Seeking creative freedom? Think twice before freelancing.

Photo: Pat Pitchaya,

Photo: Pat Pitchaya,

There’s a common narrative surrounding freelancing that goes something like this:

“I quit my job to be a freelancer in order to achieve more creative freedom.”

Sure, that’s true in some ways. But in some ways, it isn’t true. The fact is, unless you enjoy the upper echelon of commercial and critical success as a fiction writer (and maybe not even then; those guys and gals have editors, too) or you’re independently wealthy and don’t need to consider your financial resources, audience or clients when creating your passion project, you’ll have to answer to someone, somewhere, along the creative path.

When considering a freelance career, I think the real question is, ‘who do you want to answer to, and how?’ The answers will help you determine whether or not the type of creativity you want to nurture is best cultivated within a company setting or the comfort of your own home office.

Everyone’s experience with the transition to freelance writing is different, so I can only offer insight into my own foray.

In my experience, here are the ways in which freelancing helps to foster creativity.

You can diversify your subject matter.

As a freelancer, you can decide what types of things you want to write about and pitch articles according to those interests. While you might be able to write stories on one particular subject you’re interested in when you’re employed full-time by a publication, you’re not likely to pursue a diverse set of interests in that setting. As editor of a homes magazine, I wrote stories mainly about home décor and remodeling. As a freelancer, I can write on homes, but also farm equipment, kids and nutrition, plastic surgery, military lifestyles and personal finance, sometimes all in one week. That’s fun.

You can pitch stories you care about.

For example, if you read this blog regularly, you know I love to geek out on listing software and personal organization techniques. While large publications may not be devoted to these topics, as a freelancer, I can pitch the occasional story to media outlets concerned with that type of stuff and write away, blissfully, on the merits of color-coding, box-checking and getting things done using apps and programs that help readers prioritize.

Once, the designer of a listing software program I use daily and swear by, noticed me blogging my love for their product all over the place, on my own time. So they approached me and asked to try out a new version of the software and then write about it on their dime. Um, yeah, are you kidding? Of course I said I’d do it. I’m a freelancer, so I can say yes to basically whatever I want to write about.

Here’s how freelance writing does not foster creativity:

You’ll still be writing for someone else.

Be it a magazine, a newspaper, a Web site, a blog not run by you or a business looking to reach clients, each media outlet has a specific editorial voice and story angle in mind. The piece you’re hired to write will be informed by that, and you’ll be expected to write according to the outlet’s specifications.

You’ll be edited.

Some of your most creative prose, maybe the stuff you were most excited about adding to your story, may edited out. You may also be asked to add things to your story you may or may not agree with adding. But in the end, you’re being asked to write for a client, so you need to be editable. And that means compromising your own creativity from time to time in order to help achieve the publication’s goal for the article you’re producing.

You’ll be edited.

If you’re writing for multiple publications, no two editing processes will be alike, and neither will your editors, so you’ll have to be flexible. I have editors who edit heavily, editors who edit lightly, in-between editors and those who edit not at all. I have equal admiration and respect for each one, and am willing to work with them on various levels to do what needs to be done. Are you?

You’ll have to run a business.

That means you’ll have to do stuff like sales, marketing, networking and PR when you’re not being creative, in order to keep the creative work going. If you’ve never learned how to do those things, you’re likely to encounter a difficult, but not insurmountable, learning curve. I knew nothing about these parts of running a business when I began freelancing, and I had to spend a lot of time figuring it out. (True confession: I discovered I liked it.)

So, here’s the thing.

I believe there’s no “creative freedom” litmus test for freelance writers. There are no set criteria we can all use to decide if it’s the right way for each of us to explore creative expression. Instead, if you’re considering a freelance career, I suggest analyzing your own creative goals. Do you want to write on various topics, or just one? Are you interested in learning how to run a small business? Are you open to different kinds of editors and editing, and at different levels of intensity? Does all of that sound better when done independently as opposed to with a company?

It helps to gain insight from other freelancers before taking the leap, so I hope this article has helped you, even in some small way, decide if a freelance career is right for you. Sure, freelancing is a creative choice, but it deserves a measured approach.

P.S.: While we’re on this topic, I should probably tell you that some exciting change is afoot for me and my own creative work life. I’ll have more on that next week.

Have you “turned pro” yet?


I’m putting up an extra post this week because I’ve just read this fantastic book and I want to tell you all about it.

It’s called “Turning Pro,” by Steve Pressfield (Remember the movie “The Legend of Bagger Vance?” He wrote the book). And before I go any further, I need to remind you that I don’t get paid to endorse anything I read. I also don’t receive advance copies very often (this was not one) and I rarely review books.

I shelled out for the Kindle version after watching a video interview Steve did with Marie Forleo (LOVE her!) in which he talked about the concept of deciding, really deciding to pursue your beloved craft, not as an “Amateur,” but as a “Professional.”

An Amateur, as Pressfield defines it, is someone who dabbles. An Amateur paints a little (if painting is her thing) or writes a little or does whatever she loves, but without truly dedicating her self to the endeavor. Amateurs, Pressfield says, hide behind fear, believing that failing is the only option.

Some Amateurs also hide behind distraction. That’s me. I’m a freelance writer on paper, sure, and I get paid to do it. (Lucky life!) But when business gets slow, instead of going on some sort of supercharged sales campaign, I tend to coast, turning out small projects here and there in between running errands, exercising, homekeeping, cooking, shopping, caring for the dog and whatever else I can to do to churn the time away.

I fell into that mode recently. And while sometimes it feels great, luxurious even, to go do something on a whim right in the middle of the day, there was an underlying problem with the way I was spending my time: I blog about writing, I talk about writing, I have a portfolio and social media accounts to show potential clients and others what I’m writing about. Yet there were many days in which I wrote nothing or pursued nothing having to do with writing. About the time I picked up Pressfield’s book, it had all begun to feel like a bit of a fraudulent existence. (Pressfield is gentler about this. I think he would have called it an “Amateur” existence.)

Contrast that with the existence of Pressfield’s Professional, whom he writes, “shows up for work every day.” And “stays on the job all day.”

Pressfield goes on to explain that, in order to become a legit _______ (fill in your own occupation here) you have to “turn pro.” This requires taking on your work as a discipline — a practice, in the true yogic sense of the word. “To ‘have a practice’ in yoga, say, or tai chi, or calligraphy,” writes Pressfield, “is to follow a rigorous, prescribed regimen with the intention of elevating the mind and spirit to a higher level.”

He then goes on to list key characteristics he believes the Professional possesses. Here are a few:

“The professional is committed over the long haul.”

 “For the professional, the stakes are high and real.”

 “The professional seeks order.”

 “The professional acts in the face of fear.”

 “The professional does not show off.”

 “The professional dedicates himself to mastering technique.”


Pressfield also recounts stories of other individuals who have turned pro. My favorite is the story of Rosanne Cash. Unlike many books in this genre, which focus primarily on attaining success, power and / or money, this book defines success as fully realizing your ability to do your thing. Cash was already commercially successful when she made the decision to turn pro. She’d become a critical hit in the music world. Yet she knew something was missing. Though industry heavyweights and the public told her she’d made it big, she didn’t believe she’d reached the true and full expression of her art. Then she had a dream. I won’t tell you about the dream. You’ve got to read the book! But it changed her life, and she recommitted herself to being an even better singer. “I had awakened from the morphine sleep of success into the life of an artist,” she writes.

The core message of this book is that professionalism is a mindset, and one worth cultivating.

If you’re like me and you feel like you’re on the verge of realizing your true potential, but that somehow you’re asleep at the wheel of your own career, this book could be the kick in the pants you need to break through your own inertia.

Not convinced yet? Here’s that interview with Marie Forleo I mentioned earlier:

Have you read the book? What did you think of it? Do you remember the moment you “turned pro?”

The Best Writing on Work I’ve Ever Read

Photo: Nuttakit,

Photo: Nuttakit,

A lot of people romanticize the idea of doing what you love.

“Just go out there and figure out what you love to do, then make a career out of it.”

Sounds great, right?

The truth is, that type of advice rings hollow without, at least, some context and, at best, a strategy.

As someone who likes to put a framework on just about everything I do, I was ecstatic to come across the essay “How to Do What You Love,” by Paul Graham. In it, Graham discusses the complicated nature of finding work you love and actually doing it and gives some advice for beginning to think about what that thing you love to do actually is. It’s a simple, pragmatic, non-romantic approach to doing meaningful work.

I came across the essay while reading a Design Sponge profile on Susan Gregg Koger, owner of the successful vintage clothing company, Modcloth. In the story, Koger notes that she checks in with this essay “about every six months or so” to make sure she’s on track.

After reading the essay, I felt the need to share it with everyone I hold dear. I’m not going to post a review or a summary here. But I can’t help but highlight some of my favorite takeaways in the hopes that they’ll entice you to read the whole thing for yourself and apply it as it relates to your work life. So here goes:

On dispelling the myth that doing what you love is either magical or easy or both:

“Doing what you love is complicated.”

On how we teach our children to view work:

“I’m not saying we should let little kids do whatever they want. They have to be made to work on certain things. But if we make kids work on dull stuff, it might be wise to tell them that tediousness is not the defining quality of work.”

On the fairytale notion of doing what you love:

“Do what you love doesn’t mean, do what you would like to do most this second. Even Einstein probably had moments when he wanted to have a cup of coffee, but he told himself he ought to finish what he was working on first.”

On the life of total leisure:

“Unproductive pleasures pall eventually. After a while you get tired of lying on the beach. If you want to stay happy, you have to do something.”

On the satisfaction that comes from meaningful work:

“To be happy I think you have to be doing something you not only enjoy, but admire.”

On the trappings of prestige:

“Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.”

On choosing a career:

“A comparatively safe and prosperous career with some automatic baseline prestige is dangerously tempting to someone young, who hasn’t thought much about what they really like.”

On knowing if what you do is what you love:

“The test of whether people love what they do is whether they’d do it even if they weren’t paid for it—even if they had to work at another job to make a living.”

On finding work you love:

“It’s hard to find work you love; it must be, if so few do. So don’t underestimate this task. And don’t feel bad if you haven’t succeeded yet. More often people who do great things have careers with the trajectory of a ping-pong ball. They go to school to study A, drop out and get a job doing B and then become famous for C after taking it up on the side.”

On keeping at it:

“Always produce. For example, if you have a day job you don’t take seriously because you plan to be a novelist, are you producing? Are you writing pages of fiction, however bad? As long as you’re producing you’ll know you’re not merely using the hazy vision of the grand novel you plan to write one day as an opiate.”