I Failed My Way to Freelance Writing Success
Six things to remember on your road to freelance writing success . . .

Only a few years ago, I woke up at 4:00 a.m. every day despite being extremely anti-mornings. On top of that, the work environment at my last day job had grown to be a bit hostile with two many people trying to mark their non-existent territory. When I started my freelance business, I was still very much working there and wishing I could find something less stressful. I didn’t originally plan to leave my job for my freelance business, but somehow, a miracle happened, and within a year, I walked into my supervisor’s office to hand in my notice.
As easy as it sounds now that I’ve written it down for the world to see, my road to freelancing had many bumps and obstacles along the way. It did not come easy, fast, or painless.
My first attempt at working for myself found me as the proud owner of a brazilian waxing studio in 2014. This was something I was incredibly passionate about, but my personal choices led me to shutting the studio down within less than a year of being open. After that, I had no choice but to start working in a corporate salon environment. I absolutely hated it, and I had reason upon reason to regret the mistakes I made that took me there.
Not long after that, I gained my confidence again and decided to give self-employment another try. It was going okay until my personal life once again got in the way, ultimately leading to an unfortunate end to that career. At that point, I was forced to hold down what some might consider menial jobs in the medical industry, which ultimately took me to the hostile work environment at a fast-paced surgery center.
Minus a couple of bad seeds in my office, I really did start out loving my job there. Surgery was fun and exciting, and I made friends with all the nurses back in the pre-op area. In addition to that, I also had many life-altering conversations with patients and other co-workers I’ll always remember. Though that experience was mostly positive, I’ve always needed something more: I always wanted to be in full control of my life and my career. I didn’t have that there.
When I first started out as a freelance editor, I didn’t imagine it would ever turn into what my career is today. In my mind, I was just making some extra money doing something I really loved. It wasn’t until I’d been doing it for nearly eight months that I realized it could be something much bigger. That was when I landed my first five-figure contract.
Soon after that, I switch got flipped in my mind. I can really do this, I thought to myself. So, I started making plans, taking on more contracts, and working my ass off to get there. Before I knew it, I was working from early morning to midnight between full-time school (I am working on a Bachelor’s in English), single motherhood, full-time traditional employment, and my freelance business. My stress went through the roof, and my health was starting to suffer.
The pivotal point in this journey hit me like a brick when I ended up in the emergency room because of all the stress. That was the day I decided it was time. I had several thousand dollars in my savings account, so I knew I could sustain the freelance life I wanted. That next day, I turned in a two-month notice, and the stress miraculously disappeared.
The countdown had begun to my new independent life.
As I’m writing this blog, that was 15 months ago, and things have continually grown in my freelance business. I have no plans of ever returning to the 9 to 5 bullshit.
Here are some things I learned along the way:
- Never give up on your dreams. I had dreamed of becoming a writer ever since the 1990s, but I was always too afraid to make that big jump. The dream festered and festered in the back of my mind until enough crap had happened in my life. The straw that broke the camel’s back was a combination of being traumatized by emotional abuse and quitting a bad drug habit. It forced me to look long and hard at how many times I’d turned my back on the person I wanted to become. I stood up tall and said, “Not anymore.” All it takes is that one decision.
- If you don’t love to learn new things, you’d better start now. Ever since I became a mother, I had a desire to keep learning and growing. This is one of the #1 skills that ensured my success as a freelancer. When I first started working as a freelance editor, I had absolutely no clue what I was doing. But I knew one thing: all the knowledge about writing and editing was out there for me to go after, and I did just that. I took online courses, studied experts, Googled whenever I had a question, and read articles, blogs, and books regularly. If you are not willing to push yourself to compete with who you were yesterday, you will fall behind as the rest of the world moves past you.
- Find some amazing mentors who challenge you and lift you up when you need it. Being a freelancer is a rather lonely career, and without co-workers, bosses, or teachers to light the way for you, you run the risk of tripping over obstacle after obstacle. At the beginning of my freelance career, I joined an editing guild that really helped mold my career into what it is today. Though we might be alone working in our homes, we don’t have to see ourselves as being completely alone in this. There is an entire global community of freelancers out there who have been where you are right now.
- Do not let relationships hold you back from succeeding. This was a huge change for me. When I had my waxing studio, I was going through a particularly rough break-up, and I allowed that emotional turmoil to completely destroy my business. Instead of pushing through the pain to operate and promote my business, I closed my eyes and let it slip away from me. One day, I woke up and saw it slip through my fingers. By that time, it was way too late to do anything about it. Don’t wait until it’s too late to repair what’s been broken.
- Freelancing is a huge learning experience. Among these failures and many more, I went through a lot of experiments to find a balance between work and personal life, and both had many successes and failures. Even today, I am still constantly learning, tweaking, and polishing my techniques, processes, and routines. There is no perfect end state the freelancing game—you have to keep moving and shaking if you want to keep succeeding.
- Say yes to things that scare the crap out of you. I didn’t know this before I said yes, but when I said yes to a scary project, it ended up being the project that launched an entire career. So, when you start on this journey, remember that there are two different types of fear: the kind that moves you forward and the kind that holds you in place. Choose the one that brings you success.
I’ve had a lot of failures in my life in trying to pursue my dreams, but I always told myself that it didn’t mean it would lead to my ultimate failure unless I allowed it. On this journey, we have to give ourselves permission to stumble and fall as we try to achieve that ideal freedom we’re seeking. Some failures will piss us off and push us down, but others will open the door to success a little more if we let it.
If you dream of something, don’t let the brick wall stop you. Grab a sledgehammer and smash through the wall with a purpose. You will never fail to do that.