5 Worst Ways I Ruined My Freelance Writing

Freelance Writing Frustration

When I left my marketing job two years ago, freelance writing was a pipe dream that I was too stubborn to let go of. Stubbornness, in this case, brought me more grief than progress. It took me a long time to see that simple truth.

It took me a long time to see anything when it came to approaching my career in freelance writing. I didn’t see opportunity, I didn’t see budgets, and I didn’t see growth. I was ready to quit and go back to a 9-to-5 gig in just over a year.

But I didn’t.

Instead, I accepted the fact that I had ruined freelance writing for myself. Soon, I was dissecting just how I could be oh-so-miserable doing what I still consider to be my dream job.

I’ve figured out five of the worst ways that I ruined freelance writing for myself – do any of these sound familiar to you?

#1 Too Many Words, Too Little Learning

My first year of freelance writing was spent doing low-paying, fast-paced article churning. I wasn’t proud of anything I wrote, but I was being paid. I read that you have to start at this stage. In some ways, I still agree with that.

What I don’t agree with is how little I let myself learn about my new career during this time.

In my focus to get through as many words as possible, I forgot that my goal was something more significant than becoming the world’s fastest affiliate review article writer. I forgot that I wanted to become an expert that could help people do more with their company’s content.

Today, I do a better job of balancing my time (but don’t get me wrong, I still write affiliate review articles).  I take time weekly to listen to a class about some aspect of SEO marketing or headline writing that I believe can help me create a better product for higher-paying clients.

I’m still figuring this out, but the key is that I finally remember how vital it is to learn.

#2 The Fear of Increasing Your Rate

You have to increase your rates every few months.

Let me say that again for you and me: you have to increase your rates.

After my first year of freelance writing, it was past time for me to increase my rates. Instead, I was hanging on to clients who, while kind and easy to work with, didn’t pay me enough to make a decent living.

I no longer work with any of those clients, and my rate has increased by nearly 7x since that point. The key to being paid more for your writing is to increase your rate or begin applying to writing jobs in the next pay category. Without getting more money for your increased skill level, you’ll never be able to sustain yourself.

#3 Forgetting The Beauty of Regular Work

While beginning to freelance, I had an idea of what it would be like. That idea is very different from where I am today.

At first, I focused solely on one-off jobs. I didn’t feel confident enough in my time management or skills to take on long-term projects, and frankly, I felt a lot of anxiety at the thought of a big commitment.

Here’s the problem. The more one-off jobs you have, the more time you have to spend looking for clients. And when those clients aren’t paying you very much, you’re digging yourself into a bottomless hole.

Now, I divide my time between appealing one-off jobs that either pay very well or spark my interest and jobs that are given to me by regular clients. I currently have five clients that send me new work weekly. I’ve made over $10,000 from one of these clients, and I expect that we will continue working together for at least another year.

Embrace the beauty of regular work & returning clients. You’ll thank yourself later.

#4 Being Blinded by the Sun

My long-term aspirations as a freelance writer look something like this: Picture me, working on a few research articles for one of my regular clients from a small cottage in Ireland, where I’m putting together a getaway article for a new travel magazine.

Don’t laugh!

It’s cliche, but it’s true. I love traveling, and my writing goals at this time are in that sector.

When I first started freelancing, all I could think about was what it would be like when I finally reach that point. My mind would get so excited about the prospect of travel perks, exciting experiences, and lots of words to be written that I would be blinded by my own brain.

Overwhelmed is probably the right word for it.

I was continually thinking about huge ideas that I hadn’t begun to break down into manageable parts; I couldn’t get anything done. I neglected this blog for two years, I bought multiple travel writing courses that I didn’t read for months, and I barely even got my freelance writing work done on time.

The bookshelf is crucial because it holds books which hold many ideas, stories, and journeys. But it’s infinitely less useful if you aren’t ready to fill the pages, gather the books, and bind them together.

#5 Neglecting My Workflow

As of writing this article, it has been one month since I finally found a workflow that works for me. That means that it took me nearly two years to find a way to balance my part-time job, my freelance writing, my hobbies, and my future growth plans.

Up until recently, I refused to acknowledge that I needed to dedicate time to creating an efficient and productive workflow. The thought of how messily I was tracking deadlines and setting goals for myself made me feel like I was an utter disappointment, so I chose to look the other way.

The simple fact is that no matter how free-spirited you are, you need to have a way of productively tracking goals and making plans. Without it, you’ll never have a long, lucrative freelance or travel writing career.

I’m still deciding where in the spectrum of the writing world I belong, but I have finally found a way to feel like I’m making progress. And that feeling is everything.


  • Keep learning. More knowledge, more skill, more growth.
  • Increase your rate everyone two to three months.
  • Find long-term projects to sustain you.
  • Get an idea of the big picture, then work on the details.
  • Create a workflow that works for you & your future.

This list is as much for me as it is for you. I’ve written it in my journal, and I’m sure I’ll chastise myself with these remembrances at least once a week!

Have you found anything familiar in my struggles as a freelance writer? What are you doing to fight the feeling of failure in this field? Let me know in the comments!

Remember that even if you have ruined freelance writing for yourself, you can fix it at any time. It’s only up from here!

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