The Freelance Creative

Would You Rather: Freelancer Edition

Would You Rather

Life is but a series of choices. Your choice of coffee over OJ in the morning dictates how cranky you’ll be by 2 p.m. Your choice of outfit might help or hinder a Zoom interview for a dream gig. Your choice not to throw your computer against the wall after a bad client call is probably smart, but who really knows?

We are but mere pawns in reality’s collection of chaos, which is why fantasizing about what choice you would make in really bizarre situations is so much fun. Enter the timeless game of Would You Rather, where one person posits two ridiculous scenarios and another picks their poison.

I wondered what strange freelancing scenarios would fit into this game of hypotheticals and got a little carried away with the possibilities. So now, I must know…

Would you rather work with a dream client for half your rate, or pay half your rate to get a massage from your celebrity crush?

Depending on where you are in your life and career, either of these scenarios could be the start of a very satisfying daydream.

With the state of freelancing in flux due to COVID, people have become more desperate for work. It’s not crazy to imagine taking less money for a gig if you haven’t had one in a while, let alone one with a client you’ve been dying to add to your portfolio.

On the other hand, freelancers rarely get pampered, let alone by celebrities who are categorically hot. Wouldn’t it be nice to put that work on hold for a while so that a VIP can work the stress out of your shoulders?

MY CHOICE: Take the gig over the massage. This is a true test of thinking with your head over your heart. Your dream client can probably open more doors for you down the road. Plus, maybe your celeb crush is terrible at massages because they’re pampered. Maybe they think you should consider yourself lucky just to have their Midas touch all over your gams. Never meet your idols.

Would you rather type all your client emails blindfolded, or take all your client calls at a busy laundromat?

People don’t realize how sensory freelancing can be. Show up to a client meeting smelling like last night’s pool party, and you might be out of a job. Take a professional contact to a delicious taco joint, and you might nab a client for life. So, if you had to lose one of your senses during pivotal interactions, what would you sacrifice?

You may have mastered typing in grade school—or simply by existing in the 21st century. This might make you feel confident enough to rely solely on muscle memory to write things like, “Hope this email finds you well.” It’s still a high-stakes challenge, since most people judge—and judge harshly—when they see spelling and format errors.

But a zen Zoom environment is also crucial when communicating with clients. Whether they’re briefing you on a new project, negotiating a contract, or giving you crucial feedback, mishearing even a single word could derail those ever-critical “next steps.” Throw a heap of washers and dryers in the mix, and the odds for a devastating miscommunication go through the roof.

MY CHOICE: Busy laundromat every time. With software like Grammarly, dictation assistants like Siri, and general spell check built into every browser, it’s now more embarrassing than ever to deliver a poorly written email—especially if your entire profession centers around writing.

Would you rather have to explain freelancing to your grandparents every day, or have every single client explain freelancing to you?

Unless you’ve actually done it, freelancing can seem foreign. Explaining what it’s about to those not “in the know” can be tedious, but do you want to be the deliverer or receiver in this unforgiving chat?

For an older crowd who grew up in a different economy, freelancing might just seem like some hippie-dippie way to eke out a living—way too transient and variable for their Boomer blood. Explaining things to nana and pop-pop at every holiday gathering would certainly become a chore after a while, but who knows, they might up your birthday card moolah from $20 to $25 once they know you have to pay for your own health insurance.

However, when someone who is cutting your checks has never known the freelancer lifestyle, they might have wildly incorrect ideas about what goes into the work we produce. For one, they might just think of you as part of their team, which is flattering until they expect you to be at their every beck and call like a full-time employee. I think anyone would welcome the chance to correct that misconception. But whether or not clients are receptive to those corrections is a whole other thing.

MY CHOICE: Go with the client’s explanation. You have to do enough explaining to your family already, what with the internet being the internet and tattoos becoming more commonplace and all these smart scooters zoomin’ around. Hearing a client’s perspective is bound to be informative—and if their version of “freelancing” doesn’t align with yours, at least you have the free will to pass on the job.

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