The Art of Reinvention

From fact-checker to RACE-CAR DRIVER
MICHELE SHAPIRO, 38, NEW YORK CITY

EXIT SIGNS: I used to be a nitpicker. As the head of a research department at a glossy national magazine, I had to make sure every single fact in every single story was correct. So I toiled away till all hours in my windowless little office, checking things like whether it had indeed rained on a particular day 10 years ago as a story had stated. At night I'd go home and lie awake, fretting that I'd misidentified an Olsen twin. Then, one evening in 2003, when I was sweating over a late-breaking story, I decided: Enough. I thought about what would make me happy; I allowed myself to think freely, with no restrictions. And I realized I'd been dreaming about racing cars ever since I was a kid. Growing up, I'd kept a framed picture of a Lamborghini on my bedroom wall, and I'd always read Car and Driver — along with Vogue.

MAKING THE SWITCH: I decided it was time to hit the road. So I signed up for a race across the Sahara in Morocco that I'd read about online — and I haven't stopped since. My rallies have spanned the globe: I've sped from London to Ibiza (won that one) and from Beijing to Paris in a vintage 1930 Chevrolet (yup). I arrange for sponsors to help with costs and cars, and I work at a New York University think tank to support my habit. This year I'm launching a Website called Drive Like a Woman, with news on everything from female taxi drivers in Tunisia to Hermès driving gloves.

WORD TO THE WISE: It's amazing how much easier it is to pursue your dream when you remove certain obstacles — like common sense.

—as told to Abigail Pesta

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From ad copywriter to NOVELIST
ELLIOTT HOLT, 35, NEW YORK CITY

EXIT SIGNS: The first time I sold a script for a shampoo commercial and watched as six figures were spent on something I'd scribbled at my desk, it was thrilling. But by the time I was 29, the thrill was gone. Copywriting is painfully repetitive, sapping your creative juices as you try to come up with yet another way to sell face cream. I'd always intended to be a fiction writer but had restricted that pursuit to nights and weekends — the margins of my busy life. And I was afraid to quit my day job: I had great health care and a 401(k), and I was able to support myself — and my weakness for bespoke stationery, Phillip Lim cocktail dresses, and hardcover books.

GETTING SCHOOLED: I decided to go for my master's in fiction. Two nights a week, I snuck out of my Manhattan office building early to head to Brooklyn College. I loved every second — reading stories on business flights to L.A., excusing myself from conference calls to jot down some dialogue before I lost it. I was so busy, and I wasn't sleeping, but I never had more energy in my life. Whenever I hung out with my writer friends, I felt completely at home. And, cheesy as it sounds, when I wrote, I felt authentically in my own skin.

MAKING THE SWITCH: After I finished my degree, I asked my boss if I could cut back to a three-day week — I'd keep my benefits but earn 40 percent less, and I could work on a novel. "Your book is your baby," she said, and took my case to HR, arguing that my writing was the moral equivalent of motherhood. They signed off. A year later, I quit entirely.

LIFE ON THE OUTSIDE: It's scary, especially since publishing has been hard hit by the recession. But I was a good saver, and I'm renting my second bedroom to a friend from high school and doing the odd voice-over for cash. I've had people tell me they envy me because I've figured out what I really want to do. The truth is that I'm often terrified, and I wonder whether I've made a mistake. But even as I worry that I'm going to burn through my savings without a solid plan, I feel lucky because I love the work.

—as told to Lauren Iannotti

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From IT manager to THEATER ASSISTANT
ANN MUNDORFF, 30, NEW YORK CITY

EXIT SIGNS: In my first job out of college, at Hewlett-Packard, the company moved me from Colorado to San Francisco and offered me a good salary with a signing bonus. Within five years, I was managing teams in Malaysia, Italy, India, and the U.S. But the stress level was high — I'd come in to 400 e-mails each day. It was on a 5 a.m. conference call with India that I thought, What am I doing this for? So I quit my job and moved across the country to live with my cousin and her husband in Queens, NY, while I figured out how to combine my business background with my love of theater. My parents freaked; even the movers were like, "You're moving from San Francisco to Queens?"

WORD TO THE WISE: You're never too old to start over. It was the joke at the theater that I was the 27-year-old intern. But you spend so much time working that you might as well do something that you're passionate about. Now I'm a general management assistant at the Manhattan Theatre Club, learning about the day-to-day operation of shows, artist contracts, music rights, how to option a book for a play, how to commission playwrights, and how the whole creative team comes together.

THE WHAT-HAVE-I-DONE MOMENT: I took a $70,000 salary cut to do this — no more $300 salon trips. My first two internships paid zero, and once, for an opening-night party, I had to cart cases of hamburgers in a trash bag on the subway. I was like, Wow, I used to manage people, and now I'm delivering White Castle.

THE PAYOFF: I feel more at home in the theater and with the people in it than I ever did in the corporate culture of H-P, which was like the movie Office Space. Even budgeting has been good for me. I'm a lot happier in my life, and I love that crazy butterfly feeling I get watching a great show that we produced. It's like I'm up there with them.

—as told to Jessica Henderson

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From retail associate to COFFEE SHOP CO-OWNER
SONDRA POWELL, 33, LOUISVILLE, KY

EXIT SIGNS: After graduation, I was a sales associate at an upscale French antiques store. I wore little wool suits and did clerical and shop work, but after five years, I realized it wasn't going anywhere. My now-partner Christopher had the idea for a drive-through coffee kiosk, because you can't just grab a cup in Louisville — you have to find parking, walk in, and run into somebody from high school you haven't seen in eight years. I love all things coffee, so we went for it.

GETTING SCHOOLED: I stayed on at the antiques shop for a year while I researched funding and traffic patterns — stuff you'd never think about, like finding a location on the "morning" side of the street, on the right side headed downtown with the commuters. Christopher and I took a course in Idaho on buying and importing beans and learned how to work the equipment. We brought a French press on the drive there and stopped and talked to any roaster that we could find along the way.

THE WHAT-HAVE-I-DONE MOMENT: We bought a used roaster online for half of the 10 grand a brand-new one would have cost. But we did so with a credit-card check with a superhigh interest rate. When we returned from picking it up, we found out we'd been turned down for a personal loan we were counting on.

LOCATION, LOCATION, LOCATION: An old gas station came up for rent, so we cleaned it up and painted it orange. We opened Jackson's Organic Coffee at 6 a.m. on a freezing cold day in January, brewed a pot of coffee, and turned on the neon sign, hoping that people would come. Our first customer pulled up: a teacher who said he'd been waiting for us to open. We probably had 20 people that day; now we have around 200. Jackson's Organic Coffee is sold at local markets and Whole Foods, and to some of the city's top restaurants. We're in talks with a brewery to make a coffee stout from it. The Rolling Stones even drank it when they played the first concert ever held at Churchill Downs.

WORD TO THE WISE: A lot of places are closing right now, thanks to the economy, but we like to say that if you can make it right now, you can make it anytime. You have to be scrappy, do everything yourself (I joke I'm the best-dressed delivery person in town, making coffee drops in high heels), and stay positive, because just when you think it couldn't get any more stressful, something breaks.

THE PAYOFF: I wake up around 4:30 a.m. and hit the ground running; in my old life, I wouldn't get home from a night out until then. I used to sit at a desk and take messages — now I remember how hundreds of people take their coffee and their dogs' names. I'm just so proud that people want to buy something we made, and that they're rooting for us. We had bumper stickers with our logo printed, and in the beginning I'd see one and could name which friend's car it was on. Now I'll spot one and say, "I don't even know whose truck that is!"

—as told to Jessica Henderson

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From software engineer to SOCIAL-ENTERPRISE MARKETING EXEC
GLADYS KENFACK, 28, SEATTLE

EXIT SIGNS: After five years writing software at Microsoft, my job had grown predictable. Each day I'd go in knowing what I had to do, what deadlines had to be met, what milestone I was expected to hit that year. I looked at my growth and what I wanted to get out of my career and saw diminishing returns.

GETTING SCHOOLED: I started working in the evenings toward an MBA in social enterprise. I'd always wanted to effect change in my home country of Cameroon, where most people have never even seen a computer, and this seemed like a way to do it. I subscribed to an internal newsletter for a Microsoft program that brings technology to the developing world, and the more I read, the more I realized that was exactly where I wanted to be. When a job opened up in that group, I told my manager I wanted to try for it.

THE WHAT-HAVE-I-DONE MOMENT: The position I was after was way higher than the one I held; I was up against people who'd been at the company for 15 years. I sat through five interviews of one hour each, and I was so nervous because it was my dream job, but I didn't have a clue what I was doing. I kept thinking, Why should they listen to me? I'm a programmer! Do I even understand what this job requires? My manager knew I wanted to transfer — what if I didn't get the offer? But I did!

THE PAYOFF: Marketing work is completely different from software engineering. I'm still problem-solving, but where I used to use algorithms, I now use interpersonal skills. I work with internal teams at Microsoft. We seek out new countries to work in, determine what the needs are, and work with the NGOs there. The hours are technically the same, but I'm now expected to think creatively and set my own goals — and the sky's the limit. Work bleeds into my evenings and weekends. I often find myself talking about it at dinner parties, because it's my passion.

THE BEST PART: I know firsthand that tech improves lives in developing countries — we can teach farmers about agricultural best practices; we can improve education in refugee camps in Rwanda. So, yes, I lose sleep thinking about work now, which never happened when I was a programmer. But do you know what it feels like to leave for the office in the morning and think, What impact am I going to have on the world today? There's nothing like it.

—as told to Lauren Iannotti

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