Not an Entrepreneur—But Entrepreneurial
What 14 Years of Self-Employment Taught Me About Business, Identity, and the Quiet Power of Staying Small
There's something seductive about the word entrepreneur.
It suggests boldness, vision, risk. It's stitched into LinkedIn bios, podcast intros, and pitch decks like a badge of courage. Reid Hoffman famously said, "An entrepreneur is someone who jumps off a cliff and builds a plane on the way down."
That's vivid.
That's gutsy.
That's also complete nonsense if you're trying to build something that lasts.
For 14 years, I worked for myself. I had clients, not investors. I had invoices, not seed rounds. I built a business that didn't need to scale to be successful. And while I never thought of myself as an entrepreneur, I've come to realize I was always entrepreneurial.
There's a difference. One is a label. The other is a mindset.
The Skills, Not the Spark
I didn't start with a disruptive idea. I started with a certain set of skills—and no Liam Neeson punchline needed. I was a solid communicator. A strategic public relations thinker. A writer who could hold his own with anyone in market, I wasn't going to reinvent anything. I just wanted to make a living doing what I was damn good at.
Over time, I sharpened those skills and added others. I got faster, better, more efficient. I developed something akin to what Scott Galloway calls a kind of athleticism—emotional, mental, physical—that most folks with steady paychecks don't always have to flex.
If you've been your own boss, you know what I mean. You do it all. You handle the sales, the strategy, the creative, the billing, the tech issues, and the existential dread—often before lunch.
That's not complaining. That's pride.
And burnout.
Why I Never Scaled (And Don't Regret It)
I could have grown the business. I got close a few times. But every time I brushed up against scaling—hiring help, expanding services—I hated it. The minute I wasn't doing the work myself, it lost its soul.
I hired freelancers and contractors. Paid them decent wages—sometimes more than I could really afford. But I couldn't pay for deep experience, and the bench wasn't deep to begin with. That's not a knock on them—it's just reality.
One contractor nearly torpedoed a $50,000 annual contract because she felt a mansplaining client "needed to be set straight" on how he spoke to her. Whether she was right or wrong wasn't the point; I was the one left doing damage control. Turns out, some contractors who felt their personal politics or agendas were more important than keeping clients happy wasn't just a problem. It was a pattern.
That meant I had to redo work. Apologize to clients. Cover for missed deadlines and no-call no-shows. (Turns out, that's not just a fast food thing. It happens at boutique PR agencies, too).
I also learned that growth without boundaries is just chaos with a business plan. Every yes to the wrong opportunity was a no to the work that actually mattered.
So I learned to adapt. Fast.
Many sixty- to seventy-hour weeks. Nights, weekends, holidays. I smiled, spun and smoothed things over. But I wasn't building a unicorn. I was just trying to build something sustainable—and even that came at a cost.
The Business Owner vs. The Entrepreneur
Let's draw a clean line.
A business owner creates a job for themselves. They run a practice, not a product. They focus on quality, relationships, and sustainability.
An entrepreneur, in the Silicon Valley sense, is chasing scale. They're thinking systems, exit strategies, and how fast they can go from garage to IPO.
Kevin Kelly famously wrote about the idea of 1,000 true fans—if you can find 1,000 people who truly love what you do, you can make a good living without ever needing to go viral or global. That's the business owner's creed. That was mine.
Was I the best businessman? No.
If we're grading, I'd give myself a B-minus overall. Maybe a C-plus in ops, an A in client service and content. I made a living, but never created wealth.
That said, I never sold something I couldn't deliver with pride. I just didn't want to build something so big I had to lie to keep it afloat.
Entrepreneurial Inside the System
Funny thing about building something sustainable—it gives you options. These days, I work inside an organization. It's a good fit. They pay me pretty well to do things I'm great at, and mostly leave me to handle my portfolio.
But I still move like it's mine.
That entrepreneurial mindset doesn't go away. The math is simple for me: 55 hours for work (this includes 2.5 hours traveling to and from work four days a week on average), 44 hours for 6-7 hours of sleep a night, and 68 hours left over. That's 40% of my week that's still mine to shape.
Most people with my schedule would say no to maintaining a work posture in those remaining hours. I treat the time like startup capital.
Writing and podcasting easily claims another 10-15 hours; with short sips throughout the week, then 3-5 hour Saturday morning sessions when the house is quiet and the coffee is strong.
"You're very entrepreneurial," someone said recently.
I smiled. That's not a word I'd use, but I'll take it.
Because whether I'm freelancing, consulting, or on someone else’s payroll, I still tap dance. I still make it work, even when the music changes. I still care like my name's on the invoice. That's not being an entrepreneur. That's being accountable.
Final Thought: Know the Life You Want
Seth Godin said, "Instead of wondering when your next vacation is, maybe you should set up a life you don't need to escape from."
That's what I was chasing. Not the plane-in-midair chaos of the startup life. Not the comfort of a cubicle. Something in between; a creative life on my own terms, with the freedom to change course when it stopped serving me.
I'm not an entrepreneur. But I'm proud of what I built and even prouder of how I knew when to bow out. That's not failure. That's a standing ovation after a hell of a long performance.
And yeah…I still hear the music sometimes. Where are my tap shoes?