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A freelancer's taste of freedom

I am sitting in a Washington Square West coffee shop in the middle of the day with Sharon, a friend of a friend, who hands me a book - Robert Bly's Secrets of a Freelance Writer: How to Make $85,000 a Year.

I am sitting in a Washington Square West coffee shop in the middle of the day with Sharon, a friend of a friend, who hands me a book - Robert Bly's

Secrets of a Freelance Writer: How to Make $85,000 a Year


"I haven't quite managed $85,000," she says, "but it's a good book."

As I thumb through the dog-eared and underlined pages, I think of a Lawrence Ferlinghetti poem:

Constantly risking absurdity

and death

whenever he performs

above the heads

of his audience

the poet like an acrobat climbs on rime

to a high wire

of his own making.

OK, so creating advertorials is not the same as performing the secret, burning poetry of the heart, but undertaking the job as a sole proprietorship is scary. I am part of a generation of freelancers, people who choose to work on their own terms - despite the very high risk of free-falling with no safety net.

It seems I know a million people like Sharon, who tells me she was so desperate to leave her last full-time job as a writer for industrial magazines that she began applying to almost everything posted on Craigslist. Turns out it wasn't that Sharon hated the work she was doing or the company she was doing it for; she hated doing it full time. Three years later, she still writes for them - as a freelancer.

My friend Steve is the same way. He's dabbled in sales, computers and real estate. He can't remember the last full-time job he had, and he spends afternoons in nice weather in-line skating along Kelly Drive. He says he would never take a full-time job.

It just goes to show that many of us who graduated from college in the '90s and '00s think of work differently from the way our parents did. We've been taught by the dot-com boom that having a job doesn't have to mean Office Space-like workaholism. We can be productive members of society, make our rent, and never file a TPS report.

The changing nature of health insurance is one of the largest factors pushing the emergence of this entrepreneurial society. Most of the people I know can make just as much if not more money freelancing than by taking a job with a large company. Of course, then they have to pay for their own health insurance. So one of the main (one of the few?) reasons to take a full-time job is for the health coverage. I know one married mother of three who would quit her job if it were not for the insurance package.

But as companies pull back the proportion of benefits they cover, and as more affordable options and services such as become available, especially to the young and healthy, benefits packages are less and less of a draw. I get my health insurance through the Philadelphia Chamber of Commerce.

Companies, of course, love the idea of not having to pay full-time salaries and, most of all, benefits. I worked for one company for nearly four years as a contract employee. Though I was putting in more than 60 hours a week, they would never hire me, because they didn't want to pay for insurance. When a full-time job came vacant, the company often hired a contract worker as a replacement.

Freelancing also allows those of us not located in the Google-rific world of office skate parks and laptop-friendly cafeterias to work in our pajamas with clients we like at 3 a.m. at a bar, park or coffee shop. We aren't chained to our desks or roped to our neckties.

I love being able to hit a midday yoga class, work on my short stories, or take my grandmother to get her hair done and then return to my computer. I am expecting my first child next month, and I can't imagine a better way to bring in money and avoid the tortures of constant breast-pumping.

My friend Brian, whose wife is an English professor, has been able to stay at home with their daughter while freelancing. The amount they've saved in child care alone just about compensates for the shortfall from a higher full-time salary.

Since I'm just getting started, cash flow is just a trickle so far, and I am sometimes tempted to apply for anything that doesn't involve nudity. When anxiety strikes, I remind myself of Nicole, a travel writer who has always just returned from an exotic journey to upcoming hot spots such as Panama or from rating spas in the Caribbean. Her Queen Village house is like something out of the decorating magazines for which she is a frequent contributor.

Other friends aren't living quite so luxy, but are managing to cobble together an income from a variety of sources while choosing non-office lives. Meredith is a yoga instructor whose flexible schedule allowed her to pursue her dream. Last year, she helped start the wildly successful nonprofit Maternal Wellness Center in Mount Airy. Meredith isn't ready to hire Nicole's decorator, but she is able to forgo a salary from the center until its loans are repaid.

For now, a month into this balancing act, I'm taking heart in stories like Meredith's - and in Bly's advice to aim high. And I'm doing it in my pajamas.