Why you should be a freelance writer.

A few days ago, four freelance writers I admire—Megan Pacella, Liz Riggs, Jennifer Bradley and Christina Vinson—shared why someone shouldn't be a freelance writer. Their answers were as varied as they were honest. But for better or worse, all five of us are freelance writers. So why—or rather—when should you be a freelance writer?

Here's what they said:

for freelance writers

You should be a freelancer when your day job takes a backseat to how much you love running your own business.

MEGAN: For almost four years, I worked as a full-time content strategist and a part-time blogger, freelance writer, and freelance editor. After a few years of building up a client base and hand-picking which projects sounded awesome, which sounded boring, and which paid too much to pass, I realized that I absolutely love working for myself. When you wake up every day and start making the mental rounds of companies and magazines you want to write for, and then you work up pitch ideas while you're in the shower, you should be a freelancer. Because, while there are hard days (really hard, terrible days where you don't want to get out of bed), most of the time nobody is going to have to motivate you.

You should be a freelance writer when you can’t stop writing and you have a financial cushion.

LIZ: If everything you do, see, and think about lands you in front of your computer for a think piece or a blog or an email or a pitch, then maybe you’re onto something.  But, keep your full time or part time gig until you’ve got a steady stream of assignments. I was freelancing (like, seriously FREElancing) for over a year while working full time, and I after four months of full-time freelancing and zero-time salary, I am already looking for part time gigs to supplement my income —my checking account has seen a serious dip in the past few months. Plus, the social aspect of an actual job (full or part time) can do loads for your pitch ideas, social life, and morale while living the lonely life of a writer.

You should be a freelance writer when you'd be willing to do anything to make it work.

JENNIFER: I don't mean "anything" as in anything unethical. I'm talking, "I'd work at Starbucks, work at retail (which was my least favorite of all my college jobs), be a dog walker, etc..." I remember having a conversation with my husband when I'd decided to embark on this crazy freelancing adventure and he was concerned about the possible instability of a writer's income. I said, "Honestly, I'd clean toilets on the side, if it meant that I could do this for a living." If you're that committed to making it work, then go for it. [Thankfully it's never come to that – ew!] The truth is, most freelancers who are making a good income have a lot of different things in their "mix" – it's not just the exciting assignments that pay the bills. I have a couple of less exciting corporate clients, ghostwriting gigs and copywriting assignments that are well paying and consistent, and those give me the freedom to take on the "fun" gigs that feed my creativity.

You should be a freelance writer when you hate dress pants.

CHRISTINA: Let me explain. Dress pants, to me, symbolize the environment that comes with a corporate office job. I worked in that setting for six years, mostly in higher education. I bought dress pants from Banana Republic, commuted to work, packed my lunch, engaged in office small talk, and "lived for the weekend." In short, I was a "typical" worker -- and yet, I felt there could be so much more to life. The creative side of my brain felt completely trapped and I really felt that my life didn't begin until after 5pm. Sound familiar? So, I became completely determined to do whatever it would take to break into a freelance writing career. I met with other freelance writers (like Claire) on the weekends and on my lunch break. When I got home at 5pm, I began working on anything that would help me take the plunge into freelance writing, including blogging, networking with anyone who would listen, and picking up tiny writing projects. It was exhausting and exhilarating all at once. Eventually, I gained enough traction to go out on my own, into the world of freelance writing, and it's been a wild ride ever since. Today, my dress pants are untouched, in the back of my closet.

In conclusion...

So there you have it folks. Four different perspectives on why you should and why you shouldn't be a freelance writer.  I will echo these ladies and say that I haven't exactly found a way to make a feasible living off of being a freelance writer alone. All along the way, I have had part-time jobs, coaching gigs, editing stints, and one-off jobs that, and one insanely supportive husband. To know more about my journey into the wild wonderful world of words—read the "big announcement" I made a year and a half  ago, or click here to see all of my writing about writing. Ugh. How meta.

We'd love to hear your thoughts on this series. Would you want to see more about freelance writing here? Or would you rather get back to posts about poo?


Why you shouldn't be a freelance writer.

People often ask me how to start freelance writing. I always try to respond with a clear, concise, and uncalloused answer—just like Kim Green did for me. But the truth is—this job isn't for everyone. And sometimes, this "job" pays so little, that it feels like I need to get another job. And while there are many reasons people want to write for a living, there are just as many reasons why they shouldn't.

For this post, I turned to four freelance writers I admire, and asked a simple question: Why shouldn't someone become a freelance writer?  Megan PacellaJennifer Bradley FranklinLiz Riggs, and Christina Vinson all came to the table with different answers. Hopefully, together, we can dispel some of the myths of this profession and clarify the risks you take on as a writing entrepreneur.

You shouldn't be a freelance writer because you want to make your own schedule.

Megan Pacella

MEGAN: Your schedule is actually going to get out of control once you build up several clients. Without the job description or boundaries to say, "This deadline is too short," you will frequently end up turning around long stories or editing projects with just a few day's notice.

Too often, on Thursday nights when your besties are watching Grey's Anatomy (Oh, wait? Is that just me? I think everyone else quit watching in 2008), you'll be plugging away in front of your computer. You'll check your emails on vacation, and you'll work for at least a few hours every holiday while your family hangs out together around the kitchen table.  That's not to say that there are no vacation days. But for the most part, being a freelancer means being extremely flexible.

Megan Pacella is a writer and editor based in Nashville, Tennessee. She's done everything from restaurant reviews to small business profiles to full-length features to marketing copy. She loves to travel, cook and cuddle up with her golden retriever. Megan also has a sweet haircut and is an incredibly thoughtful wife and friend. 

You shouldn't be a freelance writer because you think it sounds glamorous.

Jennifer BradleyJENNIFER:  The reality is, freelancers (especially those who get to write about food, travel, fashion, etc...) do get to do some really cool things. They get to try new restaurants, see far flung parts of the world, interview interesting designers, test out spa services, etc... BUT if you think those fun bits are going to be the lion's share of your "job," you're sorely mistaken.

Being a freelancer is about running a business. You have to handle invoicing, accounting, pitching, marketing, maintaining relationships—and, truth be told, those fun assignments likely won't fully pay your mortgage. You'll probably need to take on some less glamorous jobs to make it shake out to a livable income AND you have to be willing to hustle. All. The. Time. It's a lifestyle that not everyone's cut out to lead. [Side note: it helps to have a thick skin. You'll get more rejections than assignments, especially at first, so it helps to have enough drive to push through that.]

Jennifer Bradley Franklin is an Atlanta-based writer and journalist. Her work has been featured in People, All You, American Airlines Magazine, Alaska Airlines, Daily Candy, and a long list of other publications. She also gives incredible travel-writing seminars.

You shouldn't be a freelance writer because you've "always liked writing."

Liz RiggsLIZ: Liking writing and making money off of it are two totally different things. The great part about freelancing is that you can pick and choose your own assignments (although, actually getting the assignments does seem to be even trickier than imagined), but the likelihood of being paid cash-money to do it isn’t great (at least at first).

As far as “liking writing” and then “going freelance” is concerned: just stop.  If you spend all your free time and Saturday mornings and late nights blogging, writing articles that you hope will be published, reading magazines and websites and stalking editors—then maybe it’s time to go freelance. But if you’re just thinking you’d like to put your paper-writing skills into a paying profession, try writing 1,000 words a day for at least a month and then see how you feel. Fo reals! You may be like YES, IT’S TIME! I CAN’T STOP WRITING AND NOBODY CAN STOP ME! Or, you may be crying on the floor of your bedroom because you don’t want to look at your computer screen for one more minute.

Liz Riggs, also known as @riggser, is a freelance writer in Nashville, Tennessee. Her writing has been featured in Relevant Magazine, The Huffington Post, Portable, American Songwriter, among others. She's also really funny. I mean, just check out her bio. Liz likes macaroni and cheese. And one time, I posted pictures of her face all over Georgia Tech's campus.

You shouldn't be a freelance writer because you think it sounds easy.

HeadshotCHRISTINA: Freelance writing is by far the most difficult job I've ever had, and also the most rewarding. Suddenly, you're not only your boss, but also your own accountant, assistant, communications expert, social media manager, business developer, and so much more.

There are many days where I don't do much writing at all, but am working on invoicing, networking, interviewing, and finding more gigs. It's not just about writing, it's also about owning a business -- and you have put a tremendous effort into both. You won't start out knowing everything, and this job is certainly never easy. But it's so rewarding. My mantra each day is based what Maya Angelou said, "I did then what I knew how to do. Now that I know better, I do better."

Christina Vinson is a freelance writer based in Nashville, Tennessee. She's written for The Christian Post, Bearings, Taste of Country, Native, and others, all while writing really thoughtful web content for clients across the country. She's also written back-cover copy for books, which I find fascinating. Christina lives with her husband in East Nashville and visits her twin sister, Nicole, as much as possible. She also wrote about how I said "bullshit" once.

FINALLY: Just because these four women gave you four reasons not to do the job we've all decided to do—doesn't mean you shouldn't do it at all. In fact, all four women also told me why you SHOULD be a freelance writer. Stay tuned for part II.

Courage to wear Camouflage

The book I'm currently writing is about the Army. It's also about my time at West Point—but it's not about my father. It's about three women I met while living there. So, when I flipped through a few catalogues lately, I was pleased to see page after page of old school, circa 2000, camouflage. Green, brown, and gray. Just like I remember smelling all those years ago.

I grew up around a lot of combat uniforms. Of course, this was back about ten years ago, when Army Battle Dress Uniforms (BDUs) were green, gray, and brown. These days, the  Army Combat Uniform, or ACUs, for you non-military folks, aren't green. After all, our armed forces aren't fighting in the forest. The uniforms are tan, beige, and brown—fit for fighting in the desert.

BDUs smell like mud and Old Spice. I know, because I smelled it every night when my dad got home from work. At the time, I was unaware that the memory I made wasn't gripping his core, but smelling his uniform: shoe polish, sweat, and aftershave.

In the past, camouflage has been relegated to hunters and those with a commission—but if you look around, you'll see it's popping up all over the place in the mainstream.

Now I'll be the first to admit that it's a stretch—and wearing it might just feel a little strange. But the strength of camouflage paired with soft accents is surprisingly beautiful. It's where the fierce and the feminine meet.  And in a way—it's exactly what my book is about.


1 / 2 / 3 / 4 / 5 / 6

Top photo via J. Crew

Lessons I've learned while writing.

A few months back, I boldly admitted to the world that I'm writing a book. That was probably a good decision, because the public shame of stopping has ultimately kept me from stopping. It's like going running on 12 Ave South. If I stop... I know someone will notice me walking. And I'd rather them see me jogging slowly than walking. So I keep going.

It's a positive kind of shame. Let's call it positive peer pressure.

Nashville LibraryNashville's Library. My favorite workspace.

And there are other things I've learned, too. When you take on a large project that's bigger and nastier than you ever expected—expect to get your butt kicked and you brain bent more than a few times.

Here are five lessons I've learned while writing something bigger than ever...

1. When you're staring at a blank page, just do the next thing.

There's nothing scarier than a blank page. So fill it. I've had to learn that if I'm stuck, the only way to get out of that rut is to move forward. So what happens next? What needs to happen next to move you to the next page? Write it. It doesn't have to look pretty or sound pretty (see #3), it just needs to happen.

2. If someone asks what you're working on, tell them.

Something that's been hard for me lately is feeling like I'm not doing anything of value (see #5). And when people ask me what I'm working on, I wish I could give them a measurable, understandable answer (i.e., 'Oh, I'm on summer break, becuase I'm a teacher,' or 'I just finished up three great stories for GQ, Esquire, and Vogue'). But when you're working on an extended project... you don't have that luxury. So I've had to force myself to own up to the truth. I'm writing a book. Then, it forces me to pitch it over and over again. By answering the next, logical question—what is it about?—I'm helping myself get back to the heart of what it's about. And that is a good thing.

3. Don't be your own critic. At first. 

When you start writing, it's going to be ugly and sloppy and you're going to say that your characters "sigh" a lot. Who cares. If they are sighing in your head, write that they're sighing on the paper. You can get out your thesaurus and change words and mess with it later. Just write it down now. This is why I've found that I'm better writing things by hand. Yes. By hand. That way, I can use really bad handwriting, and I can just get everything down without going backwards and editing (copy, cut, paste, delete, change) before I've even written 10 words. Once it's down on paper, I can type it. And when I type it, I can make it better. But if I start criticizing the story I'm writing before it's even written, I'll never keep going.

4.  Forget the future. For now. 

It's easy to get lost in the "what is the point of this" question. Where is it going? What is the end result going to be? Will anyone ever read it? Those questions are rough and are worth answering. But when you're in the middle of writing—those questions must be beat down into the ground and out of the room. They should be tied up and left for dead. At least until you're done writing. Because the truth is, the future doesn't matter unless the book is written—the answers are Nowhere, Nothing, and No One, unless you keep going.

5. Stop Looking at the Bottom Line. 

Money. It's a scoundrel. It also keeps me feeling like I'm not doing something of value. But in reality—money can't drive what we create. I am in research and development stage. In grad school, so to speak. Yes. I'm giving up time and energy and possible income to write a book. But it's an investment. Not a waste.


These are the lessons I'm learning. And I'm forcing myself to write them down—because I have to preach this to myself. I have a feeling these same lessons could apply to lots of different undertakings...


Writing music.

Taking pictures.

Starting a business.

Just living.

Do you agree?