It’s A Creative Business: To Freelance or Not to Freelance? ‘Tis Not an Easy Answer…

This week, Rodika Tollefson weighs the pros and cons of a freelancing career.


Ahh, the freelance life. Have you been dreaming of being your own boss, working in your pajamas, and playing hooky whenever the muse abandons you?


There’s certain romanticism about “working for yourself.” Turning every day into casual Friday (PJs or otherwise), picking and choosing your projects, and making your own schedule sounds appealing, indeed—and that sweet 30-second commute to the office can’t be beat.


But the freelance life has just as many drawbacks as advantages. If you’re thinking about making the leap, make sure you know what you’re getting into.


When I started the freelance life more than 15 years ago, I wanted flexibility while the kids were young. Little did I know about the “feast or famine” that’s inherent with self-employment, or the other costs of “flexibility.”


I’ve dabbled a few times since then with the idea of getting a “real” (i.e. full-time) job but despite the potential perks—paid vacation and sick leave, medical insurance, stable paycheck, and consistent hours—I hope I never have go back to “punching the clock.” Once you’ve been self-employed for a while, it’s tough to go back!


If freelancing full-time is on your mind, let’s talk about some pros and cons:


Being your own boss: Don’t like having a boss? Try having a dozen! Although customers can’t tell you how, when, and what to do, you are accountable to every single one of them through your deliverables. They don’t always listen to your expertise either—but, as the cliché goes, the customer’s always right.


To add to the pressure, clients often have competing priorities and deadlines. It’s up to you to meet them all.


On the other hand, being your own boss means you’re in charge of your own opportunities. If you have the self-drive and motivation to succeed, this is a wonderful thing.


Setting your own schedule: So long, vacation requests at the mercy of the HR manager! You can take time off whenever you please.


That is, until several requests pour in at the same time—which, says Murphy’s Law, happens more often than you may like, especially when you’re in the middle of packing for that extended weekend.


The beauty of working your own schedule is that nobody cares if you work in the wee hours of morning or late at night (well, maybe your family does). You can work from the beach and even from the other side of the country or world (I did that several times, and no one was the wiser).


Choosing your projects: You can turn down a potential client or project any time you want. But in reality, you’re not likely to do that regularly unless you’re so renowned in your field that you can command top dollar or earn a good living with just a few gigs here and there.


Remember that “feast or famine” nobody warned me about? After 15 years of doing this, it’s still not uncommon.


Take last month, for example. I was enjoying the slower pace the first week, even thinking I’d finally have time to do some creative writing, which doesn’t pay the bills like my commercial work does. And then, the floodgates opened and I spent the next three weeks camped in my home office, working 60 or more hours a week.


I could have turned down some of the projects, but they were all wonderful, new opportunities that could become long-term, well-paying projects. So I marched on. Besides, nobody’s paying for my time off—so making “extra” is a good way to finance that dream vacation.


Running your business: Whether you’re a freelance writer like me or an artist, musician, or any other type of creative, working for yourself means you’re running a bona fide business.


On the positive side, that means you can deduct business expenses like furniture for your home office and mileage. On the other hand, you have to pay oodles of taxes, as well as cover all your expenses, from equipment and professional development to marketing.


Without a regular paycheck, you have to plan your cash flow carefully. Even if you think you’re well prepared for the ebb and flow, all it takes to feel unstable is a longtime client pulling the plug.


I can’t tell you how many times I got a phone call or email informing me that a project I’ve done for years was moved “in-house” or defunded, or an ongoing monthly project was canceled without any notice—sometimes more than one project in the same month.


Freelancing doesn’t just take a certain kind of free spirit and self-motivation. To succeed, you need to be resilient, dogged, and thick-skinned. If you need stability, this is not the path for you.


But if you can handle some rough seas, bon voyage! You’ll be the captain of your own ship (as well as the first mate and deckhand), and where your great new adventure takes you is completely up to you.



Rodika Tollefson is a member-at-large who has a master’s degree in digital media, which included coursework in digital media law. She’s a seasoned journalist who now provides digital media content and strategy, and is currently the editor of The Pen Woman and the National Public Relations Committee Chair.

“Memo Book” by winnond/

WANTED: GUEST BLOGGERS! Pen Women are invited to submit guest posts for two new series: Creative Inspirational Wisdom and It’s A Creative Business. Please visit this link for more details. We look forward to reading your material!