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Freelance Success: Rules to keep freelancers grounded in times of crisis

How do we work and stay sane? By sticking to what got us here.

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Logic, in my experience, is one of the first things to succumb to a crisis.

When I got walloped by the Great Recession in summer 2008, I had been freelancing regularly since spring 2006 and had made the jump to full time three months before the economy, and I, collapsed. The abject horror of my dwindling checking account and vanishing clients paralyzed me. I didn’t write pitches. I didn’t diversify my skill set. I didn’t network. Instead of looking for ideas, I waited for the happy ending machine to kick into gear. If it weren’t for my parents’ ill-advised generosity, my mistakes would have had unimaginable consequences – like a cratered credit history or taking the LSATs.

I suspect many writers face this ordeal now as an incomprehensible death count and anger become normal; deep exhaustion routine. It’s understandable. Nobody wants to fall through the trap door. But it’s too easy to get consumed about taking the plunge that you miss running into the wall. We’re all trying to find the next gig to pay the rent. It’s easy to forego the unwritten rules. We shouldn’t, because they root us in our job and keep us on the path to higher ground.

Here are the ones that I feel are the first to get tossed as desperation arrives.

Don’t bitch to an editor about your rejected pitch.

Perpetually late payments without a reply? Sure, let them hear your frustration. Rejiggering lines of prose without the courtesy of a read-through? Unload! But every so often, a writer gets briny over a perfectly polite rejection.

Nobody likes to be cast aside. Someone has to lose. Sometimes that person is you. It’s nothing personal. Welcome to the game.


Have options.

Let’s stick with games for a moment. Quarterbacks Joe Montana and Steve Young built their legends throwing passes to Jerry Rice, arguably the greatest wide receiver in football history. But they couldn’t depend on him all the time. Every play had options. If Rice was blanketed, Montana or Young turned to John Taylor or Brent Jones or Roger Craig.

Employ the same mindset. If the New York Times says no, go to the Washington Post. Then try the Wall Street Journal or Slate or the local alt-weekly (if your town has one) until you find an outlet. Sometimes no one is open and you have to take the sack.

Don’t steal.

It’s not just plagiarism. According to Wudan Yan, an ace freelance writer, people apparently crib pitches. There plenty of work to go around. In fact, developing ideas is part of your job. There is no reason to steal another person’s idea, unless you’re lazy or immoral. And don’t claim desperation as an excuse. Other people are grasping onto melting ice floes with numb fingers.


Shelve your ego.

Nobody owes your their time, whether it’s an editor, a source, or a fellow writer you’ve asked for advice.

Maybe it’s because I spent years as a newspaper reporter and in retail – two occupations held in scant regard – but I rarely take offense if someone gives me the high-hat. Somebody will give you the time if you make enough phone calls. When I wrote my book on the National Basketball Association’s rise in popularity, I hoped to talk to former league commissioner David Stern, someone who had a good (albeit combative) rapport with the press. He declined. Repeatedly. Instead, I sought out his associates, friends, and colleagues, anyone who could give me insight into his business acumen and passion. Those sources were less guarded than Stern, who died in January, because they had nothing to lose. 

Ask for one favor.

The biggest casualty of the “shoot your shot” era: People have forgotten how to ask for help. I’ll never forget the aspiring freelancer who asked me to send her job postings that I passed over each day or how a total stranger asked Jen A. Miller, a well-established freelance writer, for all of her editor contacts. Everybody has a story that would make Emily Post blanch. Don’t be the star of that story.

You get one favor; choose wisely. Say thanks, follow through, and pay it forward. 


Stay curious.

I write this column for two reasons. The first is to offer advice that provides comfort or clarity to writers of all experience levels. The second is to learn something, whether it’s about legislation that threatens our livelihood or how editors go about their day or how the hell to write with an infant fastened to your hip. I read every issue of The Writer because there’s always some nugget of information that I can use – a perspective, a phrase, a potential contact – that could contribute to a triumph down the road.

You can leave at any time.

In July, Eva Holland, a stellar freelance writer who wrote a wonderful book (Nerve: Adventures in the Science of Fear) and boasted an array of dazzling clips, started bartending. Then she declared her intention on Twitter to find a new occupation. My panic and indignant pouting soon made away for empathy. Everyone’s circumstances are different. Everyone grows fatigued at different times. What we need to get through life – whether it’s financial, emotional, or social – changes. Now throw a pandemic on top of the rumbling tectonic plates that are freelancing writing.



Here’s another lesson, courtesy of Amber Sparks, the author of And I Do Not Forgive You. The act of writing doesn’t go bad. You can come back to it whenever you feel right. You owe nobody an explanation on creating the best version of yourself. Isn’t that why most of us embarked on a freelance career in the first place?

Ithaca-based Pete Croatto 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. Twitter: @PeteCroatto