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Freelance Success: How to become a risk-free freelancer

Becoming a successful freelance writer means mastering both emotional and financial components.

How to become a risk-free freelancer. This image shows a man perched upon a giant coffee cup, reaching to circle the top item on a larger-than-life list of priorities.
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Several months ago, I interviewed Dave Blazek, who draws and writes the Loose Parts comic strip. As someone who draws a nationally syndicated strip, Blazek receives his fair share of criticism. He’s not bothered by it. Anybody can make an accurate criticism once, he told me. That doesn’t mean you can draw a strip every day no matter what – when you’re sick, when you’d rather make yourself the filling in a blanket burrito and lose yourself in the pages of a thick, great novel.

In short, you have to treat cartooning like a job.

The same mindset applies to writing. You know this, otherwise you wouldn’t be reading this. But I think we also have to work at being risk-free freelancers, people who can contribute to the emotional and financial well-being of our families – and ourselves – without subjecting them to the whims of this crazy business.

To do that requires adhering to a lengthy, diverse checklist.



Don’t be afraid to take multiple assignments, because you’ll be forced to stay busy. That’s better than doing nothing, and you’ll have a cushion when the inevitable financial crisis arises – as well as the days off to recuperate from it.

Be consistent.

This separates the dabbler from the serious professional. Every day, you’re in the chair, putting words on a screen, sending a pitch, and putting forth the effort that puts you closer to getting paid or being published. It’s unglamorous, necessary work that will provide the requisite discipline to do this job well.

Fill the days with value.

When the writing lags, I do something constructive. I pay bills, grocery shop, hit the post office. These little outings make me feel useful, clear my head, and keep the household from descending into chaos. Sometimes a break from routine is the right prescription for productivity.


Follow up on everything, including when you get an assignment.

This happens. An editor will show interest in a pitch, and then the writer fades away. What? That’s like passing $500 on the sidewalk because you don’t feel like bending your knees. Follow up. Nobody will do it for you.

Recycle your pitches.

Good pitches take time and thought. If one outlet doesn’t like a story, I am not going to waste hours of effort because of one “no thanks.” Pitches get rejected for many reasons. The outlet doesn’t have space. It doesn’t fit the publication’s agenda. A writer did something similar. It doesn’t matter. If a story idea makes me giddy, I want to keep it alive. That’s why I have multiple outlets in mind for every story. I feel like every pitch has been rejected two or three times before it found a home.

If financial issues loom, address them early.

I do my best to keep money coming in, but I owe it to my wife to keep her appraised of my status so we can solve the problem beforehand instead of launching into a dinner theater production of Who’s Afraid of Virginia Woolf? when the mortgage comes due. This happened when I wrote my book. After all the dues and debts and taxes were paid, I had $14,000 left from the first part of the advance. We thought that would be enough until I finished the first draft of the manuscript. Then I could resume my freelancing schedule. The money ran out early, and I needed more time. What could have been a calamity was only a problem because Laura and I had discussed this. We made some adjustments, dipped into our reserves, and rode the rapids until I could resume a normal freelance schedule.


Practice flexibility.

As a father and husband who works from home, I am on call. I have abandoned the writerly idea that my talent only flourishes in perfect conditions. This isn’t a space shuttle launch. I write in whatever pockets I can find. That’s why I’m writing this column in the spare bedroom of my parents’ house during our holiday visit. There’s no desk, but the bed is comfortable – without inducing drowsiness – and it’s quiet.

It’s never personal.

Whether it’s an editor not responding to your emails or the babysitter bailing as your wife leaves for a business trip, no one is “out to get you.” No one has an agenda. Life makes corned beef hash out of all of us.

Make bills a motivator.

Some people look at them as grand annoyances. So do I, but they’re catalysts. You can’t get lazy when the septic tank oozes shit into the laundry room. You can’t say no to an assignment when insurance won’t cover the last $750.02 of your kid’s surgery. Yes, I know the exact amount. Yes, I got an assignment that covered it – and then some.



This checklist – or your version of it – will become ingrained. It will change. I recently read several articles touting the value of creating a business plan with long-term goals. The experience of writing a research-heavy book made me realize that I need to figure out a way to stretch the advance. And I want to start setting aside money for long-term projects that will help my career – like creating a website. I would love to teach someday.

To become a risk-free freelancer means taking the time to think ahead, to give predictability to the unpredictable. If that sounds boring to you, embrace the adventure of building your career. That can put you in a better position to feed your soul, give your work meaning, and build a life worth living. That’s worth the risk.

—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