Epilogue: The Future of Side-Gigs
LAUNCHING AN ONLINE SHOP MIGHT FEEL VERY OF-THE-MOMENT, but it's actually quite retro. People have long relied on side-gigs for security amid economic flux. The Oxford English Dictionary dates the first published use of the word moonlighting to describe “paid work in addition to one's regular employment” back to 1954.
In the 1950s and 1960s, when the workplace was still largely defined by the Organization Man mindset, which emphasized loyalty and conformity over individuality, going off on one's own to earn extra income was often framed in a negative light. In fact, most mentions of the term “moonlighting” in the mainstream press described violations of existing rules. In 1969, the New York Times reported on potential new conflict-of-interest legislation to prohibit public employees from simultaneously working for private companies. It also wrote about New York policemen who were prohibited from moonlighting at the Woodstock festival after their supervisor ruled it would violate regulations.
That judgmental attitude toward anyone seeking to earn extra money through a side-gig continued into the disco era. In the early 1970s, you were still more likely to read about moonlighting in the crime pages than the career pages. The discomfort with the concept of earning extra money outside a full-time job was palpable; it was demonized like a war enemy or a cheating spouse. It disrupted the natural order of things, and those in power—bosses, newspaper editors—resisted it.
As the decade continued, and moonlighting became more mainstream and even accepted, at least by workers looking for ways to boost their pay, the press focused more on what supervisors could do to crack down on it. The American Banker ran a feature on how to stop employees from taking on other jobs in their free time; ideas included offering them recreational programs to keep them busy. Congress passed new laws to prohibit lawmakers (along with other federal officials) from earning more than $15,000 (almost $65,000 in today's dollars) a year through outside work, such as speaking engagements. A New York carpenters’ union proposed a new rule prohibiting moonlighting, especially by public employees, presumably because it was taking work away from its members. Federal auditors complained that university professors, who consulted on the side for federal agencies, took on so much outside work for other contractors that they were short-changing the government. In a 1978 article, Newsweek described professors moonlighting as consultants as a “growing problem in the nation's colleges.”
Pop culture also reflected the belief that working side-jobs could only lead to trouble: On the Mary Tyler Moore Show, the character Murray ran into trouble after trying to boost his news-writing income by teaching a night class at a nearby college. The television station prohibited employees from taking on second jobs, and Murray was portrayed as being unable to handle the demands of both.
At the same time, reporters and editors started recognizing the legitimate motivations of many side-giggers: They were just trying to support their families during difficult economic times. A 1979 Washington Post feature profiled teachers who felt they had to moonlight to make ends meet, given their relatively low salaries. It found that in one local county, most teachers held second and third jobs. A 1979 story in my own magazine, U.S. News & World Report, reported that families were dealing with rising prices by picking up extra jobs on the side. As the article put it, “Working wives, moonlighting and overtime are the order of the day.” At the time, none of those situations were considered desirable, even if they were increasingly necessary.
A federal analysis of 1970s jobs data noted that the primary options for families looking to increase their household income were for either the wife to join the workforce or the husband to pick up a second job. Indeed, the decline in husbands holding second jobs in the 1970s was correlated with an uptick in wives holding first jobs. By the end of the decade, about 6.2 percent of husbands, and 5 percent of the general population, held more than one job, and it was usually in response to the desire to earn more money.
The first foreshadowing of the excitement and empowerment that side-gigs can bring came from the Washington Post Style section in August 1979. It profiled a forty-two-year-old car salesman moonlighting as a “hair sculptor,” a term he used to mean hair styling plus a hint of therapy. As the reporter put it, “you can get the layered look and, at the same time, get in touch with your feelings.” The car salesman had taken a standard profession and customized it, which gave him clients, coverage in the local paper, and a steady side income.
That far more positive embrace of side-gig culture continued into the decade that also embraced other rebellions, from Madonna to heavy metal. Throughout the 1980s, newspapers and magazines reported on Americans using side incomes to shore up their precarious financial states. The Miami Herald profiled a merchandise manager who started using his career skills to help neighbors organize their garage sales (in exchange for 10 percent of the sales). “Two jobs can work,” the headline proclaimed. In 1983, the how-to book by Jay David, How to Play the Moonlighting Game, came out, making further converts.
Still, many stories emphasized the hardships associated with managing more than one job, rather than the benefits. A 1989 Chicago Tribune story described moonlighting as a means of “survival,” especially for single women without the second income of a partner. It profiled one thirty-year-old woman who worked as a New York Stock Exchange sales assistant by day and chef and caterer by night. “It's a grueling pace…. But to survive in New York as a single woman, you really have to be a creative economist. Often that means taking a second job,” she said. The rest of the article focused on the stress of dividing one's time between two jobs, and even quoted a workplace psychologist on how the situation can leave women exhausted and angry.
At the same time, Bureau of Labor Statistics reports show that the number of people holding multiple jobs was starting to skyrocket and that women were experiencing the biggest surge. The economic growth of the 1980s meant that more jobs were available, and Americans embraced the opportunity to increase their income, especially after the recessions in the earlier part of the decade. Between 1980 and 1989, the number of people moonlighting increased by 52 percent, to a total of 7.2 million people, or 6.2 percent of all workers—the highest rate in over three decades.
As one might expect from the uptick in women joining the workforce at the time, women were responsible for much of that increase. The number of women who held more than one job doubled during the 1980s, to a record level of 5.9 percent by 1989. (Women who were widowed, divorced, or separated had a 7.2 percent rate of moonlighting.) At the end of the decade, 43 percent of moonlighters were women, compared to just 15 percent in 1970, the Bureau of Labor Statistics reports. The people most likely to take up second jobs were the ones in the “crunch” years of juggling family responsibilities, between the ages of thirty-five and forty-four. Affording household expenses was cited as the most common reason for doing so.
Moonlighting was further validated—and its spot in mainstream America confirmed—by Moonlighting, a television series on ABC starring Bruce Willis and Cybill Shepherd that aired during the last half of the 1980s. Shepherd's character helped run the detective agency headed by Willis's character after she went bankrupt. Like many of the side-giggers profiled in this book, she leverages her connections as a former model to make the new business a success.
Then, in the 1990s, the acceptance and even glamorization of a multi-income lifestyle really came into its own: Instead of hit men and criminals, moonlighting now belonged to the rich and powerful. In one of the first uses of the term “side-gig” in the mainstream press, a 1990 feature in the Chicago Tribune described Scott Turow's career as a bestselling novelist as a “side-gig” that accompanied his legal career. In 1999, the publication Chief Executive described a health care executive's role on another company's board as a “side-gig.”
Meanwhile, the Bureau of Labor Statistics reported that highly educated, highly paid workers were also among those most likely to pick up second jobs, partly because they tended to have more flexibility with their schedules, along with skills that allowed them to generate significant income from those outside pursuits. The rate of multiple job holding continued to hover at 6.3 percent for all workers, with the most educated jobholders—those holding master's degrees or PhDs—boasting rates of over 9 percent. The most common reasons included meeting household expenses, paying off debt, pure enjoyment, shoring up savings, and wanting to build a business. Moonlighting was increasingly a sign of success, rather than desperation.
Around the same time, career advice columnists started actively urging readers to pursue side-gigs. In stark contrast to the 1978 Newsweek article on university professors shortchanging their federal contracts because of too much moonlighting, a 1996 story in Black Issues in Higher Education celebrated professors who pick up side-gigs: “Moonlighting becomes them,” the story declared, before going on to point out that professors use their side-gigs to not only boost their income but also to get ahead in the academic world. Similarly, a headline in a 1994 Computer World confirmed, “Moonlighting gets respectable.” A 1997 Florida Times-Union article asked, “Computer programmers do it. So do carpenters, tree surgeons and mechanics. Accountants, too. What they're doing is moonlighting. So why not you?” That same year, syndicated Knight-Ridder career columnist Amy Lindgren dished out tips on how to find second jobs and how to handle the additional pressures of moonlighting. A 1999 Ebony story headlined “Success Secrets of Young Entrepreneurs” emphasized the benefits of launching a business while still employed full time elsewhere.
Self-described serial moonlighter Roger Woodson shared his advice in his 1997 book Modern Moonlighting: How to Earn Thousands Extra Without Leaving Your Day Job. “There was a time when working a second job made a person look or feel inadequate as a provider. This is no longer the case. Today's modern moonlighters are turning their time off into hefty bank accounts, new careers, and new businesses. There is no shame in working for yourself after the whistle blows on your day job,” he wrote. After working as a plumber for a company by day and taking on extra plumbing jobs at night, Woodson also built a series of other side-gigs: teaching plumbing, serving as a wedding photographer, writing, and breeding dogs. While the thrust of his argument still resonates, his advice for readers also shows how much has changed in the fifteen years since he wrote his book: He focuses on mail-order businesses instead of the world of online sales, and in-person, labor-intensive gigs such as providing diaper-cleaning services or selling secondhand clothes instead of creative services, the far more popular choice today.
Throughout the 2000s, we again saw some backlash, particularly from companies worried that their side-gigging employees were shortchanging their full-time work. “Don't allow moonlighting by workers to erode profits,” warned a 2001 article in a trade publication for contractors. In 2003, Washington Post career columnist, Mary Ellen Slayter, reminded readers that even moonlighters need to remember that “job one is job one.” In 2006, another trade publication declared, “Let's put an end to moonlighting.” That pushback shows just how firmly the concept of earning income from multiple sources had entrenched itself into our culture and had become a way of life for many Americans.
Today, many new college grads assume that they will build a side-gig in addition to whatever full-time job they are able to land. The 2011 Youth Entrepreneurship Study by Buzz Marketing Group and the Young Entrepreneur Council found that 36 percent of respondents, who were between the ages of sixteen and thirty-nine, had started side-businesses in order to bring in more income. Those businesses included freelance work, eBay shops, tutoring, baking, and web design.
That helps explain why today, side-gig culture is blowing up. Federal statistics show that the high rates for moonlighting that we first saw in the 1990s continue, particularly among those with advanced degrees, and surveys that pick up smaller-level freelance and contract work, such as the MetLife survey quoted in the Introduction, suggest far higher rates of side-gigging.
For many of the side-giggers who invited me into their homes and lives, running a side-gig felt like the obvious choice, just as getting a nine-to-five job for life might have to our grandfathers. Twenty-somethings in particular often responded to my questions about why they had side-gigs as if I asked them why they had a Facebook account. Why wouldn't they?
The belief that everyone needs a Plan B shows up even in places where you might not expect career advice. On a recent cab drive, the friendly driver asked me about my line of work, and then asked, “What would you do if you got laid off?” Many of his cab driver friends, he explained, were trained as doctors and engineers in their home countries, and, unable to find employment in their professions in the United States, became cab drivers. Everyone, he told me, needs a similar backup plan.
The rapper Slim Thug makes the same point in his 2012 personal finance e-book, How to Survive in a Recession, which was written primarily for aspiring hip-hop artists. “One hustle is never enough,” he writes. “If you're working at 7-11, have some other hustle when you're not working. Your side hustle could be anything—selling DVDs, a sports fantasy thing, or whatever you are into. You don't want to put all your eggs in one basket.”
That hearty embrace of side-gigs from so many sources makes it easy to imagine a day when side-gigs are even more widespread than they are today, as ubiquitous as smartphones or email addresses. Instead of focusing so heavily on corporate recruiting and job openings, forward-thinking college career offices will emphasize how students can build marketable skills on their own, through entrepreneurial projects. New college graduates will expect to pair more traditional office jobs with after-hours freelance work. The back-and-forth seesaw between full-time employment and side-gig might sway more heavily in one direction during different stages of life: Young entrants into the workforce might expect to pick up side-gigs in order to supplement relatively low incomes, gain experience, and support themselves if they're unable to find full-time work. After having children, parents might scale back full-time jobs and make up for lower salaries with the more flexible work of a side-gig. And retirees might ramp up side businesses to supplement savings and to stay active and relevant in their fields, especially if they were forced to retire early.
As a result, we'll probably see more double-sided business cards featuring full-time jobs on one side and side-gigs on the back, social media accounts that list primary jobs alongside freelance offerings, and personal websites that seamlessly blend those dual identities. Workers will demand more flexible schedules—and corporate rules—to provide time for their side-careers, and companies will likely acquiesce because they know that flexibility benefits them, too, by allowing them to hold onto their top employees while they gain extra skills. More detailed workplace policies will allow for that elasticity while minimizing conflicts of interest.
We can also expect to see more organizations, associations, Facebook pages, and Meetup groups dedicated to supporting side-giggers with camaraderie, marketing assistance, and brainstorming help. Home office nooks to allow for brief spurts of work, on weekends and in the evenings, will be even more popular than they already are, along with apps and planners that allow people to juggle their multiple roles. The Bureau of Labor Statistics will likely finesse its methods of collecting information on multiple job holders to more fully capture the side-gigging segment of the population, as former Office of Management and Budget director Peter Orszag recently urged. Most importantly, perhaps, any stigma or embarrassment that currently comes from acknowledging a side-gig will disappear, as politicians and economists recognize that side-giggers are an increasingly vital and powerful part of our economy—not just our personal economies.
When I checked back in with side-giggers months after first interviewing them, as I was completing this book, their updates underscored their continuous flexibility and willingness to adapt to both economic conditions and their own life circumstances. Here are their stories:
Chris Furin, the cake baker profiled in Chapter 1, has expanded significantly since I first visited his home kitchen in the fall of 2011. His cake business grew so much that he had to move it into a commercial bakery in Kensington, Maryland. He also started selling cookies and cupcakes along with his custom-made cakes. “Between my website, referrals, and positive online reviews, it's enough to keep my phone ringing and emails full of requests. Sometimes I can't even keep up with demand,” he says. He hired a part-time worker to help him, and bought a refrigerated van to make deliveries easier. He credits his success to the fact that he launched his business in a field that he already knew well from his years working in his father's deli, as well as to his wife, Dawn, who lent her own marketing expertise to help him build up his web presence.
Nicole Crimaldi Emerick, the founder of MsCareerGirl.com, also featured in Chapter 1, launched a second company, MCG Media, which offers online marketing services to companies. While Nicole initially embraced her new identity as a full-time entrepreneur after she was unexpectedly laid off from a start-up, she ultimately decided that she preferred the financial stability of having a full-time job while keeping her own entrepreneurial pursuits as a side-gig. “It's been really tough, but this year has also taught me a lot about financial management, what being self-employed is really like, and to appreciate all of the resources that bigger companies have,” she says. She recently landed a new full-time job as a senior social strategist at a digital agency in Chicago. As the agency's first and only social media specialist, she now draws heavily on her experiences as the founder of her two companies to create social media campaigns for brands. “Had I not been self-employed first, I'm not sure I'd be able to keep up with the demands of my new role,” she says.
Amy Stringer-Mowat, the Etsy seller in Chapter 2 who inspired me to open my own shop, continues to grow her cutting board shop, while also juggling being the mother to a toddler. Her sales have doubled in the last year, and she and her husband launched their own website, www.aheirloom.com, to complement their Etsy shop. The shop was recently featured in Time magazine and they have several new products in the works, too.
Emily Beach, the hockey coach and training stick inventor from Chapters 2 and 3, continues to collect orders for her Dribble Dr. sticks and will soon start showcasing an indoor version. She's so busy with her full-time job coaching hockey that she's always looking for ways to find more time to build her business at the same time.
Megan Moynihan Callaway, the public relations freelancer from Chapter 4, has settled into her dream life: She spends the winter months in Jackson Hole, Wyoming, where she and her husband ski, and then the rest of the year in New York City. She's built up her client base to four steady clients, including an Irish baby products company, and named her company Callaway Communications. “I'm reaching my capacity and readjusting to having a pretty full workload, so if I take on any new clients, they'll have to be smaller in size and I'll likely charge higher rates,” she says. For now, she'd rather stay small than hire employees or collaborate with other freelancers. Her manageable client load lets her live the lifestyle she wants: She and her husband are planning a three-week trip to Hawaii after they wrap up the ski season in Jackson Hole. “We'll work shorter days, from 8 a.m. to noon, and then surf in the afternoon,” she says.
Emily Miethner, the founder of NY Creative Interns also in Chapter 4, first reduced her hours to part time at her day job working as community manager for the website RecordSetter.com so she could focus more on building NY Creative Interns, and then she decided to leave altogether. “We just celebrated our two-year anniversary [at NY Creative Interns] and got a lot more people to come to events and more people wanting to work with us, so I felt like now was the time to take advantage of that,” she says. While she doesn't yet pay herself out of her NY Creative Interns work, she supports herself by taking on related freelance gigs—she speaks at colleges, gives workshops on social media and career management, and works with a nonprofit on internships.
DesignedGood cofounder Katy Gathright, who was profiled in Chapter 5, has moved full steam ahead with the website's launch. The company has since sold direct trade chocolate, infinity scarves, and fair trade soccer balls to their members, among other ethically appealing items. She and her cofounders are busy lining up more brands, attending industry conferences, and spreading the word about their company.
Chapter 5's Peter Davis, the college student and founder of community-building website CommonPlace, has also enjoyed rapid expansion. CommonPlace is now in twenty towns, with plans to be in every town in Massachusetts by the end of 2013. He and his team have also built revenue streams through the local “marketplace” aspect of the sites, where neighbors can find furniture, coupons, services, and tickets to events. “If we take a percentage cut from all the exchanges we facilitate, we'll be able to do a lot of things at once: Provide a revenue stream, avoid banner ads, and support local businesses and service providers,” he says. His team is also looking into potential relationships with larger organizations, such as newspaper chains and groups such as Rotary and Boy Scouts.
Professional opera singer Jessi Baden-Campbell, profiled in Chapter 6, left her meeting planner position for a new full-time job as a coordinating producer at a production company. She still sings as a church soloist every Sunday and performs at her children's school, but has scaled back her singing work because of the demands of her new job. Still, she makes use of her downtime to practice. Instead of lunchtime concerts in the parking garage, she rehearses during her forty-minute commute.
As Chapter 6's Corinne Delaney worked on updating her website and finding new clients, her alma mater, James Madison University, asked her to sing the National Anthem at the homecoming game in the fall of 2012. Standing in front of about 25,000 people in a bright red coat, surrounded by the school's marching band, she sang as her face and name were broadcast on the stadium's Jumbotron. “It was an amazing experience,” says Corinne. She continues to pick up more gigs for smaller events, as well.
Juppy inventor Jeffrey Nash, also profiled in Chapter 6, says that while revenue has not yet reached the $250,000 a year he anticipated, his company is still bringing in enough to fund his retirement, which is more than he could ever say about his former Men's Wearhouse job. He's also working on improving the Juppy model itself, as well as deals with other companies that could help increase sales.
Chapter 6's Ebony Utley, the professor, writer, and speaker, enjoyed her sabbatical so much that she says she wishes it lasted forever. She promoted her first book, Rap and Religion, while also conducting the research for her next book, Shades of Infidelity. She hasn't picked up as many paid speaking engagements as she would like, which she attributes to the economy, but she continues to build her reputation as a go-to expert on race and communication.
Ben Popken, the journalist and improv comic from Chapter 7 who experienced a layoff, landed a new full-time job as a senior staff writer and editor at NBCNews.com. He also became a dad, and decided to stop performing improv. “I did enjoy improv, but I'm not sure if I'll go back…. Improv is so ephemeral, and in some ways it seems silly to spend so much time on something that evaporates when it's over.” With the demands of fatherhood and a full-time office job, he says that if he does find time to work on comedy, it will be comedy writing, or videos. For Ben, the shift from freelancer to staffer is a welcome one: “Knowing that I have a steady stream of income to rely on, and a secure position, helps relieve some anxieties and lets us make plans for the future more boldly,” he says.
Jason Nicholas, the veterinarian from Chapter 8 who was raising money through IndieGoGo to publish his cat and dog safety books, reached his goal. He raised just over $15,000, which has allowed him to finalize publication of his dog safety book as well as market it. He recently sent it off to the printer, and he's already had a few bulk preorders. After he's promoted the dog book, he'll finish the cat safety one.
Jeff Frederick, the architect in Chapter 9 who built his freelance business through Elance.com to get him through unemployment patches, continues to run a brisk freelance business on the side. One Elance client brought him out to Nebraska to see the finished products based on his designs and to explore a new project in the same building. Connections that he made through Elance also led to new work near his home in Michigan. “Working full time and moonlighting can be time-consuming and stressful, but also rewarding. I've found that if I'm honest with my clients and tell them that I mainly work nights and weekends on their projects, they are quite understanding,” he says.
My own life has also changed since I first started my side-gig. Just over a year after opening up my Etsy shop, we welcomed our new baby son, Neal, into the world. Becoming a family of four intensified my desire to earn extra money while also making it more difficult to do so. As I took care of Neal during my maternity leave from my full-time job, I continued selling planners, sending them to customers while he napped. As he gets bigger and more self-sufficient, I plan to keep growing my shop and, I hope, my income.
Side-giggers are able to continually knock down and recreate game plans like Legos. Different skills, passions, and pursuits can be mixed and matched, like colorful building blocks, to create new revenue streams when another comes crashing down. And as a result of that flexibility, life can feel a little more stable—even in an economy that isn't.