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  Though he had finally, at the age of 31, after five years of sleeping on an air mattress on the floor, decided to invest in a real bed.

  * * *

  “Oh boy oh boy oh boy oh boy,” Gary Foster said when I talked with him on the phone in late 2016. I had just asked him how everything turned out. “Things turned out terrible is what they did,” he told me.

  Gary and I had last spoken when he’d been working as a customer service representative, the job that Terrence had helped him land. Now he was working as a truck driver. He was on his way to Washington State, sitting in the passenger seat of a truck next to his driving partner. After that he’d go to Seattle. He wouldn’t be home for a month, but he was getting paid between $800 and $1,200 per week. That was more than he made at the call center, which he’d left after disputes about his pay and insufficient hours.

  Other than missing his wife and son, he said, “It’s ok. It’s a job.”

  As a truck driver, Gary worked for a trucking company that contracted with other businesses. He wasn’t really even aware of which company’s cargo was inside of his truck. Often the contents were covered by a shield, so he couldn’t see them.

  To get the truck-driving job, he’d completed a monthlong course required to obtain his commercial truck-driving license. After that, there’d been a month of training. When we had first met in Dumas, he told me that he disliked his job at the Tyson factory because of the hour-long commute. “Now I’m doing nothing but driving,” he said, laughing at the contradiction.

  It wasn’t a bad employment outcome. Gary hoped he would save enough to buy his own truck at some point, and he was thinking about moving to Milwaukee. He had always been bored in Dumas, and his mother, for whom he’d wanted to stay, had remarried and needed less help from him.

  According to a 2014 study by the nonprofit National Employment Law Project, about 65% of all US port truckers are treated as employees but classified as contractors.1 Gary was not one of them. The long-haul truck company had hired him as an employee. On its website, it advertised medical, dental, and vision insurance, a 401(k) retirement plan, accident and disability insurance, paid vacations, and free life insurance. “We’ve never had a layoff,” the application site bragged.

  It was a decent job, but not one that was likely to survive automation.

  In some industries, the gig economy serves as a stop-gap technology, with companies employing people in the cheapest way possible until, eventually, it becomes cheaper to buy a machine. This is the case with Uber and Lyft, for instance. “The reason Uber could be expensive is because you’re not just paying for the car—you’re paying for the other dude in the car,” Travis Kalanick said on stage at a conference in 2014. “When there’s no other dude in the car, the cost of taking an Uber anywhere becomes cheaper than owning a vehicle.”2 Uber started picking up passengers in its first tests of self-driving cars in Pittsburgh in 2016. Toyota, Nissan, General Motors, and Google have all estimated that automated cars will be on the road by 2020.3

  In the United States, 1.8 million people make a living driving trucks; another 687,000 drive buses; another 1.4 million deliver packages; and another 305,000 work as taxi drivers and chauffeurs. What will they do when vehicles drive themselves?

  It’s not just drivers who may soon see their jobs, or portions of their jobs, become automated. A recent McKinsey report estimated that almost all jobs could be automated in some respect, though the extent and impact of this automation is likely to vary widely.4

  At some point, increasing automation will help power the gig economy, making it even more efficient than it is now. Though Curtis never talked about it, and I’m not sure he even realized it, Gigster’s ultimate goal is to automate as much of the programming process as possible. “In five years, maybe we’ll automate 20 percent,” said Roger Dickey, the cofounder and CEO of Gigster. “In five more years, 40 percent. Five more years, 60 percent. It will never get to exactly 100 percent, until general [artificial intelligence] is created. And then the world probably ends, so we’re moot on that point.”

  Managing roles at Gigster will be the first to go. Curtis had already received automated emails when there was a project that was appropriate for him, something that a manager might otherwise have sent. Gigster was also building an automated idea generator that would supplement its sales team’s efforts, for instance, automatically reminding a client “we notice your e-commerce website has a 30% lower conversion rate than its competitors, and we found this new feature raises the conversion rate by this percentage. Click here to proceed.” When they click, perhaps the feature they have selected, which is similar to others that human coders have already produced for Gigster projects, automatically appears and adjusts itself to fit into the new site. A programmer doesn’t need to build it again. “There’s much further we can go down that road,” Dickey said. First it might take the form of a “starter template” for programmers.

  That doesn’t necessarily mean that Gigster won’t need programmers—it just won’t need programmers to do the same things they do now. Automation could mean gigs will be more interesting and easier to find. “If you walk outside, you can see that it’s not like there’s nothing to do,” said Devin Fidler, the research director at the nonprofit Institute for the Future. “We just don’t have the right assigning technology.” He envisions a “shift from people looking for jobs to jobs looking for people,” with technology that will automatically match odd jobs with qualified workers—the gig economy, but spread across even more professions and jobs. “You turn it on like a tap,” he said. “Rather than a huge inefficient hunt any time you want to work, work is routed to you.”

  If you’re a software developer, this is easy to envision. But if you’re a truck driver, it’s not clear what those tasks would look like.

  * * *

  In July 2017, Dan created a personal syllabus of sorts that covered how work was changing. The results sat in two bulging canvas bags on his kitchen table. One was filled with manila folders labeled “platform economics” and “future of work.” They were stuffed with white copy paper, clipped together in sections with black clamps. The other was filled with books: David Weil’s book about how technology will impact jobs. A book about the second machine age. I’d chipped in a copy of Janesville, a book that followed a small town near where I’d grown up after the local GM assembly plant shut down, taking thousands of good jobs with it. Dan’s plan was to read the entire foot-and-a-half stack during a four-day solo trip to a cabin, a goal which somehow didn’t strike him at all as unrealistically ambitious.

  For now, the stacks looked like something of a centerpiece in his otherwise neglected apartment, which contained a few pieces of art and framed mementos, a dusty desk with a pile of old laptop computers, a leather couch, a bed, a minimal dresser, and a single metal rack filled with shirts and blazers. There were still holes in the floor from the time he’d converted the former two-bedroom apartment into a one-bedroom apartment with a hammer, and an electrical outlet hung from the open ceiling above the former room. His couch faced a square of faded Yogi Bear wallpaper left over from the last resident.

  Recently, Dan had propped up a surfboard in one corner. He’d been trying to take care of himself, go to yoga classes and take at least one day per week off from work. It wasn’t necessarily easy. Sometimes during evenings and weekends he’d open Slack, the workplace chat app, hoping someone would be working so he could work, too. But he’d started meeting with an executive coach, and he’d taught himself, he felt, to be less reactive. Everyone who reported to him now got a copy of his “user manual,” which attempted to explain his intense work ethic, his frustration with those who didn’t try as hard as he did, and his intolerance for sugar-coated news.

  The stakes of running Managed by Q had risen. At the beginning, Dan could have failed, but that wouldn’t really have mattered to anyone but him and Saman. Now he had 1,000 employees to let down if anything went wrong; 220 of them, hourly employees, had just
received their first stock grants.

  It wasn’t clear exactly what Dan had to gain by studying the “future of work” so ambitiously. Maybe he was, with his stack of books, preparing to promote Managed by Q as a good partner for small businesses, or for some future political campaign. “I like Bloomberg’s style,” he had told me once, referring to the billionaire and former mayor of New York City. “He cannot be bought. People can disagree with him, but they can’t question his integrity.”

  But even if there were some self-interest in Dan’s motives, I think it would still be reasonable for him to care about where our work future is headed. The full-time job—to which we’ve attached all of the rules about treating workers fairly—is dissolving, and the community of workers who are treated as second-class citizens, who aren’t protected by the same laws or entitled to the same benefits as other workers, is growing. That is a big, scary problem, and one worth studying.

  Before I left our interview, I wished Dan good luck in the woods. Then, just as more than 40 million people around the world do every month, I took out my smartphone and ordered an Uber.5 A driver named Abid drove me home. He usually drove all night, he told me, because that’s when his app tended to pay the most.

  * * *

  From the time I first heard about the gig economy until I finished writing this book, I spent nearly six years observing a sector of the economy that brought together the tremendous hopes of Silicon Valley and the disappointing reality that our support systems are not prepared to handle the major changes on the horizon.

  At the end of it, I don’t think Silicon Valley was wrong to attempt to restructure the job. Our current model wasn’t working, and the startup spirit of experimentation was necessary. But attempting to tackle the problems of the job—and yes, delivering flexibility—without fixing the support structures around it can’t quite count as progress, and it certainly doesn’t look like innovation.

  The last time our country had to reconstruct a safety net from scratch, technological progress had, much like today, just upended the way work was structured. As American workers flocked from independent rural farms and businesses to city-centered factories during the Industrial Revolution, work developed assigned hours, a central location, and a hierarchical structure. As with the evolution of work today, this change wasn’t immediately wonderful.

  Early factory workers spent 12- and 14-hour days toiling away in putrid conditions, which sometimes included breathing in smoke from whale-oil lamps (the windows were often nailed shut). As a society, we sent kids to work, locked workers inside of buildings so that they couldn’t take unapproved breaks (or, you know, escape if there was a fire), and allowed employers to pay starvation wages.

  We made the same arguments for change then as we could make today. Samuel Gompers, the first president of the AFL, wrote in 1894 that when the Constitution had been written more than 100 years prior:

  Men knew scarcely anything of the existence of the power of steam; they knew nothing at all of electricity; they had no suspicion even in the days of Adam Smith of the steam engine and the electric motor or the telegraph, the telephone, the application of steam and electricity to industry; and yet the laws that had been made in the period … are sought to be applied to modern industry and modern commerce … I submit that industry and commerce cannot go back to conform to old thoughts, old theories, and old crusty customs of law, but that the law, sooner, must be changed to conform to the changed industrial and commercial conditions.6

  The solution was not to force workers out of factories and back onto farms. It took another half century or so for the labor movement, in partnership with government and private industry, to form things like a standard ten-hour day (despite mill owners’ argument that greater leisure time would leave workers susceptible to corrupting influences), state laws regulating child labor, and requirements for worker safety. It took until the 1930s for New Deal legislation to create programs like Social Security, unemployment insurance, the minimum wage, and disability insurance.

  The gig economy, it turns out, is not the on-demand improvement to the “future of work” that its creators once imagined. But it will play an important role in exemplifying what that future might look like, and the slow, hard work that we must do to prepare for it.

  Acknowledgments

  I am grateful to the people who shared their time and stories with me for this book. Without them, it wouldn’t have been possible.

  Terrence Davenport, a great teacher in his classroom, was also a patient and kind teacher to me. Kristy Milland stuck with me during several busy times in her life, somehow still managing to return my emails within 15 minutes. Curtis Larson, whom I met at a coworking meetup, was generous enough to answer my phone calls even years later. And Dan Teran continued to make time for interviews even as his company grew in size, from our first interview to our last, by at least a factor of ten.

  Thank you also to Gary Foster, Rina Patel, Anthony Knox, Abe Husein, and Saman Rahmanian for sharing their perspectives with me during interviews, and to Ethan Pollack, Six Silberman, and Palak Shah for helping me parse unfamiliar topics. Thank you to Amy Goldstein for giving advice to a stranger.

  David Lidsky started the chain of events that ultimately resulted in this book, one of the more significant favors anyone has done me. I am also grateful to Fast Company and Quartz, my employers, for their support; to my editor, Tim Bartlett, both for seeing potential in this story and for helping to shape it; and to my agent, Alia Hanna Habib, who has also been a much-appreciated source of feedback.

  At St. Martin’s, I’d like to thank Alan Bradshaw for improving this book throughout its final stages, Jennifer Siming-ton for her thoughtful copy edit, and Alice Pfeifer for her help throughout the long editing process.

  Writing this book would have been much more difficult without the support of several extraordinary people in my life. My parents were, in a sense, my first editors, and they have been a source of ceaseless encouragement for as long as I can remember. I am so lucky. Thank you also to my brother, grandparents, aunts, uncles, and cousins, who were all supportive enough to be excited about this project, but kind enough to not remind me of my deadline over the holidays; to the Schwartz family; to Emily; and to Marguerite.

  A special thank you to Alex, who served as proofreader, chef, and therapist as needed. Your confidence in me has made all the difference.

  Notes

  Please note that some of the links referenced throughout this work may no longer be active.

  PREFACE

  1   Katz, Lawrence F., and Alan B. Krueger. The Rise and Nature of Alternative Work Arrangements in the United States, 1995–2015. National Bureau of Economic Research Working Paper 22667. 2016.

  2   Kessler, Sarah. Online Odd Jobs: How Startups Let You Fund Yourself. Mashable. December 29, 2011. http://mashable.com/2011/12/29/new-working-economy/.

  CHAPTER 1

  1   Kessler, Sarah. 13 Potential Breakout Apps to Watch at South by Southwest 2011. Mashable. March 9, 2011. http://mashable.com/2011/03/09/startups-to-watch-sxsw/#bexrtH8S0kqo.

  2   Kessler, Sarah. Who’s Nearby? This App Lets You Know. Mashable. January 24, 2012. http://mashable.com/2012/01/24/highlight/#iasBqOnotuqA.

  3   Tiku, Nitasha. Leaked: Uber’s Internal Revenue and Ride Request Numbers. ValleyWag. December 4, 2013. http://valleywag.gawker.com/leaked-ubers-internal-revenue-and-ride-request-number-1475924182.

  4   Actual salaries and wages comprise only 69.4% of an employer’s hourly cost for hiring a worker in the United States. Employers on average pay an additional 7.8% in federally required and state-required benefits like Social Security and Medicare and another 13.5% in other benefits such as healthcare (these percentages vary between industries).

  Hallock, Kevin. Pay: Why People Earn What They Earn and What You Can Do Now to Make More. Cambridge University Press, 2012.

  5   Uber Newsroom. New Survey: Drivers Choose Uber for Its Flexibilit
y and Convenience. December 7, 2015. https://newsroom.uber.com/driver-partner-survey/.

  6   Quoted in Hatton, Erin. The Rise of the Permanent Temp Economy. New York Times. January 26, 2013. https://opinionator.blogs.nytimes.com/2013/01/26/the-rise-of-the-permanent-temp-economy/.

  7   Dey, Matthew, Susan Houseman, and Anne Polivka. What Do We Know about Contracting Out in the United States? Evidence from Household and Establishment Surveys. In Labor in the New Economy, eds. Katharine G. Abraham, James R. Spletzer, and Michael Harper. University of Chicago Press, October 2010.

  8   Manyika, James, Susan Lund, Jacques Bughin, Kelsey Robinson, Jan Mischke, and Deepa Mahajan. Independent Work: Choice, Necessity, and the Gig Economy. McKinsey Global Institute. October 2016.

  9   General Accounting Office. Contingent Workforce: Size, Characteristics, Earnings, and Benefits, GAO-15-168R. April 2015. Available from: http://www.gao.gov/products/GAO-15-168R.

  10   Tiku, Leaked: Uber’s Internal Revenue.

  11   Ibid.

  12   Tsotsis, Alexia. TaskRabbit Gets $13M from Founders Fund and Others to “Revolutionize the World’s Labor Force.” TechCrunch. July 23, 2012.

  CHAPTER 2

  1   Melendez, Steven. How Uber Conquered the World in 2013. Fast Company. January 3, 2014. https://www.fastcompany.com/3024236/how-uber-conquered-the-world-in-2013.

  2   Uber has offered as much as $2,500 for a referral that meets specific conditions, such as the new driver has a taxi license and also signs up with Uber’s partner to rent a car for 12 months.

  3   Trudeau, Kevin. Your Wish Is Your Command. Audiobook. Global Information Network, 2009.