Why We All Want to Become Our Own Boss ‹ Literary Hub

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Modern culture whispers in your ears. If you listen closely, you can hear it everywhere. In ads on the Internet. From parents and coaches. From professors, politicians, and preachers. Be an entrepreneur. Start your own business. Work for yourself.

What these whispers are telling you is that you’re on your own. When it comes to getting ahead in the world today, you can’t simply go work for someone else. Real success comes to people who break the mold, seize their own destiny, and do it themselves. If you want a shot at material success, they say, you must be your own boss.

Going it alone looks different, of course, depending on where you are on the economic spectrum. At the high end, it means getting into the start-­up game. Launch a new enterprise, preferably with somebody else’s money, and then sell it for a mint. Further down the ladder? You are still in charge of your own economic future. You cannot—­and should not—­count on a stable job with good pay and benefits. “I am a millionaire in the making,” the megachurches tell you to say, but those riches can only come through entrepreneurship, through creating something new. Like Jay-­Z says, you have to be a business, man.

The whispers might sound innocuous. But underneath the bland inspiration lies a dark and alarming set of justifications. Are you underpaid? Work more. Unemployed? Try gig work. Run a side hustle. Take on debt to “invest in yourself.” Still struggling? That’s on you.

This fixation on going it alone—­the cult of the hustle, the gig economy—­has become so pervasive that we can overlook just how thoroughly it has saturated our entire culture. If you step onto a college campus like UNC-­Chapel Hill, where I teach, you’ll see its influence in all the buzz around business start-­ups. To be sure, many of the students who take college entrepreneurship courses want to learn how to get rich.

But what is striking is the convictions of the socially conscious ones, the altruistic folks who want to do good for the world. They, too, have been swayed by those whispers. For them, fixing social problems doesn’t involve political activism, legal reform, or movement building. Rather, the cure is always a new business venture.

The story of how the dream of working for yourself became so overpowering in the United States…is fundamentally a story about people.

Reality, of course, is far messier than mythology. Sometimes working for yourself turns out great, but many, many businesses fail. Some people discover a certain freedom in hustling from gig to gig, but many others get screwed, working for less than minimum wage, going into hock, or falling victim to get-­rich-­quick scams that prey on the appeal of “being your own boss.”

Of course, we can’t blame the kids. Today’s college students have grown up in a culture that is as obsessed with entrepreneurship as it is disillusioned with traditional political action. They have been told from birth that individual initiative breeds innovation, even as social problems—­from poverty and inequality to environmental disaster and war—­appear insurmountable. Their natural takeaway is that focusing on political organizing and reform efforts is naïve, doomed to failure.

What’s more, all but the most elite and privileged confront a world of work where jobs are less stable, real wage growth is worse, and benefits more paltry than when their parents or grandparents entered adulthood. Little wonder that so many are lured by those whispering voices, the ones that tell them that individual initiative, start-­ups, and for-­profit businesses are the keys to changing the world and getting paid in the process.

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This book is about those cultural whispers—­where they came from, how they became so pervasive, and how they shaped not only personal decisions but also our politics and public life. It asks how our conception of work became so individualized and how so many people became convinced that the path to success lay in working for themselves.

There are more than 33 million businesses in the United States today. Only about 4,000 are publicly traded corporations (that is, owned by stockholders), and only another 16,000 are “large” by the government’s definition (more than 500 employees). More than 99.9 percent of all companies, in other words, are “small.” And the overwhelming majority—­81 percent, or 27 million—­have no employees. The only people who work for them are the owners.

All told, the US government estimates that about 1 in 9 people in the workforce can be described as “working for themselves” today. The puzzle of this book is how that vast and unorganized community of business owners came to embody a cultural ideal, and how that ideal came to dominate our national conversation about economic life.

At first glance, we might assume that this is nothing new at all. Our history books, after all, are chock full of paeons to self-­made men (and, once in a while, self-­made women). As far back as the 1780s, Thomas Jefferson famously praised independent yeoman farmers as bastions of democratic virtue, since they controlled their own livelihoods.

“Rugged individualism” has been a central part of America’s national mythology since before the advent of the term itself, which is linked in our collective memory to the mythos of Teddy Roosevelt at the turn of the twentieth century. For many people, and for centuries, “independence” has literally meant that you don’t depend on anyone else—­a government, a family, a master, or even an employer.

Yet despite those deep roots, America’s individualistic culture has not always translated into a call to work for yourself. Although self-­interest and individual responsibility are central to capitalism, nothing about the capitalist ethic is incompatible with working for someone else. To the contrary, throughout the history of capitalism, that was the whole point—­laborers, managers, and executives alike all traded their time and energy for wages and salaries.

In the United States, the ideal of working for someone else reigned supreme as recently as the mid-­twentieth century, buttressed by a very different economy from the one we know today. In the quarter century after World War II, economic growth was rapid and, relatively speaking, evenly shared. Average incomes went up across the board. The gap between rich and poor got smaller. Rising numbers of people ascended into the middle class, with its amenities like affordable homes and cars, as well as family vacations and college for the kids.

And the central vehicle for that growth was reliable, well-­paid work—­typically at a large company—­for the (generally male) family breadwinner. For the people who were included, this was the dream. For those who were kept out, including especially people of color, women, and the very poor, it became the thing to mobilize and fight for. Success and opportunity were not defined by going it alone in the postwar years but rather by steady employment. By working for somebody else.

So, what changed? Americans in the 1950s and 1960s were every bit the ideological descendants of Thomas Jefferson and Teddy Roosevelt that we are today. Why does this individualistic ethic now push us toward self-­employment, business start-­ups, gigging, and so on, when it didn’t back then?

If it’s tempting to think that our go-­it-­alone culture has always existed, it’s perhaps equally tempting, however paradoxically, to conclude that it has emerged just in the past few years with the advent of new tech and recent economic hard times. In the first quarter of the twenty-­first century, new communications technologies—­from smartphone apps and social media to GPS and Zoom—­have upended modern life.

When you can manage your workforce, optimize your logistics, and microtarget your marketing all on your phone from the comfort of your living room, working for yourself seems easier today than ever before. Add in the long-­term deterioration of the traditional job market since the Great Recession, compounded by the Covid-­19 pandemic and its aftermath, and it would seem that the cocktail for the do-­it-­yourself economy is complete.

But while it’s certainly true that new tech and economic fragility are vital parts of the story, they don’t answer the question by themselves. Despite what we always hear—­that such-­and-­such a device or app “changes everything” or that economics is destiny—­neither technology nor economic circumstance operate in a vacuum. Neither can change society all by itself.

To really understand how history happens, to figure out where those cultural whispers come from, we have to find the people who propagate them. The story of how the dream of working for yourself became so overpowering in the United States, in other words, is fundamentally a story about people—­people with interests, agendas, ideas, and often businesses themselves. I am a historian of American business, economic culture, and politics, and I have spent decades writing about the places where those things intersect. Those kinds of people are exactly the ones I’ve been trained to study. So I set out to find them.

What I discovered was a disparate but influential cadre of individuals and organizations who, between the 1970s and the early 2000s, promoted a new vision of work. Some of them are well known: politicians, business theorists, and national lobbying associations. Others are more anonymous, from the creator of a women’s home-­based business network to consultants, how-­to authors, and journalists.

What united them, though, was their common project: to repurpose long-­held tropes about self-sufficiency and success into a public case that individual business ownership was the cure for long-­term economic decline. Their activism—­which was nearly always aligned with their own business interests—­created a new set of values about work, opportunity, and what it meant to get ahead. Ultimately, they redefined what millions of people meant by the words “American Dream.”

So while the economic crises and technological changes of the last fifteen years have nurtured our culture of independent work, they didn’t create it. Instead, today’s cultural whispers trace back less to Jefferson in the eighteenth century and more to the social turmoil and economic upheavals that began in the early 1970s. Those were the years when a series of recessions and persistently high inflation battered the country, bringing an abrupt end to the postwar “growth economy.”

Since then, even in good times, economic growth rates have never matched what people had gotten used to in the previous several decades. And that disjuncture, that gap between old expectations and new realities, has had major social and political consequences.

In terms of jobs, the American economy since the 1970s has come to center more on services than on manufacturing. Rising global trade and foreign competition put new limits on America’s once-­dominant factories, which moved production from high-wage to low-­wage regions, and eventually out of the country entirely.

By the 1980s, plant closings, unemployment, and poverty—­both in cities and in rural communities—­dominated the headlines. That process only accelerated by the late 1990s and early 2000s. The “Steel Belt” became the “Rust Belt.”

At the same time, the service sector—­from banking and professional services at the high end of the pay scale to retail, hospitality, and caregiving at the low end—­became the primary source of jobs. But since labor unions had traditionally been much stronger at big industrial corporations, that shift meant that labor was increasingly on its back heels, organizationally as well as politically.

In a historic reverse, inequality in the United States, which has been shrinking since the 1930s, started rising again after 1980. In economic terms, the “returns to capital” (that is, investing) outpaced “returns to labor” (that is, working). Rich people, who had more to invest (and lower taxes than before) got richer. Corporate consolidation, new tax policies, and old-­fashioned greed all combined to jack compensation at the high end, even as workers’ wages stagnated and benefits dwindled at large and small companies alike.

The nation suffered no financial crises between the 1930s and 1970s, but in the decades since, the economy lurched onto a roller-­coaster ride of boom-­and-­bust cycles that were reminiscent of the nineteenth century. Weaker regulations led to speculative bubbles, prompting observers to declare that the United States had become a “casino economy.” An elite few struck it rich through big bets, while most people went home empty-­handed.

As the widely shared prosperity of the postwar period became a memory for so many people, American culture turned inward. Faced with political and foreign-­policy scandals and disasters, as well as with economic malaise, people lost faith in the government, organized labor, and large corporations alike. In the same years, though, public faith in the individual was on the upswing.

From politics to popular culture to personal finance, a long-­subdued fixation on self-­reliance bubbled to the surface. Individual retirement accounts replaced pensions for millions. Personal identity, for many people, became as linked to being a “consumer” and “owner” as to being a member of a class. Not that everyone started to do it—­the self-­employment rate ticked up only slightly, and the start-­up rate for new businesses actually declined consistently from the late 1970s onward. But the fascination took over. The dream of working for yourself came to dominate our culture and politics like never before.

Putting all our faith in the promise of individual business ownership is both overly simplistic and a political smokescreen.

This book sets out to connect the dots between the changing economic landscape since the 1970s and the widespread belief that working for yourself is the key to economic success. In an era of massive global corporations, ever-­expanding big-­box stores, and high-­flying finance, how did we decide that self-­employment was the dream? How did we become convinced to go it alone?

The people you’ll meet in this book are the keys to piecing that story together. From policy activists and b-­school professors to small-­town shopkeepers and tech start-­up founders, they mobilized around a range of interconnected but distinct ways of “working for yourself.” Some were boosters for “small business”—­an amorphous concept that eludes easy definition and that really exists more as a cultural touchstone than a clear economic category.

Others focused more on a company’s newness than its size, affirming the virtues of entrepreneurship and innovation. Still others trained their fire on individual choices, encouraging everyday people to abandon the corporate rat race. Work from home, they said, or open a new business or franchise. Become an independent contractor or multilevel marketing distributor. Join the app-­based gig economy.

In the hands of this community, individual initiative and personal responsibility became powerful buzzwords that shaped public debate over a host of issues. Business-friendly regulatory reforms, weaker labor rights and worker protections, the decline of the inflation-­adjusted minimum wage, tax policies that rewarded speculation rather than work, the drastic underfunding of infrastructure, social welfare, and education—­ll of these were justified by what they would bring to business owners, investors, and entrepreneurs. The ideal of business ownership has both emerged from and fed upon a political culture that frames policy decisions as a sharp choice between “the government” and “the individual” (or, even more abstractly, “the market”).

This book is not a knock on business ownership itself. To invoke a tacky cliché, some of my best friends are business owners. My wife, my father, my wife’s father, his sons, my uncle on my dad’s side—­they all own or used to own their own businesses. I myself am a part-­owner of my wife’s company. I have no problem whatsoever with people who work for themselves in any capacity. What I do have a problem with is hype: the blind faith in fanciful promises, the unquestioned assumptions about the magic of entrepreneurship, the idea that business start-­ups will somehow solve our economic problems and help someone get rich in the process.

I take issue with a political culture that puts the burden of economic survival squarely on the individual, ignoring the root causes of economic injustice and rejecting policies like public interest regulation, worker protections, and a higher minimum wage because they are “bad for business owners.”

Finally, I disagree with the notion, so common among people who fetishize entrepreneurship and private initiative, that the big, public institutions that played such a key role during the growth years of the mid-­twentieth century, from universities to government agencies like NASA, are relics that should be confined to the dustbin of history.

Putting all our faith in the promise of individual business ownership is both overly simplistic and a political smokescreen that blocks alternative visions to addressing social problems. A political culture that trips over itself to appease business owners risks forgetting about society’s most vulnerable—­people who are underpaid, who work without benefits, who cannot pay their bills or their loans or their caregiving expenses.

I worry that, when the dominant cultural whispers tell those people to go it alone, they become convinced that they have no other options. That they should seek instant wealth online as social media influencers or freelance content creators. Or buy into the false promises of the gig economy. Or lose hope in any society-­wide efforts to make things better. And I worry that the rest of us will decide that’s OK.

I started down the road of deciphering the rise of this work-­for-­yourself ethos in the wake of the Great Recession. By the time I was writing this book, the Covid-­19 pandemic had hit, throwing an already fragile national economy into acute turmoil. Both cataclysms laid bare the economic schisms that define modern life in the United States, casting a harsh light on a system where too many people have no safety net, no steady job, no benefits.

Where some 30 million Americans earn income through online gig-­economy platforms that do not offer benefits or the minimum wage, and a third of them consider that work their main job. As we make our way through the post-­pandemic world, Americans face a reckoning over how, where, and why we work, over what we can and should ask of our employers, and over whether we should listen to those cultural whispers in our ears.

Our ability to answer those challenges depends on understanding why we think about work the way we do. Ultimately, our modern vision of employment—­atomized, individualized, precarious—­did not emerge automatically, driven by the inexorable logic of the market, or the self-­evident power of entrepreneurship, or the magical technology of our fancy phones. Instead, it was the product of people, of their intellectual and cultural movements, and of their political decisions.

I am less concerned with judging anyone’s decision to work for themselves than I am in understanding why that ideal became so pervasive, so unquestioned, and so easily exploited by today’s gig-­economy companies. By tracing today’s cult of the hustle to economic failure—­bad jobs, stagnant wages, inequality—­this book asks why and how Americans embraced business ownership as the last best defense against the ravages of capitalism.

It does so through the stories of the shopkeepers, consultants, writers, and politicians who all became evangelists for entrepreneurship. My hope is that by understanding their history, we can figure out how our blinkered way of looking at work has hampered our ability to tackle the economic challenges of our lifetimes.

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From One Day I’ll Work for Myself: The Dream and Delusion That Conquered America by Benjamin C. Waterhouse. Copyright © 2024. Available from W.W. Norton & Company.

Benjamin C. Waterhouse

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