What I’ve Learned in my First Month as a Freelance Writer

Yes, some of these things actually surprised me

You probably think this is going to be a story about how I threw everything in my life aside to pursue a dream. I’ll admit, you’re partly correct, but honestly, I’m still new and I don’t know if my dream has come true yet.

It was not as sporadic as leaving a six-figure job behind like most people seem to do (honestly, those people drive me nuts. I never had, nor do I expect to have a six-figure job).

What actually happened was I quit my job as 911 Operator for personal reasons and decided to enjoy my summer as an unemployed over-exhausted millennial. I had some savings thanks to working during Covid-19 and knew I could take a well-deserved break. Then, my roommate pushed me to get into freelance writing. After some research, I signed up for Upwork and started getting clients.

So, here I am. One month later, scared, nervous, and actually kinda doing it?

For the full story about why I left my 911 job you can read it here.

Now that you have some back story, let’s get to the juicy bits: here is what I’ve learned so far.

Everyone hears that Freelance writing is viciously competitive. Even I had always heard through the grapevine that writing was not a career anyone should pursue. It’s a skill I never advertised that I had because it never seemed valuable (but thankfully I am very wrong).

After applying to various gigs on Upwork, I’ve seen first hand how writing is an extremely viable career. Also, with the right experience and a decent cover letter, it’s actually not as cutthroat as I thought. Lots of writers are applying to jobs, but everyone has their specialties and life experience that helps them stand out.

For me, I’m knowledgeable about boardgames, podcasts, bartending, travel and so much more! These are just things I know about because I’m a nerd and love learning. When I started sending cover letters, I added my specific experiences and have found it’s to be less competitive than I thought.

If you actually think about it: Literally everything you read on the internet is written by someone.

Sure, many people think it’s easy and they underpay their writers, but many others who want quality writing do recognize that they have to pay more if they want something that is well-written.

Another thing I’ve realized is that speaking English is actually a huge advantage, especially natively. Already I’ve got a leg up because I was born in Canada and I always loved studying the English language. Lots of people don’t speak English fluently or at a high level, especially on a website like Upwork where you’re competing with freelancers around the world.

My first gig on Upwork involved editing a website for someone on the other side of the world, and the copywriter he previously hired… well, let’s just say they did an okay job. English was not their first language and it had a few issues. Luckily, it was a breeze and I impressed him by fixing his website’s typos and making the words flow better.

One other accidental discovery I made is that setting my prices higher than most and only applying to gigs worth my time has landed me far more respectful and serious clients. I’ve read horror stories online about other freelancers not being paid or being harassed with unrealistic deadlines, and while I’m sure it’s only a matter of time, so far I haven’t experienced that at all.

By extension of that, a higher price has also allowed me to negotiate and be flexible when I’m applying for an opportunity because I’m focused on gaining the experience over the finances. My first few clients liked the idea of taking a risk on me and getting high-quality writing for a good deal. It’s a win-win situation for everyone.

What has actually shocked me the most?

That my degree in Creative Writing was in fact not useless. My BFA has actually helped me stand out because it proves I had the dedication to complete a degree related to writing. It also shows I can provide more creative and unique suggestions than someone who focuses more on the technical side of writing. One client actually asked to write a short story for him yesterday. (Sorry you’re paying me to write a fun story?! Of course, I will!)

I know all this seems obvious, but I can’t help being a bit surprised that freelance writing is a real job. Sure, it’s still a lot of work and I am on my phone way too much. However, in less than a month I have already done four one-off jobs and landed three recurring clients who want me to work 10 hours a week for them.

Now, I can see why not everyone is doing this. I don’t have any health benefits, clients call me sometimes when I’m not at home, and I have to work weird hours. That said, overall, I’m actually really enjoying it.

Hopefully, I can keep it up and maintain it, but honestly, I think it’s going really well. I’ve already made enough money to cover my rent this month (granted it is quite cheap because I have 3 roommates).

If you want to follow along for my journey or if you’re on a similar one, say hello! I’m on Medium to sharpen my skills and make connections with fellow writers. We’re all in this together.