7 Things I Learned Being A So-So Freelance Sportswriter

Two weeks ago, I left the cruel and crumbling world of football scribbling to start a big boy job. I will probably still write about football from time to time, and I may even get back into it one day.

But not for a while. Not until the industry stops resembling a bit of roadkill spitting up blood on the side of a desert road.

As with many things in life, I was neither the best freelance sports writer nor the worst. I did however learn a few things along the way that I thought would be worth sharing. Please note that I don’t tend to follow my own advice, so this list is as much for me as it is for you.

1) Don’t Be a Freelance Writer

At least, don’t be one right now, and certainly don’t be one in sports. As more and more media companies lay off talented staff, the freelance pool is growing, and the routes to full time employment in sports are dwindling. Sports writing — like most high profile media jobs — follows the power law: a few recognizable names will do the vast majority of the work and earn most of the money leaving precious few scraps for the rest. Meanwhile, even the most prestigious media companies pay depressingly low rates, often a few hundred bucks for an article, whether it involves a lot of research and original reporting or not. A good bet would be to aim for longer magazine features, but that’s a far more competitive field (things are easier if you know editors).

2) Do Be a Freelance Copywriter

Yes, you won’t see your name in lights writing copy for companies (ideally in a niche subject you know a lot about), but if you need to make enough money to live freelancing you will have to consider copywriting work as a steady gig. In my experience, companies pay a lot more than publishers, and do it a hell of a lot faster. The work isn’t that bad either; it can even be fun sometimes, trying to spin gold from straw. Beware though: pitching your services to private companies is a lot harder and discouraging than sending queries to publishers, and will involve more ‘obnoxious razmataz,’ including LOIs and even — fuuuuck — glossy mailers! Which brings us to…

3) Once you Choose to Freelance, You’re No Longer a Writer but a Salesperson

Every freelancer says this to some degree, but you really have to believe it. Like, print it on your business cards believe it. I never could, and I’m sure that affected my bottom lines. Like me, you probably see yourself as a capital ‘W’ Writer, but unless you’re on full time staff with benefits, you’re not any of those things. You’re a marketer, a salesperson, a PR flack. That’s why you don’t send sloppy pitches, and that’s why you don’t pitch ‘when you feel like it,’ but every single day. That’s also why you don’t send speculative emails or lazily ask for referrals or update your website every six months. Once you accept that you’re working in sales/PR/marketing and not writing, and after you somehow find a way to wash the awful taste out of your mouth, you will start to earn reasonable coin, maybe.

4) Routinize Failure

If №3 sounds awful (it pained me even to write it), it gets worse. Because the not only do you have to sell yourself every single day, but you must also accept that you will have a very low rate of return on all your professional grovelling. Your goal, in fact, is to fail every single day — to routinize failure — usually by writing pitches whether or not you think you have the most saleable idea in the world. Freelancing is a volume game, and the hit rate is unpredictable. Some weeks editors will lap up whatever harebrained shit you pull together; other weeks you won’t even get replies, even from editors who like you. I managed to do the writing part of the‘volume’ rule really well — I have become king of writing when it’s literally the last thing on earth I want to do (except for pitching a story, maybe). But I forgot that I wasn’t a writer, but a marketer. If you do one thing every day and nothing else, make it a story pitch, not a draft.

5) Never Rely on External Validation as Motivation to Keep Going

For a while, it felt like I could do no wrong as a writer. Editors were pitching me, my stories got widely shared on social media, and I had a steady stream of nice compliments in my @ replies. And then, for whatever reason, that all changed, and I took a major dent in my confidence even though my writing output was largely the same. It took me a while to accept the cold truth: that no-one sits around thinking about your career but you. If you’re a freelance writer, your job is to pitch, write and read, everyday, in that order. Your job is not to earn plaudits and have people compliment you. By all means use Twitter, but don’t rely on it for the endorphin release. And don’t take rejections personally; just keep going. Work as hard as you can to build a good writing process, and make that process a habit.

6) If You Can’t Make Enough Money to Put Some of it Away, You’re Not Earning Enough

I mean, it’s possible that you’re spending too much of it, but if you’ve chosen freelancing as a career chances are you’re probably not the type to rack up insane credit card debt (if so, get a proper job ASAP). So if you find that you are not able to put at least 20% away of what your earn for taxes and save another 10% on top of that AND pay your bills and eat food, you’re not earning enough. So either pitch more often, pitch to more lucrative clients, raise your rates, or see number 7…

7) Know When to Call it a Day

Freelancing in 2017 is really hard. The Gig Economy is a corporate scam meant to strip workers of bargaining power, health benefits, job security, and wage growth. Therefore, what the publishing world needs is not polite, deferential types who are willing to work for pitiful rates under the idea it’s good for their ‘portfolio.’ It needs pushy, assertive people who know their worth, are willing to set realistic rates, and who have the stamina to follow up on late invoices and the financial sense to put money away. In other words, it needs salespeople, not writers. This is not for everyone. I’m fairly certain it wasn’t for me either (though it could be in the future). This is a demanding, stressful career choice that requires a lot to sustain. Sometimes it’s good to know when to call it a day.