5 Steps to Get From Freelance Writer to Published Author

The Internet truly is a great place to get started, because it's all right there for your discovery.
5 Steps to Get From Freelance Writer to Published Author

If there's one question I'm most often asked, it's "How many times have I told you that your health insurance does not cover 'accidental' insertions of your genitalia into homemade sex robots?"

But the next most popular question I get is "How do you become a writer?" The answer is, I don't know. I've only called myself a writer once in my life, and I only had the balls to do it because I was asked by another writer in my agent's office while I was holding an advance check for my forthcoming novel. I'm generally suspicious of people who are too quick to label themselves "writers." They remind me of a girl I knew in college who had business cards printed up with "poet" written under her name.

5 Steps to Get From Freelance Writer to Published Author
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"Well, part time poet, part time philosopher, and full time horrible person."

I have no suggestions on how you can become "a writer," but I can give you advice on how to go about doing something writers do -- getting published. Anyone reading this has opportunities simply unheard of 20 years ago. The Internet has taken the somewhat secret, slow, and unprofitable business of freelance writing and converted it into something fairly transparent, speedy, and still unprofitable. But the Internet truly is a great place to get started, because it's all right there for your discovery.

Pick the Place

The first step is figuring out where to publish. For reasons that will become obvious, let me suggest that you pick a site or magazine you're already reading a lot. Why? Because the bigger an expert you are on what your prospective publisher prints, the better your odds of getting published there. Why? Well, mostly for the reasons I'm going to give you in Rule 3, so I don't want to shoot my load on that now. For the time being, just imagine a big elephant that takes up a lot of space. Something like this:

5 Steps to Get From Freelance Writer to Published Author
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Got it? Good. OK. The elephant has nothing to do with this rule, but at least now it doesn't look so weird that this entry is so short.

Learn the Rules

OK, so you picked your place. Good! What's next? Well, now you have to learn the rules, and the great thing about publishing online is that most sites will tell you. I always feel awkward and embarrassed when people ask me how to submit to Cracked because it's not like it's a secret. It's right there on the website.



And most websites are like that. And if they don't have that submission information, then it's probably not the place for a new writer to be submitting to anyway. OK, so you found the link. You found the rules for submissions. Now what? Read them. And then? Read them again. Then, and this is the tricky part, do what they say and don't do what they tell you not to do.

As someone interested in writing, you probably already think you possess a unique and special talent. You are the owner of a new voice rising up to the light of publication. You can't let rules and expectations get in the way of the glory of you! Well, you may think you're unique, but guess what? Lots of people think that. Some of you are, but all of you would be stupid to think that your talent (real or imagined) gives you a free pass to do your thing. Sites have rules. Follow them. Failure to do so simply makes you look lazy, stupid, or arrogant. The end.

If the website wants a certain font, then use that font. They want attachments, send attachments. They hate attachments, don't send attachments. Give them your email, your phone number, your blood type, your first choice to play the next Doctor on Doctor Who, it doesn't matter. Read their rules and give them what they ask for.

5 Steps to Get From Freelance Writer to Published Author

By the way, if they do ask that Doctor question, please suggest my son.

Learn the Voice

Hey, remember that big elephant from above? Well, forget it. That was stupid. It was just a placeholder, but we're up to Rule 3, and it's the most important one: Learn the voice. This is why you should pick a site you already know very well. Publishers expect you to deliver content in the style of what they're already publishing daily.

When I was a young writer, I wanted desperately to get published at McSweeney's, which was then run by the lovely editor-at-large John Warner. (Today, the equally lovely managing editor Chris Monks oversees submissions.) In any event, I submitted there a lot and met with much rejection for my first 15 or so tries. And there was a reason I was getting rejected: It didn't sound like McSweeney's. It sort of kind of had a superficial resemblance to something they'd publish, but it wasn't a dead ringer. And that's what you need. Ultimately, I acquired the right sensibility, and after that, just about 50 percent of my submissions were accepted.

It was the same thing with Cracked. This was many years ago, before Cracked became the Cracked you know. Back when it was a just a collection of humor with not a list to be seen for miles.

5 Steps to Get From Freelance Writer to Published Author
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"Cracked without lists?!"

In any event, at that time, my friend Dennis DiClaudio had published this hilarious piece at Cracked, and using that as a guide, I submitted about five rejected pieces. Why rejected? Because even then, that piece, although hilarious, was not the voice of Cracked. It was a fluke. And that brings us to an important rule: Don't submit work that's similar to the obscure parts of a website. In the beginning you want to aim right for the sweet spot. Your value to a publisher is giving them what they already have, but more, with a minimum amount of work on their end to conform your stuff to what their readers expect.

Once you do that and establish credibility, you can spread your wings more and let your freak flag fly, but it's almost always a waste of time to do it off the bat.


It sounds gross, but networking can really help your writing career. Fortunately, almost all my networking has been accidental, because the thought of joining country clubs or going to symposiums still makes me want to puke. For me, it was simple. I just like funny people, so I read funny stuff. Then occasionally I reach out to the authors. (Back in the day, McSweeney's used to give email links in the bylines, but now with Twitter and Facebook, contacting people is really easy.) Around 10 years ago, all my best friends suddenly started becoming humor writers I met online. I got to see where they published, and that gave me ideas for places to submit. It also gave me insight into how to achieve "the voice." (See elephant in Rule 5 as placeholder, then jump down to Rule 3. Better yet, just go to Rule 3.) And sometimes some of my friends and acquaintances became editors and actually came to me for submissions. (That would be the case with my friend Matt Tobey, who works for Comedy Central. Of course, I repaid him by naming a borderline moronic character after him in my forthcoming novel.)

I should also mention that none of these rules I'm giving apply strictly to humor writing. Maybe you want to write for science and nature journals? Then sure, go ahead, make buds with other people who get wet thinking about photosynthesis. It can only help you. And even if it doesn't help your career, you'll make a new friend to keep you company while you both mutually masturbate to documentaries on the Discovery Channel.

5 Steps to Get From Freelance Writer to Published Author
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One last note on networking -- if you do get the chance to speak to editors or writers with the hope that they can help you land a piece somewhere, there are two rules: 1) don't get offended if you're ignored; and 2) do NOT ask them to read your blog. Why? Well, for the most part, blogs are half-baked, lazy forms of expression only half a step more legit than a dream journal or shoebox diorama. But there's another reason. Remember our most important rule? Yes, learn the voice. If you've got your eye on a specific site, don't waste a writer's time by pointing them to an amorphous collection of stuff. YOU pick the one piece that YOU think is the best fit for where you're trying to get published. Right there, you've already shown yourself to be someone who understands the value of a freelance writer -- someone who can generate content for the specific needs of a site.

Apply the Rejection

Here's the last rule: Get ready for rejection, and apply it! If your work is being judged by editors, there's a good chance they're more experienced than you and have proper insight into the merits and flaws of your work. But here's the thing -- even if that's not true, it doesn't matter. Even if their opinions are wrong-headed and short-sighted, they're still right. Because it's their magazine, and whatever they want for it is the right answer. You can let that make you bitter, or you can let that liberate you. The more experience you get, the more avenues you have to publish, and odds are, the more liberated you'll feel. You'll know what belongs where.

I've written before about Cracked's rejection of a mean-spirited (but satirically justified and amusing piece, in my opinion) of Amy Winehouse within hours of her death, but what's important to stress is that there was never a fight over it. I liked the piece, wanted to see it reach a large audience, and was disappointed, but I never had any misconceptions about the decision. Cracked's rejection was correct, because the piece was not in Cracked's voice, and Cracked's readers who have been nurtured on that voice would not have accepted it. Furthermore, the rejection led to further reflection and the publication of a related piece that I enjoyed just as much and was appropriate for Cracked. The Internet lets you feel like an all-star with your own Twitter, Facebook, Tumblr, or Pinterest (if you suck), but those feelings are not helpful for freelance writing.

If you get rejected, learn from it. Don't argue. I mean, maybe if you have a real relationship with an editor and there is a disagreement about what you're trying to achieve with the content, it's possible a discussion could lead to compromise and edits, sure. But most of the time, especially in the early stage of yay/nay submissions, just take their comments for what they're worth and think about how you can give them what they want next time. That really is the name of the game.

--Shout out to David Lindley, who read this article over my shoulder as I wrote it on the train and asked me if I was a writer right after I wrote that paragraph about people asking me if I'm a writer. Weird, huh?



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