Leadership Lessons We Didn’t Learn in Business School (Some of Us May Have Learned Them at the Bar)
I didn’t set out to build a career in workers’ compensation.
Like many people in this industry, I landed here almost by accident. I took a claims adjuster role at Aetna Property & Casualty because I wanted a stable, business‑focused job. At the time, workers’ compensation wasn’t the coveted path—property and casualty was where the “good” jobs were. I remember telling my manager I’d handle comp claims if it meant I could stay in Tampa.
What I didn’t realize then was that workers’ compensation—and more importantly, the people in it—would shape my entire career.
Here I am now, years later, moderating a conversation for a webinar with WCC with three extraordinary leaders: Sarah Meyer, COO of Bardavon; Heather Sanderson, CEO and Founder of Sanderson Firm LLC; and Artemis Emslie, CEO of CadenceRX. As we were talking, I had a realization that felt both unexpected and oddly validating.
Workers’ compensation has a very unofficial, but extremely effective, career pipeline. And maybe it can even start behind a bar.
As each of us shared how we found our way into the industry, a pattern emerged that we hadn’t planned and couldn’t ignore. Sarah bartended. Artemis bartended. Heather waited tables at Cheesecake Factory—after passing the bar exam, no less. At one point, Artemis joked that bartending might be the common denominator, and honestly, she wasn’t wrong.
There’s something about working in food service that prepares you exceptionally well for workers’ compensation. You learn how to manage impossible expectations. How to stay calm when everything is on fire. How to read people quickly and solve problems in real time—often while someone is actively upset and convinced the situation is entirely your fault.
Sound familiar?
I’ve said for years that when I see bartending or food service on a résumé, it goes straight to the top of the pile. Those jobs teach grit, resilience, emotional intelligence, and the ability to keep moving in the middle of the rush, when nothing is going as planned.
Turns out, that’s excellent leadership training.
What struck me most in listening to each story wasn’t just how we got here, but why we stayed.
Sarah talked about moving across state lines without a clear plan, taking a job she didn’t fully understand, and discovering an industry that’s constantly evolving—and one where you can make a real human impact.
Heather shared how graduating law school into a recession forced her to take whatever work she could find, eventually leading her into Medicare compliance. It’s something no one teaches you in law school, but something she found endlessly interesting because it changed every day.
Artemis entered an industry that openly told her it didn’t hire women—which, if there’s a faster way to motivate someone, I haven’t found it. She stayed because she believed workers’ compensation could be more patient‑centric than healthcare at large, and because the people made it worth fighting for.
None of these paths were linear. All of them were meaningful.
Those stories naturally led me to reflect on my own leadership journey.
At one point in the conversation, I shared something that often surprises people: I had never managed anyone until I started my own company. I didn’t step into leadership feeling fully prepared. I learned by watching others—taking the good, leaving the bad, and promising myself to do better where I could. I leaned heavily on mentors and peers, not because I had all the answers, but because I knew leadership wasn’t something you figured out alone.
Sarah spoke candidly about imposter syndrome and how often women feel the need to be fully qualified before raising their hand. That resonated deeply. Some of the most growth‑defining moments of my career came when I felt unprepared but chose to move forward anyway. Readiness, I’ve learned, usually shows up after the leap, not before it.
The conversation took a turn that made many of us laugh—and nod—when Sarah talked about being told throughout her career that she was “too nice.” At one point, she even found herself reading books about how to be less nice. Eventually, another leader reframed that feedback in a way that stuck: kindness and accountability can coexist.
Empathy doesn’t weaken leadership, it strengthens it.
In workers’ compensation, we’re dealing with injured employees, stressed employers, and systems that are already complex and frustrating. Leadership without humanity creates distance. Leadership grounded in empathy builds trust.
Nice doesn’t mean ineffective. It means human.
That theme kept resurfacing as we talked about entrepreneurship and the reality of building something from scratch. When I started ReEmployAbility, I thought my job would be to deliver a service. Instead, I found myself learning about phone systems, payroll, accounting, technology infrastructure, calendars—things I’d never once thought about before. I didn’t know what I didn’t know, and sometimes I think that ignorance was the only thing that gave me the courage to take the leap.
It reminds me of the quote by Jack Canfield that I’ve often repeated over the years, “Jump then grow wings on the way down”. To some degree, we’ve all done that—and in some ways, we continue to.
Heather’s story felt especially familiar as she described being the lawyer, accountant, marketer, sales team, and invoicing department all at once. She talked openly about panic attacks over payroll and the fear that comes with realizing other people’s livelihoods depend on your decisions. I remember Fridays spent standing at the post office box, silently hoping enough checks had arrived to cover payroll on Monday.
Those moments don’t show up in your success stories. But they shape you in ways you could never have imagined.
As the discussion shifted to mentorship, I found myself reflecting on how much the culture has changed over the years. Early in my career, the people who advocated for me were almost all men. Women supporting women wasn’t the norm, and there was often an undercurrent of competition that made trust difficult.
That’s why today’s shift feels so important.
Sarah drew an important distinction between mentorship and advocacy. Mentors offer guidance, but advocates create opportunity. They speak your name when you’re not in the room. They pull you into conversations you didn’t even know were happening. Organizations like the Alliance of Women in Workers’ Compensation, which began as a conversation and grew into a national network, exist because someone asked, “Why doesn’t this exist?”—and then did something about it.
No conversation about leadership would be complete without addressing work and life, especially for women. I’ve always been honest about this: there is no such thing as work–life balance in senior leadership. What does exist is prioritization, partnership, and the willingness to let some things go. I was fortunate to have an incredibly supportive husband, but I still missed school events, traveled constantly, and felt guilt more times than I can count.
Years later, when I asked my daughter whether she felt I’d missed too much, her answer stopped me in my tracks.
“You were there for the important things, Mom.”
Sometimes, that’s the measure that matters most.
We also spent time talking about the future—particularly innovation and AI—and how important it is that technology enhances, rather than replaces, the human side of our industry. Workers’ compensation is transactional by nature, but it doesn’t have to be impersonal. If technology allows us to spend less time on process and more time on connection, then it’s doing exactly what it should.
Toward the end of the conversation, we touched on what it feels like to be the only woman in the room. For much of my career, it didn’t even register—until one day, it did. Progress is happening, though slowly. Until true parity exists, my advice remains simple: use it to your advantage. Bring your perspective. Ask the questions others aren’t asking.
Representation changes rooms, even before the numbers catch up.
Leadership in workers’ compensation rarely follows a straight line. It’s built through unfamiliar paths, uncomfortable leaps, and lessons learned along the way—sometimes at a desk, sometimes on a whiteboard, and sometimes behind a bar. You don’t need a perfectly mapped plan. You don’t need to be flawless. You just need to be willing to show up, work hard, and say yes before you feel ready.
And if you happened to learn those skills while bartending, you’re probably more prepared than you think.
To hear directly from the women shaping the future of Workers’ Compensation, watch our on-demand webinar→ Breaking Barriers: Women Leading the Way in Workers’ Compensation
