Quitting My Job to Pursue Freelance Writing & Blogging

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I promised on Instagram recently that I would create some career-focused content soon, specifically how and why I decided to quit my full-time job to pursue freelance writing. Even people in my personal life are probably thinking “what the hell does she do all day?”, so I hope this post answers those questions and also helps anyone who wants to start freelance writing but doesn’t know where to begin.

College & Beyond

Before I dive into all of that, I’ll give a quick rundown of what lead me to this point. In 2015 I graduated from Georgia Tech feeling very lost as to what I wanted to do. I majored in Literature, Media, and Communication (named Science, Technology, and Culture when I started), which as you can guess is not the biggest major at a school like Georgia Tech. Not long after graduating, I moved out to the Bay Area and worked for free at a startup running their blog and social media. I wrote more about that experience and how I transitioned into getting paid in my article How to Be a Creative and Work for Free Without Selling Yourself Short. Over the last three years I’ve had about four jobs, so you could say it hasn’t all been smooth sailing. I’ve contracted, gotten hired, gotten laid off, gotten a new job, and quit that job. I would be lying if I said all that instability didn’t affect me.

The only constant in that time has been my desire to write. Writing is something I’ve always been passionate about, but for various reasons I was too afraid to pursue it. A huge part of that was my lack of self-confidence (something I’ve gotten SO much better at in the last six months) and a feeling of insecurity in my less-than-stellar journalism background. Thoughts like “I didn’t go to the right school” and “What if people think the things I write are terrible” clouded my opinion of my abilities and prevented me from pursuing my dreams. Also, as a self-proclaimed type-A rule follower, the lack of a clearpath was daunting to say the least.

My First Blog

My first attempt at getting into the writing game was back in 2014 when I started my first blog, A Side of Comfort. I figured if nobody would hire me, I would do it myself. The blog started as a place to share my favorite beauty products. I was inspired by the rise of major bloggers-turned-vloggers like Zoella and Tanya Burr. Let me tell you exactly why that blog failed. I never promoted it on social media or even talked much about it in real life. I was embarrassed. It wasn’t perfect, and I couldn’t bear people judging me based on my blog. In 2015 the blog pivoted and nearly became a food blog when I was at my worst with an unhealthy relationship to food. Clearly, I was lost. I didn’t have a vision, I didn’t know what I wanted, and I definitely was in no position to go after my writing dreams. Towards the end of that blog’s life, the joy of creating content was gone. I dreaded taking photos because I felt they weren’t good enough, my template was never right, and I didn’t understand how to grow my audience. I sporadically updated A Side of Comfort through early 2017, but it eventually died out completely.

The Rebrand

Last fall I decided on a whim that I would use Squarespace to create a personal website to showcase all of the articles I’d written for my job in content marketing. I made it in one night, which as a perfectionist is a huge testament to Squarespace. Around that time I also attended Create & Cultivate in Seattle and felt inspired to write a blog post about what I learned from the event on my new website. Without the pressure of “being a blogger” I felt free to write whatever I felt like. I slowly got more and more excited about blogging again, and eventually started to post every Sunday. I had never committed to a proper schedule before, and I’ve found that not having a schedule was actually more stressful than promising a weekly post. Since I re-launched my blog as a personal website I’ve been able to consistently grow my traffic every month AND have fun doing it.

Quitting My Full-Time Job

Now you may be wondering, what about the job? Yes, like many people who run blogs, I had a full-time job during all of this. And that job was actually the reason I attended Create & Cultivate, so it wasn’t all bad. But… it got pretty bad. I won’t go into details or bash the company, and in all fairness it was a mix of professional and personal reasons that caused it to turn sour. By Thanksgiving last year I was experiencing major burn out. I wanted to go back to Georgia at Christmas and never come back to California. But I did. And then shortly after, I quit. Quitting without another job was scary, but absolutely the best thing I could have done. My experience wasn’t exactly the joyous moment that many bloggers and freelancers dream of. A time when they’re finally making enough money to quit their day jobs, but as they say there never really is the perfect time.

With no new job lined up, I decided that it was now or never. I had to put my all into this whole writing dream of mine. I am very fortunate to have an incredible support system to help me out financially, as well as one more year of being on my parent’s health insurance. I totally understand that I’m coming from a place of privilege, which is all the more reason I feel like I can’t take this gift for granted.

So, that brings us to now. I’m going to say right away that this is not the fast track to money. If writing was only about the money, I would have quit after week one. I’m doing this because I love it. I’ll be super honest here and let you know that in the past month I’ve made a grand total of $75. Yes, just 75 bucks. I have some more irons in the fire as they say, but as of right now that’s what I’ve made.

Obviously, I am writing this blog post as someone who hasn’t “made it” in the field of freelance writing, but I feel like the beginning and middle part of the freelancer story is missing. You only hear from people who are ultra-successful trying to shell out tips about how to make six figures right away, but that doesn’t feel realistic. When I was starting out I found myself wanting to hear about the very beginning of someone’s freelance journey. I hope that by putting myself out there, other aspiring freelancers will feel less alone in the struggle.

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What I Did to Start Freelancing Writing

  • I researched… a lot. I found most of the resources on freelancing writing to be overwhelming, but these were the ones that I thought were the most helpful.

  • I made a plan. Again, the type-A organized part of me craves structure. If you’re also like that, you’ll learn quickly that you have to make your own structure, otherwise nothing will get done. I like to use Trello to organize my writing assignments, due dates, and ideas. (I’d be happy to share some more about my system if that’s something you’re interested in!) Similarly, I use Google Sheets to track my income. I just made a basic spreadsheet to keep track of the money I’m making, the dates I turn in my work/receive payment, and which projects it’s tied to.  

  • I searched the freelancing boards. I personally haven’t tried any of the bigger bidding sites like Upwork mostly because I haven’t heard of many good experiences with them. So far I’ve found the most interesting jobs on ProBlogger, Blogging Pro, and All Freelance Writing.

  • I pitched editors. Don’t be afraid to put yourself out there. It goes without saying, but none of the opportunities I’ve gotten have been because someone contacted me. I’ve had a pretty good success rate just cold pitching editors. All it takes is a little research.

In all honesty, I was hesitant to write and publish this blog post because I worried that potential clients would see it and realize I wasn’t as “successful” as I wanted them to think I am. I didn’t want them to know that they were one of the first people paying me to write, but why not? I realized two things. Number one, they probably won’t take the time to read this and number two, even if they did I think it’s still worth it if this helps even one person who was in my position just starting out.

Trying to succeed in a creative field of work is something I want to write more about on my blog, so I decided to create a new “Career”category on my site. I will continue to share articles about freelance writing and maybe even revist my experiences working in social media and content marketing. As always, let me know if there’s anything you want me to go in depth about and feel free to reach out to me via email or social media any time!