CHAPTER

6

Time Is Money

IT'S A GORGEOUS, EARLY SUMMER, 75-DEGREE DAY, BUT INSTEAD OF using my lunch break to get some fresh air, I'm headed to the bottom level of a hot, smelly parking garage in downtown Washington, D.C. Jessi Baden-Campbell, a meeting planner for a consulting firm by day, is using her lunch break to rehearse for her role in an upcoming opera at the Capital Fringe Festival, a local celebration of the performing arts. Jessi, a professional opera singer, invited me to watch, and learn how she combines a full-time job with an almost-full-time singing career, all while raising two children under the age of five.

As we make our way down the staircase to the very bottom of the garage, Jessi explains that she has to go all the way down to minimize her chances of disturbing people in the lobby. Her voice is so powerful that it carries three flights up, even through concrete. Since she practices three times a week, parking garage attendants have come to expect her lunchtime concerts.

She sets out her binder with song notes, iPhone, and water on a nearby Honda Civic, and presses a few keys on her piano app to get the right notes. After warming up her lips with a rolling “brrrrrrr” sound, she belts out Wagner. The acoustics are incredible: Her voice bounces off the garage walls and resounds throughout the garage. If I close my eyes, I can almost pretend I'm at the Vienna Opera house, despite the occasional roach and the extremely unpleasant smell of car exhaust.

As Jessi transitions from her Wagner warmup to the English lyrics she will perform at the Fringe, she uses her hands to gesture, and mutters mental notes to herself. “So don't breathe there,” she says, when she runs out of air at the end of a line. After taking in the full force of her powerful voice, I wander up the garage ramps, to find out just what the parking attendants can hear from the upper levels. Her voice carries around the turns of the garage, until eventually, near the top, she sounds like an ocean siren from Greek mythology, luring sailors closer to rocks until they crash. Indeed, office workers who catch a drift of her voice often wander down to see what's going on.

While Jessi, who recently turned forty, would prefer to focus exclusively on her opera career, she discovered that the lifestyle frequently required dropping everything for weeks of rehearsals and performances, often in a new city—not an easy thing for a mom to do. She also found that building a dependable income as an opera singer was close to impossible, especially after the recession hit and dried up funding for the arts. Before she had children, she was willing to take those risks, and accepted a series of freelance performances. She moved to Anchorage, Alaska, for four months to perform at the Anchorage Opera, and also performed at the Des Moines Metro Opera and Nevada Opera in Reno. She earned rave reviews in national publications; the Washington Post called her “vocally powerful and physically imposing.”

Once her daughter was born, her priorities switched. “You can't expect your child to sacrifice meals and their own comfort, so I got a full-time job,” she says. She relegated her singing career to the side while working forty hours a week as a meeting planner. She picked up steady work at a local church, which requires a Thursday night rehearsal and Sunday morning performance; she earns about $10,000 a year for that. She also sings for a local synagogue during the high holidays, which involves months of preparation and four solid days of singing. For that, she earns another $5,000 a year. She also supplements with the occasional wedding or corporate performance, which can pay up to $500 per appearance. Other workshops or performances, for which Jessi usually uses up vacation days, can pay $800 for three to four days of work, not including rehearsal time. To find potential opportunities, she stays in touch with friends in the performing arts and occasionally posts about her availability on wedding chat boards.

Jessi and her husband use her singing income to pay for household expenses, such as new windows for their house in Falls Church, Virginia, and savings for their children's future college tuition as well as their own retirement. Since they live in an expensive city with two children, that income stream feels essential to their family's financial security.

After forty minutes of working out her vocal cords, it's time for Jessi to grab lunch from a nearby food truck to eat back at her desk before her hour-long break is up. As we walk back up the three flights of stairs, Jessi mentions that she'll head to rehearsal for the Capital Fringe opera right after work; it's from 6 to 9 p.m. every night for the next month. “How do you handle that, especially with being a mom?” I ask her. That time slot seems like prime parenting hours, typically filled with dinner, bath time, and books.

She admits it's hard. “Sometimes when I get home, I cry,” she says. It's a lot of pressure, and she often feels guilty about not spending more time with her son and daughter. She invited her mother-in-law to live with the family, so she can fill in when Jessi has an unexpected performance or late-night rehearsal. Her commitments to the church choir mean that much of her weekend is taken up, and she doesn't have many vacation days left since she dedicates most of them to performances or workshops. On one recent Sunday, she woke up to sing at a 7 a.m. church service, stayed for the 10:30 service, and then drove an hour away to perform at a wedding.

But as she explains why she does it, her tone changes from one of frustration to gratitude. “I don't want to become a bitter person who had to give up her art,” she says. “I'm committed to myself as an artist and I'm also committed to my family—in order to spend time with them, and to provide for them financially, while also feeding myself in terms of my own passions and my own movement forward as an artist, I have to make the time,” she continues. Plus, she knows her kids understand, and support her. She pulls out her iPhone to show me a video of her four-year-old daughter proclaiming that she wants to be a singer just like mommy when she grows up. Jessi is clearly imparting invaluable lessons to her children, even when she's at a rehearsal.

LEVERAGING THE DAY JOB

The secret to excelling in both a full-time job and a side-gig is often to find a way to combine them, in a completely aboveboard, ethical way. That means your boss knows what you're doing and is happy about it, because it brings your employer some kind of related glory or benefit. (Exactly how much you share with your boss depends largely on the office culture in which you work, which varies widely from company to company. You'll want to get a keen sense of how side-gigs are viewed before talking up your own—and the examples that follow showcase a wide range of possibilities.)

That's not to suggest building a side-gig, even one related to a main gig, is easy. Almost all the side-giggers I interviewed struggled with finding enough time to meet their multiple responsibilities. Just as jobs have become less stable, they've also become more demanding. A 2011 survey by the Society for Human Resource Management found that instead of adding more positions when they needed to get more work done, employers instead ask their current employees to do more. Almost one in four hourly employees said they worked longer hours compared to earlier in the year. Indeed, many side-giggers work demanding jobs, putting in fifty hours or even more each week. Yet they still find ways to excel in the side-pursuit, usually because they are able to use their full-time job as a lever to boost it.

For Jennifer Teates, a law firm manager in Annapolis, that means turning her experience working on collections and bankruptcy issues into a writing career. “We have lots of people calling in and they don't know basic information—what seems to me like common sense,” says Jennifer, such as how much personal information to share with creditors who ask where you work or where you bank.

Jennifer, who's in her mid-thirties, realized she could help people by sharing information about navigating debt settlement and bankruptcy, so she started contributing articles to Yahoo! Finance and then contacted her local editors at Examiner.com about writing a personal finance column for them. After an application process, they hired her, and she soon started writing for Motley Fool as well. Since her day job provides story ideas and expertise, it feeds right into her freelance work.

To get her writing done, she wakes up around 5:30 a.m., two hours before her toddler son gets up. That way, she fits in a couple hours of writing each day before heading to the office (or telecommuting from home). That doesn't leave a lot of time for sleep—around six to seven hours—but Jennifer says that's all she needs. She insists she doesn't have a Type-A personality, and fits in plenty of relaxation time in the evenings, starting with family dinner time.

The schedule requires plenty of planning, but Jennifer says she's living exactly the life she wants. In addition to enjoying her writing, it gives her financial security: “If something happened, like my law firm decided to shut down one day, I can fall back on freelance writing. For now, I just sock away the money I bring in,” she says. She has plans to grow her writing career further, with a comedic financial planning book in the works.

One thing she doesn't plan on doing is leaving her law firm, even if her writing career takes off. “A lot of my ideas come straight from my office, so it would be really silly to drop my source of information,” she says.

That was also the case for Jeffrey Nash, inventor of a new kind of baby walker that he calls “the Juppy.” In the summer of 2011, just as my own baby was mastering the ability to walk and run, I got an email pitch from Jeffrey, who said he had figured out the best way to impart this skill to young children. He described the Juppy as “an alternative to dangerous wheeled baby walkers,” and as a paranoid new parent, my ears perked up. Anything that claimed to add to the safety of my child captured my attention (and often my money).

When I called Jeffrey to talk about writing a potential story on his product, I discovered that he had invented it while employed full time elsewhere: a suit store. Jeffrey, now in his late fifties, had spent much of his working life as a salesman, working the floors of a Las Vegas Men's Wearhouse. Then, one day, he found himself facing a major pay cut and more competition from younger, cheaper salesmen. As much as he loved his job and prided himself on his ability to make his customers happy, he knew it wasn't going to last for much longer.

One day, while watching a mother help her toddler walk, he had a big idea: What if he created a new kind of baby walker that allowed parents to give their toddlers assistance without bending over and straining their backs? Through his retail contacts, he figured out how to establish a patent and mass-produce the prototype. When mothers with babies shopped for tuxedos at the Men's Wearhouse, Jeffrey pulled out his prototype and asked them to try it, then made adjustments based on their feedback. Any time customers mentioned they were pediatricians or doctors, he solicited their endorsements. Customers who worked in marketing connected him to local news producers, who featured them on their programs. His job, while completely unrelated to his side-business, enabled him to make the connections he needed to get the word out about his product. “I showed everybody to see what they thought. It helped me tremendously,” he says. He says his supervisors didn't mind because he was working and selling suits at the same time.

During a three-week vacation from Men's Wearhouse, Jeffrey marketed the Juppy at baby product conferences and reached out to online retailers and baby stores. “Whenever I could corner you, I did,” he says of his salesmanship. During that three-week period, he sold $12,000 worth of walkers, and that was just the beginning. The Juppy has since been profiled on the Today Show and Jeffrey expected to bring in $250,000 in annual sales soon after launching, and double the following year. He eventually quit his Men's Wearhouse job and now works full time as the chief executive of his company, but not before benefitting immensely from the connections and customers at his previous employer. Says Jeffrey, “Had I not done this, I would have ended up homeless at some point in the next ten years.” Instead, he went from earning $65,000 with shrinking benefits at Men's Wearhouse to running a company that's growing fast.

Ebony Utley, an associate professor at California State University Long Beach in the communication studies department, similarly uses her position as a means of advancing her outside pursuits. In 2009, when the California State University faculty union agreed to a furlough, she found herself with extra time on her hands, and a need to earn some cash. The move meant a 10 percent pay cut for all faculty, including Ebony, along with two furlough days per month. “I said, ‘I need to make it up in another way,’” Ebony recalls. That's when she launched her second career, which involves speaking, writing, and managing her website, TheUtleyExperience.com. “Teaching is awesome, but I want to have a broader audience than just the students in my classrooms,” she says.

Ebony used her academic expertise in pop culture, race, and romantic relationships to become an outspoken expert on those topics. After emailing her friends and colleagues in academia to pitch her services, she started traveling to different universities to guest lecture on the role of religion in rap music, sexism in hip-hop, and how pop culture portrays black women versus the reality of their lives. In one lively talk at the University of Dayton, she explored how Amber Rose, former girlfriend of Kanye West and current girlfriend of Wiz Khalifa, used her dating life to get ahead professionally as a singer and model. She went on to argue that the hip-hop generation is continuing the legacy of the civil rights generation by celebrating African American culture and uniting different ethnic and racial groups.

Around the same time, Ebony started blogging for popular websites, including Ms. Magazine, Religion Dispatches, and Truthdig.com, on topics from Maria Shriver's divorce to interracial dating. She also wrote her first book, Rap and Religion: Understanding the Gangsta's God. In her author photo, she's dressed like a rapper, with a white fur wrap, dark lipstick, and huge gold earrings. If you look quickly, you might think you're looking at Rihanna.

To balance her new career with her professorial work, Ebony adopted a strict writing schedule: She gets to work first thing in the morning. “I get out of bed, have tea, and start writing,” she says. On days she's not teaching, her friends know not to call her until noon. “I learned to fiercely protect my writing time,” she says. She sets her timer for 120 minutes and makes herself write for at least that long, but often finds herself going for another few hours. Ebony keeps a log in an Excel spreadsheet of all the time she spends writing, so she can see her progress and also gauge how long it takes her to complete certain projects, such as writing an article or a blog post. “That way I know that if I need twenty-four hours for something, I can plan to do it over spring break, or in the summer. That log changed my life,” she says.

Ebony also works with what she calls an “accountability partner,” or a friend who works in her field who helps keep her on track, and vice versa. They talk about their projects, deadlines, and progress, and often swap drafts of work. “Writing is a lonely life, but having a peer give feedback makes my work stronger,” she says. (She also squeezes in some downtime every day when she's home to watch her favorite show, The Young and the Restless.)

Just like Jennifer Teates and Jeffrey Nash, Ebony's secret is that she uses her full-time job to advance her second career: “I started teaching more classes that fed directly into my public intellectual work. I designed the first hip-hop class for my department, and a pop culture class, so everything I had to learn about to teach those classes were also things I was blogging and speaking about. My students came alive more in the classroom when they saw what I do, too,” she says. If her worlds didn't dovetail, “there's no way” she could handle four classes a semester in addition to her speaking and writing work, she says.

Combining a side-gig with full-time work doesn't always go so smoothly. For Melissa Van Orman, it took a bit more wrangling, and eventually, a major life change. At first, she lived the life of a typical side-gigger: She woke up early, often before the sun came up, to get to her health consulting job by 8 a.m. or earlier. She had to bill at least forty hours a week, which meant nonstop days packed with meetings and phone calls. Then, by 5 p.m. she would rush out the door to make it to the yoga studio where she taught packed evening flow classes to the after-work crowd. She usually left the studio after 9 p.m., headed to her nearby home, and collapsed in exhaustion. “Physically, emotionally, energy-wise—I couldn't sustain that,” says Melissa, who's in her late thirties.

At the urging of her husband, she eventually left her consulting job to become a different kind of side-gigger: one who juggles a full-time yoga teaching schedule of both classes and private clients with part-time teaching work on nutrition and health at George Washington University. “I took a $50,000 pay cut, and it was right when the economy was imploding, but it was the best decision I ever made,” says Melissa. Her new schedule meant that she could fit in her yoga classes and client meetings, as well as preparation, throughout the day, instead of cramming everything into the evenings. She also recently picked up an additional freelance job as a health writer for the Centers for Disease Control, where she previously worked, which has helped make up for that initial loss of income. She noticed that when she stopped working her office job, her spending dropped significantly: She makes her own lunches, buys fewer clothes and shoes, and spends less on convenience items such as taxis and takeout. “Not working in a conventional way has really freed us up,” she says.

The reason she says she can now handle so many different jobs at once is largely because they all fit together and build on each other: Her teaching experience in the yoga studio makes her a stronger teacher in the classroom, and her yoga studies contribute to her nutritional expertise. (In addition to her advanced yoga training, Melissa also holds a master's degree in health communication.) Before, a lot of tension came from the fact that she felt that her yoga teaching conflicted with her consulting work: “I was seeing my colleagues publish papers and speak at conferences, and I realized that during the twenty hours a week I was teaching yoga, they're doing that—I felt like I was only giving half to each of those things.”

Now, Melissa's flexible schedule means that she not only gets everything done, but she also ends each day feeling relaxed and fulfilled. She typically works seven days a week, and often starts the day at 5 a.m., so she can make it to a 6 a.m. private client yoga session. She might have another client later in the morning, and go home for a leisurely lunch on her own. In the early afternoon, she'll often head over to the university to teach her nutrition class to undergraduates, or fit in her freelance writing work from home. (She can walk to both the yoga studio and university from her apartment.) Then, her evening yoga classes begin around 6 p.m. and go until 9 p.m. Her husband, who works for the government, often leaves the office to take her evening classes, so they can spend that time together. “In some ways, it sounds exhausting to have a seven-day-a-week schedule, but I also have three hours in the afternoon where I can take my dog to the woods and walk him, or grocery shop. I work when other people are off, so it makes it easy. Or I'll take a twenty-minute nap in the afternoon if I get up early for a client,” she says. What she doesn't have, she says, is time every night to watch television or cook dinner, but that's a trade-off she's willing to make.

OPPOSITES ATTRACT

When side-gigs don't feed directly off full-time jobs, there are often other ways to turn each identity into an asset that boosts the other. Twenty-something Nicholas Ignacio attributes his success with his lawn care business to one factor: that he's also a full-time college student. That fact, he says, is why clients hire him, trust him, and pay him more than minimum wage. Everyone wants to support local college students, he says.

As a criminal justice student at Marymount University in Arlington, Virginia, he joined up with a friend who suggested starting a power washing business. When they went to register at city hall, they needed a company name, and came up with “Strong Students Lawn Care,” which ended up shaping their business. His clients come primarily through his Craigslist.com listings and word of mouth.

To keep up with demand—just a few months in, his company was already fully booked three to four days a week—Nicholas hires other trustworthy college students as employees and spends his time visiting client sites, providing estimates, and taking care of administrative work. He also reaches out to new clients, including banks, realtors, and commercial companies. Still, he says, “I have to make school a priority,” which is why he schedules his lawn care work for the days he doesn't have classes. He's able to pay for his living expenses with that income. His work supports his college lifestyle, and it's that identity that allows him to land so many jobs.

Other side-gigs are so impressive—like Jessi's opera singing—that supervisors and coworkers are often happy to provide support by granting a more flexible schedule when necessary. They're proud of the side-pursuit, and perhaps appreciative for the additional glamour that it brings to the office. At the very least, they don't see the side-gig as something that takes away from the full-time job.

That's certainly the case for Alisha Williams, who competed in the U.S. Olympic 5,000-meter, 10,000-meter, and marathon running trials for the 2012 London Olympics. (You might have caught her blond ponytail racing around the track.) Alisha, who works full time as a certified public accountant for an energy company based out of the Denver area, says her coworkers and supervisors are always excited to hear about her races. Before her Olympic trials in Eugene, Oregon, her officemates threw her a party and decorated her desk with U.S.A. signs and streamers. While she didn't quite make it to London (she came in fifth place in her 10,000-meter race), they are still proud to have an (almost) Olympic-level athlete among them.

Through careful planning and Outlook calendar management, Alisha avoids conflicts with her day job, or giving her accounting work short shrift. It's not easy, given that most athletes competing at her level work only part-time jobs or dedicate all of their time to the sport.

Alisha joined an Olympic development program after college, while she was starting her accounting career, but she didn't see her times change much. “I thought of myself as just a jogger,” she says. She continued to build her career, studying for the CPA exam, earning her license, and putting in sixty hours a week at the office. Her low point was in 2007, right after tax season ended, when she ran a 5K race in what was (for her) a record slow time. “My husband watched and he was like, ‘Were you even trying?’ At the time, it was hard to do the running thing and the full-time professional CPA thing. You want to do your best and give it 100 percent,” she says.

That's when she decided to get serious. She tried for the 2008 Olympic trials but came up short, and later found out she had an iron deficiency. She joined up with a new coach and training team, The American Distance Project, a nonprofit dedicated to training U.S. distance runners. Her CPA job also became more predictable and stable, requiring closer to forty to fifty hours a week instead of sixty-plus. While she emphasizes that her top priority is her day job, she says her schedule lets her run in the morning. She typically wakes up between 5:30 and 6 a.m., drinks some tea and has a snack, then gets out for a run with her husband and dog. Four days a week, on what she calls her “easy days,” that means running ten miles in the morning, along with drills. Then, she works for eight or nine hours, and runs again, three to five miles in the evening. On the other days, she does her more intense workouts, which might consist of warming up for three miles, then running an extensive series of 400-meter sprints, followed by a two-mile cool down. She runs another four miles in the evening and heads to the pool. She saves her long, eighteen-mile run for Sunday, and swims in the afternoon.

To keep herself going, Alisha eats plenty of fruits, vegetables, protein, and smoothies. She and her husband make smoothies with spinach, Greek yogurt, and protein powder after their morning runs. Some evenings after her evening runs, she eats an almond chocolate bar. Then she tries to get in bed by 9 p.m.

If her race schedule ever conflicts with work, she tries to work ahead as much as possible. “I don't have the luxury of waiting until the last minute,” she says. She adds her running commitments to her office Outlook calendar so her colleagues know about her schedule in advance. (She uses vacation days for her races.)

Without her accounting job, Alisha could have experienced what many other Olympic-hopefuls experience after almost qualifying for the Games: crushing disappointment, and confusion over their next steps. Shortly after the 2012 Olympic trials, the Washington Post ran a story on how bereft many athletes can feel after almost making it. Only a small fraction of Olympic trial competitors became one of the 530 athletes to make to the Summer Games. The problem caught the attention of the U.S. Olympic Committee, which now offers athletes job placement help, career coach consulting, and resume advice.

Athletes like Alisha, who already have careers outside of athletics, don't need to depend on that kind of assistance. “If I had to rely on [income from running] that would be hard. I don't feel the added pressure that people who only run probably feel; the need to do well to pay the rent,” she says. Still, some years her running earnings are significant enough to add to her financial security. Those earnings come mainly from sponsorships—Alisha is sponsored by Boulder Running Company, Adidas, and PowerBar—as well as race prize money. (After speaking with Alisha, I discovered other Olympians who share her approach, pursuing full-time careers alongside their Olympic ambitions, which gives them financial security during and after their training. Natalie Dell, a health care researcher at the Veterans Affairs Department, won a bronze team medal in rowing in London. Triathlete Gwen Jorgensen is also a tax accountant at Ernst & Young.)

Now, Alisha's already planning for the 2016 Summer Olympics in Rio de Janeiro, when she'll be thirty-four. After that, she plans to continue to balance her running career with her accounting work. “I don't ever want to stop being active, and running is my favorite activity,” she says.

Corinne Delaney also found that even though her side-gig as a classical singer isn't directly related to her full-time job as a graphic designer and training analyst for a government contractor, her employers still see it as a major asset, and even occasionally use it to their advantage at company events. She highlights that she is a classically trained singer on her resume, and says that potential employers have asked her about it during job interviews. “[Classical singing] goes hand in hand with discipline, and shows I pay strict attention to detail,” she says.

Earlier in her career, when Corinne, now in her mid-thirties, was interning at the American Trucking Association, her coworkers asked her to sing “Danny Boy” at the president's birthday party. Shortly afterwards, she was bombarded with performance requests from coworkers. Not only were her supervisors impressed with her talent, but the performance helped her pick up new clients for weekend singing gigs.

Today, as a full-time employee for CACI, a large government contractor whose acronym originally stood for California Analysis Center, Inc., she performs about once a month at weddings and community events. While Corinne says she performs for the “sheer joy” of it and is often happy to donate her talent for charity, her regular paid performances typically pull in several hundred dollars or more, depending on length and location. Her voice, strong and clear, transports the listener; her rendition of “Somewhere Over the Rainbow” sounds simultaneously modern and traditional. In addition to her performances, Corinne, who has been training as a vocalist since she was fourteen, gives lessons to a small handful of students and plans to soon release a recording. She's now using her skills gained from her full-time work as a graphic designer and training analyst to develop a website that will help take her singing career to its next level.

Stephanie Theodore's second career brings a similar kind of glamour to her day job, but in a totally unrelated field: art. By day, she serves as a department manager at a major financial firm in New York City. On the weekends, she runs her art gallery, THEODORE:Art, in Brooklyn. Stephanie, who's in her early fifties, often spends her evenings meeting people, helping the artists with their installations, and getting word out about upcoming exhibitions by emailing her newsletter list or writing press releases. Her day job requires about forty-five hours a week of her full attention, although she can often squeeze in emails or Tweets during slower moments.

Her bosses are well aware of her work in the art world, and they like to joke that her management job is her “side-gig.” She gets great annual reviews and is recognized for being supremely organized and balanced. “I'm artsy for my day job and I'm pragmatic for the art world,” says Stephanie, who holds a master's degree in art history.

She avoids potential conflicts by maintaining a strict schedule: She's in the office during the day, and then on the weekends wakes up early with her dog, around 5:30 a.m. They go for a walk together, and she does some shopping, and then she bikes to her gallery from her apartment in Queens. “I build in leisurely enjoyment to the whole process,” she says. Her gallery is open to visitors on Friday through Sunday from 1 to 6 p.m. (She's there for the weekend hours.)

She also skips things she considers unnecessary. She doesn't get manicures or pedicures, she avoids television, and she doesn't spend much time getting her hair done. “My feet are not pretty, and I don't care—of you're looking at my toes, you're not looking at the art on the wall or listening to what I'm saying,” she says.

“I've always had this dual life,” says Stephanie, and she adds she wouldn't want it any other way. She gets her financial security from her office job, and her creative satisfaction from running her own business. In some ways, she's following the example of her father, who worked in advertising but would spend two-hour lunch breaks looking at art at the Museum of Modern Art. “We're all artists, and we all do what we want, but we have to be able to pay for it, too,” she says.

COMBINING UNRELATED (AND POTENTIALLY CONFLICTING) CAREERS

When the two pursuits are completely unrelated and neither pursuit seems to add to the other, then getting both done can require a bit more creativity and strict adherence to legal and ethical guidelines. But even side-giggers playing a zero-sum game find ways to make it work.

Martin Cody, a vice president of sales for a medical software company who works from home and the founder of Cellar Angels, an online wine marketing company that contributes a portion of sales to customer-selected charities, operates with extreme efficiency. In fact, before he agreed to speak with me, he asked me to answer a series of questions about exactly what I planned to ask him and what I hoped to get out of the conversation. Every night, he writes down the five things that he must get done the next day. “Normally a to-do list might have thirty to forty items, but there should be five critical ones,” he says. He makes a separate list of five for both his full-time job and his wine business, and he keeps a legal pad by his bed in case any ideas pop up during the night.

During the day, Martin, who lives in Chicago and is in his mid-forties, keeps two computers on his desk in his home office, one for each job, and he manages to respond to emails and take care of other tasks related to both businesses simultaneously, all day long. He also wakes up early, between 4:30 and 5 a.m., to get started on the day. He makes calls for his wine business after 5 p.m., when his sales job has wrapped up but the wineries in California that he works with are still open for business. He might work seventy hours a week or more between his two jobs, but he also makes time to walk by Lake Michigan, visit farmer's markets, and, of course, drink wine.

Martin's idea for the wine business came during the 2008 recession, around the time that Groupon launched. He wanted to figure out a way for wine stores to participate in the group coupon movement. “Unlike a lot of merchants, who can have a discount one day and not the next, a winery has one product a year, so they can't do that. They also get solicited by charities all the time,” he says. Since his wife runs a wine store in Chicago, he already knew the industry well.

Cellar Angels offers weeklong discounts from small, California wineries to website members (out of view to the general public, so as not to hurt the value of the wine), and also allows customers to contribute a portion of those sales to specific charities. “It hit me like a flash: how do you honor charity requests, gain exposure for wine, and solve the consumer problem of access to wine from these small wineries?” That's how Cellar Angels was born, and it's quickly picked up steam, partnering with Leeza's Place, Leeza Gibbons's foundation that supports family caregivers, and Generation Rescue, Jenny McCarthy's autism organization.

Martin plans to continue growing it, alongside his medical sales work, but because the two are unrelated, he keeps them completely separate, just like his desk setup: two different computers, working side by side. In fact, his bosses at his medical sales company don't know about his wine work. “I haven't concealed anything, I'm just not actively promoting it,” he explains. For now, that's the arrangement that seems to make the most sense, and so far, it's working.

Dana Lisa Young, a website content manager in Atlanta in her early forties, found herself in a similarly polarized situation, juggling a forty-hour-a-week office job with a growing wellness business, where she practices Reiki, reflexology, and life coaching. The two jobs are as different as wine and medical sales: Her content management work involves sitting at a desk, developing internal and external company websites, along with editing and posting content. Her wellness business consists of one-on-one client sessions and workshops where she helps promote healing and health. Since her wellness work is done mainly on the weekends or after work, when clients usually want to meet, it rarely conflicts with her content management work. Her employers are aware of her outside work, and when she worked a nine-to-five office job, they also knew that it was never scheduled during work hours, and that the work itself didn't create any conflicts of interest. When Dana worked for a professional services firm that had to abide by Securities and Exchange Commission (SEC) regulations, that distinction was especially important. She reported her business information to a database that was updated each year.

“The corporate environment and wellness business are worlds apart,” says Dana. That dichotomy sometimes led to a bit of culture shock when she went straight from the office to see clients. In the early days of her business, she often worked nonstop for weeks at a time with no days off; like yoga teacher Melissa Van Orman, she found it exhausting. And like Melissa, she eventually decided to rearrange her schedule to fit in more downtime. She went from a full-time content management position to contract work, which allows her to work largely from home and for fewer hours each week. That gives her more time to grow her wellness business, as well as to attend school events and be with her children.

Dana still does much of her client work in the evenings and on the weekends, when her husband can be with their children, and she works during the day on her content management responsibilities. That leaves her with spots of free time to squeeze in laundry or to blog, Tweet, or write a Facebook post about her business. She puts all commitments on her Google Calendar, and schedules blocks of time for work and family. When her children go to bed, she often gets back on the computer to work. She also meditates before getting out of bed in the morning, to guarantee that she fits in some relaxation for herself every day.

Dana earns less now, but, like Melissa Van Orman, says that trade-off is worth the additional flexibility. “I really objected to the fact that in most of these jobs you're required to give 120 percent of your time, even if they say work–life balance is important. At some point I felt, ‘This lifestyle isn't worth it to me,’” she says.

Some people allow that tension they feel between their full-time jobs and side-gigs to build until it explodes. When the now-famous novelist Jeffrey Eugenides worked as an executive secretary for a poetry organization at the beginning of his career, he secretly spent his time in the office writing his novel, The Virgin Suicides. New York magazine reports that he would type on office letterhead to try to escape notice. But it didn't work; his bosses noticed and he got fired. For side-giggers who like and depend on their full-time jobs, that's a disastrous outcome. It's also one that can be avoided, even when the two pursuits don't mix well, by finding ways to create time in non-work hours.

Traditionally, the thinking has been that if you're going to pursue a little something on the side, then at least have the good sense to keep quiet about it, as Martin Cody does. I even wrote about that school of thought in my first book, Generation Earn, and quoted career coach Pamela Skillings on the concept. She encourages people to keep their outside projects under wraps so no one suspects their true passions are located elsewhere. That strategy probably works best in the most traditional of office settings, where people still slowly climb the corporate ladder. In the 1960s drama Mad Men, partner Roger threatens to fire account manager Ken when he finds out he's been writing science fiction novels after hours. “Your attentions are divided,” Roger warns him. “As an account man, you have a day job and a night job.” A chastised Ken quickly agrees to stop writing. A small subset of people might find themselves in a similar predicament today. If that's the case, the side-gigger will have to make a tough decision, to give up the side-gig or find a more flexible job.

In most modern workplaces, though, this way of thinking feels as outdated as Don Draper himself. Many successful side-giggers find that their full-time workplaces fully embrace their side-pursuits and, in fact, see them as assets. That's a good thing, too, because Facebook, Twitter, and the rest of the Internet make it virtually impossible to keep secrets anymore.

THE POWER OF NO

After my first book came out, I worked hard to promote it, writing dozens of guest blog posts and appearing on as many television and radio shows that would have me, no matter how small the audience. This work could take up to ten hours (or more) each week, and of course it didn't come with a paycheck. But I was happy to do it, because I wanted to spread the word about my book.

Even after those initial months of post–book launch, I kept getting requests for guest blog posts, to appear as a guest on podcasts and online radio shows, and to speak to small groups. For a while, I kept saying yes; after all, if even just one person bought my book because of it, I felt satisfied. As a result, my typical work week, which already exemplified the harried juggle of a working mom rushing from preschool drop-off to work and then back for preschool pickup, became even more hectic. As soon as I put my daughter Kareena to bed, rushing through Goodnight Moon as quickly as possible, I'd race down to my basement office for a Skype interview with a blogger. Then, it was back upstairs to start preparing her lunch for the next day and making dinner. My husband, who was usually just arriving home from work, and I would quickly eat before collapsing in bed.

The last straw came when a local political group asked me to speak to them about getting their finances in order. Since that's one of my favorite topics, I happily said yes, even though it would be an unpaid gig. The host suggested that I sell my books after the talk, so any sales would be my compensation. I spent time preparing my speech and practicing it, and then showed up after work at 7 p.m. one evening at a nearby office building to give my workshop to about thirty young professionals.

The workshop seemed to go well, and the audience asked good questions about where to invest and how much to save. They clapped when it was over and, though they seemed appreciative of my efforts—the host gave me a box of chocolates as a thank you—no one bought a single book. As I carted my bag of books back out to my car, exhausted after a long day and missing my daughter, I thought: Why am I doing this? Why did I agree to spend hours preparing for and giving this talk, and give up time with Kareena, when I didn't really get anything out of the exchange? Sure, I love spreading financial literacy, and it feels good to be helping people, but that work was starting to come at too high a price to my own life.

After that night, I started saying no—not always, but much more often. I became more protective of my limited free time, and energy. When I felt really crunched, I even started saying no to some paying gigs, such as a freelance article I didn't particularly want to write, and a speaking event that would have required two days of cross-country travel. Yes, I wanted to earn more money, but I also needed to protect something more valuable—my time. Instead of earning $500 for that article, I spent the weekend baking popovers with Kareena, relaxing with my husband, and away from my computer.

The hard part about knowing when and whether to say no is that a lot of times “yes” might be the better choice, even if it goes against your gut instincts. The first time an organization called me to ask if I could be a paid keynote speaker at an upcoming event, I wanted to hang up the phone and hide under a blanket. While it came with a healthy paycheck, it required three things that terrified me: flying (I get nervous), leaving my daughter for the weekend (separation anxiety applies more to me than to her), and speaking in front of a large group of people. But sometimes doing the things we're afraid of is the only way to move forward, and I'm so glad I said yes—I had a fabulous weekend with my sisters in San Francisco, met an amazing group of women, and felt like I helped them get on top of their money. And I brought home a paycheck that could pay for our family's beach rental that summer.

In fact, side-giggers often say that accepting even time-consuming, unpaid gigs is what allows them to build what becomes their thriving business. Ebony Utley gave free talks on race to colleagues' classrooms before making money from it; financial coach and author Glinda Bridgforth served on organizations' boards on a volunteer basis before becoming a paid board member. Douglas Lee Miller only realized that he could earn good money consulting on social media after noticing that people came to him for free advice when they tried to build their Twitter accounts.

Now, when I'm asked to give away my time for free, I try to pause before immediately agreeing to it. But I still make big mistakes when it comes to my extracurricular activities, and sometimes, that means everything comes crashing down.