Deciding to leave a current career path is often easier than identifying a new one. My favorite framework for navigating that challenge comes from a management professor, Herminia Ibarra. She finds that as people consider career choices and transitions, it helps to think like scientists. A first step is to entertain possible selves: identify some people you admire within or outside your field, and observe what they actually do at work day by day. A second step is to develop hypotheses about how these paths might align with your own interests, skills, and values. A third step is to test out the different identities by running experiments: do informational interviews, job shadowing, and sample projects to get a taste of the work. The goal is not to confirm a particular plan but to expand your repertoire of possible selves—which keeps you open to rethinking.

Checkups aren’t limited to careers—they’re relevant to the plans we make in every domain of our lives. A few years ago, a former student called for romantic advice. Caveat: I’m not that kind of psychologist. He’d been dating a woman for just over a year, and although it was the most fulfilling relationship he’d ever had, he was still questioning whether it was the right match. He had always imagined himself marrying a woman who was ambitious in her career or passionate about improving the world, and his girlfriend seemed less driven and more relaxed in her approach to life.

It was an ideal time for a checkup. I asked him how old he was when he formed that vision of a partner and how much he’d changed since then. He said he’d held it since he was a teenager and had never paused to rethink it. As we talked, he started to realize that if he and his girlfriend were happy together, ambition and passion might not be as important to him in a partner as they had been in the past. He came to understand that he was inspired by women who were highly motivated to succeed and serve because that was who he wanted to be.

Two and a half years later, he reached out with an update. He had decided to let go of his preconceived image of who his partner should be:

I decided to open up and talk to her about how she’s different from the person I’d imagined being with. Surprisingly, she told me the same thing! I wasn’t who she imagined she’d end up with either—she expected to end up with a guy who was more of a creative, someone who was more gregarious. We accepted it and moved on. I’m thrilled to have left my old ideas behind to make space for the full her and everything our relationship could bring.

Just before the pandemic, he proposed to her, and they’re now engaged.

A successful relationship requires regular rethinking. Sometimes being considerate means reconsidering something as simple as our habits. Learning not to be fashionably late to everything. Retiring that wardrobe of ratty conference T-shirts. Rolling over to snore in the other direction. At other times being supportive means opening our minds to bigger life changes—moving to a different country, a different community, or a different job to support our partner’s priorities. In my student’s case, it meant rethinking who his fiancée would be, but also staying open to who she might become. She eventually switched jobs and became passionate about both her work and a personal cause of fighting educational inequity. When we’re willing to update our ideas of who our partners are, it can give them freedom to evolve and our relationships room to grow.

Whether we do checkups with our partners, our parents, or our mentors, it’s worth pausing once or twice a year to reflect on how our aspirations have changed. As we identify past images of our lives that are no longer relevant to our future, we can start to rethink our plans. That can set us up for happiness—as long as we’re not too fixated on finding it.

WHEN CHASING HAPPINESS CHASES IT AWAY

When we think about how to plan our lives, there are few things that take priority over happiness. The kingdom of Bhutan has a Gross National Happiness index. In the United States, the pursuit of happiness is so prized that it’s one of the three unalienable rights in our Declaration of Independence. If we’re not careful, though, the pursuit of happiness can become a recipe for misery.

Psychologists find that the more people value happiness, the less happy they often become with their lives. It’s true for people who naturally care about happiness and for people who are randomly assigned to reflect on why happiness matters. There’s even evidence that placing a great deal of importance on happiness is a risk factor for depression. Why?

One possibility is that when we’re searching for happiness, we get too busy evaluating life to actually experience it. Instead of savoring our moments of joy, we ruminate about why our lives aren’t more joyful. A second likely culprit is that we spend too much time striving for peak happiness, overlooking the fact that happiness depends more on the frequency of positive emotions than their intensity. A third potential factor is that when we hunt for happiness, we overemphasize pleasure at the expense of purpose. This theory is consistent with data suggesting that meaning is healthier than happiness, and that people who look for purpose in their work are more successful in pursuing their passions—and less likely to quit their jobs—than those who look for joy. While enjoyment waxes and wanes, meaning tends to last. A fourth explanation is that Western conceptions of happiness as an individual state leave us feeling lonely. In more collectivistic Eastern cultures, that pattern is reversed: pursuing happiness predicts higher well-being, because people prioritize social engagement over independent activities.

Last fall a student stopped by my office hours for some advice. She explained that when she chose Wharton, she had focused too much on getting into the best school and too little on finding the best fit. She wished she had picked a college with a more carefree culture and a stronger sense of community. Now that she was clear on her values, she was considering a transfer to a school that would make her happier.

A few weeks later she told me that a moment in class had helped her rethink her plan. It wasn’t the research on happiness that we discussed, the values survey she took, or the decision-making activity we did. It was a comedy sketch I showed from Saturday Night Live.

The scene stars Adam Sandler as a tour guide. In a mock commercial advertising his company’s Italian tours, he mentions that customer reviews sometimes express disappointment. He takes the opportunity to remind customers about what a vacation can and can’t do for them:

There’s a lot a vacation can do: help you unwind, see some different-looking squirrels, but it cannot fix deeper issues, like how you behave in group settings.

We can take you on a hike. We cannot turn you into someone who likes hiking.

Remember, you’re still gonna be you on vacation. If you are sad where you are, and then you get on a plane to Italy, the you in Italy will be the same sad you from before, just in a new place.

     ? Saturday Night Live/NBC

When we pursue happiness, we often start by changing our surroundings. We expect to find bliss in a warmer climate or a friendlier dorm, but any joy that those choices bring about is typically temporary. In a series of studies, students who changed their environments by adjusting their living arrangements or course schedules quickly returned to their baseline levels of happiness. As Ernest Hemingway wrote, “You can’t get away from yourself by moving from one place to another.” Meanwhile, students who changed their actions by joining a new club, adjusting their study habits, or starting a new project experienced lasting gains in happiness. Our happiness often depends more on what we do than where we are. It’s our actions—not our surroundings—that bring us meaning and belonging.

My student decided not to transfer. Instead of rethinking where she went to school, she would rethink how she spent her time. She might not be able to change the culture of an entire institution, but she could create a new subculture. She started doing weekly coffee chats with classmates and invited the ones who shared her interests and values over for weekly tea. A few months later, she reported that she had formed several close friendships and was thrilled with her decision to stay. The impact didn’t stop there: her tea gatherings became a tradition for welcoming students who felt out of place. Instead of transferring to a new community, they built their own microcommunity. They weren’t focusing on happiness—they were looking for contribution and connection.

LIFE, LIBERTY, AND THE PURSUIT OF MEANING

To be clear, I wouldn’t encourage anyone to stay in a role, relationship, or place they hated unless they had no other alternatives. Still, when it comes to careers, instead of searching for the job where we’ll be happiest, we might be better off pursuing the job where we expect to learn and contribute the most.