To my mom, the first career woman in my life.
And to Grandpa Jack, the first entrepreneur who inspired me.
"I'm not gonna spend the rest of my life working my ass
off and getting nowhere just because I followed rules
that I had nothing to do with setting up."
—Melanie Griffith as Tess McGill in Working Girl, 1988
Introduction, or how I fleel the CUBE
Back when I was a wage slave, sleep didn't come easy. Sometimes I'd spend the wee morning hours fixated on my bedroom ceiling, stressing about the three days' worth of work some joker had assigned me at five o'clock that afternoon—inevitably accompanied by sticky notes covered with red exclamation points, and an impossible deadline just twenty-four hours away. Or my sleep would be riddled with those ever-dreaded work dreams. There I'd be in my flannel jammies, slumbering far from peacefully as my dreams transported me to my grim gray cubicle. And there Dreamstate Me would be seated at my workstation, editing the same technical documentation Wakingstate Me would have to edit the next day when I actually got out of bed and dragged my bleary-eyed self into the office. Not only was I cheating myself out of a good night's sleep, I was doing the same onerous job one time too many.
Perhaps I just needed to learn to relax, take up Xanax, desk yoga, or transcendental commuter meditation. But I like to think I'm just not hardwired for office work and all the groveling, commuting, and Monday morning staff meetings that come with it. To me, the devil doesn't wear Prada—the devil wears pantyhose.
That's why, in my mid-twenties, after one fitful night too many, I got myself a pair of bunny slippers and began dabbling in all things anti 9-to-5: freelancing, temping, telecommuting, part-time work, flextime work, self-employment, you name it. As long as the work was somewhat related to writing and didn't involve sitting at someone else's desk a full forty hours a week, I was game. (Okay, maybe typing up the erotic Wiccan poetry manuscripts of art students wasn't writing, per se, but it seemed like a close cousin at the time. Plus, it meant I could work from home.)
As a cubicle expat, I still couldn't sleep, but it was because I was so amped about landing an editing project with an honest-to-goodness publisher (of calculus textbooks!) or a couple of 300-word writing assignments for some obscure, artsy newsletter with a whopping circulation of eleven. Piddly assignments soon became stepping-stones to beefier ones, though, and within a few years, I graduated to writing and editing for household-name companies and publications, effectively quelling all inquiries from family about when I was going to get a "real job."
When I started working for myself back in the Middle Ages, I didn't have a mentor, a guidebook, a Rolodex, or any freelance friends to talk shop with. Web surfing was a relatively new phenomenon (Google and Blogger had yet to debut), so I didn't have today's wealth of information at my fingertips. I also didn't have a clue, seeing as I left the cushy world of biweekly paychecks without so much as reading a book on self-employment, let alone securing a solid client base or saving up a couple hundred bucks. (Lesson learned: Leaping before you look is stupid.) Consequently, I discovered how to work outside the cube "on the job"—and by screwing up a whole lot of things, from my first few freelance projects (for ye olde college textbook publisher) to my credit rating.
By the time I finally got around to perusing the self-employment shelf at the bookstore several years later, I felt like an imposter, like I didn't belong in the DIY-career club. Where were the career manuals for creative, gutsy young women who wanted to rewrite the rules of work but weren't Cosmo-swilling Sex and the City wannabes or briefcase-toting empty-nesters with enough money to finance both a career change and a time-share in Hawaii? Where were the books that took a realistic look at how the heck you could finagle the anti 9-to-5 life while broke, rather than feeding us woo-woo, chakra-spinning visualization techniques and daily affirmations? After all, if you can't afford a box of crackers, you probably aren't going to love what you do for long.
I'm not an MBA or CPA or lawyer or financial planner. Nor am I a career coach. (Though I do seem to be the go-to gal in my circle of friends for advice on how to negotiate a project contract or how to tell their boss they'd like to slap him or her upside the head.) What I am is a gal who has been there and faxed that and can tell you what I've learned the hard way about how to work outside the 9-to-5 realm without winding up on food stamps. The way I see it, you might as well learn from my mistakes and save yourself some time, migraines, and credit card debt. If you want accredited legal and financial advice, though, you'd best consult a professional or hit up your lawyer cousin for a freebie.
That said, when I was asked to do this book, I realized I didn't want to just rely on my own experiences as a freelancer, freeloader, telecommuter, temp, and fan of all things flex. So I hit the books, scoured the web, and picked the brains of multiple career coaches, business experts, and trendwatchers. And I talked to dozens of twenty- and thirtysomething women across the country with self-styled careers or ambitions. I also squeezed in a couple chats with midlifers who have careers too fascinating not to savor. Many of these women are single, some are shacked up, and some have kids to boot. You'll find lots of their stories and suggestions woven into these pages.
No matter what their stage of life, these artists, activists, moonlighters, globetrotters, adrenaline junkies, burned-out execs, small-business owners, and aspiring superstars share the same sentiment: Quality of life trumps all else. Or as Molly Kenny, who founded a nonprofit yoga studio that serves the physically and emotionally challenged, puts it, "As far as we know, you only go around once, and I am hell-bent on not having a mediocre life." If you, too, are looking for a less cringe-inducing way to make a buck, balance a side gig or family with your day job, or crash though the glass ceiling, you've come to the right place.
You don't need me to tell you this isn't your mother's career—the days of segregated want ads, job titles like "Gal Friday," and high school guidance counselors pushing applications for colleges that attract "marriageable" men in premed are light-years behind us. Now that everyone's wired to the hilt and company loyalty, pension plans, social security, and the eight-hour workday are pretty much a historical footnote, we're far more enterprising than our parents ever were. Multiple career changes, extended travel, and entrepreneurship are de rigueur. "It's not like you get out of school and say, 'Okay, what's my forty-year game plan?'" says Kirsten Johnson, a career counselor to other twentysomethings and author of the blog Dream Big.
Still, parents, guidance counselors, and friends who've drunk the 9-to-5 Kool-Aid and are notoriously slow on the uptake can be prone to dispensing horrifically irrelevant advice. Even if they can get past pushing the MD-ESQ-MBA troika on you, they may advise you to do something as hapless as wearing a suit to a job interview on a construction site.
That's where this book comes in. I'll tell you how to research your dream job, find like-minded women to conspire with, and scrimp and save so you don't have to wait till you're sixty-five (or, worse, seventy-five) to do what you really want to do with your life. This is not an exhaustive guide, but a primer you can use as a jumping-off point—whether you want to pursue a career in carpentry, start your own dog-walking business, or finally make some headway on that novel you've been pretending to write for the past five years.
There's a lot here, so you may want to roll up your sleeves and get out your pen and notepad, or at least a pile of stickies. In fact, you may want to throw this book in your tote or backpack and take it with you on library or café research jaunts. (Hell, take it to your informational interviews, in case you need to revisit the rules on the care and feeding of your mentors.)
Know that unless you were born into royalty, you may have to make a long-range plan, even if it means crawling back into the cube for a couple years before you can escape from it. Believe me, you're not the only one who's ever had a savings account or resume deficit—I've been there, too, and lived to tell. And now I'm here to tell you that ditching the dream because you want immediate gratification is what's known as wimping out. Yes, it will take some hustling, chutzpah, and hard work to make a career change, but it can be done. Lest you feel unmotivated or overwhelmed, I've provided a handy-dandy "Show Me the Money" section and an "Anti 9-to-5 Action Plan" at the end of each chapter to give you a nudge in the right direction.
None of this is to say you shouldn't work a traditional 9-to-5 office job if you want to. After all, if it ain't broke, why fix it? But since you picked up this book, I'm going to assume you're at least a little bit anti-curious. The following pages will tell you what your work life could be like in the DIY-career trenches—the good, the bad, and the ugly. So take a peek outside your cube and see what you think. Because, when all is said and done, life's too short to stress about work when you're sleeping.
MAKE your MOVE
I WANT to find a CAREER. I'm really Passionate about
"Human beings were not meant to sit in little cubicles staring at
computer screens all day, filling out useless forms and listening
to eight different bosses drone on about mission statements."
—Ron Livingston as Peter Gibbons in Office Space, 1999
When I decided to flee the cube in my mid-twenties, I knew I wanted to do something related to writing, but I had no idea what. How I would get from point A (gainfully employed by someone else) to point B (gainfully self-employed) was a mystery. But instead of giving any of this an ounce of forethought, I blindly leapt into the anti 9-to-5 chasm. You might say I was all madness and no method.
The year was 1992. Back then, if you wanted online advice, you had to post a question to Usenet (an ancient computer network that predates the web). Since I didn't know what Usenet was (and still can't really tell you what it is), many of my questions about self-employment went unanswered. Occasionally I'd go to chamber of commerce mixers in an attempt to glean advice or maybe even a client, but I was shy as hell, I didn't know what I was doing, and I stuck out like a sore thumb among all those well-groomed adults. Once in a while a friend who felt sorry for me would give me the name of a family member's cousin twice removed who worked as a newspaper reporter or obscure book author, someone three decades older who said I could pick their brain. I'd call, and they'd gripe about what a rotten career writing was and encourage me to run for the hills at top speed.
So I fumbled and bumbled through the first few years of my so-called freelance career the best I could, bouncing from freelance jobs to temp jobs to part-time jobs and back again. Sometimes I'd say the wrong thing in meetings, or choke on my hamburger right as a potential client asked about my qualifications. Often I undercharged for my work, lived beyond my (already meager) means, and bounced my rent checks.
Once I'd mercifully put this groping-in-the-dark phase behind me, I realized I had learned a heck of a lot about carving out a self-styled solo career—and that I had made it so very hard on myself by not investigating and preparing for what I was getting into first.
That's where this book comes in. My rocky transition from employee to my own employer is not one I would recommend to my worst enemy. But I've since amassed a load of know-how about making people want to hire me—at a living wage, no less—and swapped war stories with dozens of other women who have successfully left behind the 9-to-5 grind. And I'd love to be the one who prevents you from making the same dumb mistakes I made.
If you know you want out of the cube but have no idea what your next move is, this chapter is for you. Even if you do have a career path in mind, this chapter will steer you toward some invaluable resources for scouting it out.
DO YOU HAVE TO LOVE YOUR JOB?
Of course not. In the course of writing this book, I talked to plenty of women who are happy to just collect a paycheck at some bland mercenary gig and pursue the projects they can really sink their teeth into after hours. But for every one of those women, I talked to a dozen cube-dwellers who said they'd prefer to earn their keep some way other than by wading through an inbox, snoring through staff meetings, and covering their boss's derriere.
Some, like Andrea Beyer of Seattle, crave a less stodgy, more stimulating work environment—one less inclined to cause narcolepsy. "I was tired of emailing people who sat next to me, tired of meetings that accomplished nothing," says the thirty-year-old, who left a high-profile corporate gig after three years to temp by day and learn to cut and color hair by night. "I just wanted to be more active, not so sedentary in front of the computer." She also wanted a job with more flexible hours, one that involved helping people feel good about themselves, rather than helping a department head meet some arbitrary "bottom line."
Others, like Gwynn Cassidy of Manhattan, hanker for more meaningful work. After running a beauty and lifestyle channel for a well-known website—complete with cushy office, free makeup, and A-list parties—the thirty-five-year-old came to the conclusion that "there's only so much writing you can do about mascara and lip gloss before you lose it." After giving five years of her life to "interviews about Botox and teenage acne," Gwynn began immersing herself in her local feminist community. Today she juggles a part-time telecommuting gig for the National Organization for Women with running the nonprofit she cofounded, Girls in Government, which encourages young women to accept leadership roles.
Still others, like Kate Greenen of Detroit, who's twenty-five and has worked in what she calls "the lucrative world of financial planning" since age twenty-one, find themselves asking with alarming frequency, Is this all there is? "I've been offered training, stability, and fantastic benefits," says Kate, who plans to sell everything she owns and get a marriage and family counseling graduate degree. "But I started really hating getting up. Life lost color—I was always searching for something fun to do or I was out shopping. Earn, consume, die. It was a soul-sucking circle. After years of bitching about paperwork in an industry that held absolutely no interest for me, I'd rather be broke than on the earning-spending-consuming hamster wheel."
Andrea, Gwynn, and Kate are hardly anomalies. Countless women log hour after hour in their cubes while dreaming of the day they can escape to a more fulfilling gig. In fact, a 2005 study by a leading business research group found that only half of all working Americans are happy with their jobs. And a 2006 CareerBuilder.com poll found that 53 percent of America's gainfully employed consider their coworkers, well, "a bunch of monkeys." The big question is why, in a society where most of us spend roughly 1,800 hours a year at work, do we stick it out at tedious day jobs that make our palms itch and our eyes bleed?
For one thing, most of us are hip to the fact that eating out of Dumpsters is overrated. Not getting paid is simply not an option, no matter how tempting it is to pull a Peter Gibbons (of Office Space fame) and stop showing up to work. What's more, many of us are methodically chipping away at student loans, saving our beans for that Eurailpass we've been fantasizing about, or stockpiling our savings till the day we can afford to hang our own shingle. Others are learning the ropes in an industry they hope to one day take by storm. Or actively interviewing for brighter, shinier jobs—ones that might even give us our own offices. With a window. And a door that locks.
Yet some of us are biding our time in our current dead-end gigs till that six-figure book deal or winning Lotto ticket falls out of the sky. And some of us aren't sure how we wound up in our cubicles or server aprons in the first place, much less where we should go next. If the latter scenarios ring a bell, take heart. Life in the cube doesn't have to last forever. This book will tell you how to make your way to the nearest exit.
WHAT'S YOUR COSMETOLOGY SCHOOL?
At a recent mind-numbing temp gig, my fellow short-timers and I gathered 'round the color copier to swap ghost stories of day gigs past. Trying to top each other's terrifying tales of subordination, termination, and humiliation soon gave way to true confessions of What We Really Want to Do with Our Lives. My friend Andrea was putting herself through cosmetology school during nights and weekends. Another officemate (let's call her Roz) worked four "tens" and used her Fridays off to get her home-based retail business off the ground. I, too, fessed up about my alter ego, who wrote essays and articles on the bus, during lunch, and in the wee morning hours.
The only one who remained silent was a guy I'll call George, a gung-ho, flat-topped ex-marine whose thirty-five-hour-a-week temp gig consisted of compiling some stats for a couple hours each morning, and, well, that was pretty much it. His boss hadn't given him enough to do, despite George's repeated requests for a heavier workload. Bored silly, ol' Geo would spend the rest of each day drumming his fingers on his desk, periodically reading aloud the headlines from CNN.com until 5 PM rolled around. Suffice it to say, we were all itching for him to land a more stimulating gig.
"See, I need to do what all of you are doing," George finally chimed in. "I need to come up with a career I can actually get behind. But what's my cosmetology school? I need to figure that out."
While I had a hard time envisioning even the figurative George pursuing a career in hair and makeup, I appreciated the sentiment. His question—"What's my cosmetology school?"—pretty much said it all. He didn't want to just collect a paycheck; he wanted a job that would make him feel useful, energized, like he was more than an organ-grinding monkey. If, like George, you have no idea what your beauty school is, don't despair. Though hardly an overnight process, identifying it is something anyone with the ability to daydream and write lists can do.
Of course, lists are only the beginning. From there, you'll need to investigate what landing your dream gig entails. But let's take this one step at a time. The first order of business is figuring out exactly what the heck it is you'd like to do with your life. If the only thing that comes to mind is Not this! don't fret. In this section, you'll dig a little deeper until you unearth some concrete answers.
Step 1: Go to your happy place.
Is there somewhere you do your best brainstorming (preferably away from your place of employment)? It doesn't matter if it's the can, the bus, the gym, the mall, or Costa Rica. The idea is to retreat from your cubicle to a place where you can think uninterrupted for an hour or more. Make sure you bring a pen and paper, or a laptop, with you. Whether it takes a lunch hour or a couple Saturday mornings, you're going to keep brainstorming until the blank page you started with is crammed with ideas.
Step 2: Thumb through your mental scrapbook.
You've probably heard it said that you should take inventory of every work-related and recreational activity you've done since you were the ripe old age of, say, six—from classes, hobbies, and clubs to jobs, internships, and volunteer gigs. The idea, say "those self-helpy parachute books," as a few women I talked to called them, is to note the activities you've enjoyed, no matter how small or fleeting.
For example, I used to love to draw when I was a kid, and I took all kinds of art classes at the Y. I must have subjected my poor parents to about 200 variations of the same sunset/mountainscape scene (drawn in those messy pastels that get all over your hands and clothes), which they dutifully oohed and ahhed over. The bad art continued all through high school, and by the time I reached college, there was no doubt in my mind I wanted to pursue a career in "uh, something arty." And now here I am, making stuff for a living, though I'm happy to report you won't find any badly drawn sunsets in my portfolio (maybe just some horrible poetry).
What did I love to do as a kid? Your first stop on this trip down Memory Lane should be your own childhood, from those endless Saturday afternoons spent inventing stuff to playing Wonder Woman and otherwise saving the world in your basement or back yard. Maybe you ran the lemonade-and-cookie empire on the corner. Or outfitted the family dog, cat, and gerbil in gold lamé. Or directed all the neighborhood kids in elaborate productions of Hairspray.
When you stumble on your own "Oh, yeah—I really liked doing that," write it down, even if it's some obscure task you only did once for half an hour, like fixing your Luddite father's computer when it crashed. Then ask yourself why this satisfied you so much. Was it the saving-another-person's-ass thing that made you feel good? Did you revel in the problem-solving? Or are you just one of those gadget whizzes who salivates over all things digital?
Or, if revisiting every nook and cranny of the first two or three decades of your life is too overwhelming, the remaining questions in this section can help you cut to the chase.
What do I want to learn next? Many entrepreneurs I talked to said they considered their past 9-to-5 jobs "school," only without the zits and homework. Taking gigs that teach you new skills or introduce you to people you want to meet is like "getting paid to get an education," says Michelle Madhok of Manhattan, the thirty-four-year-old founder of the shopping website SheFinds.com. For example, Michelle wanted to improve her public-speaking skills, so at her previous job she volunteered to give a lot of presentations.
But maybe, like most people, you fear giving PowerPoint presentations more than death. Maybe instead, like Maggie Kleinpeter of Baton Rouge, you have an art degree, are crafty as hell, and aspire to work for yourself one day. Unfortunately, you have the business sense of a cocker spaniel. So, like Maggie did before starting Supermaggie, her online mecca of silkscreened tees and other girlie goodies, you spend several years working for a tiny greeting-card company (or your industry of choice), where you can learn the ropes of running your own show. "That job was probably the best possible job to have because the owners pretty much showed me how to run a business," the thirty-year-old says. By the time Maggie walked away from this paid education, she knew how to talk to customers, market a product, contact wholesalers and retailers, work a trade show, and then some.
But what if you're not sure what you want to learn next? With so much virgin territory before you, the real question is, How could you be sure? When trying to figure out your next career move, dabbling is the name of the game. You can work in a dive shop and learn to scuba, like my friend Danielle did for a year. (Her consensus: Diving rocks; retail, not so much.) You can volunteer for a crisis hotline to see what you think of counseling domestic-violence victims, like I did in my twenties. (Intense, but rewarding; still, not the ultimate career path for me.) You can intern on an organic farm to see if country living agrees with you, get your EMT license and try your hand at rescue work, and on and on and on. Think of this period as an opportunity, like those electives you took in high school or college (wood shop, anyone?), but with performance reviews instead of report cards.
When was I at the top of my game? Take a second look at those projects, jobs, travels, and other peak experiences that made you feel like you could do no wrong, suggests career coach Kirsten Johnson. Coproducing The Vagina Monologues in college to raise money for local women's shelters gave her a sense of accomplishment unlike anything she did before or since.
Even if you don't have some short-lived apprenticeship with a Jedi master, far-flung Peace Corps adventure, or near brush with fortune and fame in your closet, surely there must be some past event that you occasionally replay in your mind when life at the computer monitor or espresso machine is about as exciting as watching golf on TV. (Of course, if you peaked drinking Coronas in Mexico on spring break, you may be hard pressed to find anyone who will pay you to reprise that role.)
My dream job of yore was a volunteer gig walking dogs at my city's animal shelter—hardly glamorous, yet infinitely rewarding. The dogs were happy to get out of their cages, I was happy to get my mutt fix, and the city was happy to get some free labor. To me, that job was the Peace Corps of petcare.
What do I never want to do again as long as I live? This may seem obvious, but sometimes listing all the jobs and activities that you dread and detest—or have completely burned out on—can help solidify what your next move should be. Like many women I talked to, Molly Kenny, thirty-nine, a licensed speech therapist, had seen enough bureaucracy in her six years working at a hospital to last a lifetime. "Every thirty days you do progress reports and you have twenty-two cases, and you're spending all that time shuffling papers—even though there's not that much to say after a month," says Molly, who now runs the Samarya Center, a nonprofit yoga studio in Seattle that caters to seniors and people with special physical and emotional needs. Frustrated that she was spending far more time writing about people's health woes than helping to resolve them, Molly created her own gig in the health arena, one that's infinitely more hands on and less corporate.
Enough about me, what do you think of me?