The Freelance Game

Writer Joe Donatelli drops knowledge on how to succeed at the Freelance Game.


A lot of people want to know how I did it. How did I rise to the middle of the freelance writing game? They come up to me on the street and they’re like, “I want what you got. I want an eight-year-old compact car, an old PlayStation and a streaming-only Netflix account—I want to live the life.” And I’m always like, “Slow your roll, young buck. There’s a lot about this game you don’t know.” It’s not all bylines and Facebook Likes. This is work, and it’s not easy.

For example, when you’re employed full-time by a company, you never have to ask it to pay you on payday. You just get your money. But when you work for yourself, you have to remind companies all the time to pay you your money. If it was up to them, they would keep it and spend it on a new office chair or something. So that’s one thing about The Freelance Game many people don’t realize. Everything a human resources department does, that’s on you now. Don’t know Excel? You better learn it, son, or your invoicing system will be a catastrophe.

That’s just one practical aspect. There’s also the mental challenge. You set your own schedule. That means you can wake up at 5 AM and have all your work done by 2 PM if you want to. Or you can 9 to 5 it. Or you can sleep until noon and work into the night. But it takes discipline. You have to sit your butt in that seat and put in the time. The urge to Facebook or do the dishes or drink the finest Trader Joe’s brand rum all day can be overwhelming. It’s the ability to focus on the task at hand that separates the writers like me who can afford to vacation once a year in the state where they grew up from those who can’t. When I’m on that domestic flight in the economy section eating peanuts from a Ziploc bag I brought from home, people know I’m a baller.

Some people say The Freelance Game will spit you out and break you down. Yeah. I’ve seen it happen too many times. People can’t hack just barely making enough money to stay alive. They want the fresh threads, big house, the Escalade with the putting green. That’s the mountaintop, and not everyone will reach it. So they quit The Freelance Game and take jobs as teachers or whatever. Those jobs pay more and can be very rewarding, but when’s the last time a teacher worked all day in his underwear without getting arrested? Money isn’t everything.

So what’s the key then? How do you do it? Like I’ve said, be organized, put in the work and don’t quit. And there’s another thing—the biggest thing. It’s who you know. People like to pretend it’s their writing skills that land them great gigs, but the truth is a mediocre writer who knows an editor will get an assignment over an outstanding writer who doesn’t know an editor almost every time. That’s not fair, you say? Then get the hell out of The Freelance Game! Fair? You care about fair? You chose the wrong, profession. The only fair you should be concerned about is a job fair.

Meet people. Make connections. Good help is hard to find. If you can deliver, you will get hired again and again, and your editors will refer you to other editors, and you will get assignments out of the blue. That’s when the real money starts rolling in—the we-can-afford-an-apartment-with-two-bathrooms money. Tiny stacks on tiny stacks on tiny stacks. But that’s not going to happen on Day 1, Week 1 or even Year 1. Keep on your grind and maybe someday you can be like me – rolling in so much paper you do not qualify for Affordable Care Act subsidies. The high life.

– 30-

Joe Donatelli is a freelance writer and editor. You can follow him on Twitter and Facebook