I’ve Been Earning a Full-Time Living as a Freelance Writer for Over a Decade

I wish I could tell you I'm one of those people who knew from a very early age that she was born to be a writer, but I'm not. I'd love to be able to say that earning an actual full-time living as a writer working completely for myself and by myself has been nothing but sunshine and roses, but I can't. I can tell you how I got here and how I make it work for me despite the fact that it hasn't always been an easy ride.

Earning 100 percent of my full-time living as a writer has taught me a lot about myself over the years, and it will do the same for you if you ever wind up going that route yourself. It will make you a better writer and a better worker. It may even make you a better person in some really unexpected ways, even if that "better person" does swear under her breath a lot and fight the urge to throw her laptop out the window at times. For some of us, I think that just comes with the territory, and you know what? That's OK.

I haven't always been a writer, but I have always written.

It was just something I did without really thinking about it. Like a lot of very introverted people, I was never great at expressing myself verbally, but with a pencil in my hand or a keyboard under my fingertips, it was suddenly so easy to say what I meant and get my point across. In fact, writing often felt like my own personal form of sorcery, because it made things happen.

When the child I used to be wanted to make her friends laugh, she'd write a funny story about vomit, or butts, or any number of other things that kids find so inexplicably hilarious, and poof - instant popularity.

When the teenager I grew into was sure her life was over because she'd just embarrassed herself in front of yet another boy she liked, she'd come home and write in her journal until life seemed livable again.

When the young lady I was didn't quite feel "seen" enough to suit her, she'd hop on LiveJournal, post something emo (and more than a little bit pretentious), and wait for the adoring comments to pour in.

So when the grown woman I ultimately became needed to find a way to make some extra money from the comfort and privacy of her own home, writing simply made sense. I figured I'd just use my natural way with words to conjure myself up some money the same way I always had friends, peace of mind, and easy A's when I was younger. I thought it would be effortless, fun, and completely unlike actual work, but… nope. Not so much.

Because writing for other people is definitely work.

When you write for no other reason than to express yourself, you have the privilege of not worrying about how anything sounds. Your audience basically amounts to yourself and whomever else you may decide to share your words with after the fact. As long as you like what you wrote, everything's golden. Of course, this is not the case when you have clients you need to please, especially when those clients don't know you or care how talented you think you are.

I met my very first clients on a site called Elance, which has since been absorbed along with oDesk and turned into Upwork. They were kind of a mixed bag as far as who they were and what kinds of material they needed written. One was an Australian businessman who needed his resume polished. Another was an artist who needed some copy written for his website's homepage. I also wound up connecting with a DUI attorney, a guy who ran a tutoring website, and a former salesman who wanted to try his hand at making affiliate marketing work for him, all of whom needed blogs and web content.

All of these people were about as different from one another as can be, and collectively they taught me some really important lessons on how not to go about writing for clients online. The Australian businessman and the tutoring guy were pretty much what I expected. They were professional, they paid what I asked, they were pleased with what I wrote for them, and they paid promptly. The artist was actually a dream come true. He insisted on paying me significantly more than I'd asked, because he thought my prices were way too low. (I actually would wind up raising my prices soon after based on his advice.)

The attorney and the affiliate guy were nightmares though. The attorney turned out to be a huge, abusive jerk who actually wound up stiffing me altogether because he knew I was inexperienced and that he could get away with it. (That was the first and last time I'd simply take a client at his word instead of insisting on an agreement that actually protects my interests.) The affiliate guy was nice enough as a person, but not at all realistic as far as his expectations went.

He liked the first batch of work I did for him and wanted to hire me to produce more on an ongoing basis. In fact, he liked my writing so much, he became convinced that filling his websites with my copy would make him rich via affiliate sales pretty much overnight. When that didn't happen and he eventually had to go out and get an actual day job, because this is planet Earth we're living on, he blamed my copy for it. And let me tell you, getting reamed for not being an actual magician was every bit as fun as it sounds. You live and learn though.

Writing for a living takes a lot out of you.

I would go on to have lots of clients across many different industries, because I turned out to be genuinely good at copywriting and content writing. Some of those people were sheer joys to work for, while others were odd to say the least. Most were somewhere in the middle, easy to work for and reliable, if not particularly memorable.

I wasn't prepared for how much work it was all going to be though. I always assumed that traditional day jobs were so exhausting because you had a boss, and a schedule you didn't choose, as well as customers you don't pick for yourself. Freelance writing made me painfully aware that the exhaustion comes from the actual labor you're performing, whether that labor requires you to put on real pants and arrive at an office by 9 AM or not.

Even under circumstances that allow you to make all your own choices, you still have to work when you really don't want to. You'll still occasionally find yourself committed to assignments that bore you to tears or dealing with unreasonable people that make you want to punch something. And when you're not actually writing or looking for work (which you have to do constantly if you're serious about making enough money to live on), you have your marketing, scheduling, and bookkeeping to do.

Friends of mine who know I write for a living but have zero idea how hard I really work are always saying things that make my head pound. They're aware I can string a sentence or two together, and like a lot of people, they automatically assume a little skill equals people throwing small fortunes at you just for the heck of it. They talk about how tired they are of working and how badly they wish they could "just do what I do instead".

Well, I'll tell you what I tell those friends. If you don't want a job and don't like to work, full-time freelance writing isn't for you. I've worked harder at this than I ever have at anything in my life. Sometimes it's awesome and I feel 10 feet tall because I just got to work on something I'm really proud of, like advertising copy for a big brand like Papa John's or web content for an organization that's out there doing something really meaningful. Other times, it absolutely sucks, and I will admit to having been frustrated to literal tears more than once. There have even been times I thought very seriously about quitting in favor making sandwiches for a living somewhere instead because deadlines and client expectations were causing me so much stress at the time.

In other words, you can do what you want when you're a freelance writer, but don't doubt for a second that it's work. It will feel like work too, for better or worse.

Your loved ones won't get it.

My mother's not a writer. In fact, she's not a particularly creative person at all, despite being very fascinated by people who are. Since she doesn't actually understand from experience how much a creative pursuit like writing can take out of a person, it's difficult for her to see what I do as work. After all, I do what I do out of my own home. I use my own personal computer and smartphone to communicate with clients, create content, and meet deadlines. I wear whatever I damn well please, which admittedly isn't "real" clothing anywhere near as often as it should be, and I like to have the TV on for background noise while I'm working.

From the outside looking in, there's no actual way to tell whether I'm working or doing something of my own choosing, like chatting to friends on Facebook or organizing my own thoughts in my personal journal. The great majority of the people in my life know I must work hard, because I earn an actual living and manage to keep my bills paid, but it's a real stretch to say they think I actually have a job.

My mother in particular seems to be under the impression that people throw money at me for no good reason, so she's never understood why I don't have time for a chat over Facebook during my work hours or get so upset if my internet connection suddenly dies when I'm trying to meet a really tight deadline. As far as she's concerned, if I'm at home, I'm basically free and should be happy to make myself available to anyone who'd like a piece of my time, and most of the people who have passed through my life over the past decade or so felt the same way.

Unless you happen to know nothing but other writers or creative freelancers, you can expect similar thinking from your own family and social circle. In fact, you'll probably really have to put your foot down with them sooner or later, and they won't like it one little bit. They'll think you're being a jerk for no reason, because most people really do need to see those visual cues that signal someone's working before they can take that person's job seriously - like the suit they might put on in the morning or the car they get into to drive to an office somewhere.

Eventually, some of those people will figure out that you do indeed work, but that working happens to look a little different when you do it. They'll eventually learn to give you adequate space in which to do what you do as well. Others will never actually get it, but that comes with the territory too.

You'll find out what burnout feels like sooner or later.

I still remember the first time I had one of those "wow, I'm actually a writer" moments. I was pushing a huge cart filled with groceries out of a Super Wal-Mart right after paying for the entire thing with writing money. I'd go on to do the same thing lots of times over the years until it felt completely normal, but that first time was special, because I'd never made real money doing something I enjoyed and really thought I was good at before. I felt like Wonder Woman - someone who was unstoppable and could do anything - and God knows I'd try.

In the early years of my writing career, I took on pretty much every client I could and said yes to every assignment I was offered. If I thought I could even possibly write on a topic, I took that assignment, and at first, it worked out fine. Then my schedule started reaching the point where I didn't always have time to do things I wanted to do, like go out for pizza and beer with my husband, or really get lost in a good book on a Sunday afternoon. Not ideal, obviously, but still not something I saw as a big issue. I figured it was a good problem to have - lots of business coming in and plenty of income to pay bills with.

As my client roster and my schedule got fuller still though, I started to feel genuinely stressed out. I'd never seen the need to schedule regular days off for myself, let alone set business hours that officially ended at a particular time of day. For some reason, I also felt like saying no to an assignment just wasn't an option, because that would be like flushing money down the toilet, and who does that. Eventually that meant I didn't have any time to myself whatsoever. I wrote for clients pretty much from the time my little eyes popped open in the morning until my poor, overworked head touched the pillow at night, and it caught up with me after a while.

I remember a Thanksgiving when I was close to tears all day because I was trying to juggle preparing a turkey dinner with all the trimmings for my family with yet another deadline. I remember working late into the night on one of my husband's birthdays, genuinely pissed off at the fact that I couldn't spend the quality time I wanted to with him because a client had dumped a rush order on me the night before. I started putting on weight and getting really depressed because I no longer had time to go for all the walks and bike rides I used to enjoy so much.

I also started to hate writing, not to mention my clients. It wasn't fun anymore, and I no longer felt like Wonder Woman. I just felt tired - so tired that I could feel it way down deep in my bones. Eventually, I would become pickier about the clients I took on, learn how to set boundaries, and master the fine art of saying "no" in the name of maintaining a manageable level of work/life balance, but it took me a while. It will probably take you a while as well, but starting from the beginning (instead of trying to be everything to everyone like I did) will help.

You may eventually have an identity crisis as well.

When I first considered trying to earn a living as a writer, I pictured my career trajectory going a lot differently in my mind. Before I started doing it for a living, writing was never really something I did to convey information or thought of as a service I would be providing for others. I saw myself as an artist through and through - someone who was at her best when she was writing fiction, poetry, or personal reflections. Someone like Anne Rice, or Margaret Atwood, or Alice Walker.

When I pictured my ideal future life as one of the pros, I saw myself penning bestsellers or possibly writing a column on a topic I was passionate about for some wonderful little publication somewhere. I have no idea how I thought I'd get there by writing web content, resumes, and advertising copy for random clients on Elance, but I totally did. I also naively thought it would happen without my having to actively focus and pursue that kind of work.

When my fairy godmother never materialized to sort it all out for me, I was pissed. I definitely went through a very weird, very dark period where I not only hated being a writer, but low-key started to hate a lot of my clients for no good reason. I felt like freelancing was standing in the way of my accomplishing something bigger and better, but I don't think I really knew what that was. I definitely didn't know how to get there or how to properly carve out a proper place in my busy schedule for writing I could potentially feel more excited about.

Strangely, I think it was discovering Mad Men that changed my tune. Falling in love with that show didn't just keep me good and entertained during the years it was on the air. It actually helped me come to see advertising, marketing, and copywriting as things that were creative and important in their own right. I developed a new appreciation for the work I was already doing, and I eventually learned to take a lot of pride in it.

Maybe I didn't feel like the next Anne Rice anymore, but I did feel a little bit like Peggy Olson, Don Draper, or Joan Holloway Harris on my good days. Thankfully, that's a feeling that stayed with me going forward, and led me to pursue work for bigger companies and seek out clients that were doing things I felt invested in on a personal level.

These days, my personal identity as a writer is relatively balanced. The part of me that still wants to be Anne Rice one day loves to read on the weekends and makes sure I'm taking the time to put content of my own out there. However, the Peggy Olson in me does enjoy copywriting and takes pride in doing amazing work for a lot of different clients across multiple industries. Copywriting, content production, and creative consulting are still my primary bread and butter, but sometimes I get to make money via my personal writing as well, and that also feels good.

Freelance writing really changed me, and that's a good thing.

Like a lot of creative types out there, I can't say I was always the most diligent worker. I had my head in the clouds a lot, and I definitely wasn't the best at dealing with the realities of life. I would even stay that way until I was old enough for it to be embarrassing.

The process of turning what I consider to be my only actual natural talent into a way to earn a living would eventually help me grow into a much better, more grounded person though. I'm better at reading other people than I used to be, as well as managing their expectations so that neither of us goes insane should we decide to work together. I'm financially literate now, not to mention good and responsible when it comes to running a business of my own.

I've learned a tremendous lot about a great many subjects I never thought I'd be interested in as well. I know all about kosher law now because of a wonderful gig I had a few years ago developing menu copy and advertising material for a Jewish deli. I don't even drive, but I know more about how to take care of and service a vehicle than a lot of people who do. I've written professionally about subjects I care deeply about, including beauty, fitness, history, self-improvement, and relationships. I've been lucky enough to have small and big companies believe in me enough to trust me with their brands as well.

I never pictured myself winding up where I did or taking the route I did to get here, but it's been a pretty amazing journey overall. I wish I'd learned to set boundaries with other people (and with myself) a lot earlier, as well as learned the importance of focus and planning. I really can't complain though. Words are powerful, and writing is a wonderful thing that lets a person claim some of that power for themselves. I can't wait to see what I use that power to build next.