After 8 months, I knew it was time to throw in the towel.
In November of 2015, after a few years of writing blog articles and running social media pages, I quit my job as a social media specialist at one of Arizona’s top advertising agencies and started calling myself a freelance writer. I was full of hopes, dreams, and some savings that I hoped would last until my income picked up.
A mere 8 months later, I accepted a new position at a tech company.
What went wrong?
In the hopes of helping others avoid my errors, here are the three reasons why I failed as a freelancer, and what I’d do differently to avoid those pitfalls.
Problem #1: I didn’t know how to get my own clients
For the past years prior, I had worked as a writer in a great marketing machine. Yet for all of that writing, I still had little idea how it all actually worked. You write things, you post them on social media, and they’re found by Google… right? Inbound marketing.
I had picked up a lot by osmosis, but it was all about running the accounts of big brands that already had hundreds of thousands or followers. Unfortunately, I soon realized, those practices didn’t translate to a one-person gig.
I had a few good gigs from word-of-mouth, but I was entirely dependent on other freelancers who happened to send surplus work my way. Not exactly sustainable.
What I’d do differently: Marketing doesn’t just take place online. I’d make an effort to network with more freelancers in my community. My city has a vibrant community of freelancers who I could have involved myself with.
From there, I would have blogged more regularly on my own website and guest posted on teaching others how to write their own marketing copy. I would have started an email list with gusto, rather than as an afterthought. This would have established myself as an expert in my craft and built toward a more sustainable future for my one-woman business.
Problem #2: I didn’t know what I actually wanted to do
I said I wanted to be a freelance writer, when in reality I was burned out on blog articles. So instead I started copywriting websites, but I was never involved closely enough with the design and planning process to feel I was doing much more than filling in the blanks.
Now I know that I’m someone who thrives on big-picture strategy and meaningful client interactions. No wonder this was such a buzz-kill!
When copywriting wasn’t as interesting as I’d hoped, I thought I’d do some one-on-one marketing coaching, which seemed like a natural fit for my personality. But while I could give a great overview of the basics, I hadn’t actually run a full marketing campaign myself. It became clear that if I tried to do more than just the basics, I would soon be running a dishonest business selling techniques I hadn’t tried myself.
What I’d do differently: Instead of trying to jump on the coaching bandwagon right out of the gate, I would have done my time building my own client base and working as a true freelancer. Then, I’d have much better perspective on how to market a one-person business, which would be the perfect experience for helping other one-person and small businesses succeed as well.
Problem #3: I didn’t get out enough
I’m an introvert. I can stay home all week with an interesting project and be perfectly fine.
However, my work wasn’t always interesting. In fact, with all of the unknowns, it was more often than not stressful. I had monetary goals, but no clear idea how to meet them.
All of the above coupled with the fact that I live a good 30–40 minutes outside of where all the freelance meetups happened, I stayed home a lot. I got a dog, which was supposed to keep me company but also ended up keeping me even more tethered to my apartment. He’s lucky he’s cute.

shy boy.
The result of all this was that I was uninspired, trapped in my own confusion as to how to make this whole freelancing thing work, and very bored.
What I’d do differently: While I loved where I lived and the logic for moving there made sense (closer to friends, closer to the man who is now my husband, cheaper rent), the reality is that I was limited by my location. Honestly, there was nothing different that could have been done in this situation—I did exactly what was right at the time. However, let this be a word of advice to anyone who’s considering their own freelancing career: Location does matter.
Many consider freelancing because you get to work from home. However, you’re going to be far more successful if you have the opportunity to meet with your clients in person. Or at least get out and try a bunch of coffee shops. If you can, start your career where the opportunities and inspiration are.
Freelancing was still the best career move I could have made
In spite of these challenges, freelancing taught me so much more than I’d have learned if I had stayed in my old position. I learned the basics of working with a client on a website, how to charge what you’re worth, and what it felt like to be in charge of your own business growth. But most importantly, freelancing helped me realize that I still had a lot to learn.
Seeing my weaknesses clearly created an outline for what I needed to learn. When I then joined a team full-time again, I was able to rapidly fill in the gaps and be a far more effective marketer than I would have been had I stayed in my original role.
Freelancing gave me the kind of perspective you’ll never have it you spend your career locked into corporate career trajectories. If you’re looking for someone to tell you to take the leap, allow me the honor of saying go for it.
Also published on Medium.