The Fine Art of Failure

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A few months ago, I wrote a tongue-in-cheek guide to freelancing for the online world. Jokes and utter lies aside, I offered tips on how to identify and win over the gatekeepers for most sites, the folks known as editors. Executive summary: use Twitter and email *tactfully. Since then, lots of other folks have chimed in on the conversation. Most of these people are/have been/will be much more successful than me.

For the record, I freelance part-time and enjoy a day job serving impoverished, at risk communities in Houston. My income from freelancery is not insignificant, and I’m writing here about why things you have read elsewhere about the game of writing for cold hard cash just may be lies. Filthy, dirty lies.

I came to writing in a very internetsy way. I did not attend a j-school or write for a university newspaper. I did no internship nor have I done a fellowship. Instead, I liked soccer, a hurricane in 2008 made work impossible at my day job, so I started a blog at GoDaddy dot com. Then, if you ask any established staff writer and/or editor at a legacy publication, I made a Cardinal Sin that should have spelled doom: I gave my content away for free.

People will always tell you that you need to charge for what you write. However, the people who say this after the ones who have already 1) Refined their prose, 2) Found their voice, and 3) Gotten past the gatekeepers (aka “editors”). I love the Longform site, but the recent discussion on freelancing boils down to: (a) I have a hard time coming up with ideas so I play around on Twitter and (b) raise them rates/get that green.

These are all true, but only good tips for somewhat established writers. Most folks asking about “getting into writing” have not fallen into the j-school funnel. They are beginners. If you say the word “pitch”, “copy” or “lede”, they will stare at you as if you were speaking a foreign language. So when somebody tosses out that Cardinal Rule – never write for free, take it with a grain of salt.

Allow me to illuminate your world with some examples of writing for free turning into writing for money:

Years ago, an editor pitches me to write two articles for exposure on Fox Soccer. I do it. I am not paid. Time passes. Days turn to weeks turn to months turn to years. That same editor lands at Fusion and sends a stream of paid work my way.

Years ago, I wrote a few articles at the Good Men Project, again for exposure. I am not paid. One year later, that editor scores me a sweet World Cup commission for Pacific Standard and almost fed me a story at Grantland before the implosion.

I wrote for both The Classical online and the magazine, and two of those editors there have moved on to VICE. Guess what? They’ve greenlighted plenty of stories that pay that cold hard cash.

Of course, there’s a balance: you can only write for sites that promise exposure a few times before anybody would feel somewhat exploited. However, having your own site and other sites featuring your work and showing your ability to work with editors to turn out slick copy helps get you through the gates, so to speak. Plus just writing for any audience regularly will help you refine your skillz. Then you can start talking about rates and accountants and contracts and rights.

I understand that I come from a place of privilege where I could dedicate serious time and effort to a passion: writing. Although, ahem ahem, I have turned down job offers (just closed on a house in Houston, so no marriage proposals involving relocation or fall weddings please), but my own site allowed me to 1) Refine my prose, 2) Find my voice, and 3) Get exposure. My first paid freelance gigs came thanks to editor(s) contacting me on Twitter who had read my site and/or unpaid work.

So, that is my path to failure. I am, of course, a failure because I started a blog and wrote for some sites that did not pay me early on. Reams of my unpaid articles float around the webs still, mocking me. Pity me.

The good folks at Paste Soccer published a feature last week by me on the pedestrian greatness of one Thomas Muller. Check it out here. And yes, I was paid. Two weeks ago I published a feature for The Guardian on why more Americans should ignore the EPL when chasing a soccer dream in Europe.

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