Do a YouTube search for “be your own boss,” and the results seem to go on forever.

“HOW TO BE YOUR OWN BOSS IN 2021 (MUST WATCH)”

“20 BUSINESS IDEAS FOR 2020 T0 FINALLY BE YOUR OWN BOSS”

“BE YOUR OWN BOSS! How we escaped the 9-5 ft. Chris Hau”

“MAKING $2,000 IN ONE DAY!”

Most people who try to follow through on this dream fail. Even if they scrape together the starter capital for their own business, 70 percent of businesses go belly up within their first decade of operation. And most that do make it don’t net their founders “$2,000 IN ONE DAY!”

But one interesting thing about this genre of videos is that relatively few of them are really about getting rich. Most people who dream of being their own boss are imagining starting the smallest of businesses — ones where they would still be doing most of the work. The dream, after all, is to be your own boss, not to simply be “the boss.” The focus is often less on money than autonomy.

A video collecting “be your own boss” tips from Canadian businessman Kevin O’Leary starts with O’Leary telling a story about his “first real job.”

I was working once in an ice cream parlor when I was about fifteen years old . . . and on the second day I was asked to scrape the gum off between the Mexican tiles on the floor, and I said to the woman who owned the store . . . “you didn’t hire me to scrape gum, you hired me to scoop ice cream.” . . . And she said, “What are you talking about? I own this store, I’ll do anything I want with you, get down on your knees and scrape that gum.” 

O’Leary refuses to scrap the gum, and he gets fired. It was the last job he ever had. “I don’t like to work for other people,” he tells his audience of would-be entrepreneurs. “I hope many of you here inherit that.” While he assures them that there’s nothing wrong with being a worker, “If you want to control your own destiny, you work for yourself.”

That’s inspiring — but the problem is that, under capitalism, it’s impossible almost by definition. If the ice cream parlor was an ice cream stand on a street corner, it might be a one-person operation, but by the time it expanded to having even one employee, one of the two people scooping ice cream would no longer be living O’Leary’s dream. The owner could use their economic power to make the other get down on their knees to scrape gum.

In an 1861 speech, Abraham Lincoln argued that there was “no such thing as a free man fixed for life in the condition of a hired laborer.” Lincoln wasn’t a socialist. His vision was limited to replacing slave labor in the South with capitalist wage labor. But he was uncomfortable with the idea that some people could spend their entire lives in such a subordinate position. He thought wage labor was compatible with real freedom not because the wage laborer was a fully free person in charge of their own destiny, but because someone could work for wages “awhile” and then “save the surplus to buy tools or land for himself.” 

The idea that everyone could eventually be an independent farmer or small businessman was already becoming a bit anachronistic in Lincoln’s day. But today, the idea is manifestly absurd. It would be structurally impossible to maintain a modern economy with a labor force that consisted entirely of future independent proprietors working a few years at a time before striking out on their own.

That leaves us with a stark choice: either we have a society where, as even capitalism’s most ardent defenders like Kevin O’Leary admit, the vast majority of people are powerless employees who don’t “control [their] own destiny,” or we can transition to a society where people collectively control their destiny.

We can see what the second vision looks like in the few islands of workplace democracy that exist within capitalism, like the worker-owned Mondragon Corporation in Spain or the worker co-ops in Italy’s Emilia-Romagna. In these enterprises, workers democratically decide on pay scales, elect managers, and vote on operating agreements — the equivalent of a union contract but without a separate owner on the other side of a negotiating table. If someone has to scrape gum off the floor, everyone at least has some democratic input about who will be asked to perform which kind of tasks, when, and under what circumstances. There isn’t a separate owner whose word is law.

Under capitalism, businesses organized this way are a relative rarity, and they face structural disadvantages when competing against traditional firms. Look, for example, at Baltimore, where even as the restaurant industry as a whole was pushing to reopen well before the vaccine rollout, worker-owned Red Emma’s Bookstore and Coffeehouse was stubbornly closed for indoor dining. When the owner of a restaurant can simply tell their workers what the owner of the ice cream parlor told Kevin O’Leary — “I own this store, I’ll do anything I want with you” — those workers are far more likely to see their health and safety sacrificed to the firm’s bottom line than they would if they had a voice and a vote in the matter.

Creating a society where worker control is the economic norm therefore requires political action. A future socialist government could do things like bring banks under public ownership and direct these nationalized banks to only give out grants to new businesses that were organized as worker co-ops.

Libertarians and conservatives would naturally scream their heads off that such a government was making us all less free. But as the thriving genre of self-help videos about becoming your own boss vividly demonstrates, the opposite is true. 

Under capitalism, most of us don’t get to control our own fate. Realistically, the only way we can all achieve a greater degree of freedom is to collectively be our own bosses by transitioning to democratic socialism.