What running a business actually takes

Hey there -

There's a conversation I've had more times than I can count over 25 years of freelancing: someone with real, marketable skills tells me they'd love to work for themselves, and then tells me all the reasons they can't. And it's almost never the work itself - they KNOW they can deliver. What stops them is everything wrapped around the work: forming a company, taxes, contracts, bookkeeping, insurance etc. The "business side." In their head it's a second full-time job, a giant obligation that hangs around their neck, eats their evenings, and leaves them broke if they get any of it wrong.

I understand this fear because I had my own version of it. When I started out, the business side scared me far more than the work did. For me, given my personality type, the scariest part was other people. I dreaded client calls. "Doing sales" sounded like a personality I didn't have, and I was sure I'd say the wrong thing and lose a project. Underneath all of it sat a vague dread that running a "real business" required some enormous body of secret knowledge that everyone else had been handed and I hadn't. I read every business book under the sun, thinking that I needed to know everything about running a business. I don't regret reading those books, but it was mostly a waste of time because, in reality, running a business turns out to be much, much simpler than I imagined. You can read 100 books to learn how to ride a bike, or you can just get on one and go. You may scrape a knee along the way, but by the end of the day, you'll know everything you ever need to know about riding a bike.

So let me put actual numbers on the "business side," because after 25 years of running one, the reality is almost embarrassing compared to the fear. Forming my LLC took less than an hour. I mean that literally - in most states you fill out a form on the state's website, pay a filing fee, and you're done (approval takes a few days to come back, but that's the state's time, not yours). And the ongoing burden people imagine? Once you're organized, the actual management of a one-person business - invoicing, expenses, quarterly tax estimates etc. - takes me an hour or two a MONTH.

The rest of "running a business" is just doing the work. The same work, in the same hours, you'd otherwise be selling to an employer. You already spend 40-plus hours a week making somebody else's business run - freelancing points those same hours at your own. What's genuinely new is a short list: health insurance, retirement, and setting aside the taxes nobody's withholding for you. And each one is a line item with a known and fairly straightforward solution, the kind of thing you set up initially and then revisit once a year rather than carry around every day.

And here's the thing about this kind of fear - it thrives in the dark. "Running a business" stays terrifying only as long as it stays undefined, because your mind fills that vacuum with an obligation of unlimited size. Nobody ever hands you the actual list, so you never find out how short it is.

But don't take my word for what's on the other side of that list - ask the people already there. Gallup puts US employee engagement at 31%, which means roughly seven in ten American employees aren't engaged at work. Meanwhile, in MBO Partners' 2025 State of Independence survey, 86% of full-time independents said they're happier working on their own than at a traditional job, and 67% said they feel more secure working for themselves, the exact opposite of what the fear predicts.

My advice? Stop arguing with the fear in the abstract, because in the abstract it's unbeatable. Write your actual to-do list instead: form the entity, open the business bank account, sort your insurance, set up quarterly taxes etc. Then look at what you wrote. It's an afternoon of setup and, once you're organized, a couple of hours a month. And on the other side of it, your working hours finally belong to you. To me, that's one of the most liberating trades a working adult can make.

So the question to carry into your week: what, specifically, is on YOUR list? Write it down. Anything that makes the list is a task. The rest was fog.

More from the trail next week.

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- Brendan

P.S. For most people the biggest line on that list is health insurance and the rest of the benefits an employer used to hand you. I wrote up how to replace every one of them here: How to Replace Your Corporate Benefits as a Freelancer