What’s freelance writing for a living really like?

My summer office

I recently read this blog post by a man who hasn’t held any writing job more than two years.

And David Handelman is no deadbeat:

When Aaron Sorkin left The West Wing in 2003, I was the only writer of 11 who immediately cleared out my office. I didn’t want to have to go back to fetch things later if I was let go. As it turned out, eight of us weren’t asked back.

The experience — and, I’m sure, my then-recent divorce — taught me it’s better to assume a job isn’t going to last, and be pleasantly surprised when it does, than presuming the opposite and being caught without a parachute.

As I look around me, more people of my generation seem to be in the same boat. Whether it’s editors who pinball from one job to another, college professors who are forever “adjunct” instead of tenured, newspeople who jump from network to network, it feels like there’s little security. I just happen to be one of the more extreme versions.

I lost my last staff job in June 2006, at the age of 50.

After sending out 48 resumes — with no reply — my heart just wasn’t in it. Like many people, I hate job-hunting. I do not interview very well when on the other side of the questions.

I returned to working freelance, picking up the pace with some long-time clients and finding new ones.

Then the recession hit, slashing my income to 25 percent of my staff salary. Major (i.e. well-paying) magazines were disappearing or cutting their freelance budgets.

My income is, thank heaven, steadily rising, now 50 percent of my old salary. But many print pay rates are lower now, and the costs of living a lot higher so, like many freelancers, I’m running to stay in place.

Bear in mind that some people have several regular columns and/or an advanced degree (allowing them to teach), or write for film or television or do corporate work, (all much more lucrative), none of which I’ve yet tried.

So what’s the freelance life like?

You do need to write well, as American novelist Francine Prose’s book, “Reading Like A Writer”, points out.

Kelly James-Enger, an American friend, colleague and savvy and successful freelancer, has published several helpful books on how to write freelance for a living. Her blog is also filled with good tips.

The one thing you never ever do is make shit up — like the two interns recently fired for outright fabrication, one of them working for The Wall Street Journal. If editors can’t trust you, you’re toast.

It’s a non-stop hustle.

My current income comes from:

Newspaper articles. I write for The New York Times as often as I can find an editor willing to assign, usually 3-6 times a year.

— Magazine articles. I don’t do a lot of magazine work these days. It’s often a hassle of multiple, unpaid revisions and the top rate — once $3/wd is usually, at best, $2/wd, meaning a check of $5,000+ is very difficult to attain when most pieces run at 700 to 1,200 words. Editors only pay you after they’re happy, so I try to work only with editors who like what I submit initially.

Web writing. I recently picked up my first-ever steady gig, writing a personal finance blog for Canadians.

Photo editing. I began my photography career at 17 selling three cover photos to a Toronto magazine and have since had my work published in Time, the Times and the Washington Post, among others. I also studied interior design, so am doing slideshows for HGTV.com, a wholly new way to finally integrate my skills.

Editing others’ work. People come to me to read and critique their own writing. Last year I edited a thriller translated from Spanish, sections of a business book and a few chapters of a memoir. (I charge $150-200/hour.)

Writing books. My last advance payment on “Malled” came in in April 2012. Time to sell the next book!

Speaking engagements. I’ve addressed three retail conferences so far, with my next one at the University of Minnesota on October 30.

Television option rights. My retail memoir, “Malled: My Unintentional Career in Retail” was optioned by CBS as a sitcom and a pilot script written. Like most pilot scripts, it didn’t make the cut. But I got some cash for the option, a one-time payment.

I’d ideally like to add a few more reliable revenue streams, like teaching writing at a college and/or holding my own writing workshops.

If you want, or need, to earn your living freelance, it takes almost daily client relationship building. And each client — unlike your one or two bosses at a staff job — has a different personality, billing cycle, narrative style. You have to adapt constantly.

And, yes, you need to be on LinkedIn; here’s why.

If you want to sell books to commercial publishers, you’ll need to find (and manage) an agent. If your work has value to film or television, you’ll be working with another agent, (who will claim even more of your income) and you might, (as I did), also pay an entertainment lawyer to review your agent-negotiated but possibly dense and incomprehensible contracts.

Freelancing also means a major shift in how you conceptualize work and labor — you’re selling time, talent and skills. They’re not “giving” you a job.

And financial success relies less on office politics (none), than your ability to find, nurture and retain profitable clients, while spotting or quickly shedding the PITAs (pain in the asses.)

People fantasize wildly about how great it is to manage your own time. It’s pleasant indeed to work, as I’m writing this, in a T-shirt and shorts in the cool morning on my balcony in silence.

But the only paycheck you get is the one you did the work successfully, and invoiced for; people with weekly paychecks too easily forget to make sure you also get yours in a timely manner.

Which is why when people offer you “exposure” instead of cold, hard cash for your skills, you must chuckle audibly at their naievete — and remind them that “exposure” is not yet accepted as legal tender anywhere.

You also have to man up enough to ask for more money on a regular basis — because some people with “real” jobs still get raises, bonuses, promotions and commission.

Freelancers only get what they are willing and able to negotiate — and your “value” is a highly subjective and relative term.

And, sadly, you’ll have to deal effectively with cheats and deadbeats.

I live near New York but have hired lawyers in Vancouver, Canada and Kansas City, Missouri to successfully sue two such publishers who, like some of their ilk, assume freelancers are weak, powerless, naive or too nice (hah!) to come after them.

After one in-flight magazine’s editor tried to wriggle out of paying me, I wrote to the airline CEO — and was sent a free ticket to anywhere they flew.

I’ve also hired assistants, who help to keep me productive. Freelancing brings with it a fair amount of administrative work but I don’t need to be the one doing it. I recently filled that position — with five offers within minutes — by posting it on Facebook.

Here’s an excellent blog if you work freelance in any capacity.

Do you freelance for a living?

How’s it going?

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23 thoughts on “What’s freelance writing for a living really like?

    1. The most essential thing to remember — you are running a small business. Too many people focus on the “creativity” of writing when, frankly, some of it IS going to be tedious drudgery — but pays the bills! The freedom from the cube adds a whole new world of other responsibilities.

  1. Although I admire freelancers for their tenacity, I like to have a steady pay; that’s why I’m happy I work in the financial aid office at school. Gives me a paycheck and allows me to write in the evenings.

  2. i for one have always had great respect for freelance writers…im just starting out and its just so difficult, so many people refuse to take me seriously and even my family members, especially my parents keep lecturing me about considering a ‘serious’ career ….also i live in pakistan so careers like writer or artist are very opposed…inshallah maybe things will look up 🙂

    1. Tell them it IS a serious career and you’re just getting started! Seriously, no one needs to put that kind of pressure on you (and I hear this from other ambitious South Asian female friends.)

      If you’re still broke-and-starving in 12 months, time to step back and re-consider. But it will likely take at least that long to: 1) find some assigning editors; 2) assemble enough good samples of you work to get even more assignments; 3) gain the confidence to go for larger and better-paid markets.

      If you have EXCELLENT English skills and know how to report (two big IFs), you might also focus your energies on selling to American, Canadian or British editors, print or radio. Might be a lot easier and better paid than domestic markets…

      1. for now im doing various jobs in local magazines and online but the main problem is that before twelve months my dad might lose his patience and force me into med school unless i can get something a bit bigger and show him i did plan on trying american market but im not really sure they would give the time of day to a completly unknown pakistani girl….i really appreciate your support though 🙂

      2. At gunpoint? Seriously, force you into medical school?

        It’s your father…but if this is what you want to do (do you actually want to go to medical school?)…

        Everyone is “completely unknown”…until they are not. If you want it ferociously enough, you will make it happen. Or not.

    1. Very true. Some are utter wankers…but the good ones quickly pull away from the herd.

      I feel I’m not doing nearly as much as I could or should. I just left the volunteer board of a national writers’ group after (whew) six years of service….but my financial blog gig came about as a direct result of working closely with another board member who referred me to her client…:-)

  3. Thanks for the peek into your freelancing life! I’ve been considering giving it a go for quite some time. Previously, I found the prospect of constantly looking for work too daunting (and very similar to my old life in theatre). But changing projects constantly is actually more natural for me than being stuck in one spot, thinking about the same things day after day. I’m realizing (maybe a little late?) that everything worthwhile is difficult and that there’s no such thing as a free pass. You’ve got to work hard to get what you want. Trouble is, most people don’t want to do all of that heavy lifting.

    I love your practical, no-nonsense posts. Your blog is well-written and so refreshing. Thanks!

    1. “I’m realizing (maybe a little late?) that everything worthwhile is difficult and that there’s no such thing as a free pass. You’ve got to work hard to get what you want. Trouble is, most people don’t want to do all of that heavy lifting.”

      First, thanks for the kind words — Miss Freshly Pressed! Your blog is excellent and your audience super-engaged. Very cool.

      Now…clears throats, looks stern/annoyed/doubtful. Surely (???) you knew already that only a very lucky/connected few blaze through on connections or charm. And they’re toast when people realize they do not have many skills after all. If you’ve (?) been surrounded by people who flew into prime spots, you’ve been rooked into thinking…I can have that too! Because as soon as you lift your foot from the pedal (so to speak), people like me (driven as hell) will breeze past you, and we may be far less pretty/smart/educated/whatev…but determined!!!!

      Much of my relative success has been NOT giving up (and Jesus, there were many, many times it looked attractive.) Both of my (well-reviewed books) were each rejected by 25 (yes) publishers before they sold to major NYC houses. What if I’d given up after 10 or 13 or 18 or 24?!

      So it’s really up to everyone to decide — is it worth all the hard work? How badly, really, do you want it?! I left Canada for the U.S. (as you left the U.S. for Canada)…and people then expect you to rock it, hard. Do you really want to slither back “home” with little to show for the grand adventure that fizzled? Pas moi.

  4. Wow … this has been a popular post. Not surprising when you write in such a no-nonsense fashion. Great tips in there and your honesty shines through in the work that you produce. I like it and I’m glad I found your blog … it’s a font of refeshment.

  5. Very sensible advice, as always! And yeah, it’s a whole paradigm shift from ‘day job’ work. Here in New Zealand there’s been a shift in recent years – the freelance editorial/proofing market is pretty full as people spin out of the media amidst downsizing. Freelance rates have dropped to the point where newspapers pay less than it costs to write the stuff. That’s apart from the way editors (who know it’s a tight buyers’ market) treat their contributors.

    The local book-writing market is more lucrative for authors but limited by scale – the real money’s overseas. A few have done it. One very successful Aucklander writes vampire romance fiction and, I’m told, does better out of it, financially, than in her previous life as a law partner – she hit the NYT best selling lists. There’s another who does well writing Mills & Boon romances – hack-work as far as the snobbish literati are concerned, but this woman gets to pay her power bills and they don’t, so hey…

    1. It’s interesting (if depressing) reading your comments as they reflect my experience in Canada — a nation of 30 million — versus those in the US with 300 million. I left Canada because I knew, even at 30, it was a severely limited market with about 10 people in power in journalism and I’d already been working with them for a decade. One editor sat in his very powerful chair for 30 years — then the woman who took over was the daughter of one of Canada’s most august writers. I had very little patience for that tiny a cabal.

      Living and working in NY (although many highly successful writers here do not perch on its doorstep as I do) is wholly different. Americans welcome a direct approach, which makes Canadians flee and avoid you. I have been able to move easily from one market to another, find new agents as needed, share info with people I trust…there is simply more work to be had, even in a recession. Typically, this week, I’m interviewing a source this morning for my book, made dinner plans with a powerful and connected woman who runs an NGO and am meeting another thought leader for breakfast. I don’t think I’m anyone terribly special, nor do I have much social capital compared to them, so I am very grateful indeed that anyone at their level is willing to make some time for me and my questions.

      When I try to make these (possibly mutually useful) connections in Canada, people freak and flee. Who needs it?

  6. “exposure is not yet accepted as legal tender anywhere” — Love that.

    Fantastic post. I always learn so much when you write on the business of writing. Thank you for sharing your expertise.

    I wished you’d do a post on how to negotiate successfully!

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