Freelance Writing 101

New to writing for hire? Take this hard-earned advice and run with it.

Freelance writing 101
Follow the lessons in this article to find success freelance writing. Image by Ilyafs/Shutterstock

I suspect that some readers skip over this column. The name “Freelance Success” suggests a certain level of experience is required: I mean, how can you have “success” at an endeavor you’ve just started?

Here’s the secret. If you get paid for writing something, you’re successful. Even if you’ve decided to pursue freelance writing as a full-time career, you’re successful, because for so many this is a hopeless pipe dream, like teaching our current president the concept of compassion. 

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The only barrier to entry is your willingness to succeed.

A writer friend of mine once remarked that freelancing is like swimming in the middle of the ocean: It’s simultaneously liberating and frightening. I agree – with a slight amendment. To start freelancing, you need a raft. So, newcomers, this column is for you. Stay afloat with these instructions I’ve fashioned out of my mistakes and experience.

1. Look, look, look again. Then leap.

Life without a regular paycheck is an adjustment, so after you’ve decided to freelance, wait a month or two (or more) if you can. Garnish some of your paycheck toward a small savings fund you can tap into when things get tight. Begin reaching out to colleagues and friends to indicate that you’re looking for work. You also might want to land a menial job that allows you time to write while providing a base salary. 

I got lucky when I started in 2006. My grandmother had set up a mutual fund in my name. It wasn’t much – maybe $5,000 – but it went right into my checking account. I grabbed a full-time job at Borders, which provided health insurance and breathable hours that allowed time to write. I spent 18 months following that game plan. 

2. Set up a work routine.

If you don’t, you will binge on the indulgences – cable and internet, a bed – that come from working at home. Get up at the same time every day. Set up a list of tasks. Stick to it. Jobs have routines, you say. Well, guess what? This is a job, even if you work in socks.

3. Keep home and work separate.

When I started, I lived in a one-bedroom condo. I put my desk in a corner of the living room. My sound interior design decision turned into a horror story, because I was reminded of deadlines and to-do lists all the time. Looking back, I should have written in a library or a coffee shop, some place that signified work. When my wife and I moved in together, she insisted we get a two-bedroom apartment, so I would have an office. That has continued in every place we’ve lived in since. 

4. Diversify how you find gigs.

The internet is great for research, but it also makes you think that the only opportunities exist online. Not true – plus everyone flocks to those job postings. Write pitch letters. Keep reaching out to old editorial contacts. Tell friends and family members you’re on the lookout.

An ugly truth about freelance writing is that a good chunk of time is spent not writing. In time, you’ll find the right balance.

5. Get ready to write pitch letters.

“But can’t I ping the editor through LinkedIn or Facebook?”

No, that’s the purpose of the editor’s email account.

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“What about Twitter?”

Good lord, no. I can’t list what I had for breakfast in 280 characters.

There are two times you can use social media for pitching. The first is when an editor says they want to receive pitches via social media – and that is rare. The second is when the editor follows you on a platform. You can write a short message along the lines of “Hey, I’d love to write for you. Are you accepting pitches?” 

The rest of the time, construct a pitch letter that is one part blueprint and one part sales pitch. Sorry.

6. Rejection is part of the beat.

Yes, freelance writers are really in sales. To use Taffy Brodesser-Akner’s wonderful phrase, we’re “idea vendors.” Some days, buyers are interested. Some days, not so much. Get used to hearing “no,” but remember how good it feels to hear “yes.” The latter is your fuel. 

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Please don’t act indignant when an editor rejects your idea. It’s never personal. Just write “Thank you very much. I’ll be in touch when I have a better idea” and hit reply. 

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After that, regroup. Study the publication to see what kind of stories run and what they have in common. More importantly, learn the best section for new writers. Many resources, including this very magazine, talk to editors about exactly that. A common mistake new freelancers make is they offer a vague idea (“I want to write about global warming.”) or a thinly veiled demand (“I want to interview Anna Kendrick!”) rather than a detailed plan on reporting and writing a story. 

Following these rules won’t make you impervious to rejection, but it will make an editor eager to hear from you in the future. “This isn’t for me, but please keep pitching” means you have an ally.

7. Take taxes seriously.

Thirty percent of every paycheck goes to taxes. (I put my money earmarked for taxes into an online account strictly for that purpose.) This way, you won’t miss the money and you won’t have to pay a back-breaking bill at tax time. Quarterly taxes, where you pay a pre-established amount to the IRS every three months, further helps ease the discomfort.

The most important piece of advice: find a good CPA, one who’s current on tax laws and returns your phone calls. 

8. Be prepared to fire clients.

Priceless advice from my friend and colleague Jen A. Miller: Just because somebody gives you work and pays you doesn’t mean they have permission to abuse you. Totally unreasonable requests. Broken promises. Bounced checks. Leave.

9. Respect the other side.

Film critic Sam Adams once remarked that a writer’s job is to make an editor’s job easier. Make deadlines; be accountable when you can’t. Editors hate working with flakes and divas. Act like an adult.  

10. Take your time.

Freelance writing should be about two things: making a decent wage and having fun. Your contemporaries might be landing book deals and getting gigs at high-end outlets while you edit medical directories. Don’t let their success contaminate you. Everyone’s timetable is different. The minute you get consumed by the success of others, envy becomes your new employer – and she is an awful boss. 

 

Finally: What if you discover you hate freelancing? Step away. Your happiness matters most, and at least you know what you don’t like. Now you can find the job that is the right fit –something that will provide more than just vacation time and casual Fridays. 

But for those who end up loving freelancing, take the time to help someone else set sail. After all, there’s plenty of room in the ocean.

 

Veteran freelance writer Pete Croatto (Twitter: @PeteCroatto) is working on his first book for Atria Books, an imprint of Simon & Schuster.