The Heartbreaking Truth of Being a Freelancer

Back in 2009, I began my freelance life. I wasn’t single at the time, but I wasn’t in a deeply emotional relationship, either. I was solid with my group of friends and they weren’t going anywhere. My family was in town and in tact. In a nutshell, nothing was breaking my heart.

Freelancing was a means to an end in the beginning (or, truthfully, for the first two years). It was a way to unwind after a difficult experience at my former “real” job. It was a way to move out of my parents’ home and in with my best friend. It was a way to pay for dirty martinis and hang out with my other single-ish friends every night of the week. It was a way to live, though the job itself was simply surviving.

None of my clients were actually mine. I worked as a ghost content writer for sometimes as little as $5 per article. It didn’t matter. The articles were written in practically no time and the payments came in on time. That’s all I needed and all I wanted. This experience would serve me in the future in unexpected ways, but for the time being I had enough money to pay my rent (albeit late), buy a few groceries at the start of the week, get my brother a seriously belated wedding present and, most importantly, afford dinners and drinks with my nearest and dearest. I guess if I thought about it, I wouldn’t say this was a life-long plan, but honestly, I never thought about it.

It wasn’t particularly easy to work for myself, because it was nearly impossible to get myself to work. If I could write ten 400-word articles per day, I would make an exciting amount of money. Turns out, though, that when you’re not used to that extent of writing, getting through two or three articles a few days a week feels like a challenge. I did the bare minimum and made the bare minimum. The hard part was motivating myself to do even that and the hardest part was dealing with my lack of enthusiasm, motivation and, of course, money. The less I worked, the harder life got.

Still, I kept this pace for a while. My roommate and best friend wasn’t always happy with me, but she wasn’t a great friend to begin with, so I wasn’t making things much worse than they already were. My family was disappointed in and maybe even embarrassed by me, but they wouldn’t go so far as to abandon me. My boyfriend at the time wasn’t thrilled that I was practically always broke or over-spending, but frankly, I didn’t care. I knew life wouldn’t be like this forever, but it was like this for now, and everyone would have to accept it, myself included.

Then the bottom dropped out. I had been working primarily for two content mills. One of them paid a decent amount and was where I made most of my income. The other paid next to nothing, but there was a ton of work and I used it as my backup income stream. The high-paying content mill decided to completely revamp their structure and, as a result, their team of writers. Even though I had a good track record with them, I was now back amongst the newbies who had to start from scratch. The application process was long, the approval process was longer and it wasn’t a realistic way to make money anymore. I had to rely solely on my fallback content mill, which meant three times the amount of work for the same amount of pay.

Eventually my friendship and my living situation with my roommate fell apart. I stuffed my stuff in storage, slept on the floor of my old bedroom-turned-miscellany-room for a few weeks, worked hard enough to barely afford a deposit on an apartment and, finally, moved into my own place. My crappy job and income followed me, but I had a home to call my own, enough of my own furniture to make it livable, hand-me-downs to fill in the rest, a home office and some breathing room to process the toxic friendship I was still mentally working through. Things were better, but now it was me alone in this apartment. If I couldn’t afford Kleenex or coffee or dish soap, I didn’t have a roommate’s stuff to fall back on. It wasn’t long before I took a good look at my job situation and had a stern talk with myself. The outcome was this: if I was going to make freelancing work, really work, I would have to find a more sustainable, higher-earning and long-term solution.

The level of unprepared I was for freelancing could fill an entire book. I had no. idea. what. I. was. doing. Truth be told, I had no idea what I was doing from the day I decided to never go back to a traditional full-time job and throughout those first two years, but when you decide to take what’s essentially a paycheck and turn it into a full-blown career, you realize how far the water is over your head. The learning curve never seemed to end. (Honestly, it’s still there, but much more manageable now.)

I started with what I had: the content mills. By now, I was writing for an additional one, which was even crummier than my crummy one, if that was possible. The good news was that this one made it somewhat easy to find contact information for the clients who posted assignments. I got in touch with a few to offer the same writing services for the same amount of money. The benefit to them was that they could work with the same writer each month instead of rolling the dice and probably paying for an article that was written by someone whose first language obviously wasn’t English. It worked. I got a few clients and a regularly-replenished PayPal account that would support for my new life, Starbucks drinks and new shoes and beach vacations not included, of course.

I didn’t know this at the time, but from the moment I started collecting my own clients — ones that I would deal with directly, utterly vulnerable and without the protection of the content mills — I would open myself up to a brand new kind of heartbreak.

Now look, I’ve been through it. I’ve had more breakups, sleepless and sobbing nights, rambling boy-focused conversations with my mom and my girl friends, and self-help books than I’d like to admit. I’ve also had over-the-top arguments with my closest family members and one exceptionally bad friendship breakup that left me reeling for days, weeks, months and years. Heartbreak and I are familiar frenemies. Nothing prepared me for the heartbreak I would feel from freelancing, though. Not only was it unexpected — this is a damn job, not a broken engagement — but it was profoundly painful. My-life-is-over, what-do-I-do-now, I’m-a-complete-loser painful. What does that sound like? That’s right: a real, bonafide, relationship-worthy heartache. That’s what it feels like, too.

Here’s what no freelancing how-to book tells you (or maybe they do, but I’m usually so overwhelmed by the “Setting Your Rate” and “Contract Negotiation” sections that I haven’t read that far): it’s just you, all the time, and it’s extremely, unfathomably hard.

When I was living with my old roommate, her fun, rambunctious, loud and utterly charming three-year-old son was our third roomie. One day, she said to me, “It’s really hard. It’s just you and this kid every day.” She was on the verge of tears, which was unlike her. There’s a lot of bad stuff I can say about my ex-BFF, but she somehow managed to have a child with an [insert any expletive you like] guy, become a single mom from practically before the baby was born and still, magically, stay her uncomplaining, let’s-get-this-done self. She retained her interests and her personality, she stayed relatively grounded and her crying days were few and far between. Even now, though I’ve done plenty of reminiscing about the nonsense she put me through, I find myself bringing her up often and mentioning, kindly, the mothering skills she had that I hope to someday possess.

On days when my heart is split in two thanks to my career, I think about what she said that day: It’s really hard. It’s just you and this kid every day. Except instead of “kid,” it’s “job.” It’s just you and this damn job every day.

I get that I’m not a single mom and that having a bad day here and there work-wise does not, in any way, compare to what she and other single parents must feel when their life goes sideways. Getting through a shitty eight hours of work is nothing like taking care of a child all by yourself. She had it harder, hands down. What I do relate to is the aloneness she felt, the lack of companionship, the missing help that so many other people have but she didn’t, how everything — everything — weighed on her shoulders. It’s not the child or job that’s difficult, it’s the world surrounding it. Around this humongous responsibility is a world that’s not helping you out one bit, no matter how much you want it to. To me, nothing has been lonelier than that feeling.

Luckily, though many days are difficult when you’re self-employed, work from home and make your living freelancing, you eventually settle into the toughness of it all. You figure out a work schedule, you find online tools to help you out, you pay for a bit of outsourcing, you make friends with a freelancer who understands your plight and you actually manage to sit down at your laptop every single day to be productive. All of that is hard, but if you’re in this type of career, this is the kind of hard that suits you. For me, this kind of hard is mentally easier than what was essentially a cushier job in my 9-to-5 life. I had a steady paycheck, on-the-house lunches, sick days, two-week vacations, weekends off and freakin’ free health insurance. The logistics were a million times easier.

I was miserable, though, not to mention constantly over-tired and sick. Thank God for that free health insurance, because I took advantage of it. Not only did I hate my bosses (and eventually most of my co-workers) and waking up with dread at having my entire work day spanning before me, but I also hated the job itself. The saddest part of the day I finally quit was that I didn’t care. It didn’t matter one bit that the files I left un-filed or the paperwork I had yet to scan or the phone calls I didn’t return were going to remain un-done. The realization that I had spent the last three years doing busywork I couldn’t care less about for people I would never see again was sadder to me than figuring out how to pay for my family’s Christmas gifts that month. Though that wasn’t the exact moment I decided to freelance full-time, I believe that was the moment I decided, somewhere in the back of my mind, that I wouldn’t waste my time anymore.

You could argue that the first two years of my freelance career was time wasted, but I guess that depends on your definition of “wasted.” I didn’t have a lot of money and I did hang my head a bit because of it, but my social life was overflowing and I had a ton of fun. I felt free, I slept late, I went out and I lived. I also healed — from a job that treated me like garbage, from a stale breakup that I was still reeling from and eventually from the bridge that I had to burn between me and the best friend I’d had since childhood. While I wouldn’t ever go back to that paltry income or lack of career goals, I do hope to eventually have that type of freedom and mental space again one day.

My boyfriend often says to me, “You hate your job. You complain about it all the time.” I don’t, though. Complain? Yeah, probably. But hate it? Not at all. I love my job. I’ve fallen so head-over-heels in love with writing in the past seven years that I feel like I’m married to it. On the days when I have a deep sadness reminiscent of my worst breakups but instead caused by a lost client, an impossible project or a rejected article submission, I remind myself why I continue to stick with this career. Unlike before, when I hated my job but loved everything surrounding it (paychecks, heath insurance, on-site gourmet cafe, beautiful campus), now I love the root of my job and sometimes have trouble with only the elements on the outskirts.

Creating your own schedule, staying organized and getting your butt to your desk every single morning is a challenge. Figuring out how to manage the business side of a creative career is endlessly exhausting and confusing and filled will hard-earned lessons. Pouring your heart into a piece of writing or a work project only to have it rejected or harshly critiqued is soul-crushing. That may sound dramatic, but that’s what it’s like. When you write, whether it’s a memoir or a press release, it feels like you’re on the page, not ink. You can have the thickest skin in the world, but when someone doesn’t like the words you’ve slaved over, you can’t help but question yourself. Every time that happens, I say to myself, “These are the days when people quit.” At those moments, I couldn’t understand more why some people choose to not live with this type of career. It can be a heartbreaking, punishing, bitch of a job.

To me, though, what’s worse than all that was leaving my job that Monday morning and feeling so much relief. I didn’t want that relief. I wanted to be emotionally invested in what I had spent my time doing. I wanted to be dragged from a job, kicking and screaming because I didn’t want to leave. I wanted an internal struggle over should-I-or-should-I-not quit that went beyond, “How am I gonna pay my next cell phone bill?” And while I took a big ol’ break for the next 24 months, eventually I found myself still wanting that.

Being a freelance writer is being on a deserted island. It’s just you, all the time, with this beast of a job. There’s nobody to help you. There’s barely anybody to talk to about it. Mom may lend an ear while you vent, but nobody’s going to call that difficult client back or chase down an unpaid invoice or fix your broken printer or vacuum the office floor while you go out to happy hour. There is nobody to lean on for support or to take the pressure off. The most help you’re going to get will be from books and blog posts written by people who have been through it before, but even that isn’t going to prepare you for what’s coming.

The biggest help you’re going to get will be from yourself. On busy days, you’ll plant yourself in front of your computer at 6 a.m. and power through a pile of work until the sun sets. On heartbreaking days when you can’t think straight, you’ll give yourself the afternoon off to cry, complain and, eventually, revisit your business plan. Each morning, you’ll wake yourself up, along with your internal writer and your internal boss, and you’ll face this job. Because no matter how difficult those heartbreaking days can be, you’re completely and hopelessly in love with it.

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