What If You Were Never Meant to Have Just One Career?

Leslie Barber started writing her book Unemployable: The Psychological Toll of Proving Your Worth in 1998. She had just finished graduate school, was collecting rejection letters, and assumed that eventually she would land the right job, find her place, and build the career she was supposed to have.

More than 25 years later, she finally published the book. In between, Leslie accumulated something far more interesting than a conventional résumé.

She’s been a social worker, organizational development consultant, grant writer, coach, baker, cooking instructor, gym operations director, and high school track coach. She’s started businesses, taught classes, and reviewed grants. Today she’s working on multiple novels, preparing to launch a podcast and considering how she can make travel a larger part of her life.

Leslie describes herself as a multipotentialite, someone with many interests and abilities who doesn’t necessarily want to spend an entire lifetime doing one thing. For people like her, the traditional advice to “pick a niche” or find your single calling can feel less like guidance and more like a constraint.

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Our conversation explores what happens when you spend years trying to fit yourself into a system that doesn’t quite fit you. Leslie has experienced toxic workplaces, corporate bureaucracy, the dot-com crash, automated rejection systems, ghost jobs, and the strange transition from once being considered too young for opportunities to suddenly wondering whether she’s now considered too old.

At one point she found herself applying for jobs she already knew she didn’t really want, then feeling terrible when she was rejected from them.

That realization became one of the most useful lessons from our conversation: if you already know you don’t want to go in a particular direction, why are you working so hard to get there?

For Leslie, contract grant writing has provided something valuable. She’s good at it; it pays the bills, and she can do it remotely. But she’s stopped insisting that the thing paying the bills also has to represent her entire identity. Writing increasingly feels like the next chapter, while portable work gives her the flexibility to explore it.

Leslie’s story also challenges the idea that changing direction means you’ve failed at whatever came before.

She ran a sourdough bakery until circumstances changed. She coached track until an injury changed that. She has repeatedly picked something interesting, gone deeply into it, learned from it and eventually moved somewhere else.

That isn’t necessarily indecision. It may simply be how some people are built.

Now, with adult children and a growing desire for “more traveling and less paperwork,” Leslie is again figuring out what comes next. She recently returned from three weeks in Europe, wants to spend more time abroad, and already has work she can theoretically take with her.

Her advice for anyone facing the same uncertainty is refreshingly practical. Trust your gut. Pay attention to what you already know you don’t want. Ask people for help. Try something. Create momentum. And when the path stops making sense, give yourself permission to choose another one.

As Leslie says, there are many paths to the top of a mountain.

You don’t have to take the path your friends chose, the one your parents expected, or the one society told you was sensible.

And perhaps that’s one of the most important lessons of midlife recalibration: you don’t necessarily need to finally figure out what you’re going to do for the rest of your life.

You only need to decide what you’d like to try next.

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