Why I Stopped Hating Freelance


Many of you know that I spent a good chunk of my early twenties struggling to find a decent writing job. I’d just graduated from college (Uni for non-Stateside peeps) smack dab in the middle of that financial crisis we so gently called a ‘Recession’.

I remember the exact moment that I realised I was screwed. It was my junior year of college, and I’d already committed to my major: English Literature.

Go on, get your laughs out now.


Moving on. I was doing my year abroad in the UK, and decided to go visit a college friend in London. We oh-so-innocently decided to go see Avenue Q. Some of you know where this is going.

The scene began. The song? ‘What Do You Do With A B.A. in English?/It Sucks to be Me’

For your viewing pleasure:


As the song continued, I began sinking lower and lower in my seat. My friend, who was studying Physics and boasted a 4.9million GPA, laughed harder and harder.

I had a sort-of existential crisis. What was I going to do with a BA in English?

Screen Shot 2019-05-28 at 13.39.46
Oh, how naive I was.

Fast-forward another year or two — shiny BA in hand, applying for any job I could find. What I landed was not what I’d had in mind: insurance agent assistant (lasted two months before nope-ing it out of there), sales associate at a candy store (okay, free chocolate wasn’t so bad), and a freelance gig at one of those e-news mills.

That last one was, what I’d thought at the time, my “big writer beak”. I’d had no real idea what freelance meant, especially for my taxes, and at a mere $10 an hour, part-time, there was no way I’d be able to support myself.

I was there eight months before they ended my contract. It was December. Christmas lights twinkling, Frank Sinatra singing about snow that didn’t exist in San Diego. I had to scramble to get full-time work at the aforementioned candy store, which thankfully wasn’t too difficult that time of year.

But it definitely wasn’t writing. I was heartbroken.

Worse, I was learning just how hard freelance status would be on my pay check. I went to an accountant for help with any write-offs, but she pretty much laughed me out of her office. It was then, based mostly on the self-employment tax ridiculousness, that I vowed never to go back to freelance.

And because these writer mill contracts were so easy to get, I began to see freelance as  as the black hole of the writing world. The place that only the desperate and despairing sought out, and probably never escaped from. Obviously, the better choice was stable, full-time employment at a reputable company.

So I stayed at the candy store for a few years while I sent my short and sweet resume to hundreds of companies. I did land a couple of jobs during that time, but they didn’t work out, either because the company itself went broke, or the boss was legitimately abusive to his staff.

I was usually disappointed, but there was always another emotion simmering underneath, which I tried my best to ignore. It was a sense of relief. Freedom from the 9 to 5. Getting away from that stale office environment and into the sunshine. No more bosses micromanaging my every move.

Back then, I thought it was just laziness. Obviously nobody wanted to work full-time.

This guy hates working full-time, too.

So I kept at it. I found a stable job as a copy writer and stayed for just over a year. My reason for leaving was thankfully nothing to do with failure or firing – I was moving to London!

That job made me feel like I could legitimately handle a 9 to 5. So I figured it wouldn’t be a big deal to do it again while living in London.

That’s when I landed the perfect job. This was the one I’d been hoping for, the one that Avenue Q had made me question ever finding.

And I hated it.

There was no reason. Everything about the job was fine. My boss appreciated my work and let me manage many projects on my own. I was even working with my now-husband. And the salary! The benefits! Even better, they were in the process of granting me the coveted Tier 2 visa to stay in the UK.

I felt like an idiot for wanting to leave. So I forced myself to stay. I felt the stress inside me rising, and this dread for something I couldn’t name. With that came a self-hatred for all those feelings, because this job was perfect.

Then I got sick. Like, passing-out-and-being-rushed-to-the-A&E (ER)-sick. Doctors diagnosed me with acid reflux/gastritis/IBS. I couldn’t eat most foods for a month, was feeling sick all the time, and really couldn’t do my job the way I used to.

I knew that for both my mental and physical health, I had to leave.

It was around that time that I began looking into freelance. I missed working from home, and was starting to weigh the benefits of that against the frustrations of the associated tax.

The former was winning. It was a weird feeling, wanting to leave my dream job for freelance. Basically a 180. But I was learning things about freelance that I didn’t know before. This time, I would do the proper research and go about this business legitimately.

I think that now I’m seeing freelance the way it really is: a legitimate business venture that many writers are choosing to partake in. They, like me, aren’t comfortable with the 9 to 5 office life. They want to choose their paths, their projects, and manage their time their way.

Looking back, I feel like I was a little naive to believe that those writing mills were the primary outlet for freelancers. There’s obviously more out there, but I was too focused on that old-school, comfy job to see the bigger picture.

Freedom to work outside! In the fresh air! With a half-pint! 


That’s not to say that I regret having avoided freelance for so long. Back then, I was definitely not ready for it. I’m not claiming to be Miss business-savvy now, but when I was just out of college, I had absolutely no idea what to do or how to do it. Even more importantly, I had no motivation to figure those things out.

Ten years later, and I see things differently. I’m excited to start managing my own business. The process of setting up an LLC, talking to accountants, opening a business bank account — all of it is giving me the happy feels. Does this mean I’m adulting?

Eh, probably not. But regardless, here I am, pursuing my goal of *gasp* freelancing!

Fellow freelancers, how did you feel about starting your own business? Any tips or tricks? Leave ’em in the comments, please! I can use all the help I can get. 😀

3 responses to “Why I Stopped Hating Freelance”

  1. Yay boo boo! I, too, will eventually join you on this freelance journey and we can share ALL the tips and tricks. Lol! All I know is to not sell yourself short and think strategically! Bwah! There is a freelance book by these two designers that you can check out. I haven’t read it yet but it may be helpful?

    Oh! Spruce up your LinkedIn and try to join their Profinder services.

    Sorry to hear about the struggles, especially with your health, but I’m glad it’s better now. I’ve always seen you as the freelance type since you can choose WHAT you want to work on and WHO you want to work for. Creatives need to feel satisfied with what they do. 9 to 5 is just not normal and I don’t know how much longer I can do it. *sigh* *cough*

    Congrats on this new journey. Please keep me posted! I already spread the word out that you’re freelancing too. *wink* BEST OF LUCK!

    • Thank you for the congrats 😀 I’ll check out that book for sure!! And yeah I cleaned up my LinkedIn a little but I still have a long way to go there -_- Are the LinkedIn Profinder services different from their general job search tool?

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