How Failing at Freelancing Helped Me Succeed at Freelancing

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In the fall of 2016, I was struggling.

Three months before, I had quit my job as the program and social media coordinator of a small non-profit to set out on my own and become a freelance writer. Living in my apartment downtown, I envisioned myself living the life of Carrie Bradshaw, albeit without all the smoking, expensive shoes, and male-related drama.

I had always loved writing, and I was good at it. And if I was good at writing, I thought, the jobs would simply find me.

So I waited. And waited. And instead of, you know, finding opportunities for writing jobs, I spent that summer waking up at 10 AM, watching old episodes of Game of Thrones, and telling people I was writing when in reality I was submitting zero pitches to any publications and had even all but abandoned my once-beloved blog.

By fall, with my savings account dwindling, I got a job as a part-time receptionist. I told myself I would still try to freelance in my spare time. Guess what? I didn’t.

In fact, in the almost two years I spent claiming to be a freelance writer, I submitted less than 20 articles (none of which got picked up) and applied to approximately three writing jobs.   

I wasn’t embarrassed that my writing wasn’t being published; I was embarrassed that I wasn’t even trying. It’s one thing to try and fail - it’s another to defensively tell your family members and friends that you’re working as a freelancer when in reality you are spending barely an hour a day doing just that.

But I wasn’t ready to give up on freelancing, and somehow I transitioned into my current job as a freelance web designer where I actually work hard, stay busy, and yes, even find clients.

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I failed at freelance the first time around.

But looking back, I’m now able to see why I failed and have used the opportunity to turn those first mistakes into second successes.

You see, the first time I tried freelance I had no plan.

I didn’t have accountability.

I wasn’t disciplined.

I didn’t have the right mindset to keep me motivated.  

I was more obsessed with the “free time” aspect of freelancing than the actual freelancing.

I was isolated from other self-employed people.  

And eventually it occurred to me that as much as I loved what I was pursuing (writing), I wanted a freelance job that entailed a different kind of day-to-day life.  

And so, after spending almost two years feeling sluggish, unmotivated, undisciplined, and anything but successful, I had had it. I didn’t want to feel this way anymore, so I dove into something else I loved: helping creative women own their talents and passions through stellar online design and presence.  

I became accountable to my time during the day to my husband.

I began planning out the entire weekly to-do list the Sunday before.

I set goals and intentions that actually made me excited.  

I joined a gym to keep me energized and on a schedule.

I flipped my mentality from “I’m just trying out freelancing” to “This is a real job and I’m going to treat it like one.”   

I set up an office space to help me feel like a professional.

I treated my daily schedule like a real 9-5 to keep me on track, saying “no” to certain things during the day.

I began to reach out to other freelancers to form a network of community, inspiration, and support.

And suddenly, the things I had struggled so deeply with the first time began to fall more and more into place, until I was no longer someone who was failing at freelance: I was someone who was succeeding at freelance.

As difficult as it was to feel like I had failed the first time, I truly believe my job as a freelancer would not be where it is today had I not failed. I learned what didn’t work for me, and thereby what it would take to work.

Therefore, I highly encourage those considering freelance to not assume their business must always be on an upward trajectory, each month building easily upon the last. It was failure that projected me towards success - and sometimes that’s what it may take for us to reach our goals at all.


Julia York is the founder of Creative Crumb, a freelance web design, copy and brand identity business. She loves helping creative and entrepreneurial women find their voice and own their talents online. She lives in Spokane, WA, with her husband, cat, and a collection of various cheap wines. Connect with her on Instagram and check out her website.