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Should You Work For Yourself? A Cheat-Sheet for Creatives

by Jordan Rosenfeld
featured, freelancing

should you work for yourself

Many creatives dream of quitting the drudgery of a full-time job for what seems like the ease and flexibility of working for yourself. And many freelancers will tell you that they don’t regret going solo, despite its sacrifices. Before you take the leap, however, see how many of these crucial freelance qualities you can say yes to:

1. Every job you’ve ever had makes you miserable. Yet you’ll delightedly spend a whole day researching some obscure piece of information for your own project.
You might want to make the leap to self-employment when other people think you’ve got “a great job” but you’re just slogging at someone else’s agenda. Freelancers are notoriously drawn by their own powerful creative directions. Designer/Maker Klay Arsenault accepts this trade-off. “Working for myself, I continuously experiment and redefine what I do for money. I feel less like my personal talents or abilities are being wasted. In many ways taking on the risk of [freelancing] has also helped me follow through better and be more present in my daily life.”

2. You like organizational systems, even if you’re the only one who can understand your own.
Working for yourself may mean no more interpreting a boss’s finicky organizational system, but you still have to organize yourself. Though your own version may involve lots of stacks and colorful Post-it notes, so long as you can keep track of key information and not get overwhelmed, you may be a freelance candidate. Marilyn Cole, a freelance writer, editor, and translator suggests, “You know you should work for yourself if you constantly find that your way of doing things is better than the way you’re told to do them by your boss.”

3. You are comfortable with uncertainty and the unpredictable nature of your income.
Perhaps the trickiest element of working for yourself is knowing that your income may not come in steady paychecks the way it does at a regular job. Going freelance means knowing, or learning quickly, how to budget and plan for the inevitable lean times. Whitney Pintello, a visual artist says, “To me, there’s something romantic about me and my partner looking at each other and saying we need to tighten our belts and hunker down the next two months so we can pay the bills.” But, cautions Marilyn Cole, “before you quit your job, make sure you have a couple of repeat clients lined up.”

4. You know how to hustle after new projects and drum up work in the slow periods.
When you’re working a regular job, you might be full of ideas pressing to be created when you just get the time. Then, when you finally go freelance, the pressure is on to dream up new ideas all the time. Rachel Kramer Bussel, a freelance writer who focuses primarily on sex, dating and popular culture, draws from her own life as often as possible. “I try to use topics I’m genuinely passionate about to fuel my work,” she says. “I don’t go after stories so far outside my storehouse of knowledge that it feels like reinventing the wheel.”

5. You can make use of your time in the slow periods rather than sinking into a binge-watching stupor.
When you work for someone else, you may covet those “slow” work periods, but as a freelancer they can mean your bills go unpaid. If you can use downtime to create fresh work or improve your business model, you may be ready to go solo. Lisa Rowan, a freelance writer, editor and vintage clothing shop owner says, “Slow periods can be scary if you’re not yet in a position to be saving more of your freelancing income than you’re spending. But if you have projects that keep your creativity going, it can ease the pain of a dry spell and maybe even get you additional work.”

6. You’re an optimist.
It’s not required, but it helps. Staying hopeful about the future is key to motivating yourself through drought and stuck times. It’s not necessarily a skill you can learn, but if you already lean in this direction, you’re ahead of the game when it comes to freelancing.

7. You are self-motivated. To work for yourself, self-motivation is non-negotiable, because now there’s no boss to crack the whip (though there are clients).
Food and travel writer Mary Luz Mejia socializes to keep herself motivated. “The more people you know and manage to include in your own personal “network,” the more likely they are to be able to suggest you for a job or think of you when something comes up,” she says. “I always try to return the favor.”

8. You don’t mind giving your money to the IRS.
When you work for yourself, it’s up to you to pay your own taxes every quarter. However, you may be surprised to learn how many deductions you can take. Finding a good CPA who knows your particular creative field will help.

9. You love freedom and independence.
Though you work harder than at any other job, you have a lot of room to do what you please as a self-employed person. Lux Alpatram, a freelance writer, consultant for sex tech companies, comedian and co-founder of the conference Binder Con has always hated operating under someone else’s rules. “Working for myself means that I don’t need to worry about keeping myself busy just because I’m supposed to work an eight hour day. And there’s also the benefit for being able to work when I feel most productive, rather than forcing myself into a 9-5 schedule.”

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Jordan Rosenfeld

Jordan Rosenfeld is a freelancer writer whose work has appeared in Mom.me, The New York Times, The Rumpus, The Washington Post, Writer's Digest, and more.