CHAPTER

9

Endgame

WHEN I ASKED PEOPLE ABOUT THEIR LONG-TERM SIDE-GIG GOALS, they often said that they just wanted more of what they already had: a full-time job that provides a stable home base while they experiment and expand on the side. “I really enjoy what I do during the day. I love art, I love technical stuff,” says singer Corinne Delaney from Chapter 6. She has no plans to ever leave her day job.

Chapter 3's tax guru Jason Malinak gave a similar response. “I'm happy, and I love my job. I consider my passion my career and my Etsy shop my hobby,” he says. Still, he adds, he intends to continue growing his customer base as much as possible.

Sydney Owen, the skydiver and career coach from Chapter 3, plans to continue jumping and coaching indefinitely. So too does writer and law office manager Jennifer Teates (Chapter 6), who gets her writing ideas from her day job. Martin Cody (Chapter 6) also wants to continue building his online wine business on one computer while he takes care of his medical sales responsibilities with another. These side-giggers all found a balance between their two pursuits that is stable enough to support and fulfill them for the foreseeable future.

In the process, they are redefining financial independence. It doesn't mean bringing in a million dollars a year, or earning enough in royalties to retire to Belize at age thirty-five. Instead, it means knowing that a single boss, single employer, or single paycheck isn't the only thing keeping the bills paid each month. It means knowing at least one income stream will always be there, regardless of the economy's fluctuations or an employer's bottom line. It means knowing that we, not our employers, have ultimate control over our financial well-being.

That's why the question for many side-giggers isn't so much: “When can I leave my full-time job?” as it is: “Why would I ever want to leave my full-time job?” Full-time work offers safety and stability, in contrast to riskier after-hours entrepreneurial pursuits. In addition to a steady paycheck, my own full-time job offers retirement and health benefits, free coffee, camaraderie, tech support, and, perhaps most important, room to learn and grow within an established company. While my own side-gig is fulfilling and profitable, it could never replace all those benefits—financial, social, and emotional.

It's the combination of the full-time job and the side-gig, after all, that provides the greatest financial security. Each gives us a backup plan in case the other suddenly fails us. With only a full-time job, we are walking on a high-wire sans safety net; with just a side-gig, we can find ourselves lolling in the safety net, unable to climb to the greater heights that the connections, support, and backing of an employer can provide. As Silicon Valley tech manager and nonprofit founder AJ Thomas put it, having both a side-gig and a full-time job means “you can glide and soar, and then come back to the cliff when you need a jump.”

It's hard to do both, but the alternatives— suffering through an extended layoff without a trickle of earned income, or being bored with the monotony and languishing pay of a thirty-year career—are even less appealing.

BREAKING THE FALL

Some side-giggers, though, don't have the luxury of maintaining both pursuits forever. Their side-gig income saved them when their main jobs disappeared. Cake designer Chris Furin (Chapter 1) focused on his cake business when his father's diner shut its doors. Nicole Crimaldi Emerick (Chapter 1) turned to her own side-business, Ms. Career Girl, when she was unexpectedly laid off from her start-up. Chhayal Parikh, a former coworker I wrote about in Generation Earn, would have suddenly lost all of her income when she got laid off from her job as a video producer had she not already been teaching fitness classes on evenings and weekends. Those classes brought her close to $10,000 a year, and when her day job disappeared, she picked up new classes to keep her solvent until she landed her next videographer job.

Indeed, the boundaries between side-gig and full-time job are increasingly fluid, and side-giggers frequently move back and forth between worlds without much difficulty. When Jeff Frederick, father of three in Troy, Michigan, got laid off from his architectural firm in 2008, he signed on to Elance.com, the freelance website, to look for project work. “I wanted to keep up my skills while I was looking for a job,” he says.

Jeff soon landed work designing small projects for residential and commercial clients; one of his first jobs was designing a deck trellis for someone's backyard. “[The client] was looking for something out of the box, different from what he could find at Home Depot,” says Jeff. After leaving that client a satisfied customer, he started landing more jobs through the site, including office design work for a company in Omaha. He didn't earn as much as he does when he's working full time at a firm, but he says that extra income was essential to getting his family through his layoff. On average, he earns around $50 an hour through his Elance.com work, for a total of over $10,000 since he started.

Once he found a full-time job at a different architecture firm, he didn't stop his Elance work. “I can work a couple hours a night, and over a week I can get a project done,” says Jeff, who puts the extra earnings into savings and general household costs. When he got laid off a second time, he again focused on Elance.com—full time; and now that he's once again employed at a company, he continues his freelance projects on evenings and weekends. Maintaining that side-gig gives him flexibility to move between being a full-time employee, freelancer, and side-gigger with relative ease.

Other side-giggers decide to leave their jobs voluntarily. That was the case for Michael Carvin, who started working on his concept for a new personal finance tool while he was working full time in private equity. He was planning to buy his first house, and, even as someone who analyzes finances for a living, found the process extremely confusing. “I thought if anyone should understand the economics of it, it should be me, but it was enormously more complicated than I anticipated,” says Michael, who's based in New York City. But with realtors urging him to consider homes that were well above the budget he felt comfortable with and multiple mortgage options, he decided he needed to build his own financial model, similar to the models he builds for companies in his day job.

As Michael created that model, which incorporates tax savings, mortgage rates, and the expected future value of real estate, among other factors, he started sharing it with friends and family members, too. That's when he realized there was a market for the kind of personalized financial guidance that his tool provided. “We had great feedback, which gave us a lot of confidence, and working on new technology in personal finance felt like a big leap forward. We felt like we could help people make big decisions,” he says.

So Michael, along with his cofounder Philip Camilleri, worked on building out the model in more detail, adding detailed projections on taxes, expenses, liabilities, and income. He worked on the evenings and weekends for about eight months before deciding to leave his company. While the financial training and experience he got from his full-time work was essential to helping him build his business idea, he says, “It became obvious about two months before we quit that to take any next steps we would need to become ‘full-timers’…. I was certainly worried about losing the financial security of being on someone's payroll, but we had exhausted what we could do while still working.” The new website, SmartAsset.com, needed new business partnerships and investors. “It is hard enough to get people to take your phone call when you are just two guys in an office, but if you tell them you are moonlighting, it becomes even more difficult to be taken seriously and make important connections,” says Michael.

Today, with a staff of five and coverage in major publications, including Fast Company and PC World, Michael knows he made the right decision. “If I knew then what I know now, I would have left sooner,” he says. Along with his cofounder, he's expanded the site to include guidance on credit scores, retirement, and renting versus buying, and plans to expand soon to even more areas, including life insurance and investing. While initially sustained by investors, the site aims to eventually become profitable by referring people to financial products, such as mortgages, that make the most sense for them. At thirty, Michael's own financial life is looking promising: He owns his own thriving business.

Maria Sokurashvili from Chapter 4 made a similar choice when she decided to leave her information technology job to work full time on her website, dcurbanmom.com, along with her husband. Between being a mother of two, her full-time job, and her popular website, she says, “I had no extra time, so I realized the situation could not go on.”

Todd Henry, the founder of The Accidental Creative from Chapter 2, says he decided to leave his full-time job as creative director at a nonprofit when he simply no longer had time for both, given the rate at which his business was growing.

For acupuncturist and therapeutic masseuse Lucinda Lyon-Vaiden (Chapter 5), time was also the deciding factor. She worked as a meeting planner during the day and holistic healer from 4:30 to 6:30 for ten years, and then realized her schedule was holding back her business. “People were disappointed; they couldn't get in, and I traveled for work sometimes and couldn't see clients. So I was happy when I could add more hours to my day,” she says, which she did by quitting her day job.

Not everyone makes an either/or decision. Dana Lisa Young from Chapter 6 scaled back her content management work by moving from a full-time position to contract work, which allowed her to focus on building her holistic health business. Yoga teacher Melissa Van Orman (Chapter 6) replaced her stressful consulting job with part-time university work to supplement her yoga income. Alexis Grant (Chapter 8) left her full-time journalism job when another company hired her to write and edit career-related content several days a week, giving her time during the rest of the week to build her own website, write digital guides, and work on her social media business. “That offer made me feel financially secure enough to go off on my own,” she says.

SEEKING SATISFACTION

When I asked side-giggers what makes them feel fulfilled in their work over the long term, they almost always pointed to signs that they were making a positive impact on the world, even in some small way. For the side-giggers who launched public service pursuits, such as Emily Kaminski of frugalpharmacies.com or AJ Thomas of Infuse Program Foundation, their positive impact was obvious, but it's also apparent for many people whose primary goal is more business-oriented. While financial security usually plays a key role in why people build side-gigs, they often find a deeper payoff along the way, too, especially if they choose a pursuit that is closely aligned with their skills, values, and dreams.

As her jewelry business took off, Febe Hernandez (Chapter 3) started hiring young people from her home in the Bronx to work on her social media accounts and graphic design. When they get together, the members of “Team Febe” don T-shirts with her company's logo: “Sacrifice nothing.” Helping young people is one of the most gratifying components of her business, she says, and one she plans to continue long after she retires from her career in national security.

For children's book publisher Calee Lee (Chapter 3), the satisfaction comes from passing out royalty checks to her writers and illustrators, as well as connecting young readers with new role models. “I was raised to see the value in employing others, so on some level, writing royalty checks is one of the most exciting things I do. I am building the economy on a tangible level for artists, and it's important we value artists, and give them a way to earn a living wage,” she says.

Maia Heyck-Merlin, the teacher-turned-organizer from Chapter 2, says she knew she had to continue giving workshops to teachers about how to be more organized when teachers said it helped them want to stay in the classroom. Keeping teachers from quitting is a huge problem in education, and Maia feels like she's doing her part by helping them learn how to juggle messages from parents, homework assignments, and administrative tasks. “Just hearing those individual teacher stories made me feel that I had to continue,” she says.

Prakash Dheeriya, a finance professor at California State University-Dominguez Hills, found a way to pass on a legacy of financial literacy through his side-gig. He started writing finance books for his two elementary-school-aged sons as a way to teach them basic money skills, such as risks and returns, opportunity costs, and credit. He thinks of it as the legacy he is leaving his children. He soon realized that other children could also benefit from the lessons, so he created a series of books that he sells through his website, finance4kidz.com.

“All we do is teach kids to save and budget, but we rarely teach them the relationship between risk and return, and then someone like Madoff comes around and says, ‘Let me give you the opportunity to make tons of money.’ That comes with risk. We need to teach kids that,” says Prakash. He feels like he's found his calling by sharing these financial lessons, which connects his decades of experience teaching finance with the demographic that is perhaps most in need of these skills.

Melissa Van Orman, the former consultant and current yoga teacher and university instructor, gets a similar type of satisfaction from her new mix of jobs. Unlike at her consulting job, which took place in what she describes as a stressful, hostile work environment, Melissa finds her time in the yoga studio and classroom to be deeply fulfilling, largely because she can see the transformation she's helping to foster in other people's lives. Her classes are vigorous; she says her goal is to keep people fully engaged, which “helps people create distance from their mental habits and maybe create space for something new or more helpful to emerge.” She achieves that effect through her instruction, voice intonation, lighting, music, and physical assists. One of her students, whom she teaches in private sessions as well as group classes, found that yoga helped her to stop dieting and instead have a more intuitive relationship with food, which allowed her to sustain a healthy weight loss for the first time in her life. Another student decided to leave her twenty-year communications career to teach yoga full time; another went from living off of burgers and takeout to being a vegan. She's noticed similar transformations among her college students, who have switched degrees from business to public health and quit smoking. “I seek to set a supportive tone and provide resources where students feel inspired and confident to make changes on their own,” she says, adding, “I view my role as creating a space people want to return to again and again—repetition is a powerful and effective way for this kind of self-reflective work to occur.”

Her students are so grateful that they often leave her little gifts or thoughtful notes; her Facebook page is filled with thanks for a great class or for her “juicy assists” on the yoga mat. While she's soft-spoken, Melissa has a gentle strength and authority that comes through when she's teaching; she inspires students to push themselves just where they need to go. “Part of why I went into public health was because I wanted to make positive change in the world, and I saw people in the yoga studio making huge changes in their lives, and I was a piece of that. It's so exciting to be a part of that transformation for people.”

Melissa's experience resonates with some of my favorite research on career satisfaction, which comes from Jamie Ladge, assistant professor of management and organizational development at Northeastern University's D'Amore-McKim School of Business. Instead of focusing exclusively on the financial rewards of work, she explores more subjective measures of career success, including how satisfied people say they are with their work. Satisfaction, she says, is not just about income, but about what she calls “personal rewards.”

Her research can be interpreted as supporting a new, more flexible model of work that incorporates periods of work for a full-time employer, part-time work combined with a side-career, and periods of freelance or contract work only, along with various combinations of those options. “We're taught from an early age that there's one linear career path to success, and you go from one step to the next,” she says, but this alternative career model instead suggests that there are many different ways to be successful, and each person should define that path for themselves. Part of the new model also involves adapting the mentality that you work for yourself, even when you work for others, Jamie says—a philosophy that applies perfectly to the career-plus-side-gig model.

That lesson is driven home to me, over and over again, every time I sell another planner, write another freelance article, or plan my next speech. My full-time reporting job is still where I spend most of my time and it provides the bulk of my income; it's also where I find much of my satisfaction, especially when I hear from readers who find a story I wrote useful, or when an article takes off on Twitter or Facebook. With the backing of my employer, I can reach far wider audiences than I ever could on my own. Still, the glee I feel over finishing a new planner, or selling one, or giving a well-received speech, provides a different kind of joy: Creating my money planners and giving talks on money depends on me finding my own voice, and my own skills, and figuring out how that best intersects with what people find useful. That, as the career research suggests, is incredibly satisfying.

If I'm having a bad day at work, all I have to do is scroll through my Etsy feedback for an espresso-level pick-me-up: “So helpful! Love how easy it is to use!” Michelle wrote about one of my money planning kits. “So well thought out and makes managing money more fun,” said another customer about my money planner. “As a recent graduate school student, I need a little help to get on track. So far, the worksheets are easy to use and include just enough not to be too overwhelming. Thank you!” wrote another. A woman planning on soon becoming a single mom wrote to me after reading my baby planner, asking if I had any specific advice for single expectant moms. (I told her to be sure to find child care she felt comfortable with as soon as possible.) A customer in Barcelona, Spain, wrote to let me know she was excited to sit down with a cup of coffee and study the money planner. “Thank you for your effort, it is totally worth it!” she wrote. Another Michelle, who purchased the personalized version of my one-page planner, wrote me an enthusiastic email: “You are sending me in the right direction and this is greatly appreciated at the perfect time…I can't wait to put the ideas into action.”

My planners also helped me accomplish my original goal: greater financial security. In the year since first launching Palmer's Planners, my shop received almost 20,000 page views and sold $2,000 worth of planners. Thanks to my freelance and speaking work, I was able to bring my total outside income to over $10,000, exceeding my original goal. Not enough to sustain me or my family without my full-time job, but a significant figure that I could probably increase if I ever needed to.

The other side-giggers that I met along the way continue to give me inspiration. They convinced me that mixing traditional and new economies into a hybrid career is right for me, and that it's probably right for a lot of other people, too. In another ten years, having a side-gig could be as essential a tool for modern workers as knowing how to type, or how to send email. The good news is that it's also a lot more fun.