Four Lessons From 10 Years of Freelance Writing
“Welcome. Your office is here in the back.”
The manager of the college bookstore led me through racks of clothing and shelves of books before squeezing into a room uncomfortably lit with blinking fluorescents and outdated computer monitors.
“It’s really more of a storage room with a desk, but don’t worry, you’ll get used to it.”
God, I hope not.
It was 2008. I had just graduated from college in the middle of the Great Recession. My degree? Film and television with a focus on editing.
I’d contacted nearly every studio, news outlet, production house, independent film company, offering up my freshly pressed resume and credentials.
But nobody was hiring new editors. I received more, “any other time we’d love to have you but” responses.
I would have rather been told my demo reel was trash. At least that I could work to improve on.
That response told me to pack it in.
So I ended up expanding my application reach, including the “Web Manager” for a college bookstore.
After just a few hours on the job, I discovered a Web Manager was nothing more than a guy who grabbed orders from the printer, collected what the person ordered, then shipped them out.
Basically, I was an Amazon employee with fewer benefits and worse lighting.
Thankfully I took the job in the summer, so orders to the college bookstore were limited. This left me sitting at my Windows XP computer screen for hours on end. After the first day of updating every Web browser and media player, I shifted my attention to making additional money on the computer.
It started with paid surveys, but those were annoying, paid pennies, and I never really knew when I’d finished the survey or not. That’s when a buddy of mine pointed me to a new writing platform. I could make $15 a pop for writing some how-to articles.
I write one, skeptical. Why would someone pay me $15 to write how to plug a VCR into a Magnavox television?
Well, they did, and it marked the beginning of my work as a freelancer. Now, over a decade later, here are some of the lessons I’ve learned and what I’d do differently.
Don’t Get Too Comfortable
I can’t tell you how many writing platforms I’ve been associated with over the years. When first starting I assumed these platforms were iron-clad locks to last forever. None of those original platforms now remain.
Eventually, I found my way back into the world of film and television (well, in this case, video) when I landed an online job producing cooking and travel videos for a division of the New York Times. I loved that job. The pay was great, I was actually using my degree. I was cooking.
And within a year that platform had been sold and they replaced me with a grandma-type host. I can’t even argue with the decision.
But it left me scrambling, looking for new work. I’d become complaisant. Comfortable.
I learned my lesson after that. It’s also one of the most important bits of advice I can tell anyone getting into freelance writing.
Never get comfortable. Because that’s usually when the ground drops from under your feet.
Write For Yourself
There’s a sense of perpetually chasing the work carrot when freelancing. It’s this need to always have work coming down the pike. It can become all-consuming. And the quest for immediate financial gratification may prevent long term success.
For years, I wrote for other platforms. Other agencies. Other individuals in need of a hired gun. I did my work, I cashed my check, I moved on. Much like an old west bounty hunter. Always drifting, always searching, never settling, or laying down roots.
It’s one of the reasons why I love Medium. It lets me write what I want to write when I want to write it. I have other writer friends I talk to. I tell them to get on Medium. Usually, they post one thing, make zilch in the way of money, then abandon ship.
They want that instant gratification.
I get it. Seeing that money hit the bank account is a nice feeling. Especially when it’s a bump up from what normally finds its way through my routing number.
But I’ve been in this game long enough to know it’s essential to build up your own brand. Because the last thing you want is to be writing for a decade and suddenly realize you’re right where you started.
Standing Up For Your Professional Self Is An Essential Skill
Working just about any day job comes with some kind of interaction with fellow employees and a boss. I haven’t had one of those in well over a decade now. Before making the move to full-time freelancing (and before that short stint at the bookstore) I worked in a mailroom at the college I attended.
Mostly I stuffed envelopes with catalogs, selling promises to unsuspecting high school students in hopes of winning large chunks of cash from parents and lenders. I worked with some great people.
When you’re force-feeding the mouths of envelopes for hours on end there’s nothing else to do but talk. Talk welds together relationships, even if the two pieces wouldn’t normally go together. And if something ever went wrong, we’d have each other’s backs.
That’s not the case in the world of freelancing. You’re on an island. There’s nobody there who will support you. Sure, there are all kinds of freelance groups on social media (at least there are now. When I started up MySpace was still scraping and clawing for survival against a surging Facebook while AOL AIM remained the go-to IM service). But when dealing with a client who’s trying to take advantage of you, you either fold and give them free work, or you stand up for yourself.
I didn’t do that early on. My work a house of cards, if I failed to do whatever a client wanted it might disrupt the construction and pancake my entire career. Sure, I might curse at the computer screen while walking away, needing a respite from work, but I’d eventually relent and do the work, for free.
It took me a while to learn I needed to stand up for myself, and that yes, I absolutely needed to. Because there are far too many clients who will push and probe and search for those freelancers who won’t. Who will cave and offer up free work out of fear of losing the client.
Fear is the anchor of a freelancer that keeps you from achieving greatness.
Don’t be afraid to stand up for yourself. To defend yourself. To cut yourself loose from clients who don’t respect you. Even if you lose a few dollars here or there your mental state will thank you.
Don’t Lose Sight Of Your Dream
Few writers want to be freelance copywriters for the rest of their professional lives.
I know I don’t.
The work took over for a backroom office, but in a way, it, for a while, became its own windowless office. Focused so much on what I needed to do, I forgot what I wanted to do.
What I’d dreamed of doing.
Losing that travel and cooking video gig was a gut punch. I knew something like that would never come around again.
Yet it was the best thing that could have happened.
It shook me awake amid a fog. Every day I worked that gig the fog became thicker, blocking out the fading lighthouse of my dreams.
People don’t remind you of your dreams. They might not even know what they are.
But you know.
I don’t make the kind of money I did with the lost work. Nowhere near it. But it’s better that way because I’d replaced my dream with money, and no amount of money can buy my dream.
It’s a pitfall along the road of freelancing. Perhaps freelancing is your dream. Then you’ve accomplished it and it’s time to craft a new one. But if it’s not. If it’s a means to an end you haven’t yet figured out, be careful. It may try to pull you away from your ultimate goals. You just need to keep your eyes on what really matters.
