10 Quick and Dirty Tips for Freelance Writing

Let me start this post by confessing how uncomfortable I am with giving advice — specifically career advice. But countless EM readers have emailed me for posts on how to make it as a writer or how to grow a blog — and I watch my colleague bloggers talking on panels, and other bloggers hosting web seminars and online classes, as if the formula is neat and simple, like handing someone a paint-by-number picture of success.

But I feel like I'm still chugging along, like anyone else. I feel like the variables are impossible, and that, quite simply, I might jinx myself. More than that, I feel just as Dorothy Parker did:

"That would be a good thing for them to cut on my tombstone: Wherever she went, including here, it was against her better judgment."

It might be true that ever single one of my major life decisions has been met with raised eyebrows and hunched shoulders. Eek. Are you sure you want to do that? 

If I had been a sane, rational, careful person, I never would have ditched a semester of classes to chase a life-changing job opportunity and been as inappropriately persistent in my pursuit. I never would have left a stable dream job with (in hindsight) incomparable benefits for the long-shot life of a freelance writer — especially with an infant at home depending on me. Hell, I never would have gone through with my pregnancy. Or gotten married. Everywhere I've gone, including here, has been against my better judgment.

But it's been right.

That being said, I've had a handful of editorial jobs — regional, national, print, online — in the office, as well as working from home. I've been on both sides of the computer screen — editing other people's writing and having my writing edited. I've had bylines in national magazines, high-traffic Web sites, and books. So maybe I have learned a few things along the way. (Dear Universe, be kind to me.)

First: Freelance writing. I can't tell you how to get a specific job, or even encourage you to mic-drop your 9-to-5 for the flexibility of freelancing. (Oh there's that uncomfortable feeling again.) But I can tell you this...

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1. Whatever it is that's making you feel like you're not enough of a writer to be a writer, just stop it. Stop comparing yourself to other bloggers and freelance writers who splash their credentials across their Twitter bio. Stop beating yourself up over each and every rejection. (Rejection happens, a lot, especially in the beginning.) Stop holding yourself back. You have full control over your life — this is it, right now, right this very second — so make it happen. There are a lot of terrible writers doing it. (MY GOD there are a lot of terrible writers. Have you read Twilight?)  You're better than that. (This is where I slap your ass as you file out of the locker room.)

2. Pitch better.

A) At the very least, pitch to the right person. Go grab a magazine and take a look at the masthead. Do you see those names way at the top? With important titles like EDITOR IN CHIEF and DIRECTOR and EXECUTIVE? Keep it moving, sister. Those are most definitely not the people to contact. Even those middle-of-the-road editors typically aren't the right contacts. You want someone with the word ASSISTANT in the title. Editorial Assistant is best, but Assistant Editor is better than nothing. Find the department that you're looking for (beauty? features?) and then follow this handy cheat sheet that I never told you about:

Condé Nast (Glamour, SELF, Allure, etc.) :  firstname_lastname@condenast.com

Hearst (Marie Claire, Seventeen, Good Housekeeping, Cosmo, etc.):  FirstInitialLastName@hearst.com

Time Inc (People, InStyle, etc.):  firstname_lastname@timeinc.com

Meredith (American Baby, Family Circle, Parents, etc.):  firstname.lastname@meredith.com

Bonnier Corporation (Parenting, Working Mother): firstname.lastname@bonniercorp.com

B) Make sure that the masthead/online contact info. is as current as possible, because editorial jobs have a faster turn-over than a Ruby Tuesday on Friday night. (Any other Ruby Tuesday veterans here? Holla.)

C) Make your pitch short and concise. Confidently state previous writing credentials right in the intro. If you'll be interviewing experts, say who they are. Tailor your pitch to the individual magazine, rather than sending out a general mass blast. (This should go without saying, but you'd be surprised.) Don't get crazy or fancy with the subject lines. If a subject is too long, or if it feels like a mass PR blast, it will likely get ignored. An easy subject line is something like: "Idea for ____ Section," which proves that you know about a magazine or Web site's different sections. Sending in a full essay? Embed it into the body of the e-mail because, #1, if your title and intro are catchy enough, he/she might get hooked, and #2, no one likes downloading attachments from strangers. (You might want to include an attachment AS WELL as embedding, because, options? Always good.) And, if you have them, include links to your other work (including, yes, your blog).

D) Follow up. Editors are human, you guys. Humans inundated with an ungodly amount of emails. Things fall through the cracks. PERSISTENCE PERSISTENCE PERSISTENCE.

3. Timely pitches are good for online media, but they can be trickier for print. Typical lead time is 3 months — which means if you have a February deadline, it most likely won't be published until May/June/July. (But that's a helpful tip in case you're pitching a seasonal story.) Want a sneaky little secret? (of course you do.) Search through past issues of a print magazine — not just months, I'm talking years — and find a nice evergreen piece. Take the basic concept/topic and add your own unique spin to it. It won't always work, but you have a better chance than pitching an out-of-the-box choice, considering magazines tend to have specific voices and topics that they like to recycle. If nothing else, fully research a magazine or Web site before pitching — including tone and typical topics.

4. If you want to make a good, steady living as a freelance writer, the best route is a steady gig. You want to get to a point where editors are asking you for work, not the other way around. You want to get so many writing offers that you have to start turning some down. Living on a pitch-by-pitch basis can be stressful and frustrating — especially if you have a family counting on your paycheck — which is why either a steady staff writing/blogging position is ideal. The good news is that once you get to a certain level — whether it's a reasonable social-media following (for online) or an impressive collection of writing creds (for print), it can snowball from there. The more experience you have — and the better you do your freelance jobs — the easier it will be to snag a steady gig.

5. But what if you don't have any writing clips whatsoever? I remember being so incredibly frustrated with this, way back when (or 4 years ago). HOW AM I SUPPOSED TO GET WRITING CLIPS IF I NEED WRITING CLIPS TO GET PUBLISHED? I just needed a boost, I thought. I just need someone to give me a shot, and then I'll prove my worthiness.

I totally relate to that feeling, but at the same time, start a blog. Wait, scratch that — start an online magazine. Write an e-book. Show that you, yes, can write, but you also have the ambition and vision to create your own writing space. Why not?

6. Paying your dues might be necessary. I'm all for writers demanding their worth — which, I've been told, should never be less than $25/hour — but you might need to write for free to get some clips. And I'm not just talking about those e-lance sites that promise (cough) "big bucks" for soul-sucking medical writing and instructional manuals. I'm not talking about the Craigs List ads that ask you to submit something as a "test" and then steal it without giving you money or credit. Whether it's guest posting or becoming a regular contributor to a favorite Web site, or even working a low-paying internship-like gig, these are all stepping stones. And, let's be honest, they're clips. And clips are what you need.

That being said, don't work for free for too long. Know your worth, and demand it.

7. Ed2010.com. If you want an editorial job, this site is invaluable. They also regularly post freelance/blogging/editorial job openings — some of which are remote, although most are in NYC.

8. MediaBistro. This is where you'll find the meaty job openings and freelance opportunities. They also have a membership option, which, in my opinion, is really only worth it for their "How to Pitch" section — where editors tell you exactly what they're looking for, when they're looking for it, and who to contact. I found it really useful in the beginning, but I'll admit to letting my membership expire awhile ago.

9. Freelancer's Union. Besides offering services like health and dental insurances, the Freelancer's Union has a wealth of resources — especially for nitty-gritty issues like taxes (ugh), retirement planning, and networking. (But seriously, you guys. Taxes. Don't mess around.)

10. Just keep writing. And reading. And researching. And pitching. And writing some more. write write write write write.

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Are you a freelance writer? Any tips to add?