Every American knows the story. A guy starts building something in his garage. Maybe it's a computer, a delivery service, or some kind of better, faster software. He has no investors or even anyone who believes in his idea. Twenty years later, he's on the cover of a magazine, and the journalist writing the profile calls him "self-made" as if the concept were novel instead of foundational to the entire national mythology.

We love this guy. We put him on motivational posters. We name business schools after him. We tell our kids about the young man who walked into a CEO's office with nothing but a pressed suit and a firm handshake and walked out with a career. We treat self-reliance like a sacred American value, right up there with free speech and the Second Amendment, and we should, because it is.

So why does everybody act so confused when seventy million Americans actually go out and do it?

The American Ronin

In feudal Japan, a ronin was a samurai without a master. He carried the same sword, wore the same armor, and possessed the same training as any lord's retainer. The only difference was that nobody was signing his checks. The romantic version of this story is the wandering swordsman who lives by his own code and answers to nobody. The actual version involved poverty, suspicion, and a society that respected his skills but had no idea where to put him. A ronin was dangerous precisely because he was unattached. No lord could vouch for him. No institution would claim him. He was both useful and threatening, a duality that made everyone uncomfortable.

Ronin describes what is happening in the American labor market better than anything a think tank has produced in the last decade.

According to MBO Partners, roughly 72.9 million Americans now work independently, accounting for nearly 45% of the labor force. By 2027, projections suggest that number will clear 86 million, making freelancers the outright majority of American workers. The independent workforce contributed approximately $1.5 trillion in earnings in 2024 alone. This is a massive, accelerating shift in how Americans earn a living.

These are not teenagers driving for DoorDash between classes. Twenty-eight percent of skilled knowledge workers now operate as freelancers or independent professionals. Thirty-seven percent of skilled freelancers hold postgraduate degrees, nearly double the rate of salaried employees. The median income for full-time freelancers hit $85,000 in 2024. And 85% of them say they would choose self-employment again if given the option.

On its face, society approves of this trend. It’s the American dream in action. But your dad was right when he told you not to listen to what people say; instead, watch what they do.

The reality says America has built precisely zero infrastructure to support these people, and in many cases, the system is actively structured to punish them.

The Day the Deal Died

Everybody lived through 2020. Everybody remembers, much as the architects of that powergrab wish we would forget.

The government shut down your livelihood and dared you to complain about it. Governors held press conferences explaining that your barbershop, your restaurant, your gym, your small business was a threat to public safety, while big-box retailers stayed open because, apparently, the virus respected square footage. Your pastor couldn't hold Sunday service, but you could stand shoulder to shoulder in a Walmart checkout line. The rules made no sense because the rules were never about science. They were about control, and who had it, and who didn't.

Then it got worse. Companies that had been dragging their feet on remote work for years discovered in about forty-eight hours that most of their office workers could do everything from a laptop in their living rooms. Productivity held. Actually, in most cases it increased. Workers could, if they had a mind to, hold TWO full-time remote jobs at the same time, delivering all needed work without fail for both. In many cases, profits went up. And then those same companies spent the next two years demanding everybody come back so that middle management could justify its own existence. Or to support the commercial real estate industry.

Amazon's CEO eliminated tens of thousands of corporate roles while mandating five-day office attendance, and the move was widely understood inside the company as a strategy to force resignations without paying severance. A Unispace study found that 72% of companies with return-to-office mandates saw higher employee attrition than they anticipated, and 29% were struggling to recruit at all. The mandates said "come back to the office." The subtext said "we would like you to quit so we don't have to fire you."

The social contract between employer and employee had been fraying for decades. Covid was just the death blow. We could all make excuses about the longtime IBM employee who got axed without severance. “Of that silly Boomer stayed at a company too long. That won’t happen to me, smarter, more agile Gen X/Millennial.” But then the government stepped in and said, “None of you are essential.” The old promise that if we showed up and worked hard, the company would take care of us was shown to be nothing. Worth less than your at-will employment agreement. 

The institution will sacrifice you the second it becomes convenient. Every single time. So it made sense that more Americans, of all ages, decided to go their own way. If putting up with HR, open office layouts, and that bitch who heats up fish in the communal microwave didn’t provide the barest hint of stability, then why bother?

The Ronin Tax

The answer to that question is going independent in America means the federal government treats you like you're pulling a scam.

A W-2 employee pays 7.65% in FICA taxes, and the employer covers the other 7.65%. When you go out on your own, you pay both sides. The self-employment tax rate is 15.3%, and it hits before your income tax even enters the conversation. For 2026, the Social Security wage base is $184,500, which means every dollar of self-employment income up to that ceiling gets taxed at 12.4% for Social Security plus 2.9% for Medicare, with no cap on the Medicare portion. On $100,000 in net self-employment income, you're looking at approximately $14,130 in self-employment tax alone, before you've paid a dime in federal or state income tax.

The IRS wants its money four times a year. Quarterly estimated payments are due in April, June, September, and January. If you guess wrong, if you underestimate what you owe, they charge you penalties on top of what you already owe. You are simultaneously the employer and the employee, and Uncle Sam collects from both sides of that transaction. 

If you want to reduce your tax burden, that means hiring a CPA to find the right loopholes, file your taxes for you, and tell you which purchases to make and how to claim them as a business expense. Depending on your business, MAYBE the CPAs annual fees will cost you less money than the taxes would have.

In my humble opinion, I’d rather pay Brian the CPA than give one more penny to the government coffers, as the experience of being a taxpayer in this country has become increasingly difficult to justify.

Consider the homeowner in a city that was safe and functional ten years ago. Property taxes have gone up (and thus so has the mortgage payment). Services have gone down. The schools are worse. The roads are worse. There are encampments on streets that used to be walkable. You are paying more for your home than it has ever cost, assessed at a value that reflects a neighborhood that no longer exists in the form it was valued at. The money goes somewhere. It certainly goes to someone. But the services you were promised in exchange for what you pay have degraded in ways you can see with your own eyes every time you walk to your car in the morning.

Add to that, depending on which state and/or city you live in, if someone breaks into your car or camps on your property or harasses your family on the way to school, you are expected to call the same institutions that have demonstrably failed to prevent any of it. 

If you handle the situation yourself, even without laying a hand on anyone, the state that couldn't be bothered to protect you will suddenly discover an impressive capacity for swift legal action. Against you. The government can't keep drugs off your block, but it can absolutely file charges if you tell the guy selling them to move along. You are simultaneously expected to fund, through your taxes, the services that no longer function, and to refrain from providing those services yourself because that's the government's job.

The ronin pays the lord's taxes and gets none of the lord's protection. More people figure this out every single year. And every year, more of them decide to stop pretending the arrangement makes sense.

The Dignity of Your Own Failure

American culture and “rugged independence” are unique in the world because we were founded by a self-selecting group of individualists. Our forbears would rather risk a measles outbreak on a ship, then freeze in an untamed wilderness, ax in hand to carve out a way of life for themselves… vs staying in their homeland where they were told how to live, how to worship, or to pay a lord who neglected them.

They would rather fail (i.e., die a horrible diarrhea death) in their own mission than live forever serving someone else’s. 

The modern employee faces a similar choice, with the stakes sometimes being just as high. You can stay an employee, or seek to become one, and wait for the inevitable day that someone you have never met looks at a spreadsheet and decides your salary is more useful as a budget reduction. You gave them years, maybe decades, and they gave you a box and a security escort to the parking lot. That specific kind of humiliation does something to a person that is very hard to come back from, because the humiliation is total. You did everything right and it counted for nothing. You’ll still lose your house, and maybe your family too.

If your own business goes under, that has high stakes too, but the failure hits different. You bet on yourself and the bet went south. There is grief in that, but no humiliation. You own the failure because it's yours. You can look at the decisions you made and understand where things went wrong and learn something from the wreckage. The independent worker who fails is still the author of their own story, and you have the option to write a better one next time.

The corporate employee who gets laid off in favor of AI or offshoring only has the hope of finding a new job in the same industry, with the full knowledge that the pink slip may (will) come for them yet again. 

Eighty-six percent of independent professionals say they're happier working on their own than they were in conventional jobs. Eighty-five percent say they'd choose self-employment again. Eighty percent believe they work more efficiently than full-time employees. You can dismiss those numbers as self-selection bias if you want, but people who leave institutional employment and succeed on their own terms do not, as a rule, go back. The ones who tried going back mostly tried because they needed health insurance or a mortgage approval, which tells you everything about what institutional employment actually offers versus what it claims to offer.

Millions of people choose this life because they weigh the risks and decide that the uncertainty of independence is less degrading than the certainty of dependence. That tells you everything you need to know about how bad the alternative has gotten. 

The masterless class in America is growing, and they are not going back. We have seen what compliance and “go along to get along” gets you, and have, in one unified voice, said no thanks. Maya Angelou once said that when people show you who they are, believe them. Both the government and corporations showed who they were during Covid, and even the most loyal company man has no choice but to believe them, no matter how much it hurts. 

The question is what will you do with that hurt? Swallow it and keep going? Or make a change in how you live your life?

Choosing the ronin path doesn’t come from losing a master. Truth be told, there’s pretty much no way to fully do that. But you can live and earn in a way to keep his interference to a minimum. Millions have already decided they can do better on their own path, and for the most part, they were right.