One Person/Multiple Careers: A New Model for Work/Life Success

Chapter 1

I'm drawn to computer programming because it involves solving puzzles and the beautiful abstract understanding of complex things. It's what I spend a lot of my free time reading about. But after a while that work can feel arid, and I get really excited to get back to the theater where I work with people, telling stories, bouncing things around. But rehearsals are all vagueness and uncertainty, with all of these egos. And after a while of that, it becomes compelling to go back to a place where things are clean and simple. With the programming, even though I have collaborators and clients, in the end there's a sense that's just mine. There's something really nice about just solving a problem in my head that doesn't depend on if the paint color works, everyone remembers their lines, and the audiences like it. Basically, if I weren't doing both things, I'd get bored and antsy.
-Dan Milstein, computer programmer/ theater director

Dan Milstein, thirty-nine, moves between his work as a computer programmer and a theater director with elegance. By pursuing his multiple passions, his career nourishes him. But like most slashes, he has built his unique career over time, tweaking it as he goes along. When he spoke the words above, he was at a resting place, observing what was working to keep him in balance for that moment in time. Milstein's approach is an appealing way to think about a career, and about a life.

Milstein was always interested in lots of things. As a high school senior he took math classes at Princeton University at the same time as he edited his school's literary journal. When he arrived at Yale, he focused his coursework on math and computer science but gave all his free time to the theater. "Yale was the ideal creative home for me," he said, "the sort of place where all these high achievers would give thirty to forty hours a week above their coursework to some extracurricular activity. And the people who thrived were those who ran things on their own, which turned out to be perfect training for a life where no one gives you a job and tells you what to do."

He toyed with graduate school and was even offered a fellowship that would have paid for continuing his education in math and computers. But the computer department wasn't where his friends were, and such a focused course of study didn't seem like it would be satisfying. "It just didn't feel like a full life," he explained. Milstein also had a hunch that he might no longer be the star performer at the next level and that only the stars in academia had control over their lives. "I guess I didn't love it enough to think that I'd be satisfied doing the work if it meant living anywhere I was offered a job."

For several years after college, Milstein had a period you could easily refer to as floundering. He settled in Boston and got a job in a coffee shop, working the late afternoon shift so that he could devote the mornings to writing short stories. The writing didn't take off. "It was a period of lots of self-doubt," he said. "I wasn't sure if I could consider myself an artist, yet it was so compelling to me to be an artist."

Around the same time, he decided to use his computer background to get a day job that was more likely than his job at the coffee shop to pay off his student loans. He tried his hand at various jobs in the computer field and was disenchanted by a lot of what he saw-people who had become experts in doing one thing and were paid to do just that one thing, and jobs in tech support that weren't at all creative and where the staff looked universally unhappy.

Slowly, the tide began to change. It was the early nineties, the heyday of the dot-com boom, and programmers were sought after. Gig after gig materialized for Milstein, often through his coffee shop contacts. In one instance, he was literally hired off the street when he ran into a friend who brought him aboard a startup. "You know HTML. Come with me," was the basic pitch. Around the same time, Milstein abandoned his attempts to write fiction and turned his attention to the theater, from which he had drifted since his college days. Once he began directing plays, he knew he had found his creative home.

At his day jobs in the technology field, however, Milstein grew tired of worrying that his bosses would catch him on the phone stealing time to manage crises with the plays he was working on. He also realized he needed to work for and with people who valued the end result of what he did enough so that they didn't care how many hours he worked each day or where he did the work. Fortunately, work was so plentiful that Milstein realized he could be employed quite well without a "job."

He partnered up with a buddy and began a consulting business. Fast forward to today. He's working about thirty hours a week on programming (largely dedicated to a business he's helping to create) and up to sixty hours a week on Rough & Tumble, a theater company he founded-although the hours in any given week can vary wildly. The income split between the two hardly reflects the way he spends his time (he makes about $1,000 a year from his theater company and about fifty to a hundred times that from his consulting work). He identifies equally with each.

One of the reasons Milstein's setup works for him is that he is in control of both aspects of his life. In his artistic life he writes, directs, and produces what he likes to call "theater that doesn't suck." On the theory that theater should be accessible and fun, Rough & Tumble's plays involve physical comedy and often employ innovative approaches to language and expression. (One play I saw was an improvised Austin Powers-type caper in which "blah blah" was the only utterance by the actors-it was still possible to understand everything happening among the characters.)

Having two fully developed careers may sound like a recipe for workaholism, but Milstein is as passionate about his time off as he is about his twin vocations. For years, he took summers off to travel, and he's always made time for ultimate Frisbee and other hobbies. His philosophy is that being well-rested and well-rounded is part of what makes him excel at his jobs.

Milstein believes he wouldn't be a good fit for a client who would be impressed by how overworked he is. "There's a certain culture in programming where managers think they are doing a good job if everyone is working overtime," he said. "After being a programmer for ten years I've learned that is sort of a big lie. The most productive team is the one that closes down at five every day and has a clear head in the morning to see their way through problems. It's more like an art form than building a house. If you have a problem with a novel or a play, the solution isn't necessarily to write more pages. Often what you're doing when you're working on a novel or a play is looking for that burst of insight. And you won't get those unless you are fresh and unstressed."

Whether or not they are actual entrepreneurs like Milstein, serving as their own boss in their various endeavors, most slashes show an entrepreneurial streak at the heart of their stories. These are the kinds of people who are not satisfied to rest once they've achieved competence or milestones in a given field. They are inherently curious, eager to engage and immerse themselves in a multitude of areas. The notion of finishing up one thing and moving on to the next doesn't seem to exist for these folks. Instead, it's about building a complex identity, adding a new layer with each slash. Milstein's choice to abandon serious scholarship in computers is also emblematic of slash thinking; by keeping computers in his life in a less academic way, he was able to make room to pursue other things that are important to him. Sometimes removing yourself from the fast track, or just slowing down a bit, is an ideal way to allow another passion or vocation to flourish.

Mary Mazzio, forty-four and an Olympic rower-turned-lawyer/ filmmaker/mother, can't remember a time when she wasn't pursuing multiple interests at once. She attributes it to an unusually high energy level. "I was a slash to the tenth in high school and college and always wondered if that would lead to mediocrity," she explained in her signature rapid-fire speech. When she recited the list of activities she pursued in those years-ballet, elocution, cello, piano, tennis, swimming, "anything you can throw a lesson at"-she attributed it to her Italian-American dad and Irish-American mom: "They wanted to produce children with a higher pedigree, almost to an obsession." Mazzio didn't disappoint.

She went to law school directly after college, where she had dedicated a lot of time to rowing. During a semester in France, she joined a local boat club, and after law school, while working on successive fellowships in Yugoslavia and Korea, she found her way to rowing communities, training among (and often coaching) the best of each country's female rowers.

Back in Boston, Mazzio began to work as a real estate lawyer in a large firm. By then she knew she was a good enough rower that, with proper training, she could compete in the Olympics. She pursued both her legal career and the rowing (with a lot of support and accommodation from her law firm), and in the summer of 1992 she rowed in the Barcelona games. She didn't take home a medal, but that experience gave her the validation that she was a serious athlete, and it gave her a sense of commitment that has traveled with her in all her subsequent endeavors.

After the Olympics, Mazzio put aside the competitive oars, but the promise of a full-time legal career didn't appeal to her. "I was a lawyer, but I never thought of myself as only a lawyer, which seemed so narrowly defined," she told me. At the time, she was spending a lot of time on pro bono work, helping displaced tenants get their homes back. It was gratifying at first, but after a while she felt she was hearing the "same stories with different faces."

"I got so depressed, I just felt like I wasn't making a difference," she said. "That prompted me to think bigger, about how I could impact change on a larger scale. I had always been profoundly moved by film ever since I was a little girl. The power was so overwhelming in a way that made you think."

Within months of returning from Barcelona, Mazzio enrolled in an MFA program in film and began studying "on the sly," taking mostly evening classes or daytime classes during a time slot that could be disguised as a long lunch. (She feared that if the firm's partners knew she was studying film, they would question her commitment to the law and it might affect her chances of being promoted to partner.) "I had the best secretary at the time," Mazzio told me, switching to a workingclass Boston accent. "'Mary is so busy,' she would say, protecting me from anyone who wanted to bother me."

She began writing screenplays with the goal of bringing new kinds of female characters to the screen. "I always thought the women in the movies didn't look like women I knew," she said. "They were gorgeous, but bland, insipid, and two-dimensional." Mazzio wanted to write about the women she knew, women who were "irritatingly smart," but who might have big thighs or be cranky with their periods from time to time-"basically real women with their whole range of characters and emotions."

Mazzio made some progress on the road to being a screenwriter. Several of her screenplays bounced around Hollywood and Mazzio had a series of meetings with the bigwigs. "All this stuff happened and then, in the end, nothing happened," she explained. "I kept feeling I was so close, but I wasn't really close at all." Concluding that the Hollywood odds were not in her favor, Mazzio took matters in her own hands. Ultimately, it was a true story-about a 1976 revolt by female rowers at Yale- that turned her into a filmmaker. She developed the idea in her classes, stepping up her work on it while home with her second child on maternity leave. "I was itching to get out of the house and those film classes were the perfect escape," she said.

Mazzio's legal background and connections came in handy during this period. Being a lawyer (and a female athlete) provided expertise in the film's subject matter, Title IX, the law enacted to bring equality to women's sports. And through her business relationships, she found both the technical experts and financial backers to get her film off the ground. Using contacts and knowledge from one career to build another is a common slash technique.

Having a supportive husband, who always encouraged her and who shared her philosophy on things like having a full-time nanny even when she was working part-time, was also very important to her being able to pursue her many passions. As she put it, "My husband knew I wasn't the type who'd have a home-cooked meal on the table every night."

Mazzio's maternity leave got her through preproduction on the film. By the time she returned to work, the film was in the middle of production. She had an inkling that her days as a lawyer were numbered. With two young children and two fullblown careers, Mazzio knew she was at the edge. "If I didn't make a change soon, something would suffer, not the least of which would have been my health."

Once the film was aired and press coverage began, Mazzio realized that she could resign from the law firm, the post she was holding on to to hedge her bets. As a filmmaker and a mother, she had as many slashes as she could handle, and because she runs her own production company she can control her schedule more than she could as a lawyer.

Leading a slash life often requires shedding a slash to make room for something new. For Mazzio, rowing and the law had run their respective courses, but each remains a fundamental part of who she is, as a mother, a filmmaker, and an entrepreneur. She's made films about athletes, mothers, the law, and even the intersection of these various themes. Her legal skills serve her well as a filmmaker.

If Milstein and Mazzio represent the arrival at a destination, Jenny Vacchiano, thirty-five, is the embodiment of the journey. Writers and artists almost always have "that thing they do until they don't have to do it anymore." For Vacchiano, that thing was painting houses. I met her just at the moment when she was trying to wean herself from a fairly successful painting business she had built up. "I'm feeling kind of scared," she said several times during our conversation. The goal was to get the business down to half-time to make more room for writing. With several short stories published and a novel in the hands of an agent, she was moving in the right direction-if only the money gig weren't so consuming.

Vacchiano fell into painting houses her first summer after college when she moved to California and needed some steady income. Painting houses (interiors and exteriors) was easy, temporary work for someone still in the wandering stages of life. And for many years, through a master's program in Boston and even after graduate school, painting was the ideal side job. "I just love painting a room a color, a really bold color, and seeing the before and after. When you're working with your hands, your mind can just go," she explained. "And you're keeping your body in shape rather than sitting at a computer all day in an office and coming home to write on top of it." Plus, she was able to work for a few months straight-the spring through fall, when business was plentiful-and save up enough to spend the winter months on her writing.

Once she settled in Denver, the painting work became so steady that she started her own business rather than just taking jobs from other people. For a while, she enjoyed the entrepreneurial feeling of building something for herself. But soon, managing a business that was not her passion discouraged her. When business was good, she could be painting fifty hours a week, which left her physically tired. It was also hard for her to switch from the painting to writing mind-set within the same day. "If I was mid-project, it was disturbing to return after a week of painting to a day of writing. Sometimes it took me a whole day to remember where I left off and find my voice again. I just started to resent the painting. Writing gives me a purpose and to not do it, I'd think 'this is my life, this is it.'"

Vacchiano knew it was time to readjust, but readjustments don't happen overnight. When we last spoke, she was in the middle of the transition, hoping to set up a life with more slashes connected to writing. She'd made the decision to take on fewer clients, focusing on single rooms and jobs small enough that she could do them without hiring other people. To compensate, she was copyediting, getting her feet wet in freelance journalism, and stepping up her teaching commitments at the Lighthouse Writers Workshop, a writers' community in Denver.

Her life as a painter has seeped into her writing, though. On the day I first interviewed her, the Denver Post published an article Vacchiano had written about a professional color consultant whom she met through her business. She's even made one of the characters of her current novel a housepainter. "Camille works in a library and she's fed up with where she is. Sick of her boyfriend. Sick of her job. Sick of her life. She goes off to the shore, paints the house she's staying in, and gets a painting job with a crew of guys. She likes it, just like I did when I first started out," she explained, then added, "As for me, perhaps I'll work in a library like Camille did before she got hooked on house painting."

Though Vacchiano enjoys the painting work, she hopes to get to a point in life where she can give it up completely. She's comfortable with the idea of having slashes, but she would relish a life in which all her slashes could be connected to writing, like the teaching and freelance journalism work she's now pursuing. It's all part of the constant tinkering that goes on in any kind of slash life.

Near the end of a group hike, a tour of an organic vegetable farm in Tecate, Mexico, I got into a conversation with Scott Sharkey, my guide. After a few hours of watching him, I thought I had him pegged. The ruddy-faced outdoorsman was all smiles and positive energy, awed and pleased by everything around him. Passing an open field, he pointed out a mama peacock protecting a new flock of chicks. On a dirt road, he shouted Buenos dias to the locals doing their brisk morning walks. I imagined he was in his late twenties, living in Mexico as a guide and fitness instructor at a local resort while figuring out what he would do with his life. As it turns out, he was in his mid-forties and for him, a life of wandering and using his talents for guiding and entertaining was an end in itself.

Growing up in Orange County, California, Scharkey knew he didn't want to end up like his father, who joined the navy to get an education, worked for one company his whole life, and, once married with children, fell into a routinized grind of work and home chores. Mowing the lawns on the weekends was his only brush with physical activity. Exercise was a memory of boot camp.

On graduating from high school, Scharkey seriously considered joining the police force, but after riding along with some middle-aged officers, he decided the men had no passion for what they did. He then focused on nurturing his talent for dancing and performing. In his twenties, he went to work for Disneyland, where his penchant for hamming it up with strangers made him a charismatic parade leader. Performing gave Scharkey a chance to travel-a stint in Okinawa, Japan, in the cast of a traveling musical; a sojourn in Argentina with another show; time in New York City, where steady work with flexible hours as a fitness instructor at high-end gyms allowed him time to pursue voice-over work and acting gigs. Ultimately, the combination of fitness training, leading hikes (like the one where I met him), and performing has allowed him to connect with people, remain youthful, and see the world. But recently he discovered he also has a knack for refurbishing real estate properties and selling them, a lucrative sideline.

For Scharkey, following his interests has led him to a place of balance-a life in which the journey and the destination are the same. He could never have planned the course he ended up on. The notion that you can't plan everything is a hallmark of slash thinking.

Carrie Lane, thirty-nine, a Pilates instructor/art consultant (and one of my oldest friends), is living proof of that. For most of her adult life, Lane followed a path that meshed with the expectations of her Ivy-educated peers. She studied art history as an undergraduate, took a series of internships and entry-level jobs at museums, and ultimately pursued a doctorate. Out in the world, she soon discovered a business opportunity in the large number of people who want to collect art but don't know where to begin. Thus was born Carolyn K. Lane & Associates, the consulting firm she founded with a twin mission: helping people make educated choices about art and helping up-and-coming artists find markets for their work.

Lane has always been athletic. Through high school and college she was a champion equestrian, competing in events on a national level. After a broken collarbone diminished her enthusiasm for riding, she turned to running, filling her free time with marathon training, scouting out races in other countries, and improving her finishing times. Next came mountain climbing. Then, a new form of fitness training, Pilates.

Like many people, Lane treated her work-the intellectual stuff she did with art-as distinct from her hobbies-those athletic pursuits that kept her fit and fueled her competitive spirit. People who knew her well often told her she would be a great trainer, but she felt she already had a career. With increasing frequency she started to wonder if it had to remain that way.

Around the time of the September 11 attacks, Lane was working with a private Pilates instructor; the exercises helped ground her in that time of turbulence. She was attracted to the theories behind Pilates, which uses specially designed pieces of equipment to increase core strength, enhance flexibility, and improve posture. One day it just hit her: coaching others in some kind of physical work had to become a part of her professional life. As she explained it, "With the art, I'm helping people and educating them. But I was feeling the intense need to help in a more hands-on kind of way."

The idea of putting her business on hold to develop a new slash was daunting, but she didn't overanalyze it. "I tend not to think too hard about things I want to do," she said. "I usually just move forward and then worry about how to deal with it later."

Becoming certified to teach Pilates is one of those immersion experiences, like basic training for the military or graduate school, when friends and family learn to do without you during your period of initiation. "During my training, I had to put everything, even a lot of my art stuff, on hold," she said. "I had to complete six hundred hours of training and wanted to do that quickly. Life was solidly Pilates for about six months."

Today, Lane is fully established in both vocations, with a parttime job at a health club, a small group of private Pilates clients, and her art business. She's busy, to be sure, but she rarely says no to an opportunity. In 2004, she was hired to write a scholarly book about the nineteenth-century American artist William Merritt Chase. That project, which occupies around twenty hours a week, will last for about three years. The challenge for Lane these days is deciding which of her slashes gets the most attention. "Sometimes I worry about spreading myself too thin, but it's cyclical," she explained. "When I have a new art client, my mind is preoccupied with art. But after a Pilates seminar, I'm reinvigorated by that and feeling more identified with my teaching. When I'm thick in the research for a Chase painting, the city could be aflame around me, but I'm stuck in the 1880s, wondering about the identity of a mysterious figure in a painting."

Though Lane often feels pulled in many directions, each of her vocations has benefited from the other. Many of her art clients originally met her through Pilates and vice versa. "Often, when a client in one work context hears about my other life, they are curious and want to know more," she said. Synergies like this are such a common part of slash life that an entire chapter of this book (chapter 7) explores those issues further.

One of the trickiest parts of writing a book about slash careers is that often I'd check in with one of my subjects some time after an interview only to learn that he or she had ramped up one activity and scaled down another, or added an entirely new slash to a seemingly full plate. Lapses of time could mean that someone was finishing up a campaign to run for office, in graduate school getting an advanced degree, on sabbatical to write a play, or taking a break from paid work to parent full-time.

Thus, having a slash career requires being comfortable with beginnings. Sally Hogshead, a branding expert/author/ consultant, refers to this principle as being the "dumbest person in the room." While nothing about Hogshead strikes me as dumb, she told me that's exactly how she felt when she went from high-flying creative director to fledgling author. "Nothing was handed to me. In advertising, it had been years since I had to make cold calls or explain why someone should hire me. But I was back at level one. I had to earn my credibility from scratch," she recalled. "I wrote a book proposal. People didn't like it and it got rejected. They told me career books didn't work like this. Anytime you're trying to add a new slash, before you even start to dip a toe into that, you have to get comfortable with the idea that people may not think you should move into that area. I collected so much evidence that I shouldn't be an author. I'm sure anyone who's leapt into a new zone goes through that. That's innate to the process. I hired a writing coach to help me do the proposal. She said, 'You don't have this whole writing thing down. I don't think anyone will buy this book.' I had been making my living using my writing skills for over a dozen years and I had shelves full of awards telling me I was a good writer. Still, when my agent first saw it, it took weeks for him to call back and then weeks to even comment on it. I created proposals for a living at the top agency in my field and I went through a heart-wrenching year-long process."

We all have those moments of dumbness, as Hogshead calls them. They're the times of trying on new identities and navigating new worlds. Herminia Ibarra's book Working Identity distills the process people go through when they shed one identity and take on another in the process of career reinvention. She observes:

Most people experience the transition to a new working life as a time of confusion, loss, insecurity and uncertainty. And this uncertain period lasts much longer than anyone imagines at the outset. An Ivy League Rolodex doesn't help; even ample financial reserves and great family support do not make the emotions any easier to bear. Much more than transferring to a similar job in a new company or industry or moving laterally into a different work function within a field we already know well, a true change of direction is always terrifying.

Despite those feelings of "confusion, loss, insecurity and uncertainty," the only way people discover new identities is by facing down those feelings and moving past them. Marco Canora, a chef/restaurateur, talked to me about this when I met with him at his New York City restaurant Hearth in the summer of 2005. Canora was at a crucial point in his career, figuring out what to do next in a time when being a player on the restaurant scene seems to require the amassing of slashes.

Canora became known in foodie circles after he helped launch the successful restaurant chainlet Craft. But a good track record doesn't seem to be enough for someone to be considered one of the greats. Today, successful chefs are marketing empires, breaking out of the kitchen to build their brands by teaching cooking classes, writing cookbooks, and launching food-related product lines. Canora spoke candidly about the challenges of building a career in the age of celebrity chefdom.

To the outsider looking in, Canora was sitting in a coveted spot: he and his restaurant were attracting media attention at a steady pace; he had recently been invited to give master cooking classes in Melbourne, Australia; and he was being courted by agents for books and other media projects. In short, he was on the celebrity-chef fast track. Yet when we spoke, he was filled with apprehension. Restaurants thrive and die. There is pressure to open the next place, to expand the empire, to break into television and radio. "What if I make the wrong move?" he wondered aloud, in a moment of unguarded musing.

So many people avoid growing their careers for fear of being in just this place-giving up the known, the secure path, the steady income, the thing you know you're good at. The beauty of taking on a slash is that you can make a foray into new territory and still embrace the established career that gives you confidence, income, or whatever else it is that makes you want to continue doing it.

GETTING TO SLASH ////

• An entrepreneurial streak is at the heart of most slash stories. Even if you work for someone else in some areas of your working life, building a slash career means you are taking charge of the mix of things you do.

• Sometimes taking yourself off the fast track in your primary career opens the door to building a second one. As an added benefit, you might avoid the burnout and narrowness of focus that often plague the highest achievers in a given field.

• Contacts and knowledge from one career can give you a leg up as you build another.

• Leading a slash life often requires shedding a slash to make room for something new; be prepared for a life of constant tinkering.

• Get comfortable with the idea that you can't plan everything.

• Synergies between various vocations are a common part of slash life; when they emerge, recognize the opportunities they afford.

• Embrace being a beginner. We are all insecure and filled with doubt when taking on new challenges. The only way to overcome those feelings is to acknowledge that they're part of the process and move past them.