Why I Keep Leaving Jobs That Finally Feel Easy
Professional growth ends when comfort takes over—recognizing this is when you must move forward.
Throughout my career, I’ve built things that worked, earned the respect of colleagues, built up clients, and understood the system—then walked away. I left competence for uncertainty, clarity for confusion, and a steady paycheck for unpredictability.
And every single time, in that first year of the new role, I’ve wondered if I made a catastrophic mistake.
This isn’t about job-hopping for money or titles. It’s about those pivotal, uncomfortable moments when comfort becomes the riskiest move—and choosing to act, even when it feels wild.
Let me walk you through three major turning points in my career, each marking a clear transition.
The Associate Years: Trading Security for Autonomy
The first time was 2007. I was an associate veterinarian at a two-clinic practice in Huntington, West Virginia. The owner paid me 22% of gross revenue—not net. Gross. For six years, I ran one of his clinics essentially as my own, and that commission structure meant I was earning a substantial income. I knew every client. I knew their dogs’ names and their kids’ names. I could diagnose by phone half the time.
It was a beautiful trap.
Though I earned well, I controlled nothing that mattered—no policies, hiring, or shaping the culture and medicine. I was middle management dressed as leadership.
The safe move was to stay. The paycheck was reliable, and the work was predictable. I could have done that job in my sleep for another twenty years.
So, I made my first big transition: I started my own practice, leaving employment behind.
And spent the next year learning what ownership actually meant. Financially, I did well. But suddenly every dollar mattered differently — because it was my money on the line. Every equipment purchase, hiring decision, and client who didn’t pay their bill came out of my pocket now, not someone else’s.
But I owned it. Every mistake, every success, every hard call — it was mine.
That’s the price of autonomy: surrendering comfort for the weight of real responsibility.
The Teaching Years: Leaving Easy for Meaningful
The second time was 2015. I was teaching at Mountwest Community & Technical College in West Virginia. It was, without exaggeration, the easiest job I’d ever had. I taught veterinary technology courses. I mentored students. I went home at a reasonable hour. The pay was low, but the demands were lower.
My soon-to-be wife and I bought our dream house on a golf course. We’d spent six months finding it. It fit us perfectly — the layout, the location, the light. We closed, unpacked, and started imagining our life there.
One month later, my mentor from Purdue called.
They were looking for a director of veterinary nursing programs. He thought I’d be a perfect fit.
This was no lateral move. It meant leaving West Virginia — my family, my hometown, where I’d spent 19 years building my professional life. It meant leaving the house we’d just bought and a stable job I knew inside out.
I remember sitting in that house, boxes still half-unpacked, thinking: What the hell am I doing?
But I knew the answer. At Mountwest, I taught twelve students. At Purdue, a consistently top-ranked veterinary nursing program, I could influence hundreds and make a global impact. That platform mattered.
So we moved. The learning curve was vertical. The politics were complex. Expectations were enormous. I missed that easy teaching job more than I’d expected.
But the scale was different. The reach was real.
The First Year Tax
I didn’t expect these transitions: even when you know they’ll be hard, you’re never prepared for how hard.
Every time I’ve made one of these moves, the first year has been a gauntlet. I’m finishing my first year at Iowa State, and it has been no exception. I’ve questioned my judgment more times than I can count. There have been multiple moments where I’ve thought I had it good at Purdue. What was I thinking?
The learning curve is steep. Mistakes are public. Expectations are high, and credibility remains low until you prove yourself. You’re starting over in every meaningful way.
Those first-year struggles are the unavoidable price you pay for real growth.
Competence is comfortable. Mastery feels good. But neither one teaches you anything new. You can’t expand your capacity by doing the same things you’ve already figured out. You can’t become a better leader, thinker, or version of yourself by staying in the lane you’ve already paved.
Every time I’ve left an easy job, I’ve seen comfort as a ceiling—and I’m determined to keep growing.
The Uncomfortable Truth
So why do I keep doing this?
Settling for comfort always means giving up growth.
The alternative is spending the next twenty years doing work I could do in my sleep, collecting a paycheck, maintaining the status quo, and becoming the professional who peaked at 45 and spent the next two decades reminding everyone how good he used to be.
I’ve seen those people. Hell, I’ve worked with them. They’re not bad people. They’re not lazy. They’re just… done. They found their comfort zone and decided to stay there.
And I’m not ready to be done yet.
Knowing you must leave comfort is different from actually doing it. The real question is: Will you pay the price of growth?
There is a price. And it’s steep.
I want to discuss next what these leaps actually cost, why I kept making them anyway, and what I learned about betting on yourself when the stakes keep increasing.
If you found this helpful, there’s more.
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