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By Root 114 0

employment center at the local community college, I was able to drudge up scores of stopgap work handling rich people’s bills, phone messages, laundry, childcare, and workshop registration (because in Marin County, California, you’re nothing if you don’t teach some spiritual enlightenment workshop or other). But I don’t hold a monopoly in the supplemental odd job department. Seattle-based graphic artist, cartoonist, and author Ellen Forney worked the night shift on a psych ward during her first couple of years as a freelancer. Novelist and Los Angeles Times columnist Meghan Daum wrote everything from press releases for a state-funded mental health organization to web copy for Always Maxi Pads during her early freelance years. Molly Crabapple initially supplemented her fledgling freelance illustration business by working as a nude model for artists and photographers on the side.

Trading in your 9-to-5 for a more flexible day gig that gives you mornings, Fridays, or any other window of time off during regular business hours can make getting your freelancing business off the ground infinitely easier. Otherwise, you’ll have to wake with the roosters or burn the midnight oil (and likely invest in a restaurant-grade espresso machine) to get your freelance projects done. Staying in touch with clients can be tricky too, unless you limit all communications to email, cultivate some customers in a time zone earlier than yours, or furtively sneak in a couple of calls on your cell during lunch, as I’ve been known to do.

How do you know when it’s time to jettison your day job for good? Pick up a traditional business book and you’ll probably hear that it takes a year or three before a small business owner starts pulling in enough profit to pay herself an annual salary. But as a freelancer who sells a service to companies and individuals, you won’t necessarily have an avalanche of business expenses. So assuming you don’t max out your credit cards buying a $7,500 computer system, and assuming you’re charging your clients enough and getting paid on time, you should start seeing a profit within the first two quarters. It might not be anything to write home about, but it’ll still be money in the bank.

So should you wait till your freelance income equals 30 percent of the money you need to live on before you jettison the 9-to-5 job? How about 50 percent? Or 75? And how long will all this take anyway?

There’s no universal formula. “Even after I’d been published in The New Yorker, I still went in to temp jobs. Quite often,” Meghan says. And it took Molly, the illustrator/nude model, three years to completely phase out her modeling gigs. On the opposite end of the spectrum, Erin, the virtual assistant, nabbed her first client within two weeks of opening her doors and had enough business to quit the corporate world six months later.

In other words, it depends on how much time your day job leaves for building your freelance business, what freelance profession you’re getting into, how hard you hustle, how much cash you have saved, and how much of a risk taker you are.

My motto: When freelancing on the side has you scrimping on sleep and taking caffeine intravenously, it’s time to ditch the day gig. Yes, cutting the cord will be scary. Most things worthwhile in life are. But look at the bright side: When it comes to finding the extra time to grow your freelance business, you’ll hit the jackpot.

Chapter 3

Get a Room Already!

Solo office smackdown: Working from home vs. putting on a pair of pants and leaving the house

“Whatever work you do at home, take every precaution to put it away properly

and safely between sessions. I know of one horrible catastrophe that befell an

author who had taken the only existing copy of his new novel to a typist. The

dog chewed it clear through from page 100 to the end, and naturally after that

the author changed typists.”

—Elmer Winter, Women at Work: Every Woman’s

Guide to Successful Employment, 1961

There are many reasons not to work from home: The overflowing laundry. The