What Unusual Jobs Taught Me About Hiring, Retention, and the Talent You’re Overlooking

Paddy Fanning never set out to become one of the best sheepdog trainers in the world. He was a cowboy working on a Canadian cattle ranch when he came across an old book on horsemanship that described the magical give-and-take between humans and animals. Back in Ireland, as he worked to recover from a drinking problem, he put those lessons into practice with a border collie on his father’s sheep farm, and, in the process, discovered a new sense of purpose.Twenty years later, Paddy has represented Ireland in international herding dog competitions and earned a reputation as one of the finest trainers alive. “I’m probably still a bit unemployable,” he told me, laughing. “You hear my job there, and I don’t really have one. And yet we do okay. Dogs have given me all that. I just feel glad with the way the whole deal turned out.”For the last six years, I’ve been writing about work. How people get their jobs and how they lose them, the relationship between employer and the employed, and how all of us find meaning in our work. I frequently meet people who are unhappy with their careers. But I noticed something: People who have unconventional jobs often are happy with their work.So I started searching for the people who have jobs they don’t tell you about in school, roles that don’t show up on job boards: the death doulas, sheepdog trainers, puppeteers, and Foley artists of the world. And I made a podcast about it, called How to Be Anything.Each episode tells the story of someone with an unusual job, and after interviewing 15 of them, I realized their lessons aren’t only for people whose careers take them off the beaten path. Their wisdom and experiences are relevant for anyone working today–including those in corporate America. Some of my findings: Self-Determination Is a Powerful Retention ToolFrom Day One contributing editor and journalist Emily McCrary-Ruiz-Esparza takes you inside the world of unique and unexpected jobs in her podcastAlmost everyone I spoke with chose their job intentionally. Sometimes it took years (or decades) to find, but in the end they carved out space to do work they found meaningful. That self-determination is a powerful reason they stay.Puppetry artist Heidi Rugg built a career by weaving together all the art forms she loves, and her work became stronger once she focused on the environmental themes that deeply matter to her. On the TV Show Dimension 20, lorekeeper (kind of like a script supervisor) Skye Smith designed their own system for tracking the plot, a process they owned from start to finish. For Smith, the real satisfaction comes from being taken seriously. “If I have opinions, I get to say them and they get taken into consideration, which I think is a huge blessing, especially as someone who's young and I didn’t finish college,” Smith told me.And when veterinarian Cindy Otto worked at Ground Zero after 9/11, she saw firsthand the need for better medical care for search-and-rescue dogs. Backed by the University of Pennsylvania, she launched an entire research program to address it, and now is on the leading edge of working-dog science. When workers have the freedom to pursue ideas that matter personally to them, they’re far more likely to stick around.Everyone Needs to See the Fruits of Their LaborWork feels meaningful when you can see its impact.Forensic artist Melissa Cooper has seen her sketches lead directly to the capture of violent criminals, and she draws joy from knowing she’s giving power and a voice to survivors. Gavin Cox, a research scientist who works a mile underground searching for dark matter, described the satisfaction of spending a month designing a procedure to safely move liquified xenon gas, a high-stakes task that required precision and patience. “That’s when I feel proud of my work,” he told me.Employees don’t need a dramatic story to feel accomplished, but they do need to see that the outcomes of their contributions matter.I asked veterinarian Cindy Otto what she thinks of her career now that retirement is in sight. She told me that at a recent veterinary symposium, a presenter asked the crowd for a show of hands: Who had been affected by the Penn Vet Working Dog Center and the work they’ve done? Every single person in the room raised their hand. “I think about it a lot,” she told me. “I’ve made a difference. I’ve made an impact,” she said. Excellence Requires Freedom to FailNo one starts out as an award-winning sheepdog trainer or an award-winning Foley artist. You start as lousy, and then you become okay, and then you become good–and then you become great.That’s why the famous Jack Welch mentality of routinely cutting lowest performers (a practice now back in vogue in 2025) is so damaging. It sends a message to your employees that stumbling is a punishable offense, and eliminates the top performers of the future.Organizations that want innovation have to accept that employees will struggle, or even fail, on their way to mastery.Careers Are Built on Soft SkillsBrendon King has been climbing 500-foot cell towers for more than a decade. The hardest part isn’t fixing the electronics, it’s staying calm when the steel tower sways like a noodle in the wind. Patience, composure, and a little bit of thrill-seeking keep him safe. The technical skills, like repairing fiber optic cables and network switches, those are things he learned on the job. But the best part? “It’s a constant adventure, no matter how you look at it,” he said. “I’ve been in places where people have lived there their entire lives and they’ve never once seen the view that I get to see. It’s amazing.”Similarly, Erin Bishop spent two decades in market research before becoming a death doula. You might be surprised that running a focus group translates quite well to conducting community discussions about death and dying. “Having a career that helps me be a better person in the world—I never thought I would have that in my life,” she told me.Too often, employers seek out candidates who have direct experience, and miss out on remarkably talented people with unconventional career paths.Work Should Be EnjoyableBusiness leaders love to talk about purpose and meaning. They want employees to connect to the company mission, touting its ability to increase engagement and retention. It’s true, and there’s evidence to back it up. But purpose alone isn’t enough.The people I spoke with not only find meaning in their unconventional jobs, but enjoy them in the moment. An employee may love working at a company that saves lives with medical equipment or helps people afford homes. But if the day-to-day is tedious, they won’t stay. Meaning is important, but fun doesn’t get enough credit.Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Featured photo courtesy of forensic artist Melissa Cooper)