One Day I'll Work for Myself: The Dream and Delusion That Conquered America

by Benjamin C. Waterhouse

From side-hustlers to start-ups, freelancers to small business owners, Americans have a special affinity for people who make it on their own. But the dream has a dark side. “One day I’ll work for myself.” Perhaps you’ve heard some version of that phrase from friends, colleagues, family members―perhaps you’ve said it yourself. If so, you’re not alone. The spirit of entrepreneurship runs deep in American culture and history, in the films we watch and the books we read, in our political rhetoric, and in the music piping through our speakers. What makes the dream of self-employment so alluring, so pervasive in today’s world? Benjamin C. Waterhouse offers a provocative the modern cult of the hustle is a direct consequence of economic failures―bad jobs, stagnant wages, and inequality―since the 1970s. With original research, Waterhouse traces a new narrative history of business in America, populated with vivid characters―from the activists, academics, and work-from-home gurus who hailed business ownership as our economic salvation to the upstarts who took the plunge. We meet, among others, a consultant who quits his job and launches a wildly popular beer company, a department store saleswoman who founds a plus-size bra business on the Internet, and an Indian immigrant in Texas who flees the corporate world to open a motel. Some flourish; some squeak by. Some fail. As Waterhouse shows, the go-it-alone movement that began in the 1970s laid the political and cultural groundwork for today’s gig economy and its everyone should be their own boss. While some people find success in that world, countless others are left bouncing from gig to gig―exploited, underpaid, or conned by get-rich-quick scams. And our politics doesn’t know how to respond. Accessible, fast-paced, and eye-opening, One Day I’ll Work for Myself offers a fresh, insightful cultural history of the U.S. economy from the perspective of the people within it, asking urgent questions about why we’re clinging to old strategies for progress―and at what cost. 6 charts/illustrations

Genres: Nonfiction, Business, Politics, History

304 pages, Hardcover

Published January 16, 2024

About the author

Benjamin C. Waterhouse is assistant professor of history at the University of North Carolina, Chapel Hill.

Reviews

[Emily St. Amant · Rating 4 out of 5]

A history of the self-employment phenomenon in America. This is a (mostly) neutral history on the topic, and I could tell the author struggled to hold back on suggestions for better alternatives, but for the most part this is a good “what happened when and why” rundown. He does call people who want an economic system other than a capitalist one “radicals” at least twice, and the irony of this isn’t lost on me. He clearly outlines many radically terrible things about our economic and political systems. It seems that imagining that our current system is literally the only way would be what’s deemed radical, since it’s so staunchly closed minded, but whatever. An interesting read that offers a lot of good historical context to the current job market.

[Jim]

‘One Day I’ll Work for Myself’ Review: The Risks of Going It Alone https://www.wsj.com/business/entrepre...

[Tina Panik · Rating 4 out of 5]

A strong analysis of why we believe what we believe about this aspect of the American Dream. Hopefully Waterhouse will write a follow up piece on the impact of the Covid-19 Pandemic.

[Todd · Rating 4 out of 5]

Certainly not the type of book that I generally read, but the title and cover looked interesting and I dove in. A succinct, recent-ish economic history of the United States, with its focus on small business and entrepreneurship, this was extremely elucidating in putting a lot of pieces together. Both in terms of governmental and NGO entities, the author lays out the ways that Americans have been, rightly or wrongly, led to believe that working for themselves will bring them prosperity and peace of mind.

For all that background, I think I would have liked to hear more of Waterhouse's own take on all this, rather than subtly leaving the reader to make their own conclusions. He clearly doesn't buy into various iterations of going out on one's own; still, I feel like the book could have benefited from a more obvious point of view.

If you're looking to better understand this aspect of American economic history, I highly recommend this book! I learned a lot of things that I had only a superficial knowledge about and I believe that most readers will, too.

(Oddly enough, this book was featured in United's "Hemispheres" onboard magazine's Jan 2024 issue, and I finished it on a UA flight this past weekend!)

[Joseph Stieb · Rating 5 out of 5]

An interesting mix of history and socio-economic critique: BW explores the rise of a variety of different kinds of "work-for-yourself" sectors of employment as well as their pitfalls and advantages (mostly the latter). The story begins in the postwar era of bigness, when the dominant job format (at least for white guys) was working for big, faceless, but stable companies for a salary plus benefits in the middle class range or, if you were working class, for a factory that also provided a decent level of pay and long-term security. The main benefit of this kind of job was stability, but people also had critiques and anxieties about them. They were often soul-crushing and impersonal (think of how many movies there are about this), leaving little room for personal expression and independence.

So when this employment model fell apart in the 1970s and 1980s with the recession/inflation crisis, many Americans were already culturally primed to find ways to work for themselves. BW shows a number of self-employment formats that either emerged or expanded: working at home, starting a small business, sub-contracting, entrepreneurship and so on. There were numerous boosters of this new set of approaches, which was supposed to be more flexible and dynamic than the stolid old economy. Universities started entrepreneurship programs. Small businesses were lauded by politicians of both parties to an almost absurd degree. New technologies, especially the rise of the Internet and the smartphone, made this seem more feasible, although the craze took off well before these technologies went mainstream.

BW's main insight is that the work-for-yourself trend took off because it seemed to offer an out or an answer for the structural economic crises of the era while also lining up well with the cultural zeitgeist, which was becoming more individualistic (the "me decade" of the 70s) and more averse to "bigness" in both economics and government. The results, however, are incredibly mixed. WOrking for yourself is something that people seemed to want to make available to others but not really do for themselves. It's incredibly hard to build a business from the bottom-up, and almost all forms of working for yourself come with a high level of precariousness. BW does a great job exploring the racial and gender dynamics of this issue, where the WFY ideal only intensifies unequal opportunity rather than rectifying it. Finally, the gig economy has proven to be a scam for actual workers and a massive boon for the companies that run it.

Anyways, this is a well-paced and enjoyable cultural and economic history.

[Matt · Rating 2 out of 5]

Honestly, not for me. I kind of wanted a book about stories of entrepreneurship, and how to achieve something similar for myself. At least a framework maybe of that, including how to do it modern day. Instead what I got was mostly a political history lesson about how small business representation in government came about, how administrations like Raegan and Clinton approached small businesses, ending with the Obama administration, and how different economic conditions spurred people to work for themselves.

Ultimately, if your looking for more of a political history of entrepreneurship in government, then this book is for you. If your looking for cool stories about entrepreneurs and how you can become one, I wouldn't recommend this book.

[Angela Wirth · Rating 4 out of 5]

Very informative but took me forever to read because it wasn’t very exciting. A lot of names and dates and statistics, made me want to fall asleep. But I do think it was worthy information which is why I stuck it out and I’m glad I did. I now have a much better understanding of the country’s cultural mindset and the downsides to owning a business and contract work. This book isn’t for everybody, but it is if you’re interested in starting your own business or a history buff.

[David C · Rating 3 out of 5]

1/23/25: read almost half during recovering from flu

Felt a bit dry, but main takeaway was:

- up until late 1880s: working for yourself is common in poorer countries and even in the US
- 1930-1970: big companies were preferred post world war
- 1970-1990: non profits that support minorities and small businesses pushed agenda of starting your own thing will fix America’s problems

[Rolf · Rating 4 out of 5]

An effective exploration and critique of how the self-made-man myth plays out in contemporary U.S. life.

[Sharon · Rating 3 out of 5]

Nice review of history but central argument felt unsubstantiated and full of gaps

[Morgan · Rating 5 out of 5]

As someone who was always a bit confused about the glorification of self employment, this book filled in the gap of what I was missing. From the 1970s onward, economic failures pushed people to find a different way of making ends meet. I really enjoyed how the stories of freelance/franchising/ MLMs intersected in multiple ways.

[Pete · Rating 3 out of 5]

This book did not solve my existential dread. It was a history lesson that did not provide suggestions on how to handle things going forward. It showed us the things that led us here and asks if we will repeat history or learn from it. However there seems to be little that a regular individual can do to affect things. How can we override the government policies that support capitalism and the winners of capitalism? Waterhouse also highlights the popular individualism attitude in Americans that predispose them to trying to go it alone.

Ultimately, each era of work and attitude about work was a response to the economical situation that Americans were born into. Each generation wants to set itself apart from the previous generations. Younger people, like myself, feel no loyalty to companies and are always looking for the job that serves them best. Whereas the previous generation valued and gave their loyalty to the big companies because the job stability, benefits, etc..

It was interesting to learn how the ball started rolling and the little different stages throughout history. We went from cottage industry to industrial revolution to dot.com bubble to app-based gig economy and all throughout that the idea of entrepreneurship and running things yourself has persevered. I found myself in agreement with the author whenever he allowed himself to express his feelings and I wished he did more of that. Overall, this was a good read to make myself more aware.

[Morgan · Rating 5 out of 5]

As someone who was always a bit confused about the glorification of self employment, this book filled in the gap of what I was missing. From the 1970s onward, economic failures pushed people to find a different way of making ends meet. I really enjoyed how the stories of freelance/franchising/ MLMs intersected in multiple ways.

[she.who.reads.plans · Rating 3 out of 5]

Interesting read it’s something I will come back to and read again. It did take me a little bit to read but it was still good.