My So-Called Freelance Life

How to Survive and Thrive as a Creative Professional for Hire


By Michelle Goodman

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Tired of clocking in and losing out? Want to pursue creative, fulfilling work on your own time and also make a living in the process? My So-Called Freelance Life is a how-to guidebook for women who want to avoid the daily grind and turn their freelance dreams into reality. 

Michelle Goodman, author of The Anti 9-to-5 Guide and self-proclaimed former "wage slave,” offers tips, advice, how-to’s, and everything else a woman needs to pursue a freelance career. Confused as to whether you should tell your clients that the odd gurgling sound during a conference call is emanating from the infant sleeping on your shoulder? Goodman answers all of the unusual questions that may arise for women exploring the freelance world.

Far more than your normal business guidebook,My So-Called Freelance Life blends candid, humorous anecdotes from a wide variety of freelancers with Goodman’s own personal experiences as a creative worker for hire. Whether you’re a freelance first-timer or a seasoned creative professional, copyediting queen or web guru,My So-Called Freelance Lifeis an invaluable resource for anyone interested in freelancing.


For anyone who’s ever hit the snooze button
five times in a row on Monday morning.

To fulfill a dream, to be allowed to sweat over lonely labor, to be given a chance to create, is the meat and potatoes of life. The money is the gravy.”
—Bette Davis
The two most beautiful words in the English language are ‘check enclosed.’”
—Dorothy Parker

Eat, Pray, Quit
When I was twelve and writing in my diary about how much I hated my braces and loved Arthur Finkelstein, I fantasized about someday publishing the whole hot confessional mess. My book, The Bride Wore a Night Brace, would be acclaimed the world over.
Girls would write me sentimental notes about how I’d helped them learn to smile again, despite the ten pounds of hardware obscuring their teeth. Boys would send me lengthy missives about how I’d convinced them to take a second look at that gangly girl in the corner, the one who could pick up twelve different radio stations with her headgear, and ask her if she wanted to dance. High school teachers and college professors alike would make my treatise on preteen angst required reading in their classrooms. Politicians would buy it for their sons and daughters. I’d be invited to the White House, interviewed by Barbara Walters, and—once the movie version of my opus grossed a billion dollars—given my own star on Hollywood Boulevard.
Not for one minute did I think that someday I’d be trapped in a 9-to-5 (or 5-to-9) job, fielding thirty dozen emails a day and straining to stay awake during staff meetings. Not even for a nanosecond.
Then I finished school and cruel reality set in.
Occasionally, my older, wiser coworkers would stop debating whose carpal tunnel was worse long enough to share their hard-won pearls of workforce wisdom with me. “I used to be like you, thinking that one day I’d pursue my own writing or take up painting again,” they’d say. “But eventually, you learn to let go of those silly dreams. You gotta grow up sometime and get a real job like everyone else.”
Why? I remember thinking. What’s so juvenile about actually liking what you do for a living? What’s wrong with designing your own career if you can’t stomach the one you’ve got or can’t figure out what kind of a job you want in the first place? Isn’t that a better bet than hanging on to a 9-to-5 that makes you feel like you’re crawling over broken glass sixty hours a week?
I’m guessing you can relate. You want more control over the work you do, who you do it for, and where you do it. You don’t want to be told what the pay range for the job is—you want to set it yourself. You want a flexible schedule so you can devote more than fifteen minutes a day to your family, the canine couture empire you’ve been hoping to launch, or the screenplay you’ve been nursing for the past decade. You want to work in your bunny slippers with your dog lying at your feet. Most important, you want off the corporate hamster wheel and you want it now.
You certainly wouldn’t be alone. Only one in two Americans are happy with their jobs, reports The Conference Board, one of the world’s leading business think tanks. Not surprisingly, in 2007 the U.S. Census Bureau found that almost twenty-one million Americans work as self-employed professionals or independent contractors.
Some of us turn to freelancing in the wake of a layoff. Others turn to it as a way of easing back into the workforce after having a child. Others have simply found that traffic snarls cause them to froth at the mouth and fluorescent lighting gives them a bad rash.
This isn’t one of those “I am perfect and you can be too” books where I tell you how rich and slick and esteemed and redeemed I am (don’t I wish), or how I did everything right when I first fled the cube in 1992 (nothing could be further from the truth). If you’ve read my first book, The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube, a guide to fleeing the cube farm for flexible, temporary, overseas, social service, or self-employed work, you know I was hardly the poster child for self-employed success during my early freelance years. When I left my day job in the dust at age twenty-four, I had the business sense of a beagle, the paltriest of portfolios, only one client to my name, and no money saved.
Thanks to a crazy little thing called trial and error, I fortunately got with the freelancing program and figured out everything from naming my price and structuring my time to wooing clients and whipping my contracts into shape. To help you do the same (only without all that fumbling in the dark), I packed as much of my freelance know-how as would fit into this book. So consider this your crash course in becoming gainfully self-employed.
Every great story has three acts—even the story of your shiny new freelance life. In this book, I’ve laid out those acts for you chapter and verse. In Part 1, you’ll find details on those first key steps you need to take as an indie professional, from making a budget and setting goals for yourself to getting a business license and building a web portfolio. In Part 2, we’ll talk about landing the work, from marketing yourself like mad and getting in the referral game to negotiating rates and contracts like nobody’s business. And in Part 3, we’ll cover all the day-to-day details of surviving and thriving as a creative professional for hire—in other words, staying sane, solvent, and off the IRS’s shit list.
Whether you’re on a fact-finding mission, eager to learn how this newfangled way of boss-free working works, or already freelancing on the side and wondering how soon you can turn in your letter of resignation, this book is for you. Even the seasoned freelancers in the bunch are sure to pick up some tips and tricks here. After all, what freelancer doesn’t love a little dirt on how her self-employed counterparts deal with missed deadlines, clients from hell, and checks that are MIA?
For the record, I’m not an accountant, financial adviser, or legal professional. I’m a journalism major turned freelance writer who makes her living writing articles, books, and corporate marketspeak, with the occasional editing or teaching gig thrown in for variety. While I touch on some of the legal and financial gobbledygook of working for yourself in these pages, my advice isn’t meant to take the place of the advice of a trained financial or legal pro (in fact, my own legal adviser made me type this very sentence). So for tax, financial planning, and legal help, please, hire yourself a good accountant or lawyer who can keep you out of debt and out of jail, okay? Don’t waste your one phone call from the pokey on me.
Instead, learn from my sixteen years of hard-won freelance wisdom and the missteps I made while scrambling to gain a foothold on my so-called freelance life. As far as I’m concerned, you might as well benefit from the biggest lessons I learned and blunders I made and save yourself some time, agita, and bounced checks in the process.
Because diversity is a beautiful thing, I’ve also included the war stories and sage advice from several dozen of my full-time freelance heroines (and a couple of moonlighters), from a pet photographer to a personal trainer, writer to web developer, visual artist to virtual assistant, rocker to radio producer, animator to auctioneer. Many of these freelancers are the main breadwinners in their households, regardless of whether they’re single, shacked up, or somebody’s mom. Many have mortgages and kids to put through college. All of them rely on their freelance income to make ends meet; you won’t find any hobbyists or trust fund babies here.
To round out the discussion, you’ll also hear from a handful of clients, financial pros, and legal eagles. And since no DIY career book would be complete without a little homework, you’ll find a few exercises to do along the way (no deep breathing or “creative visualization” techniques—I promise!). So get out your pencils and Post-it notes, and get ready to dig in.
I realize that you may be afraid. Afraid of not having enough money to pay your bills. Afraid of giving up your health insurance and 401(k). Afraid no one will hire you. Afraid you’ll go nuts working alone. Afraid you’ll work all the time and have no life. Afraid you’ll take the leap and your parachute won’t open.
I was too when I started working solo. But I quickly learned that a little planning (and a whole lot of chutzpah) goes a long way, especially when it comes to chasing your freelance dreams and dealing with the financial realities of life without a steady paycheck.
So allow me to be your tour guide as you strive to get your so-called freelance life on track. Let me tell you what to do with those business card designs you’ve been sketching on the back of a pink “While You Were Out” notepad and how to transform that useless corner alcove into a fully functional home office. Because wanting to make a living as a freelance cartoonist, clothing designer, or computer programmer isn’t silly. It’s dreamable, doable, and damn good fun.
What’s silly is giving up the dream because some overworked officemate who lives to bitch about her carpal tunnel syndrome said you should. Now enough stalling, let’s get to work.

You fled the cube - now what ?
Freelancing isn’t just about selling your talents, advice, or wares. Working for yourself as a creative professional also means playing chief executive, bean counter, sales rep, marketing maven, tech support, contract manager, and admin assistant.
Or, as author and journalist Lynn Harris puts it, “People think that freelancers sort of sit at their desks all day and just have ideas. But we’re running a business. It’s a business I can run in my socks, but it’s a business.”
While I’m all about running the best possible business one can run in her socks, I’m not about doing things the traditional (tedious, expensive) way. Business plans that double as paperweights? No thanks. Three-thousand-dollar executive desk/hutch/swivel chair set? Not on your life. Instead, I’ll give you the quick-and-dirty list of what you need to consider and do right away to get this freelance party started—and what plans, purchases, and services you can back-burner till your business grows a smidge bigger.
In a perfect world, you’d plan, ramp up, and build your freelance business on the side while keeping a steady paycheck. After all, if you quit your day job today, it’s highly unlikely you’ll have a full freelance workload tomorrow. But not everyone has ten to twenty spare hours a week to moonlight. And many creative professionals find themselves diving into the freelance pool headfirst after getting laid off, becoming a parent, or getting so fed up with their 9-to-5 they accidentally blurt out where their boss can stick it. If you count yourself among that crowd, not to worry. Many freelancers before you have started their solo careers without a lick of planning and lived to tell the tale (yours truly included). With the help of this book, you’ll be a lean, mean, freelancing machine in no time.
Even if you’ve been freelancing on the side or full-time for a few years, you’re going to find some useful pointers here. As creative pros for hire, it’s easy for us to get caught up with the project work on our plate but gloss over the business side of things. If your website, office space, or income could use a makeover, this section will serve up some suggestions. And if you’re bored with your current workload, these chapters could give you the kick in the pants you need to shake things up.

Chapter 1
Business Plan To Go
Even Thumper had goals
“Smart kid like you. You got to have a plan. Some kind of a dream.”
—Peter Gallagher in The O.C., 2003
I used to think business plans were for people who preferred pumps and pearls to slippers and sweats. When I started working for myself as a freelancer, I wasn’t looking for a bank loan or an angel investor, so, I figured, why would I need some wonky thirty-page tome? How the heck was a hefty mission statement going to help an independent professional like me land better clients and make enough money to pay my rent?
Then I was asked to write a story on business plans for NAFE Magazine, a publication aimed at female execs. In the interviews I gathered for the article, business guru after business guru griped about the way so many self-employed people operate on autopilot, leaping at every opportunity that falls into their laps—the good, the bad, and the ugly, intention and ambition be damned.
Melissa Krinzman, who runs Venture Architects, a New York-based firm that helps entrepreneurs looking for seed money develop their business plans, said something that stuck with me: “A business plan helps you focus on selecting the client rather than waiting for the client to select you.”
In other words, commit to paper your latest and greatest freelance goals—why you want to work for yourself in the first place, and what projects and clients you hope to land in the process—and you liberate yourself from thinking you have to jump on every gig that comes your way.

A Cure for the Common Waffler

I’m a waffler at heart. Show me a decision that needs making and I’ll show you a woman capable of flip-flopping three dozen times in the course of an hour. You might say I’m a lot like Tevye, the lead character in the musical Fiddler on the Roof. Gifted with the ability to examine any situation from about nineteen different angles, Tevye was freakishly fond of the phrase “on the other hand.”
Dangle a sweet-sounding gig in my face, and you’ll witness this modern-day Freelancer on the Roof in action: Let’s say HotShitStartup .com contacts me out of the blue and offers me serious cash to write web copy for the next two weeks about some newfangled wireless gizmo I don’t give a whit about. In deciding whether to take the job, my thought process might go something like this:
Hmmmm, wasn’t just on the front page of the business section? That gig suuuure would look spiffy on my resume. On the other hand, I’m so over high-tech corporate work; didn’t I swear it off back in 2007 (and 2006, and 2005)? On the other hand, the pay is phenomenal—twice as much as I’ve made on any other project this year. On the other hand, if I take the gig, I’ll have to burn the midnight oil since I already have four magazine articles due this month. On the other hand, it’d be cool to have this new client in the hopper in case I ever need some high-paying tech work to fall back on. On the other hand, I already have enough dull-as-dirt corporate work to fall back on . . .
And that’s just in the first fifteen minutes.
That’s why the idea of getting my goals down on paper resonates with me. Regardless of whether you’re a waffler, if you want to work solo, you too need a written game plan—what I like to call a Business Plan To Go. It doesn’t have to be War and Peace; the CliffsNotes version will do just fine. All you need is a short list of your freelance goals for the year—a roadmap of where you want your career to go, and some directions for how to get there. It might be all of three hundred words. It might be posted on your blog. It might be scrawled on the back of a beer coaster. Point is, jotting down your freelance hopes, along with your to-do list for making those dreams a reality, will help remind you why you’re here, working at home in hot pink pajamas with three-day unwashed hair (or, uh, maybe that’s just me).
Keeping my one-page plan tacked to the wall above my desk ensures that the next time calls, I won’t get bogged down with all that Tevye-like indecision. Instead, I’ll glance at the game plan I wrote long before some flashy webpreneurs with deep pockets began parading a wheelbarrow of carrots in front of me, and I’ll assess. Quickly. Sure, this sounds like a great gig, but is it a great gig for me, given what I want to accomplish this year? If the answer is no, I won’t take the gig; if the gig isn’t in line with my overall freelance goals and I’m not starved for work, why derail my creative hopes and dreams for the next few weeks or months?
Here’s an example, one of the biggest goals from my own Business Plan To Go for 2008:
Game plan:
Introduce myself to the editors of Fancypants Magazine and, whose names a couple of freelance friends kindly passed along over the holidays.
Pitch an article to any of the aforementioned editors who take the bait.
Continue filling my story-idea well by actually reading those online press release and news alert services I’ve subscribed to (Newswise, Google).
Write one new humor essay a quarter and shop it around with doctor’s-office-worthy publications.
Limit corporate gigs to one a month, if that. If I have a gap in my schedule but I’m hitting my monthly financial goals, use the free time to troll for bigger, better journalism gigs and work on aforementioned essays.
If you’re an illustrator or interior designer who just fled the cube last year, your biggest goal might be boosting the amount of bacon you’re bringing home. (We’ll get to the how of making moola in Part 2.) If you’re an event planner or e-commerce programmer on her third year of full-time freelancing, you might be more concerned with beefing up your green client base and phasing out any planet-busters on your roster. If you’re a photographer who’s spent five years making a name for herself on the wedding circuit, you might want to branch into editorial work, stock photography, or portraiture.
Just like our 9-to-5 counterparts, we freelancers should always be moving toward something, be it more money, more free time, bigger and better clients, or those dream projects that are so much fun to work on that we can’t stop pinching ourselves. Operate like a reactive robot-for-hire who gobbles up every gig lobbed her way and you grow stagnant, stale. Instead, you need to give yourself a promotion every now and then. Because if you don’t, who will?
I’m not saying you should aspire to be the next mommy millionaire or overnight YouTube sensation. In fact, I sincerely doubt the glass ceiling is the sole reason only 3 percent of the 10.4 million women-owned businesses in the United States pull in $1 million or more in annual revenue. (For comparison, 6 percent of male-owned businesses clear the million-dollar mark.) I’m saying that one size does not fit all self-employed people. Not all of us want to be the next big thing. Some of us just want enough cash to keep a roof over our head (and a few new pairs of shoes in the closet). And some of us just want enough downtime to devote to our creative habits or kids.
I’ll leave it up to you to define—in writing—how you’ll know when you’ve truly arrived as a creative professional for hire: four-hour workweek, six-figure income, ten employees on your payroll, twenty Fortune 500 clients in your portfolio, front page of the business section, home page of Digg, opening night at Sundance, top billing at Madison Square Garden, New York Times best sellers list. . . . It’s your freelance career, so it’s your call.

Do Try This at Home: Business Plan To Go

Ready to roll up your sleeves? It’s time to write your own Business Plan To Go. It can be all of a paragraph or two. All you need to do is list at least three of your freelance goals for the next year. Bonus points if you also outline your game plan—your to-do’s—for reaching each one. And none of this vague “I will publish a best-selling graphic novel/pull in six figures with my catering business/win three Grammys” crud. Yes, ambition is a beautiful thing, but you still need a roadmap if you want to arrive.
Think tangible, realistic, bite-size pieces. Here’s an example:
Game plan:
Put myself on a weekly illustration schedule, starting January 15. Start with thirty-minute sessions first thing in the morning on Wednesdays and Fridays, and see if I can increase the session length and/or amount by March. Aim for a rough sketch of at least one panel per session.
Sign up for that cartoon-publishing class at my local media center.
Read blogs by and interviews with my illustrator/cartoonist heroines to see how they got their start.
Here’s another:
Game plan:
Revise online portfolio to reflect what experience I do have publicizing sustainable businesses and products.
Start blogging about green businesses, products, and consumer tips to boost my street cred.
Join the planning committee for my local home improvement and garden show to get my name out there.
Print up new business cards and introduce myself to all the green businesses in town.
Give each item in your plan a start date and a deadline. Break down the steps into bite-size pieces you can tackle each month, week, or day, and give them deadlines too. Set up whatever reward system you need to prod yourself along (vino! cupcakes! John Cusack movie night!). If you can’t wrap your brain around anything beyond the next ninety days, write a three-month plan and rinse and repeat at the end of the quarter. (If you’re brand-new to freelancing, consider reading Chapters 2 through 10 before taking a stab at this exercise.)
Make a spreadsheet, a wall chart, or a 3D diorama to track your progress. Take a page from Molly Crabapple and get your friends in on the act: “For big, long-term goals, I’ve found loudly bragging about what I’m going to do makes me do it,” says the award-winning illustrator for such fine institutions as Marvel comics, The New York Times, and Playgirl. “Otherwise, I have to face the humiliation of public failure.” (Talk about incentive.)
Bottom line: You’re a smart kid. So if you don’t have a plan about how you’re going to meet this so-called freelance life head-on, time to get cracking.

Chapter 2
Forget Fuzzy Math
Get real with your finances—and get over the notion that artists have to starve
“Making money is art and working is art and good business is the best art.”
—Andy Warhol
A couple years ago I attended a business conference for writers and visual artists. One of the main panels was on how to blend creativity and commerce without winding up on your office floor in the fetal position, a shell of the woman you were before you served your soul on a silver platter to the Man. After forty-five minutes of hearing half a dozen painters and illustrators elaborate on how it’s next to impossible for an emerging artist to cobble together a living on watercolors and lithographs alone (no way!), someone in the audience asked what each of the panelists did for fallback income. One up-and-comer on the panel copped the “I am an Artiste!” attitude that drives me nuts. It goes something like this: “I don’t have a fallback. Having a fallback is like falling down, or admitting defeat. It’s like giving up on my artistic ambitions altogether. I might as well just trade in my easel now if I’m going to fall back.”
So basically this Vincent Van Schmo would rather sell his paintings at the farmers market and eat Saltines for dinner than taint his Talent with any lowly commercial work.
Yeah right. And I’m the queen of Sheba.

The Beauty of Bread-and-Butter Work

If you’ve read The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube, my book on alt career paths, you know that although I’m a big fan of following your creative bliss, I’m also a big fan of fallback skills, backup plans, and bread-and-butter work that keeps you clothed, fed, and warm at night. I mean, what’s so noble about starving? Where’s the honor in sleeping on a subway grate?


On Sale
Nov 10, 2008
Page Count
240 pages
Seal Press

Michelle Goodman

About the Author

Michelle Goodman writes about careers and pop culture for publications such as Salon, Bust, Bitch, The Bark, and the Seattle Times. Her writing also appears in the anthology The Moment of Truth: Women’s Funniest Romantic Catastrophes (Seal Press, 2002). To keep a roof over her head, Michelle wrangles text for book publishers, high-tech companies, and peddlers of New Age philosophy. She lives in Seattle.

Learn more about this author