Think of the hardest choices you ever had to make. They probably weren't questions of which supplier to go with or whom to hire. These are serious decisions, but we generally know how to make them: the best supplier saves us money and hassle, a good employee does great work and isn't a jerk.

The hardest choices, instead, are those where we don't really know what we value. Should you stay in your hometown or move to a distant metropolis, for example? One alternative offers deep personal ties, the other adventure and opportunity. Which do you value more? These are the choices that keep us up at night.

So what's the best way to make them? That's the topic of a recent, fabulous New Yorker article from Joshua Rothman. It's well worth a read in full, but one distinction Rothman makes is useful for anyone who has ever faced this sort of tough choice (i.e. all of us): when making these decisions, focus on aspiration rather than ambition, he argues.

The difference between ambition and aspiration

These words are basically synonyms in everyday life, but Rothman shows they aren't the same. An ambition is something we know we want to achieve. 'I want to make partner,' for example, or, 'I want to sell X dollars of product.' An aspiration, on the other hand, is something vaguer but bolder -- a desire to become a different kind of person.

Chasing an ambition doesn't change who you fundamentally are. Chasing an aspiration does. If you decide to move to across the country, you're not sure exactly what your life will be like in that new city, but you're betting the move will transform you. The day you say 'I want to become a parent' you have close to no idea what you're getting into, just an aspiration to start a family.

Which is the problem with chasing aspirations. You're pushing towards becoming something but you're not there yet, and being that half formed can be uncomfortable. Rothman, drawing on the work of philosopher Agnes Callard, offers the example of a person who decides they want to appreciate classical music and signs up for a class.

"Some of the people taking the music-appreciation class are ambitious; they enrolled not because they aspire to love classical music but because the class is an easy A. From the first day, they know what they value: their grades. The ambitious students find it easy to explain why they're taking the class," Rothman writes. But what explanation can the aspirational students give for why they're there?

"You would be overreaching if you said that you were moved by the profound beauty of classical music. The truth, which is harder to communicate, is that you have some vague sense of its value, which you hope that some future version of yourself might properly grasp," he continues.

The same is true if you take a leap into a new career, decide one day you want to become a parent, or finally rent that U-Haul. You're not sure exactly what you're going to become, you just sense that you want to become that sort of person. And when you're just getting started, it's totally awkward.

Or as Rothman memorably puts it: "Being a well-meaning phony is key to our self-transformations." Which is probably one reason a lot of us avoid identity-stretching aspiration.

A pro-con list will never give you control over your life.

Rothman isn't the only one making the argument for messy aspiration over straightforward ambition. In a TED talk another philosopher, Ruth Chang, makes a very similar case. Hard choices, she explains, often stress us out because we feel like we lack information. Will I be happier at home or in that new city? Should I work at an investment bank or a charity?

We look for the data that will make the right choice clear, but no data can possibly help us because these are questions of identity and value. There is no "right choice." Instead, you are at a crossroads: What kind of person do you want to be, a banker or a do gooder, a city dweller or a small town hero?  

Instead of making and ignoring pros/cons lists when faced with these sorts of choices (please tell me other people do this too), Chang and Rothman both urge us to accept these decisions as aspirational moments when we can actively choose who we want to become.

Yes, that's going to make you look and feel like an unsure, clumsy newbie for awhile. And yes, aspiration is way harder to talk about without sounding like a cornball. But aspiration, not ambition, is how we take ownership of our identity. It's how you transform your life.

Sorry, feeling like an awkward phony for awhile is part of the deal.

Published on: Feb 6, 2019