Stop Obsessing About Having the Perfect Career Plan

The paths we thought we knew are crumbling fast. Maybe it’s time to think differently about getting ahead.

Get the degree, get the job offer, get that first promotion. Then what?

The set paths that used to shape so many careers are eroding fast these days. Instead of handing out fancy new titles at every performance review, companies like Meta Platforms are cutting layers of middle managers. Law firms are testing watered-down partnership models

A Washington, D.C., area lawyer I talked to said that even partners at his firm were gripped by uncertainty about keeping pace on the corporate treadmill. A police officer in Tennessee told me his career path felt more like a narrowing tunnel. Positions above him never seemed to open up, and the raises he’d expected felt just out of grasp. 

No matter the profession, the promise of a system propelling you steadily forward is now often a facade. Companies are changing strategy on a dime—from hiring at breakneck speed, to cutting jobs just as fast. Technology like artificial intelligence is reshaping the value of white-collar work. 

“The idea that all of us could continually step up the career ladder was a false promise,” says Helen Tupper, chief executive of a global career development and training firm.

Instead, Tupper suggests asking yourself: What is it I want to be known for?

The answer might be a brilliant presenter or a decisive leader. Exactly where is less important, she says. Look for not just new roles but projects that expose you to new people, like sitting on a committee or helping out an international office. Preserve your earning power by negotiating a raise with a lateral move, or ask for money to use toward education. Think of this moment as an opportunity to have more choice in the work you do, rather than following a trail someone else carved out. 

And level with yourself. Trying to embody some perfect LinkedIn profile, with a cascade of titles in stair-step order, might just be a fantasy. Hitching yourself to one path leaves you vulnerable when things change.

“Not every move you make has to be absolutely perfect,” says Tupper, co-author of the book “The Squiggly Career.” 

Certainty meets reality

Alex Robb spent years checking the boxes to becoming a vet: getting into a prestigious college, doing surgical research in veterinary school, matching into postgraduate training. 

The work was grueling, but “I had this sort of comfort and certainty around everything,” he says.

Alex Robb, shown here with a patient, climbed a steady path in his veterinary career before hitting a roadblock. Photo: Marina Valdes

He landed at an animal hospital in Denver and settled in. Dreaming of running the whole organization one day, he got his M.B.A. on the side. Then an acquisition and restructuring hit the hospital, eliminating the department head position he’d been interviewing for. 

“What am I going to do now?” he says he thought. 

He left and spent a year testing out different work settings as a contract veterinarian. The exploration led him to a job he loves: co-founding a group of animal hospitals and running his own location, which he opened in 2021. 

Looking back, he wonders if there were some downsides to hewing so closely to a set path. Could he have been more well-rounded or creative if he hadn’t been so laser-focused?

The new tech era

Many people in Western societies mistakenly believe we have more control over the world than we actually do, says Adam Alter, a professor of marketing at New York University who’s studied how blindsided we are by change. Fueled by our belief in science and medicine, we subscribe to the idea that “things just get better if you are virtuous and do the right thing and follow the right path and listen to your parents.”

The problem is that technology has turbocharged the pace of everything, he says. The rules of success—study this, pitch the boss that—used to last generations. Now they might last five minutes.

He recommends taking an audit of your work and life every couple months. Ask yourself how much things have shifted since you last checked in. Are there changes afoot? How can you prepare? 

“You’re not more powerful than the world around you,” Jarrod Farmer says he learned after being laid off from Meta last November.

He’d spent more than seven years in big tech and planned to never leave. The experience prompted him to transition to a public-sector job, which he hopes is more stable.

As firms invest in AI, their hierarchies flatten, according to a recent National Bureau of Economic Research working paper. They bring on young, educated folks with fresh tech skills, increasing junior roles by 10%. 

Meanwhile, the technology helps workers at all levels make decisions and seamlessly gather data, leaving less of a need for middle managers, says Tania Babina, an assistant professor at Columbia Business School and one of the authors of the paper.

The questions we all ask

Riley Sheehey, an education major with an artistic bent, remembers being terribly jealous of her girlfriends the summer after college graduation. They’d parlayed internships into jobs in big cities or were gearing up for grad school. Meanwhile, she was working at her same old summer camp and trying to figure out what to do with her life. 

Twelve years later, Sheehey is a successful watercolor artist with her own line of fabric and wallpaper, and has watched those same friends question their paths. She’s glad she faced the reckoning early. 

At some point, she says, you’re going to ask yourself: “Even though this is laid out for me, is this what I want to be?”

Write to Rachel Feintzeig at

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