How to Become a Freelance Writer in 900 Simple Steps – Part 1: Risky Business


Let's be clear: I am not a freelance writer—yet, and I don't yet know how to become one. This is the first in a series of articles in which I drag you, dear reader, along with me as I try to figure out how to set up a freelance writing business. Over the past 2 years, you've come to me for grammar advice and random musings on craft, but join me now as I attempt to enter the business world as a freelance copywriter. Let's get started.

WTF is a Freelance Copywriter?

I have proven the existence of a once-thought mythical creature—the paid writer. Sure there are novelists and celebrities that make cash for books, and there are a few people out there who get a buck or two for helping magazines fill pages and websites create content. There are screenwriters and speech writers, but generally speaking, writing is not a lucrative career choice.

What exactly do freelance copywriters write? Everything!

Or so I thought. A few years back, I met and befriended Kristin O'Neill ( through a volunteer gig. She lived near me, and she had the most astounding job title I'd ever heard of—freelance copywriter. Not only that, but she was friends with other so-called freelancers. At first, I admit that I didn't really understand what she did. But then at party at her house, I met another freelancer, Amber James (, who'd been successfully supporting herself with full-time freelance writing for several years! What a thought!

What exactly do freelance copywriters write? Everything! From ad copy to newsletters, from policies to blogs, from business proposals to brochures, and from catalog blurbs to t-shirt taglines, there's nothing off-limits. James told me she's worked on everything from tweets for non-profits to ghost writing a book for a motivational speaker to writing taglines for Nike. So, if you are after variety, it appears that the freelance thing delivers. Sure, some freelances have specialties, but generally speaking, they are just really skilled at writing and they help businesses who need someone with that skill to produce written content. Unlike traditional writers, these people don't get their names in the byline, but they do get paid hourly for their work. Did you catch that? HOUR-LY.

James also turned me on to a book by longtime Atlanta-based freelancer, Peter Bowerman. Bowerman's book, The Well-Fed Writer, goes in-depth about how to set up and be successful at being a freelance writer. James said that although she started on her path to freelancing before reading the book, Bowerman's insights helped her go from part-time to full-time. While I haven't had the opportunity to read the book all the way through, Bowerman does do a great job of making it sound feasible while still striking a tone of realism. He also talks about how he has done jobs for large corporations, who you'd assume have fully-equipped marketing departments for this sort of thing. But, apparently, even the biggest businesses need a little help here and there on special projects without adding a whole new person to the payroll. This, my friends, is good news.

Risks and Rewards

I confess, I am not much of a risk-taker. I like to know all the possible outcomes before I embark on a project, so assuming that it is even possible to know everything, I do feel it necessary to pull out the ol' Composition Book and do a Risk vs. Rewards list to help me get the proper perspective.

When I asked Amber James to elaborate on why she decided to go freelance in the first place, she told me that after moving a lot, she was tired of starting over in each new home.

I wanted to have a job that could grow as I grew, and that I could take with me wherever in the world I might be. Knowing that my interests revolved around reading and writing, I decided to become a freelance copywriter.

Let's face it, this is a global economy, and to get ahead, you have to be willing to change location. I have lived in four states in ten years, and while I love Portland, I sense this isn't my last stop. Besides, I'd like to be able to travel or, I don't know, spend winters somewhere warm, or summers in my hometown. Now I'm dreaming a bit big, but really—it's in the realm of possibility, and that's something.

More realistically, however, the flexibility of location James talks about doesn't always mean traveling or moving. As a newish parent, finding flexibility in my career has become a really high priority. No longer can I stay late or come in early, travel, or even commute long distances as easily as I once could. Between kid colds and day care schedules, my time is limited by more factors than it used to be. Thus, being able to work from home when the kid (or I or the husband) has a cold/flu/chicken pox/lice, etc. is a huge bonus. So let's put flexibility in the Rewards column.

Also, I love the idea of losing the cubicle. Having spent the last three years between three greyish-beige—let's call 'em greige—walls, I'm ready for a little light, a little color! If I worked from home or from my own office space, I could have more control over my work environment—which I find incredibly attractive. Often, during my maternity leave, I would meet up with Kristin at her "office"—a booth at a local coffee shop. She rented her own desk in a shared office space, but she was able to cross the street and grab a latte and crack the laptop any time she wanted without taking some mandated 15-minute break, or worrying that the boss would catch her "slacking." So, I'm also putting no greige/latte-friendly work environment in the Rewards column.

Now let's take a look at the not-so-great parts of going freelance. I asked James what was the best and worst part about working for herself.

The best thing is having complete control of the work you create, the clients you work with, and the rates you get paid. I would say that that is also the worst thing! It means that at the end of the day, you are the one responsible for your success, progress, or lack thereof. You can't point fingers at a lazy co-worker or an unfair boss. As your own boss, your business is your responsibility. Sure, you'll encounter less than awesome people who make your job harder, but as the boss, you decide whether to set them straight, cut them loose, or put up with the abuse. It's all on you for the bitter and the better.

I take this insight to heart. I have never worked for myself, and so I have had the pleasure of blaming my failings on bad companies, bad economies, or bad bosses—but as my own boss, when things go poorly, I'll have only myself to blame. I'm not going to lie—that scares me. So let's put having only yourself to blame if it all goes to shit in the Risks column.

Speaking of risks and responsibilities—it is nice having someone else sign your paycheck. You show up, do whatever they tell you to do, and voila!, you get paid. What's not to like about that? Sure, you are at the mercy of your employer, but if you have a good one, then there's not much to complain about. And while you'll always run some risk of getting laid off, the risk-taking and responsibility for keeping the company afloat is in the hands of the owner—not you. Being my own boss may sound wonderful, but it carries with it a LOT of responsibility. Am I ready? Let's put being my own boss in both columns.

As for keeping the company afloat—well, getting started, I have to face fact that I am starting at zero—zero dollars, that is. When you report to a job, you get paid just for being there. When you work for yourself, you end up doing a lot of work that is not paid. You could spend hours on something that amounts to nothing—and by nothing, I mean zero dollars. I love to write, but I am a practical sort, and I know I need money in the bank to pay my bills. I have taken on some pretty craptacular jobs over more appealing but lower-paying jobs because I racked up too much debt in college to live on minimum wage. My psyche is constantly at war with itself—creativity and freedom versus practicality and a paycheck. It's not often that these two things come in the same package. Going freelance is, to me, a big financial risk versus finding a decent paying job. I'm putting zero dollars in the Risks column.

On the flip side of the money question, though, is the fact that I could actually make more money in the long run as a freelancer. When you are in a job at a company, you can often get stuck in a particular job title or duty. When you are ready to move up, there may be nowhere to go, or your employer may not be willing to dole out a raise when you think you deserve it. As a freelancer, you can give yourself a raise whenever you think it's appropriate. You can go after bigger, better jobs. You can give yourself the most high-falutin job title you want, and you can move up on your own terms. There is room to make more than you would in any regular job—so I'm putting more money in the Rewards column.

There is one more Risk that, personally, doesn't scare me as much as it should—the paperwork. For some reason, I've always had a bit of a secret love for the mundane task of filling out paperwork. I've done my own taxes since I was a teenager, and I've always been pretty good at that aspect of life. That said, I've never set up my own business before, so I should not ignore that it will be a challenge to figure out business licenses, taxes, etc. without a legal team to make sure I don't fuck it up and end up owing the IRS my ass(ets). I'm putting set up in the Risks column, even if I am a freak of nature who likes to fill out forms. (I know, weirdo.)

So What's the Hold Up?

Well, until a week ago, having a full-time job that put money in my bank account was the biggest factor (excuse) keeping me from pursuing this freelance thing as a real option. But.....then I was laid off! So now I have more time than I originally planned to give this some real consideration. While I am worried about the reality of depending solely on freelance work to make income, I am excited by this sudden bonus of that most elusive of substances—TIME! So while I planned to work on going freelance gradually, this process may move faster than I'd though it would.

Stay tuned to LitReactor over the next couple of months. I'll update you on my progress as I get into the nitty-gritty of setting up a freelance business. I'll keep you in the loop as I select a business name, apply for a license, set up a website and domain, search for clients, and continually doubt myself and the decisions I make. Should be fun! (and really, really scary—and possibly hilarious. Oh god...what have I gotten myself into now?)

If you have advice for me or words of encouragement (or discouragement, as the case may be) put 'em in the comments.

Taylor Houston

Column by Taylor Houston

Taylor Houston is a genuine Word Nerd living in Portland, OR where she works as a technical writer and volunteers on the marketing committee for Wordstock, a local organization dedicated to writing education. She has a BA in Creative Writing and Spanish from Hamilton College and attended Penn State's MFA program in Creative Nonfiction. She has taught writing at all levels from middle school to college to adult, and she is the creator of Writer’s Cramp, a class for adults who just want to write!

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kej5009's picture
kej5009 from Pennsylvania is reading Parlor Games January 24, 2014 - 7:48pm

So excited to see this! I just started the process of becoming a freelancer myself. Looking forward to hearing your experiences and maybe pick up some tips!

Edit: Just saw you're a Penn Stater; that's my alma mater and current employer. We are!

Sanbai's picture
Sanbai from the Midwest is reading The War of Art January 24, 2014 - 10:00pm

Hmmm. Interesting. I look forward to hearing more from you - and hopefully not a "6 months later, I gave up on Freelancing"...

InfoInsomniac's picture
InfoInsomniac from SoCal is reading everything January 26, 2014 - 4:39am

Hi Taylor, 

It is always exciting and scary embarking on a new adventure. One thing to remember is that this will be an adventure. Additionally, how you see everything will also be important. Is it a problem or is it better to view it as a learning experience? Things will go well and things will go badly (it just happens), but you need to work on maintaining a positive attitude and realizing that there is plenty of work out there.

It's also great to reach out to others and network with other writers. They can be a wealth of information and contacts. 

Excited for you! Welcome to the club!


.'s picture
. January 28, 2014 - 1:53pm

Cool article! I've landed my first freelance gig that is ongoing for the moment. I haven't given any thought to marketing myself as a freelancer. That would be a good idea. Just bought The Well-Fed Writer.

Amber James's picture
Amber James February 14, 2014 - 7:09pm

Hi everyone! This is the aforementioned Amber James with a few more bits for you (and your readers), Taylor.

Paperwork & Start-Up Cost: Easy.

  • Very likely you'll establish your freelance copywriting business as a Sole Proprietorship or LLC (Limited Liability Company). It'll cost you $100 to set-up, and $100 every year to renew. You go here to register your business and they send you your business social security number (called an EIN) that you'll need for tax purposes.
  • Regarding taxes, get a CPA. Or at least get a CPA to walk you through how a freelancer should structure their taxes and then you can take over from there.
  • As far as a contract goes, Freelancers Union has a Contract Creator that allows you to generate a contract with fields to be filled-out with the specifications of the project. You can also connect with any freelance copywriters you know (wink wink, nudge nudge) and they'll very likely be able to help you with this. ;)
  • The biggest expense a freelance copywriter incurs (in my experience) is buying a computer. Assuming you already have this, the remaining cost is around $200 (I know this because I've calculated it before) for a basic setup.

Had you been employed full-time, I would have recommended starting your freelancing as a side gig. Build it slowly, but seriously, until you get to a point where you're at capacity and you can't not go full-time freelance. 

Sorry if that ruined your plans for the next few posts! You should come back to the Copywriter Conclave meetings. Questions like yours are the very reason for our existence! ;)