3 Lessons I Learned From My First Week as a Freelance Writer

Cody A. Churchill
Freelance Ladder
Published in
4 min readFeb 17, 2023
Photo by Jamie Street on Unsplash

Let’s talk about my very first week as a freelance writer. It was hectic, but it taught me three valuable lessons that I’ve used in my business ever since.

But first, here’s some context, and why I’m writing this series:

Beginning in 2020, I ditched the 9–5 grind and became a freelance writer to put myself through grad school. In 2021, I dropped out of grad school because freelance writing gave me the same level of success as my degree could. This blog details my journey so you can take what you need for your own success.

This is installment 4.

After week one, I realized I had a new normal on my hands. I got up and made the long commute of… fifteen steps to my home office. I did my best to brainstorm potential leads for writing work. I built my social media profiles and website, and started proposing for jobs on Upwork.

I reached out to everyone I knew on Facebook who had some kind of business or called themselves an entrepreneur, and asked if they needed any help with writing and editing. I pitched about five jobs on Upwork each day. I sat there thinking about ways I could get more work and praying that it would just fall right into my lap.

It didn’t magically materialize, but soon enough, the work of reaching out to people paid off.

I connected with someone who wanted to take a chance on me, and they began assigning me blog posts to write. After thirteen rejected Upwork proposals, someone hired me. One of my old friends wanted me to rewrite his website.

I’ll never forget the feeling of seeing the money land in my PayPal account for that first blog. From there, I was hooked.

This first week taught me a few valuable lessons:

The first thing I learned is that 1) there is a ton of information out there about beginning your own online business, even something specific like a writing service. There were countless websites, blogs, videos, social media accounts, and articles telling me the creator had unlocked the secret to becoming a successful, wealthy entrepreneur. Most of them wanted to sell me an online course. Others wanted to sell me individualized coaching sessions.

(There’s nothing wrong with any of that, but I would urge you not to spend too much at the beginning of your journey. Instead, let the money you make from your business pay for extra learning material.)

The fact that there’s a ton of information isn’t a bad thing, either. I would rather find way too much information, and need to apply critical thinking and research to figure out what’s true, than search for hours and find nothing helpful. I probably spent half my time that week simply learning and reflecting. I listened to 15 podcast episodes about freelance writing and online business. I probably read twice as many blogs and articles on getting started.

What did I learn from all this research? 2) The internal work is just as important as the external work.

Here’s what I mean: It is important for a freelancer to generate leads, acquire clients, do a great job for them, follow up, rinse, and repeat. It’s also good to hit the books and get information and training. However, all of this leads to nothing if a freelancer doesn’t actually believe they can succeed.

It seems like many new freelancers and entrepreneurs fail not because of practical reasons, but because they stop believing they can make it. Then, that belief starts affecting the way they behave, in a weird form of self-sabotage.

And man, I felt that, especially at the start. I feel it these days too sometimes.

Back in the first week, I had a little voice in my head telling me I would fail. That I wouldn’t know what to do or how to do it. That I’d mis-invest my time and energy into something that would end up costing me. Every time I read a new article that told me something I was doing wrong, or something that I wasn’t doing at all, the temptation began again.

That feeling showed me that 3) setting goals is the only way forward. During my first couple of days on the job, I was directionless. This led to me not really knowing whether I had accomplished much. As somebody who didn’t have any coworkers anymore, that made me feel lonely.

So, I started setting specific and measurable goals to accomplish by the end of the first month. Some goals were outcomes (like getting a certain number of clients), but most of the goals were inputs (like reaching out to a certain number of people for work, or putting in a certain number of Upwork proposals). This way, if I didn’t reach all the outcomes I wanted, I could adjust my efforts.

From that list, I broke it down into goals I could accomplish on a weekly basis. Finally, I broke that down into daily goals. This meant that if I could take it one day at a time, and hit my daily goals for just that day, then I would be on track to hit my goals for the month.

Where are you on the journey? Feeling the information overload? Doing the internal work? Setting your first goals? Whatever you have going on, keep going!

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Cody A. Churchill
Freelance Ladder

Founder of Telltale Writing Services. Author. Storyteller. Big ole nerd. codyachurchill.com