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Freelance Success: What the hell is ‘freelance success,’ anyway?

You’re doing OK. Really.

Freelance Success
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Freelance success – the term, not the column – is a murky concept. Most 9-to-5 jobs feature easy-to-identify highlights: a glowing, life-affirming performance review, a raise, maybe a promotion. Your boss likes you, so she lets you work from home or gets you that sweet parking spot. Perhaps you get a sizable gift card for your birthday.

I never got these perks. At my last full-time job, birthdays were marked with the same apple cake served on plastic plates in the boss’s sad, sterile office, the final scene in a Raymond Carver story. It was fitting that the office sat next to a cemetery.

All those dizzying amenities made it easy to go freelance in November 2006. I love what I do now, but I’m frequently floating in space – in a dreamy kind of way, not the terrified Sandra-Bullock-in-Gravity way. That’s the permanent occupational hazard of this set-up. You must provide the tether office workers take for granted: finding health insurance, paying taxes, setting up an office schedule.

Recognizing accomplishments fall under that category, and they’re just as important to keep you grounded. Some are obvious, like if you leave your steady job to write full time or find a publisher for your book idea. Here, I’m more concerned with acts that get overlooked in the daily slog toward legitimacy and away from insolvency.


Remember to take pride in these small triumphs; no else will do that for you.


A stranger praises your work. Twitter is frequently awful if you’re a realist, a grammar nerd, or not a straight white man, but it allows the stay-at-home writer to feel less alone. (Fellow freelancer Jen A. Miller refers to it as her water cooler.) Anytime a stranger shares your story or offers a compliment, savor it. Someone who isn’t a relative or a friend or a parent read your words and was moved by them. What we do can have an impact, a concept more energizing than any byline.


A stranger slams your work. The flip side of writing for outlets with larger audiences, and writing well, is being increasingly prone to blowback from readers. That’s the price of having a higher profile, and I’m happy to pay it, because editors are getting readers and my work is eliciting a reaction beyond indifference. It’s a good hurt.



Out of the blue, an editor invites you to write for their publication. This is a close relative of the previous points, with two additional benefits. First, this appreciation comes with money. Second, you don’t have to spend hours crafting a pitch or courting editors; you head to the front of the line.


An editor shuts down your pitch but opens a window. A pitch can be rejected for many reasons: the story was done before, it doesn’t fit with the magazine’s editorial mission, the editor hates the subject. But if that editor gently lets you down and then offers the chance to pitch her again, that’s a tremendous consolation prize. You have another ally, someone who knows your name and will look forward to your email. Plus, you know an editor who responds to emails, the Bigfoot of our profession.



You leave an inadequate client. Knowing for the first time that you can find more satisfying work is your bar mitzvah. I fear new freelancers view terrible pay or despotic editors as conditions of the business, like invoicing or W-9s. They are not. The same tenacity that led you to this place can be channeled into finding jobs that don’t diminish your self-worth or your savings account.

You get published in places people know. It doesn’t matter how much talent or self-confidence you possess, it’s hard to feel like a success when the response to places you’ve written for is either “I’ve never heard of them” or “Do they even pay?” These comments shouldn’t rankle a salty veteran like myself, but they do. An identity crisis over a plate of pigs in a blanket is a real thing.

These people are nitwits. Writing for national publications is not the key to happiness. It’s doing what you’re meant to do, and not talking about possibilities until they ferment into regret. As Stephen King wrote, “If you wrote something for which someone sent you a check, if you cashed the check and it didn›t bounce, and if you then paid the light bill with the money, I consider you talented.” That’s as useful a measurement for success as I’ve encountered.



Finding work is no longer your main priority. You have several steady gigs. Editors know to hit you up when they need a job done right. A quick note to a familiar editor serves as an effective pitch. A long-term project covers your expenses for three months. The amount of success you have is inversely proportional to the time spent on job boards,, and Sweet Baby Jesus exposure is not a form of compensation! Why is this still a thing?! It’s been years!


Getting gigs becomes an expectation, not a fluke. I am aware that many factors – from editors I’ve met to whom I married to my family’s patience and benevolence – have put me in this position. But I also know that I’m good at this. Nobody can do anything for this long because of luck alone. Besides, luck becomes a shabby excuse if it’s not flanked by talent and discipline.



And that work feeds your passion. If you’re writing just for money, you will be more than a little bit disappointed.

Other writers come to you for advice. People aspiring to succeed in a field don’t seek counsel from the incompetent, unless “teaching via cautionary tale” is corporate America’s hot new mentorship trend. I don’t know. I’m not on LinkedIn much these days.


You will find other landmarks for success, ones that will cause you to sit back and take pride in what you’ve done on your own and the accomplishments that lie ahead. No parking space or apple cake can replicate that feeling.



—Ithaca-based Pete Croatto (Twitter: @PeteCroatto) is a veteran freelance writer who has written for The New York Times, The Christian Science Monitor, Publishers Weekly, Columbia Journalism Review, and many other publications. He is also working on his first book.