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4 Mistakes I Made in My First Year as a Freelancer Writer

4 Mistakes I Made in My First Year as a Freelancer Writer

The other day, I posted a blog post about the things I believe helped me find success as a freelance writer. And I do think I did a few things right but let’s be serious, I also made a lot of mistakes along the way.

This list is far from complete because I’m sure there are dozens of other mistakes I have yet to realize I’m making.

My Biggest Freelancing Mistakes

Here are some of the biggest mistakes I made in my freelancing business:

1. I continued to do work for a company that owed me money

About six months ago, I started writing weekly blog posts for a pretty large company. At that point, I had mostly worked with small businesses and solopreneurs so working with that company was a different experience.

For one thing, they always mailed me checks rather than just sending payments through PayPal. I figured that was the reason why it always took them so long to pay me.

Right from the start, their payments always arrived at least a week past the due dates on the invoices I sent. Because I enjoyed the work so much, I overlooked it when that company fell behind on paying me.

Finally, after two months of not receiving any payment whatsoever, I realized that I couldn’t continue to work for free. I tried to contact the company but didn’t get any response.

It was then I discovered that the company had filed for bankruptcy and that all the employees had been let go. It kind of sucks that I didn’t get paid but I should have stopped doing work the minute the first invoice become overdue.

2. I didn’t set boundaries with my clients

I had a client who communicated with me primarily through a team Slack channel. I would make a point of checking Slack every day to see if I had any messages from him and if I did, I usually responded right away.

In the beginning, I tended to always be “on call” for my clients; answering emails at 10:00 at night or on weekends. Needless to say, I got pretty burnt out on this and one weekend, I decided to completely unplug. I didn’t check my email, Slack channels, Skype, or any social media accounts all weekend.

On Monday, I saw that my Slack client had sent me a message on Friday night. When I didn’t immediately respond, he sent several follow-up messages and they all looked something like this: “Hello???????????”

At first, I was annoyed that he couldn’t just wait until Monday morning for me to respond. Let’s be serious, there are no real “writing emergencies” and I’m sure whatever he needed to tell me could have waited.

But then it hit me that my client wasn’t really doing anything wrong. He was just engaging in behavior that my actions had told him was okay. After all, I usually answered when he sent me messages on a Friday night.

It was then I realized that if I don’t like the way my clients are treating me, then it’s kind of my fault. All that means is that I’ve done a poor job of setting boundaries and I need to do a better job communicating.

These days, I give every new client my “How I Work” document which clearly outlines how soon I will respond to emails, how they can communicate with me, etc. The best way to stop any inappropriate behavior is to keep it from happening in the first place.

3. I did a job I disliked for nearly a year

One of my first clients was a really nice guy and a very consistent source of income. I really admired his business, how organized he was, and I always appreciated how prompt he was about paying me.

But I hated writing blog posts for him.

I found the subject so incredibly boring and I dreaded doing the work every week. But he was a nice guy and I like getting paid every week so I told myself I needed to suck it up and stick with it.

Then he did us both a favor and hired an SEO specialist to manage me and the other team of writers. Let’s call this particular person Greg.

I could not stand working with Greg. I’m not going to go into the details about why I disliked Greg because honestly, it doesn’t really matter. And I definitely bear a lot of responsibility for our constant head-butting.

But it came to a point where I began to realize that I couldn’t work with someone I disliked and do work I disliked. My client seemed to sense the friction between me and Greg and he ended up deciding to let me go.

And looking back, I can see that it was in both of our best interests. I do think that there are times when you just have to suck it up and do things you don’t like. Boring jobs pay the bills as well as interesting ones.

But I can also see that I never did my best work for that client which wasn’t fair to him. And because I disliked the work so much, every blog post took two to three times longer than it should have taken.

I could have saved us both a lot of time and energy if I had just decided to move on months earlier.

4. I didn’t follow up with my previous clients

As a freelancer, one of my strengths is bringing in new work. I’m very consistent about looking for work every day and I have a pretty good system in place so it doesn’t take up too much of my time. As a result, I never really have any dry spells where I just have no work whatsoever.

But one of the areas I really struggle is in following up with clients who fell off the grid. When you work with someone for long periods of time, it is inevitable that at some point, they will want to take a break.

And I never really gave following up with them much thought because I always assumed that if they needed something, they would contact me. Then I read a blog post on Medium and it really made me realize how much I have been missing out by not following up with clients I have already worked with.

What’s funny about this is that I have written dozens of articles about customer retention. But I guess I just somehow thought it didn’t apply to me. It’s easier and more exciting to find new work whereas following up is pretty boring.

But it’s also more time-consuming and difficult to only look for new work. Clients who I have already worked with already know and like me, I don’t have to convince them that I can do a good job. I also don’t have to sell them on my rate.


For a long time, I avoided taking actions in many areas of my life because I was afraid of making a mistake. But what I have learned is that mistakes are actually a gift.

I honestly feel grateful for the lessons I learned from every one of these mistakes. Decision-making is a self-correcting process and the only way to start making good decisions is to learn from the bad ones.

If you are a fellow freelance writer, do you resonate with any of my mistakes? Let me know in the comments.  

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