just can’t know what it is, so the best move is always to go with the safer option.” Instead, Chang says, hard choices are genuinely hard because no best option exists.

But that doesn’t mean they’re both equally good options. If two options are equally good, then you could decide by just flipping a coin, because it really doesn’t matter which you choose. But can you imagine ever choosing your career based on a coin toss? Or flipping a coin to choose whether to live in the city or the country, or whether to marry your current partner or that ex you’ve been pining for?

Of course not! We intuitively sense that that would be absurd, because we’re not simply choosing between equivalent options.

So what’s really going on? In a hard choice, Chang argues, we’re choosing between options that are “on a par” with each other. She explains:

When alternatives are on a par, it may matter very much which you choose. But one alternative isn’t better than the other. Rather, the alternatives are in the same neighborhood of value, in the same league of value, while at the same time being very different in kind of value. That’s why the choice is hard.

To concretize this, think of the difference between lemon sorbet and apple pie. Both taste extremely delicious — they’re in the same league of deliciousness. The kind of deliciousness they deliver, however, is different. It matters which one you choose, because each will give you a very different experience: The lemon sorbet is delicious in a tart and refreshing way, the apple pie in a sweet and comforting way.

Now let’s consider your dilemma, which isn’t really about whether to do nonprofit work or to become a corporate lawyer, but about the values underneath: advocating for marginalized populations on the one hand, and feeling financially secure enough to raise a family on the other. Both of these values are in the same league as each other, because each delivers something of fundamental value to a human life: living in line with moral commitments or feeling a sense of safety and belonging. That means that no matter how long you spend on a pro/con list, the external world isn’t going to supply reasons that tip the scales. Chang continues:

When alternatives are on a par, the reasons given to us — the ones that determine whether we’re making a mistake — are silent as to what to do. It’s here in the space of hard choices that we get to exercise our normative power: the power to create reasons for yourself.

By that, Chang means that you have to put your own agency into the choice. You have to say, “This is what I stand for. I’m the kind of person who’s for X, even if that means I can’t fulfill Y!” And then, through making that hard choice, you become that person.

So ask yourself: Who do you want to be? Do you want to be the kind of person who serves profitable clients, possibly to the detriment of marginalized people, in order to be able to provide generously for a family? Or do you want to advocate for those who most need an advocate, even if it means you can’t afford to own property or send your kids to the best schools?

What is more important to you? Or, to ask this question in a different way: What kind of person would you want your future children to see you as? What legacy do you want to leave?

Only you can make this choice and, by making it, choose who you are to be.

I know this sounds hard — and it is! But it’s good-hard. In fact, it’s one of the most awesome things about the human condition. Because if there was always a best alternative to be found in every choice you faced, you would be rationally compelled to choose that alternative. You would be like a marionette on the fingers of the universe, forced to move this way, not that.

But instead, you’re free — we’re free — and that is a beautiful thing. Because we get the precious opportunity to make hard choices, Chang writes, “It is not facts beyond our agency that determine whether we should lead this kind of life rather than that, but us.”

Bonus: What I’m reading