Traditionally, moonlighting was something you did when you were short on money and needed to meet the monthly bill cycle. My experience is that now it is the very well educated and very secure people who are in the best position to be able to do multiple things because we’re the ones with access to the technology and support to do one job flexibly while having time for another passion.
—Karl Hampe, management consultant/aspiring cartoonist
Ruth Roche, my hair stylist, was showing off her rather buff arms while cutting my hair one afternoon. When I asked how she stayed in such good shape, she told me she worked with Oscar Smith, a personal trainer who owned a one-on-one training studio around the corner from her salon in New York’s Tribeca neighborhood. Roche said the most intriguing thing about Smith was that he had a “whole other life,” working the night shift as a narcotics officer.
What intrigued me most is that his personal training is the slash that came first. Police officers commonly have other jobs, but usually they fit an extra-money gig around their work in law enforcement. Smith, cop by night and trainer of Victoria’s Secret models by day, has flipped that notion on its head. I had to meet him.
I interviewed Smith at O-Diesel, the sleek studio where he trains his supermodel and CEO clientele. As we talked, with a waif warming up on the stationary bike nearby, he explained that his job with the police department was the perfect way to build up his credit in order to get financing for his personal training business.
Smith joined the police force at twenty-nine. If he sticks it out, he’ll qualify for a pension and retire by the age of forty-nine, practically mid-career by today’s standards. Rather than taking on a job just for the money, Smith chose something that would feed his desire to help people and serve the community. Smith had worked as an ocean lifeguard since he was in high school and had saved thirteen lives over the years; protecting people from danger as a police officer was something he knew he would like.
Not everyone could do what Smith does. Working an evening shift that lasts from 3:00 to 11:30 p.m. and then training his clients in the early morning hours at his studio gives him very little sleep during the week. Still, Smith said it works for him because he takes good care of himself and reaps the benefits of working in two occupations that give him different kinds of satisfaction. I couldn’t help noticing that he looked completely rested and relaxed. His tanned and toned body didn’t show any signs of overwork, and I believed him when he told me he’s caring for his body even as his sleeping habits violate every health rule in the book. It helps that he’s a gifted napper. He returns home to catch up on sleep whenever a client cancels or he has a two-hour open slot, which happens often for personal trainers.
For Smith it was all about finding a job that he felt good about doing, as well as something that would give him the security to take on the risk of a business. Smith was used to putting in grueling hours, so for him, the relatively cushy schedule of a civil servant feels almost part-time. Shifts are eight hours long, but by tacking on an extra thirty-five minutes a day, he earns an extra day off each month. Add those twelve days to the eighteen he’s already got coming and that’s five weeks of paid vacation. All the more time for O-Diesel. His combination may not make sense for anyone else, but all that matters is that it works for him. For this point in time.
The prior chapters focused on building slash careers to cultivate passions or make room for competing interests, but that isn’t the only reason people have slash careers. Many people take on a slash to provide extra income or security while chasing a dream, pursuing a creative endeavor, or working in a low-paying but rewarding field. These folks are different from the moonlighters of earlier generations. Forget cobbling together dreary day jobs or night jobs to make some extra bucks; today’s moonlighter shops for the perfect slash (or collection of slashes) that best accommodates the passion that occupies first place.
With actors, writers, and entrepreneurs earning steady income working as lawyers, real estate agents, or Web site developers, it’s getting harder to tell the difference between a day job and a dream job. Smith chose one path, a job with security to complement the risk of his business, but many modern moonlighters are drawn to work that can be done flexibly or remotely. Or work that gives them wide open swaths of time to work on their own projects.
These folks say they know what comes first. But sometimes what begins as a money gig evolves into a full-blown second career. This chapter will look at the many ways people are thinking creatively about finding an ideal money gig to complement a passion or high-risk venture.
When Sarah Graham, thirty, decided to become a journalist, she knew she was entering a field notorious for its low pay. While she was finishing up journalism school, she took the advice of one of her professors and picked up a skill—Web site design—that would give her a way to make some extra cash on the side. That professor, Sreenath Sreenivasan, who teaches new media journalism and is a general journalism gadfly, was also responsible for supplying Sarah with a bevy of journalists and authors who were eager to have her build their Web sites. When she began her consulting business, she hadn’t even secured a job in journalism; for a few months Web design was her full-time job. But once Graham got a job as editor for the online branch of Scientific American magazine, Web design moved to second position.
Even with a solid journalism job, the extra income has made a big difference to Graham. “Living in New York is painful. While I could live on my salary, I just wouldn’t be saving any money,” she explained. “With this, I can basically do it on the side and it’s almost one hundred percent savings.”
I’ve been Graham’s client since I launched my own Web site (or more precisely, since Graham launched it for me) a few years ago. And though I always knew she had another life, she rarely talked about it. We communicated only by e-mail and I knew that even if I never heard from her during business hours, once an evening had passed (and she had been home), the changes to my Web site would miraculously appear. To my mind, she had discovered the perfect slash to complement her job. Her Web work is virtual, portable, and flexible, a desirable triumvirate for any slash; and even though she started it up to make extra money, she’s discovered that she enjoys it. “I get to use a different part of my brain. It’s sort of like people who tinker in their tool shed on the weekend. It feels kind of like that because you’re making something. And one of the best things,” she said, “is that you never get production block the way you get writers block.”
Graham’s sideline works for some other reasons as well. Because she’s an entrepreneur with a Web business, the business gives her a sense of autonomy and control often missing from a job. She has also built up some technical skills in her business that have helped in her career. Recently Graham took a new position at the New York Times. When she made that move, it turns out that the experience she brought from her Web business was just as valuable as the skills from her editing job. When I last spoke to her, she was steeped in the learning-curve phase of a new job, putting in long hours, and therefore not so interested in bringing on new clients. But she says there is no reason to give up the business.
If Graham experienced the side gig as a pleasant surprise, Ann Guttman won the modern moonlighting jackpot. Guttman, a professional musician, got into selling real estate as the proverbial backup. By her mid-twenties, Guttman, now fifty-one, was at the top of her game as a performer. She was playing her French horn regularly with the New York Philharmonic, the Long Island Philharmonic, and in the pits of Broadway musicals. At about the same time, a musician friend with a touch of the pragmatic began to rib her: “Look around. See any women in their fifties doing this? And if you do, do we want to be them, schlepping our instruments from gig to gig?” That teasing, coupled with the low periods of waiting between those prestigious freelance jobs, made Guttman wonder if it might be wise to nurture another career alongside her music.
Following the advice of all career experts, she looked to her interests. She was president of the board of the apartment building where she lived and decided that dabbling in real estate sales might suit her. Nearly twenty years later, her real estate career is as much her identity as her music. Initially, she always said she was a musician when she met new people, but over time that changed. She now relishes her role as a senior manager in a large real estate firm, mentoring the younger associates and enjoying the thrills of helping people find the perfect home.
Just two years ago, her life took a sudden twist when she contracted focal dystonia, a debilitating illness that often strikes musicians and others who overuse certain muscles. Guttman went through an excruciating period, dealing with both the pain of the disease and the emotional turmoil of retiring as a musician. Then, just around the time she was coming to terms with that, she was given a promotion at Coldwell Banker, where she now manages one of its busiest offices. “I feel so lucky. At a stage of life where I could be mourning this loss, I don’t just have a fallback job, I have a career I love,” she told me.
Guttman’s experience shows that while you can never know when a job will turn into much more than that, you can stack the odds in your favor. Guttman didn’t become a real estate agent solely for the promise of a good income. She chose it because she loved talking real estate, meeting new people, and getting the chance to visit all kinds of living spaces. This kind of self-awareness usually leads to smart career choices. But so many people don’t bother with that kind of thinking when they are focusing on how to pay the mortgage.
Guttman isn’t the only performer who’s figured out that real estate is a very slash-friendly sideline. In New York City, where she lives, real estate has been touted as the “new waiting tables” for some time. This quote from an article in the New York Times makes light of the ubiquity of the actor/Realtor combination:
In this city’s central casting office, few stock characters are more set in their roles than the slick and savvy real estate agent and the starry-eyed starving artist waiting tables. But increasingly, the two high-risk, high-gain professions are becoming a mutually beneficial hybrid. The real estate agent at the open house may have a familiar voice because he was selling shampoo on television the night before.2
The article goes on to explain the reasons that actors are drawn to real estate brokering: flexible hours; a low barrier to entry (taking a brief course and passing a licensing test is usually all it takes); and the appeal of a professional rather than service-oriented job, among others. The phenomenon isn’t limited to performers. Entrepreneurs are also widely represented in the ranks of part-time brokers, as are parents looking to keep their fingers in the work world during a period of hovering near home.
Working as an agent is only one avenue in real estate. Investing or refurbishing properties, becoming a landlord, or even running an inn or hotel are other ways that slashes use real estate to complement other pursuits.
Robert Sudaley, forty-four, has been an earth science teacher in middle school for more than twenty years. He became a teacher out of a desire to share his passion for education, but over the years his enthusiasm waned as he became frustrated by the aggressiveness of parents and the pressure to assign higher grades. Still, early on he realized that teaching was a career with a lot of tradeoffs. “Teachers may not make a lot of money,” he told me, “but the structure of the job affords a lot of opportunities because (1) you work limited hours; (2) you have summers available to do other work; and (3) you have a guaranteed annual pay increase as well as a secure income, which is attractive to lenders.” In his early years as a teacher, Sudaley enjoyed the hours and lifestyle of the teaching life. He stayed after school coaching the volleyball team and tutoring students in math and science, all of which came easily to him and brought in some extra income. During summers, he worked as a leader on cross-country bus trips, getting paid while touring the United States. After about a decade of teaching, he started to understand the economic value of the third point—the benefit of having a guaranteed income when buying property.
Sudaley lives on Long Island, New York, and in the summers he would drive around the Hamptons looking at houses. He already owned a house in Huntington, near his school, but he wanted to own a second home near the beach. Everything he looked at was beyond his reach, until he decided that he would buy a plot of land and try to build a house on his own. Sudaley isn’t an architect or a builder, but he knew he was good with numbers and following a budget, so he hired a builder and went ahead. When the house was completed the builder happened to need a place to live for a while, so Sudaley rented it to him. The next summer, he had another tenant. All along, Sudaley was watching the housing market rise. He sold that house after the second summer season and used the proceeds to get to work on another house.
Managing his properties soon consumed more and more of his time. Since school let out at 3:00 p.m. (and he had given up all after-school activities), he was able to focus on his real estate projects in the afternoons; he also could work full-time during vacations and summer months. As his own boss, he scheduled meetings with banks and lawyers around his teaching job. And then finally, in the year I met with him—the seventh of his slash arrangement—he had decided to take a one-year leave of absence because his business grew so big that it needed all of his time.
I asked him whether it was hard to be his own boss in one corner of his life while adhering to very strict rules in another, wondering if that shift was a difficult one to manage. “I’m so used to the rules I’m supposed to work under as a teacher,” he explained. “I just know what’s expected of me. But my success outside of school has empowered me within the school. When I sit down with parents, during union negotiations, in whatever context, I talk from a position of strength. It allows me to say things that other teachers often won’t say, things people are afraid to say. I teach in an affluent community and as homes go up in value to millions of dollars, I’m willing to fight for our raises. I’ve learned that if you don’t stand up people will walk all over you.”
Sudaley says his experience as a builder has increased his confidence in addition to expanding his bank account. He now wants to teach others how to follow his lead. Sudaley believes so strongly in the idea that all teachers (and other civil servants) should supplement their income by investing in real estate that he has self-published his book, Financial Wellness for Teachers, explaining his philosophy. Sudaley plans to be the pied piper of teacher slashes.
Sudaley’s story is interesting from the flipside as well. Teaching, in its many forms, is about as slash-friendly work as you can find. In Sudaley’s case, teaching was his starter profession. The security and steady income from teaching allowed him to develop his real estate investments. But just as often, people come to teaching as a part-time post to complement something else they are doing.
Sometimes, the ideal slash isn’t just one activity, but rather a collection of them. Victoria Matlock, twenty-seven, left Salt Lake City to try to make it in New York as an actor and has been working on building up a few businesses to offset the uncertainties of an acting career. Even though Matlock has had some early signs of acting success, she says she was raised to think about her fallback options. So, she followed her father’s advice and majored in computer science. Now she’s grateful she has the degree because it has allowed her to bypass the restaurant work route that she says she isn’t cut out for.
Her computer background led to her first slash—building Web sites for actors and others in the theater community. In addition, she works as a photographer, specializing in actor headshots. She’s also started to design a line of handmade purses, which she sells through her personal Web site. Matlock has been able to support herself through these budding businesses for the past few years. Equally important, she enjoys everything she does. In fact, she told me that if she died tomorrow, she’d be content with what she’s achieved. That’s a big declaration for an actor on the rise in the most competitive city in the world.
A key ingredient in Matlock’s happiness is that each of her “backups” involves creative work and keeps her connected to people in the arts. “It helps me to work with people who are interested in what I’m interested in,” said Matlock. “It wouldn’t be as much fun to me—actually it would feel more like work to me—if I didn’t. The best part is that I make my own hours; I find that working for someone else or in part-time jobs becomes intrusive. Even if I became a big star on Broadway, I might still like to take photographs and build Web sites. They’re both something I enjoy doing. Though they’re side gigs, I think of them as businesses and intend to nurture them and help them grow. I’m investing in upgrading my equipment to professional standards, and I’ll take a class or two when I can afford to. I’m a bit hesitant to advertise because I don’t want any of these businesses to explode and become my full-time job. Word of mouth seems to be working fairly well for me. But if the time comes when I need to advertise, I will.”
Grace Lisle-Hopkins, a photographer, was frustrated after several years of moving from temp job to temp job, only to move on when the inevitable happened—she’d be offered a full-time job. That’s great, if you want a full-time job. But for Lisle-Hopkins, thirty-two, jobs were only a means to an end. So she would quit periodically to focus on her art. Finally, she realized that the way to end that cycle was to find a job that followed that rhythm—a job where she could work for a few months straight and then have an expanse of time big enough to get some of her own work done. It turns out that academia was the answer.
As Assistant Dean of Admissions for the School of the Museum of Fine Arts in Boston (where Lisle-Hopkins studied), she works about thirty hours a week, accruing enough hours to take off all of January and then from June through August. The job offers three valuable benefits: (1) expanses of time to work on her art and organize shows; (2) travel to conferences, which affords lots of opportunities to take photographs; and (3) health insurance, the Holy Grail of an artist’s life. Another nice piece of the equation is that Lisle-Hopkins works for a Boston institution, earning a Boston-based salary, but she lives in Maine, where the cost of living is significantly lower. For some extra income, she also does administrative work for a library, which also slows down in the summer.
Bonnie Duncan, a teacher/dancer/puppeteer, is married to Dan Milstein, the computer programmer/theater director from chapter 1, and the two of them have talked a lot about what it means to live slash-filled lives. Duncan, thirty, looks at the three different things she does the way a money manager might look at a balanced financial portfolio. Dancing is the high-risk, high-reward activity. It is extremely challenging, but it brings her the most pride and satisfaction of all the work she does. Teaching is the safety net, the work she was educated to do so that she would have a way to support herself. Luckily, she also loves it; but working with young children (whom she teaches to read using drama techniques) would be draining if she did it full-time. As an artist in residence, she works a part-time schedule, splitting her time between various schools that offer the programs she creates. When she needed money (as in before she met her husband, whose higher earnings give her some freedom), she took on more teaching hours. In the future, if she ever needed to support herself, she would add more teaching to the mix.
Dancing and puppetry are artistic expressions that complement each other nicely. Dancing is generally the thing Duncan mentions first and the profession she most identifies with. (She is a dancer with Snappy Dance Theater, a modern dance company that blends theater and dance with acrobatics, puppetry, and martial arts.) Making puppets fuels another part of her artist identity. “I think I wanted to identify myself as my own individual art-making person when I’m not dancing,” she explained. “And with puppetry I can do it. Because I can do it in my living room. I can do it by myself. I can do it in small venues. And I don’t have to be in tip-top physical shape. If I get injured or if the company falls apart, I’m self-sufficient. And that’s what I think I’m figuring out as I get older. That what is important to me, more so than touring the world or being the best, is just making art that satisfies me.”
Everything Duncan does is seasonal and cyclical, with busy periods and slower periods. Occasionally, she has to rejigger her schedule, like when she delayed the start of one of her programs with her students so that she could travel for three weeks to take part in a workshop for artists in Florida. “It really wasn’t too difficult,” she explained. “The schools love having working artists teach the students and they recognize that to do that I need to work on my art.”
How many times have you said to yourself, “Gee, I’d really like my job if I could only figure out a way to do less of it”? Geoff,* thirty-six and a lawyer/actor-director, seems to have figured that out. I met with him at the offices of Weil, Gotshal & Manges, the law firm he works for in New York City. Aside from the orange messenger bag near the window and his funky sneakers (a suit was hanging on the door, presumably for client or court appearances), he looked the part of a typical lawyer. But unlike the other lawyers at his firm, he has another job. Whenever he’s not at the firm, he’s working as a theater director.
“I always enjoyed practicing law, particularly engaging in intellectual debates and parsing words and all that kind of stuff, but it was never the center of my pleasures,” Geoff told me. He became a lawyer for the same reasons so many people do. In fact, as he told me his story, it reminded me of how I felt about my legal education and the time I spent practicing law—interesting on some levels, intellectually stimulating, but failing to provide a deep sense of fulfillment.
After law school, Geoff spent a few years traveling and then settled in New York. He started devoting time to writing, first short stories and plays and then moving into freelance journalism. Along the way, he got interested in acting and went to acting school, where he discovered he had some talent. That led to directing and eventually a job with the school of the Atlantic Theater, where he directs several student shows a year. All the while he didn’t focus on a career path in the law; instead he took temporary legal jobs to help pay the bills, or, more accurately, to allow him to enjoy the trappings of being a corporate lawyer while working as a director. Writing came easily to Geoff and he applied that skill to preparing legal briefs. Having a marketable talent and taking great care in his work distinguished him from other candidates and made him desirable to temp agencies.
One of his placements was with Weil, Gotshal & Manges, who liked Geoff so much, they made him an offer to join the firm as a part-time employee, working by the hour. The work is plentiful, which means he can modify his hours depending on how much he wants to work. And since his work consists completely of writing legal briefs, it’s portable. He pointed over to the cell phone, BlackBerry, and laptop on his desk. “With these three things, there’s no difference between me sitting anywhere on the entire planet Earth with an Internet connection and sitting here. Most days, I come because it’s quiet, they have all the office supplies, and I have a secretary.”
What he’s traded by working the way he does as a lawyer is a certain amount of career advancement. “I’m not up for partnership consideration, obviously, because that would be absurd,” he told me. That’s just fine with him, because he wouldn’t accept that offer if it were made. His theater work comes first, and though the law is stimulating and has allowed him to buy a house and enjoy other financial goodies, he’s got a plan to shift full-time to theater at some point.
Geoff has found a way to practice law that works for him. And one of the main reasons he enjoys being a lawyer is that he isn’t doing it full-time. The legal field isn’t the only profession where this kind of arrangement could exist. So many professional-sector jobs—from management consultants to bankers and engineers—could support the same setup. If you can imagine negotiating a part-time arrangement to spend more time with your children, why not imagine doing that to make room for some kind of work? Come to think of it, people who go part-time for child-rearing reasons face increased expenses at home, but if you go part-time to pursue a slash, there is actually the promise that your slash will become income-generating even if it’s never as lucrative as your primary vocation. (Geoff says he makes about half his law firm salary in the theater.) The key is to build enough skills and contacts so that if you ever wanted to shrink your working hours, you would be able to negotiate a part-time arrangement with an employer or you could work for yourself as a consultant. Chapter 8 will give some tips for how to do this.
One of the only people who asked to use a pseudonym for this book is a woman I’ll call Julia Lloyd. She had a high-powered job as a marketing professional while trying to build her own interior design business on the side.
After five months of phone and e-tag, Lloyd, thirty-one, finally e-mailed to say she was ready to get together. I met her through a mutual friend so I thought she was making time for me in her hectic life out of loyalty to our mutual friend. But I realized that part of the reason she wanted to talk to me was that she was trying to make sense of the bifurcated life she was leading. As I questioned her about the various layers of her identity, she was hungry for insights I could share about how other slashes managed to keep it all together.
High energy and bubbly, Lloyd welcomed me into the restaurant she chose for lunch and guided me through her favorite dishes on the menu. She took control even though I was the person who had asked for the meeting. Throughout our lunch, which covered everything from juggling jobs to bicoastal living to dating and children (where and how to fit that in), Lloyd glanced down every few minutes at her Treo, positioned between us on the table. She explained, “The technology is key” in allowing her to meet the responsibilities of her high-powered job while building up her own interior design business. The trickiest part: her clients have no idea she holds a day job and her colleagues are in the dark about her business. She didn’t plan for this kind of career.
As part of business school recruiting, Lloyd accepted an entry-level marketing job for a major consumer products company in New York. While most of her classmates were enjoying the relatively carefree life of business school nearing its close, Lloyd was restless to get into the real world even though her job didn’t start until the following September. Lloyd had always been interested in design and now that she had some time on her hands, she explored the fields from many angles. She threw herself into working on a television pilot for a reality television show (her idea, “Bachelor Pad Makeover,” didn’t sell, but Lloyd was onto something; about a year later, Queer Eye for the Straight Guy put design reality television on the map). Next, she found herself working on the remodeling of a friend’s home, and before long other design projects started flowing in—a room for a prestigious design show; a penthouse apartment. With no formal training but a good deal of artistic flair and savvy, a business was percolating.
Still, she went through with her plan to move to New York and begin the corporate job. “The job allowed me to move to New York City. With my own business, I couldn’t even rent an apartment. You need years of tax returns. It’s just a tough city to break into as an entrepreneur,” she said. The job also provided other benefits—health insurance, a community of other young professionals, and a structure—somewhere to get up and go to every day. “It also let me use the skills I acquired in business school.”
At that stage of her business, she spent a lot of time running around to design centers to pick up fabric swatches after hours and during lunch. “Imagine Martha Stewart’s early days,” she said. “There was a lot of just baking pies.” Her plan was to stay at the job long enough to sharpen her skills in the corporate world. She told me she’d know the right time to move on, which would be when her business was big enough to support a staff.
Meantime, the day job she described didn’t exactly win points for slash-friendliness. “If they need you for fourteen hours, they have you,” she explained. “The pace is so fast—if you miss an hour, the e-mails just pile up.” Because she noticed that the company made accommodations for colleagues with small children (and because she doesn’t yet have a family of her own), Lloyd justified the rare instances she responded to a client during business hours by treating her business as a “family substitute.” Still, she said, she never used company time to handle a client matter without working through lunch or staying late to make up the time. At the close of our lunch, she confessed that she couldn’t sustain her current pace indefinitely. “I’m in a transitional phase, a straddle period until I can dedicate myself fully to my business.” Before she went back to the office, I asked her what kind of personality a person needs to live her kind of life. “You need to be completely insane, almost like a chameleon, and really driven—knowing why you’re doing it—because it’s really tiring.”
What Lloyd described was working for her, but just barely. When I caught up with her about a year later, her plan had materialized. She had left the corporate job and was now firmly rooted in her own business, though one with many strands. First, there’s the straight interior design work for clients. She is also writing a book, working on a pilot for a design-oriented reality television show, and in discussions with a major newspaper about writing a column. “Basically I’m still a slash. But now the slashes are all for me,” she said. “I can’t imagine doing just one thing.”
Lloyd’s story, like so many in this chapter, underscores the importance of remaining flexible and knowing when it’s time to shake things up. She held on to her corporate job long enough to hone certain skills and bridge a financial gap, but she was willing to adjust as soon as she felt her business was ready. She still approaches her career with a slash mind-set. Whenever I call her to check in, she tells me about a different mix of projects that is pulling her in different directions. The ability to move easily between diverse projects—crucial when she had both a job and a business—is serving her well as she now pursues diverse opportunities all under the banner of her own company.
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* He asked that his last name not be used.