In Death of a Salesman (1949), Willy Loman idolizes and mythologizes his brother Ben, an entrepreneur of “vicious audacity.” Willy imagines a conversation where Ben says, “When I walked into the jungle, I was seventeen. When I walked out, I was twenty-one. And, by God, I was rich!” Willy responds, “That’s just the spirit I want to imbue them with! I was right! I was right!” Benjamin Waterhouse believes that Willy was wrong then and wrong now, and that the notion of successful self-employment is, as his book’s subtitle indicates, largely a “dream and delusion” that has morphed over the years.

Waterhouse, a history professor at the University of North Carolina, knows that proponents of personal economic independence include Franklin, Jefferson, and Teddy Roosevelt, among many others. But he posits a significant change in the past 50 years or so: “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” (p. xvi). That “someone else” was a big corporation offering a salary, benefits, and job security. Then, with the disruption of this order in the 1970s, “an influential cadre” of lobbying associations, politicians, women’s groups, management theorists, and journalists repurposed long-held tropes: “Earlier generations had venerated local shops and individual proprietors as guardians of free competition, hard work, thrift, and community. For the boosters of the 1970s, however, small businesses also became something else: economic saviors [and] sources of innovation, job creation, and dynamism itself” (pp. 22–23).

Waterhouse notes that categorizations of “small business” by the Small Business Association (SBA) and others are “so vague as to be mostly meaningless” (p. 31). But his treatment is also definitionally promiscuous, encompassing small retailers, other solo proprietors, consultants, remote workers, outsourced customer service agents, franchisees, people in multi-level networks such as Avon, gig workers, and others. This is not necessarily a fault, since his project is to document “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” (p. xv). By “cultural whispers,” Waterhouse means something like “zeitgeist.” His book has the benefits of that approach (a wide-angle perspective on disparate groups) and its tendency to posit a common currency of discourse and values to very different actors and activities.

He distinguishes starting versus owning a business and focuses primarily on the latter. But many of his claims about cultural change rely on the adulation of startups. Most chapters begin with an example of someone attracted to a form of self-employment, a deeper dive into the reality of that line of work (which is less remunerative and attractive than advertised), and then what the example tells us about motivations and the changing ideal. Some examples are more convincing than others, and some seem reframed and reinterpreted at the end of that chapter.

One Day I’ll Work for Myself is a much better book than most on this topic, which are mainly pop effusions about “free agents” and “personal branding.” Waterhouse places the topic in the context of evolving work patterns, what people say about those patterns, and the political and social causes and consequences of that discourse. As such, his book makes claims and warrants evaluation as economic history and as cultural criticism.

As history, the book is silent about what are arguably some bigger determinants of infatuation with startups and business ownership throughout US history and in the post-1970s period of interest to Waterhouse.

For instance, as explained by Bruce Mann, attitudes toward commercial bankruptcy changed in the early years of the nation.Footnote ¹ The bankruptcy law of 1800 was a response to the imprisonment of Robert Morris, the “financier of the revolution,” for unpaid debts. Previously, bankruptcy was treated as a moral failure punishable by forfeiture of property and jail. Since 1800, however, US law has generally viewed business failure as a common consequence of risk-taking, and it has evolved into a process where declaration of bankruptcy is accompanied by an “automatic stay” (a period in which creditors cannot file claims against debtors), followed by repayment procedures overseen by third-party judges and trustees. This reorientation made bankruptcy into an opportunity for reassembly and recovery rather than a reason to be chased down. In turn, relatively flexible bankruptcy law spurred business ownership and what Waterhouse calls “America’s national mythology” (p. xv) of figures such as Ben Loman. In other words, that ideology has legal and institutional foundations.

Waterhouse attributes a shift in attitudes toward entrepreneurs to a cohort of “boosters” in the 1970s comprised of journalists, think-tank pundits, and events such as Jimmy Carter’s White House Conference on Small Business. But there is a more consequential story in that decade about startups. In the late 1970s, amendments to the Employee Retirement Income Security Act (ERISA) gave pension funds more leeway to invest in risky asset classes, creating a large and sustained boost to venture capital. In addition, lower capital gains rates in the late 1970s and early 1980s supported the shift. As Tom Nicholas notes, “in terms of occupational choice, lower capital gains taxation could make potential entrepreneurs more willing to switch out of wage-work and into entrepreneurial activities, and in turn expand the pool of opportunities that venture capital firms could invest in,” and he cites studies of the impact of tax law on the supply of entrepreneurs.Footnote ²

Patterning the past with chronological boundaries is core to historiography, but Waterhouse moves the goal posts as his book proceeds. We are told that the shift in attitudes occurred in “the mid-twentieth century” (p. xvi); then as a consequence of “the boosters of the 1970s” (p. 23); then “only in the 1980s and 1990s, when upward promotion at a traditional job became out of reach for so many people” (p. 162); and again “in the early 2000s” and “the crisis years of the early 2010s,” when a “despondent economic environment” made gig work attractive (chapter 9). There were boom-and-bust cycles in American history long before these alleged shifts in cultural ethos.

In using economic precarity as a motivating cause, moreover, Waterhouse assumes that “self-employment tends to correlate negatively to a country’s wealth” (p. 8) and that progress means wage work. But as global poverty fell from 1980 onward, patterns differed. In some countries (e.g., Mexico, South Africa) transition into wage work indeed accounted for the bulk of poverty decline. In other countries (where the numbers are bigger: e.g., China, India, Indonesia), being self-employed was a major way out of poverty.Footnote ³ And in the United States during this period, self-employment patterns changed: away from industries with higher startup capital requirements and opportunities for returns-to-scale (e.g., agriculture, hotels) to lower-startup-capital businesses in construction, childcare, and personal services.Footnote ⁴ Rising debt from student loans and housing prices may have discouraged certain types of self-employed entrepreneurship.

As cultural criticism, One Day can undermine its thesis as Waterhouse, an honest broker of the evidence, unfolds his critique. He argues that “we are still in the grip of an ethos that exalts above all the people who take their economic livelihood into their own hands” and attributes this to a cultural change “that conquered America in the last fifty years” (p. 208). Waterhouse cites the data: self-employment in the United States fell from 1948 to 1970 and then “ticked up modestly, perhaps a percentage point or so between the mid-1970s and the early 1990s. By 1990, approximately 10% of the American workforce was self-employed and that figure has remained roughly the same ever since” (p. 143). Is that percentage point evidence of significant change or plus ça change? He also notes the decline in business formations and share of US employment in new companies during this period (pp. 89–90)—evidence of decreased entrepreneurial activity. He cites data to support his thesis from business schools: In 1970, 16 schools taught entrepreneurship courses, and “By the early 21st century, 1600 business schools taught more than 2200 courses on entrepreneurship” (p. 74). Are course catalogs evidence of a guiding cultural ethos? If so, what about increases in the same period of computer programming, “data science,” and finance courses aimed at employment in big corporations?

The evidence raises other questions about the social analysis. Channeling Jane Austen, Waterhouse emphasizes that “It is a truth universally acknowledged that new business ventures are the beating heart of modern capitalism. In a political culture that cannot agree on anything else, there is virtual consensus that entrepreneurs are the risk-takers, job-creators, and industry-disruptors that make the world go around” (p. 66). The evidence cited is mainly ads and recruiting brochures from entities such as franchisors, Chamber of Commerce and small-business trade organizations, multi-level marketing firms, and gig platforms. But “creating jobs” was and is political justification for many policies, ranging from green-energy subsidies for auto makers and other big corporations to tariffs that protect incumbents and raise entry barriers for entrepreneurs. Most of what Waterhouse quotes from commercial sources reads like standard ad copy touting benefits while minimizing risks of a purchase or career change. Does this confuse marketing slogans and political boilerplate with “cultural values”? Are fairly routine pitches from diverse sources evidence of a collective will to transform the ethos of work?

His critique indicts these sources for misleading and motivating people to abandon a salaried job, start a business, and find that it is more work for less money. His case studies follow someone along this path, and Waterhouse can sound like Engels on Manchester factory workers: “Americans embraced business ownership as the last best defense against the ravages of capitalism” (p. xxii), and “burned by the greed and incompetence of slick bankers and massive corporations, Americans turned inward, doubling down on the promise of independent work” (p. 197). Yet, multiple chapters end by revisiting the protagonists, who do not regret their decision because they value being their own boss. Waterhouse eventually cites work by a University of North Carolina (UNC) colleague indicating that motivation for self-employment is often not financial. “Rather, many are motivated primarily by a desire to control their own time and the conditions of their labor, and they will frequently limit the work they do to accommodate their lives [and] achieve that precious thing that folks in the corporate world call ‘work-life balance’” (p. 190). Studies about post–coronavirus disease 2019 (COVID) work also support this interpretation.Footnote ⁵

Most small businesses fail—about 20% in the first year, 50% within 5 years, almost two-thirds within 10 years—and those have been the rough numbers since the Bureau of Labor Statistics started counting. Well, as Damon Runyan said, “All life is six-to-five against.” Meanwhile, work patterns change, and capitalism, especially in the United States, keeps generating more options and permeability between wage work and self-employment. Benjamin Waterhouse’s book is a serious starting point for a more nuanced chronicle of an important economic activity and cultural value in American history.