I started freelancing in 2016 with no college degree, no professional experience, and no writing samples. I had a goal to earn $1,000 per month, and once I hit that, I decided I wanted to reach six-figures.

That story sounds so inspiring and straightforward in a blog post, but believe me, I stumbled through my first year as a freelance writer. I made mistake after mistake, and somehow, just kept pressing forward.

So I thought it might be helpful to share a few of my mistakes and what I learned from them. This list is far from all-inclusive because if I wrote about all of them, it would end up being a long, very dull novel.

4 Mistakes I Made as a Freelance Writer

So without further ado, 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

In 2017, I started writing weekly blog posts for a large event marketing company. I was still figuring out my niche, and at the time, I thought I might want to explore marketing.

Up until that point, I had mostly worked with small businesses and solopreneurs, so working with that company was a different experience. For one thing, they had a very slow and tedious payment process in place.

The way it worked is that I would write four articles a month for that company. At the end of the month, I sent them an invoice, and payment was due within 14 days. The payroll department would process the invoice and mail me a check.

Right from the start, the payments always arrived at least a week late. And over time, the invoices started coming later and later until one day they just stopped arriving altogether.

At this point, the company owed me $700. And when you’re a new freelancer and still not earning that much, $700 feels like all the money in the world.

I emailed my client, but she didn’t respond to me, which was alarming. I called the company and left multiple messages, but no one got back to me.

So I did what any good freelance who wants to get paid does -- I stalked them on social media.

That's how I discovered that the company had filed for bankruptcy. All the employees, including my client, had lost their jobs.

Needless to say, those final checks never arrived in the mail.

It sucks not to get reimbursed for your hard work, but I learned a valuable lesson from that experience. First, I learned that you cannot be passive when it comes to getting paid.

If someone doesn’t pay you, you should stop doing work for them immediately. Your client doesn’t do free work for indeterminate periods of time, and neither should you.

I also learned that you need to trust your instincts. I knew it was a problem that the company had stopped paying me, but I ignored it because I wanted the work.

2. I didn’t set boundaries with my clients

At the beginning of my freelance writing career, I struggled to set boundaries with clients. I did a poor job of communicating, and that led to many misunderstandings that could have been avoided.

For instance, one of my very first clients communicated with me primarily through a team Slack channel. I made 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. I answered emails at 10:00 at night and on the weekends.

That was fine at first, but after a while, I got tired of responding to messages and emails all day. So one weekend, I decided to unplug completely.

I turned off my Slack notifications, I didn’t check my email, and I didn’t even look at social media all weekend.

The problem was, I didn’t let any of my clients know that I wouldn’t be checking or responding to messages. So that Monday, I saw that my Slack client had sent me a message on Friday night.

Obviously, I hadn’t responded, so he had sent several follow-up messages, and each one became increasingly irate and demanding.

At first, I was annoyed by his response. Why couldn’t he be patient and wait until Monday morning for me to answer? There are no writing emergencies, so whatever he needed to tell me could have waited.

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

I realized that if I don’t like the way my clients are treating me, then 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.

I’ve noticed that setting boundaries are a problem many freelancers struggle with. When you’re eager for new work, it’s easy to avoid setting boundaries because you want to seem accommodating and easy to get along with.

But the truth is, setting boundaries will make clients respect you more, not less. After all, we teach others how to treat us.

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

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

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 the team of writers. Let’s call this individual 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 matter. And I 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 Greg and me, 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 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 job 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 rarely have any dry spells where I have no work whatsoever.

But one of the areas I struggle is in following up with clients who fell off the grid. Every client has a lifecycle, and it’s inevitable that at some point, they will stop needing as much work from you.

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, and it made me realize how much I was 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 exciting to land a new client, but following up with an old client 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 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.

Bottom Line

If there’s one thing I want to leave you with, it’s that your journey to a successful freelance writing career will be riddled with mistakes. And that’s exactly the way it’s supposed to be.

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

I 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 the right decisions is to learn from the bad ones.