How to thrive as a freelancer

I share the unvarnished truth about how to reach your dreams

Not long ago, I sat in a hotel room looking out a picture window straight at Diamond Head, the volcanic peak that looms over Waikīkī. I had just finished my morning constitutional to the Kapi‘olani Park fountain and back. Stretching ahead of me was a day of zooming around Honolulu interviewing actors, directors, and professors. In the evening, I’d watch a rehearsal of Twelfth Night. Then I’d take a night swim under a Pacific sky and call it a day. A workday.

I was writing a story about Shakespeare in Hawai‘i, an article for an airline magazine published during a yearlong celebration of the Bard’s 400th year. My airfare, hotel, and expenses were paid for, and I would make $2,000 for the story. I felt engaged, creative, incredibly lucky. And free. This, I told myself, is what I’ve been working for all these years.

Moments like that morning in Waikīkī are not the standard in my cobbled-together writing life, so when they come they are sweet. A freelance writing career rarely offers fame, riches, or awards like “Employee of the Month.” But if you are willing to work hard, think strategically, roll with punches, and innovate, those Diamond Head moments do come.

The foundation: Know thyself

When we speak of freelance writers today, we refer to self-employed writers who do a variety of writing projects not as part of a publisher’s staff, but rather on an hourly or a per-project basis. (In medieval times, a “free lance” was a mercenary, a free agent who offered his lance to someone who needed fighting power and offered the highest bid.)

Freelance writers are free in the sense that they do not have to work nine-to-five, attend endless meetings, sit stewing in rush-hour traffic, or obey the strictures of a “boss.” They are not free in the sense that they succeed by finding people who appreciate their skills and experience and who are eager to pay for quality work.

One of the first requirements in thriving as a freelancer is to sense which of your affinities will make it easier to be a solo venturer, which will make it harder, which you will rely on the most, and which you might want to work around. There is no one “Freelancing Personality Style.” Depending on what you know about yourself, you might seek work that requires online databases and library research, or, conversely, lots of interactive reporting. Your tolerance for financial ups and downs might lead you to have a reliable gig for ballast.

Serious freelancers work hard and meet deadlines, but they can work in their pajamas, set up in cafés, or design their offices to their own liking. Morning people can blast through their work early and get to the gym well before dinner. Night owls can sleep in and work in the wee hours. A freelancer can do riveting work in intense bursts or parse ho-hum work out among other tasks – be they gardening, shopping, or dance classes.

Successful freelancers enjoy the combination of right- and left-brain activities. They love independence but are astute time managers. They revel in the world of ideas but are practical about the value of their work. They love books and are decent bookkeepers. They care about commas and etymology, but also current events, plot, character, and controversy.

More about strategies.

The next step: Know thy publications

If you want to write for a particular publication, figure out fast whether it relies on staff writers or freelancers. (Hint: Look for freelancers on a magazine’s contributor’s page. Look at the masthead and see if it lists “contributing writers and editors.” Those are freelancers.)

The process of selling a story idea can be tricky. Sometimes you can feel like you are carrying around a plug (the idea), desperately looking for the right socket (the publication). Understanding a few key things about a publication before pitching an idea will give you an easier time fitting your plug to their socket:

Style. Is the publication journalistic, like Time, with articles that focus on current events and hard news? Is it literary, like The Sun, with a combination of fiction and nonfiction, poetry, and art? Is it commercial, like Costco Connection?

Genre of articles. Does the publication print long reported articles, essays, how-to or “service pieces,” personal stories, or all of the above? Afar, a travel magazine, publishes all of the above. Via, a regional travel magazine in the West, publishes fewer long articles and essays.

Specificity. Is this a general interest magazine, like Huffington Post, intended for a wide audience interested in a variety of stories about different subjects? Or is it a niche magazine, intended for a narrower audience of people with a specific interest, like tennis (Tennis), technology (Wired), knitting (Knitting), or food (Saveur)?

Audience. Who reads this publication? Mostly men (Men’s Journal) or mostly women (Self )? Does it reach a national audience (The New York Times), a regional one (The California Sunday Magazine), or a local one (San Diego)? Look not only at the style and content for this, but at the ads. These will give you hints about its readers. Are they the mass audience of sports fans (ESPN) or the targeted audience of men 18 to 34 who buy fast cars, expensive watches, and cigars (GQ)?

Distribution. The way a magazine reaches readers can also tell you something about who those readers are. Is it bought at a newsstand in the financial district, or in a bookstore, or in a grocery store? Is it mostly sold by subscription? Does it come to you if you belong to AAA or AARP?

Freelancing as a vocation, not an avocation

All of us love to write – even if we struggle with the writing. But there’s a big difference between writing as a passion and writing as a profession. Ideally, you keep the passion alive even when writing is your job. But being a professional writer is indeed a job.

All serious freelancers work hard and meet deadlines. This requires incredible discipline: Showing up every day, early, and staying in the chair at least five hours; plugging away at writing every one of those hours, no matter how much we hate staring at the empty page; focusing, intently.

I often unplug the phone in the early hours; I manage email very carefully, so as not to let it rule me; I discourage friends from calling me during my work hours; I never bring personal chores (doing bills, scheduling appointments, dealing with health insurance) into my writing space.

It helps to have an office. When I started my career as a writer, I worked on a wooden table in my bedroom. It was set right in front of the window, so when I sat down to write I could ignore the rest of my life, packed into that small apartment. When my boyfriend moved in, I realized I needed a discrete office and not just a desk in my bedroom or the kitchen table—or even a table in café.

Today I have an office with a desk, bookshelves, a window, a couch—and a door that closes—in a cooperative workspace called The Writers Grotto. Arriving at my office helps me click into gear, and I appreciate working in proximity to other freelancers. I take quick lunches there, and I’ve been known to nap on the couch. It’s the perfect workspace for me and allows me to be quite productive.

Hang your shingle and think long-term

To get started in the writing, set a schedule and stick to it. To start making money, check out things like job boards and Craigslist. Answer ads, and take any writing gigs you can to build your confidence and experience. Place ads to solicit the kind of work you seek. Research publications, develop some ideas, and start pitching.

Don’t forget: freelance writing is a business. You must be brutal about the monetary aspects of this career, because no one else is going to be thinking about this—except, perhaps, your family, which needs your financial contribution.

Making a living as a freelancer is tough. I’m in my third decade, and I’ve never earned an annual salary even in the high five figures. I average between $30,000 and $50,000 a year. (That said, I spend my workdays having a lot of fun, I travel on someone else’s dime, and I get to learn about fascinating things without having to pay for multiple graduate degrees).

Let’s get practical, though, about the money part. I’ve always said, somewhat jokingly, that to succeed as a freelancer you must have a housing scam. You must figure out manageable, low-cost digs. It might mean buying a house in a sketchy urban area, as I did. It might mean staying put in a rent-controlled apartment or moving to the wilds of Wyoming. Think carefully about your long-term needs and come up with a plan.

Freelancing often involves a feast-or-famine workflow, and relatively low pay. Few freelancers rely solely on income from writing, unless they’ve been lucky enough to have a bestselling book. Many rely on:

—a spouse who supports them;
—an inheritance;
—savings from a previous career;
—a day job;
—a night job or a teaching gig;
—related part-time work in editing, technical writing, corporate writing, or grant-writing.

Figure out where your financial ballast will come from. I make money from my writing, and I always try to negotiate the pay upward. But I rely on editing for predictable income.

In plotting how to make the monthly nugget, some use what I call the MBA approach: They draft a business plan. They make a pie chart to figure out how to portion out different kinds of work. They make lists with goals and metrics.

Some use what I call the MFA approach: They keep massive bulletin boards. They make collages that help them imagine all the ways they will find creative satisfaction. They prepare for financial ups and downs.

Here’s a checklist for freelancers’ business must-dos.

Get going, but don’t go it alone

Succeeding as a freelancer is not just about hanging your shingle and savvy pitching. It’s also about being a good writer, not giving up, growing, and continuing to improve at the craft. (Some editors keep their eyes on certain writers who show talent or verve, watching them develop. One editor at The New Yorker told me about a writer who pitched him 15 times before getting an assignment. The editor watched as the writer kept publishing in other places, getting better and better at his game. And then he landed an assignment at the prestigious magazine.)

Take writing classes at a local salon, a writers’ collective, or a university “extension” program.

And find moral support as you set higher and higher goals. You can improve your skills, meet more writers, and learn more about various markets by taking classes. Writers’ conferences are a great place to see editors and agents in the flesh and to have face-to-face conversations.

You can find models by going to readings at bookstores or attending literary festivals with inspiring panels and talks.

You can shadow someone to learn the ropes or apply for an internship. You can join professional groups to learn about opportunities. There are all kinds of groups—like Left Coast Writers® in the San Francisco Bay area, or chapters of the California Writers Club up and down the state, or the American Society of Journalists and Authors, which is national.

If you’re like me, you’ll find the right mix of work, publications, and people that keeps you inspired without getting in the way of your disciplined daily routine.

Of course, I’m still plotting what’s next. If I stay focused and disciplined, and if my luck continues to hold, I expect that soon I’ll be staring out some new picture window, amazed that I’m getting paid to go somewhere new and write about something that allows me to fire on all cylinders.

—Constance Hale

{A version of this article first appeared in The Writer in December 2016.}

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