This week we’re asking our audience whether they have 5- or 10-year plans for their careers. While I’d usually wait for the results to write something up, I feel this topic warrants more immediate discussion.
We all entered the workforce with some expectations for our careers. But in economic downturns or near-impossible job markets, the feeling of what could have been intensifies.
The internet might be obsessed with romantic yearning right now, but to yearn for a more defined, secure, or higher-paying career and not feel like the opportunity exists for you is its own kind of grief—especially after growing up amid "bootstrap" or "grind" ideology.
I’m sure asking about 5- or 10-year plans at this particular moment doesn’t help, either. You might be thinking: "Well, I did have a plan until… (gestures at economy)."
That sentiment is more than valid.
Still, I don’t think this is a hopeless moment—I think it’s just a different one.
Careers aren’t unfolding the way many of us were raised to expect. The trajectory isn’t as linear, the milestones aren’t as predictable, and the timelines don’t always make sense anymore.
Which is why I keep thinking about something from landscape architecture: desire paths.
Desire paths are unofficial, human-worn paths that appear when people, over weeks and months, trek across the same strip of land. You’ve seen them everywhere, but the most striking examples are on college campuses. There, despite sidewalks, desire paths appear along cut corners or amid extended greens because students, racing to class, often take the line of best fit to their destination.
In fact, some landscape architects observe desire paths before laying concrete. (A famous example is The Ohio State University’s Oval paths, which were paved after students forged their own paths across the grass.)
What I like about desire paths in the context of careers is that they often exist whether or not there was ever a plan.
Even on my favorite running trails, eroded paths curve next to designated walkways because at some point, someone thought, “I see where I’m supposed to go, but that doesn’t make sense for me,” and they changed course. Others followed.
That impulse is instinctual.
What if we approached our careers the same way? Instead of forcing ourselves into a trajectory that no longer fits the moment, what if we allowed ourselves to veer—without over-explaining it, without waiting for permission?
What if the goal wasn’t to follow a plan, but to get to our desires—security, fulfillment, work-life balance, whatever—by any route that gets us there?
As a woman and a millennial, I know what my designated path looked like—for my career, for my life—because it was mapped for me at a very young age through culture and media.
Yet all I see around me now are desire paths forming: more women opting out of marriage, choosing to be childfree, buying homes on their own, changing careers, entering male-dominated fields. Making the choices that work for them.
To me, the path to “success” hasn’t disappeared—the map itself has been redrawn. By all of us. Collectively.
And if that feels unsettling, that’s completely normal. Any time you step off a walkway, you sink a little, the ground is uneven and harder to tread. Uncertainty is the reality of creating something new.
In last week’s polls, we asked our audience what defines their identity outside of work. One response made me smile:
“All of it. My life is my work. The relationships I build are work, the meals I make and the home I keep together is work. The books I read and the journals I write and the photos I take are work. A job should pay for the life you build. Building a life is work. It's the only work.”
That is the desire path. Not a plan at all, but something you build by following what you want.
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