Solopreneur: Year One vs Year 20

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I just started my 20th year as a solopreneur.

But 2006 looked very different than 2026.

My first six years as a solopreneur were part-time while I worked a full-time job in Corporate America, and studied full-time for a bachelor’s degree.

I started at zero. No savings account. No prior experience. No connections.

My very first project was a website build-out from scratch. It took me over three months to complete and I earned $600 for the entire job.

Fifteen years and over 100 websites later, my typical website was priced around $25,000 and took around six weeks on average to complete.

That growth wasn’t luck. It was obsession — years of learning, improving, messing up, and starting again.

I remember so many late nights when I wanted to throw my computer out the window of my apartment from frustration.

My first role as a social media manager paid $150 a month, and that was after they talked me down from $200 a month.

But every week, I showed up, took new photos, and crafted new stories. And every month, I’d deliver the data from my work with my invoice, and the data never lied.

Fifteen years later, my average rate for social media management was $5,000 a month. The difference wasn’t the market; it was my work.

Looking back, the story of my career isn’t “I made it.” It’s “I built it.” I did this by starting with one underpriced project at a time, and one client (on a budget) at a time.

Through all of it, the same truth kept showing up: nobody owed me anything.

The bottom line that clients always knew they could trust: I kept my word.

I stuck to my timelines. I never sent extra invoices for unexpected work. I showed up for meetings on time. I did the work without anyone checking on me.

Last week, I was at the bank making deposits into my business accounts, and a new teller (Henry) looked up at me with big eyes and said, “Can I ask you business advice real quick?”

I smiled. “What’s up?”

Henry: “I’m guessing, based on the names of your companies, that you work in the digital world?”

Me: “I do.”

Henry: “If you could give me three pieces of advice for working in that field, what would they be? I’m going to school for it.”

Me: “I’m going to be completely honest with you. Show up on time, complete your projects by the deadline, and put a subject line in a your emails.”

Henry: “Really?”

Me: “Really. If you do those three things, you will be successful. It doesn’t matter if it’s digital or not. The bar is low. If you do those three things, I promise that you will have success beyond your wildest dreams.”

I smiled at him and walked out of the bank.

It was the truth.

Be obsessed with your work — the way my dedicated friends are obsessed with their kids, the way people get obsessed with whatever show they’re binging, the way so many are obsessed with staying inside their comfort zone so they never have to feel uncomfortable chasing their dreams.

I remember the stress I used to feel in Corporate America, and I thought, “If I’m going to be stressed, I want it to be from the fear of the unknown while I’m chasing down my dreams not because I am making money for other people.”

I traded the frustration of pushing paper and uninspiring cubicles for the fear of wondering if I could pay my rent or if anyone would ever hire me.

My body didn’t know the difference; the stress hit the same.

But my bank account felt the difference.

And so did my life, especially when I started wanting freedom more than I wanted money.

20 years later and I can honestly say that I am just as obsessed with the work (from the little tweaks to the big unknowns) as I was in 2006.

I hope that curiosity for excellence never dies, and I love when I experience it in others.

Whether you are creating a website for the first time or working the night shift in a factory, people pay attention to obsession done well.

Remember these three things:

1. Nobody owes you anything.

2. The bar is low. You have the opportunity to stand out by being the best you that you can be.

3. Stress is unavoidable. Pick the stress that gives you the life you really want.

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