Weird and dreadful freelancing tales

6 min read
Brian Dunn

Freelancing is a desperate undertaking for desperate individuals. At least it always has been for me. Every freelance job I’ve taken has been to fill a void that loomed large in either my wallet, portfolio, or creative psyche. I’ve only ever been a moonlighter, that stripe of freelancer who, armed only with a fistful of yellow jacket energy pills, comes home exhausted after working a legit day job only to don his freelancer chapeau and work furiously until the sun rises in the east. (Let’s not even broach the subject of full-time freelancers, who are their own flavor of bat-shit crazy).

I’ve sworn off freelancing entirely, but three jobs still provide nightmare fuel on a regular basis. Are you sitting down? Then allow me to share these harrowing tales of perversity and greed. Heed my warnings, lest similar agony and humiliation befall you. Beware!

Weird tale #1: I was haunted by Alex Trebek

One of my first freelance writing gigs was for a buddy who needed a funny short film script. He would cast, film, and edit it for his client, a business owner who wanted something to show at the conclusion of his company’s quarterly sales meeting. After two days of stuffing half-drunk salespeople into a conference room at the Hyatt and subjecting them to team-building exercises and sales presos, I suppose a chuckle or two is needed.

I spun up four clever, budget-conscious ideas. Before I could pitch them, my buddy called me up and uttered the six words that are certain death to any project: “The client wants a Jeopardy! sketch.” I reeled and almost retched. A Jeopardy! sketch? What kind of person hires a creative guy and then hands him such a played-out premise? A CEO who’s dying to show off his Alex Trebek impression in front of all his employees, that’s who.

Knowing you can't compete with an executive vanity project, I didn’t curse my misfortune.

Instead, I immersed myself in the client’s business (software) and Jeopardy! episodes, all while loathing every minute. The result was a very funny Jeopardy! sketch that captured Trebek's nuanced delivery and spilled over with company inside jokes and industry references. The drunk sales reps loved the resulting film. The client was overjoyed at his 10 minutes of fame. When it was over, my buddy and I slapped each other on the back, while I silently promised myself to never again work on a such an ego-driven assignment. Horrible.

Warning:  Don’t be the wedge between an executive and his showbiz dreams.

Secondary warning: Collect endorsements on the spot. I deleted the client’s voicemail in which he gushed about my work. Asking him to gush again later so I could write it down was…well, awkward.

Weird tale #2: The client with two faces

I had the misfortune of freelancing for a now-defunct, content-driven website run by an unscrupulous business owner. A developer friend of mine vouched for the guy, so I felt I was on solid ground. The job was easy enough—just write some seed content for the site to get things rolling.

The initial ominous sign? The company mascot was a donkey sitting on a toilet. His name was Dumpy the Donkey. I am not making that up. Red flag number two showed itself when the client instructed me to “just make a bunch of stuff up”—fabricated stories, over-the-top details, phony contributor names. Foolishly, I pressed on.

When I finally delivered my words, the client was all smiles. When it came high time to pay me, however, he balked. The company vision had changed, he explained, without a hint of irony that a business using a donkey mascot was laying claim to "vision." They might not use all of what I wrote, he told me. Not my problem, I informed him. The client hemmed and hawed like a, well, donkey. Desperate, I drove across town to the company’s squalid strip mall office and announced that I wasn't leaving without a check in hand. I’m convinced I wouldn’t have seen a dime had I not shamed them into it. Terrible.

Warning: Take your money early and often, especially if your client is an ass.

Secondary warning: If and when you get paid, sock away a good chunk for tax time.

Weird tale #3: Death was almost my editor

A good friend of mine sought me out to write all the content for his company’s website launch. It should have been a dream gig. I’d be using the irreverent voice/tone that I love, and a healthy budget had been set aside for my services. My moonlighting talents were finally being given the respect they deserved.

The catch was that they wanted a 150+-page(!) website, all of which demanded fresh, clean, and funny writing. Oh, and they needed copy ASAP. I agreed to insane delivery milestones because I liked these guys and they liked my writing. I told myself to just schedule my time intelligently. All would be fine.

All wasn’t fine. I fell behind right out of the gate and immediately resorted to all-nighters.

For three interminable weeks, I’d sit at the kitchen table after dinner, already exhausted, facing the task at hand—pushing myself to write witty, pithy prose until 3:30 a.m., resisting even the basic human need of going to the bathroom. My delirium kept compounding until late one night I saw death himself seated across the table. He mouthed the words, “Make it funnier.” Harrowing.

Warning: Don’t promise to wear a cape just because the client makes you feel like a hero.

Secondary warning: Don’t resist the basic human need of going to the bathroom.

Keep the horror at bay!

I don’t know what this little trip down freelancing memory lane means for me, other than the inevitable recurrence of my awful night terrors. It’ll all be worth it, though, if you simply heed the warnings herein. Do so and you’ll never have to look across your kitchen table and see death staring back. But if your project deadline starts to slip and you’re forced to face the reaper, just tell him, “Get lost. It’s funny enough.”