My BIGGEST Freelancing Screw-Up (Don’t Let This Happen To You)

Let me be real for a moment.

Most of the advice I give y’all here on Paid to Write 101 is based on some kind of mistake I made in the past.

You know what they say! Every failure is a step on the road to success! (Haha, at least that’s what I tell myself.)

But today, I want to tell you about my biggest, baddest freelance writing mistake. It’s the worst one I ever made and almost made me quit writing for-ev-er. For-ev-er. FOR-EV-ER. (Sorry, I’m having a Sandlot moment. Anyone else?)

Joking aside, this failure was an epic #facepalm comprised of several minor mistakes that ended up having a huge effect on my life. I’m not joking when I said that I almost gave up freelance writing because of it. I even went on a few job interviews because I was so depressed about what happened.

It all started with a job that seemed too good to be true…

My Biggest Freelancing Screw-Up

Mistake #1 happens pretty earlier in this story. The entire gig seemed way too good to be true. Always listen to your gut, writing friends!

At the time, I was making, on average, about $15 per 500 words. Not great by any standards, but I was paying my bills and had some pretty excellent long-term clients.

I even was in the beginning stages of forming my writing company, which would eventually send out regular work to anywhere from 10-20 writers per month. At this time, I had 3 writers who would help me do some jobs on a very occasional basis. I would typically pay them $10 per 500 words and take my cut of an “editor’s fee” of $5 per 500 words. Again, not a ton of money, but it helped me scale up the amount of work I could do for my clients.

Then, I saw a gig advertised for $50 per 500 words. The person posting the job said that they were looking for several writers to complete hundreds if not thousands of articles per month. Basically, all-you-can eat for the right writer or team of writers.

Red flashing lights were going off in my brain, but I resisted the urge to click away from the page and instead I applied for our little team.


I was hired to do a batch of 100 1,000-word articles to start, due from myself and my team in 6 weeks. In total, the payout would be $10,000, and of course my team would get some of it, but I still stood to make a pretty awesome chunk of change in just a month and a half.

Wait, Who Were These People Anyway?

In the acceptance email she sent to me, the project manager (we’ll call her Melissa) told me their backstory (i.e. why they needed so much work). See, this was back in 2007 when blogging networks were all the rage and niche print media like specialty magazines were in real trouble.

What her boss, the founder of this new company, envisioned was a network of subscription-based websites in a sort of blog format, but with monthly issues like magazines. He wanted the websites to be extremely niche topics. For example, not just an automotive site, but a “classic cars” site.

Melissa said that if things took off, we would be hired to create content for this network indefinitely. He wanted enough content for the first few “issues” and then would see what was working and what wasn’t.

I was a little skeptical. Other people were trying to do the subscription-based thing and it really wasn’t going well. Remember, this is the moment in the history of the Internet where you still had a good number of magazine options, but free blogs were popping up everywhere, in every niche.

Mistake #2 was taking a job where I felt the person wouldn’t see a return on investment (ROI).

Basically, I didn’t think the person would be successful, but I told myself that I didn’t care. If it ended up not being a long-term job, so what? At least I would have that one-time gig.

And while we’re at it, Mistake #3 was my willingness to overlook the fact that I couldn’t find anything about this company or dude online. I mean nothing. He had a pretty common name, so Google was no help; his business name brought up no search results, and none of his sites were live yet.

Yet, I forged on.

Signing the Contract

Melissa didn’t initially didn’t send over a contract. She just sent me topics so I could get started.

But I insisted on a contract. Look at me, all professional and smart!

Well, at least it was the right direction, I guess.

She did send over a contract at my insistence, but I didn’t put enough thought into reading it and the payment terms were “upon publication.”

In my defense, at this point in my career I had probably signed 7 contracts at most. Almost all the work I was doing came from 2 long-term clients. So I didn’t have a ton of experience.

I thought “upon publication” sounded reasonable. I mean, no reason to delay publication, right? They wouldn’t make money unless they had my content published.

Well, that was Mistake #4.

For the record, some clients, especially if you are working in print, still do pay upon publication. This is a valid way to pay writers. However, these contracts typically have what is called a kill fee, which means that if you turn in the work and they end up not publishing it, you still get paid a small amount, and sometimes retain the rights to your work.

This contract had no kill fee. Of course it didn’t. But I didn’t even know to look for one. I signed it and sent it off to Melissa.

Off to the Races!

I talked to my writers, and we excitedly discussed terms. I would pay them $60 per article they turned in and keep a $40 editor’s fee. They would have batches due every week, so I could make sure we stayed on track to complete the entire project.

I asked my client’s project manager if she wanted to receive articles in batches, but she said it wasn’t necessary. They would take the entire 100 articles when we had them done.

Mistake #5 was agreeing to do such a huge project in one big gulp, instead of in little steps. It just doesn’t make sense if you’re working with a new client. At the very least, you should do a test piece of about 10% of the work to make sure your client is on board with what you are doing.

Instead, I distributed topics to my writers, and we got started. Week one, they turned in their first batch, and I edited and paid them. Week two, they turned in their second batch, and I edited and paid them again. We had a few bumps here and there with the writing, but nothing major. It was during week three that the shit hit the fan.

The Beginning of the End

We weren’t even half-way through the project when Melissa emailed me. Sometimes, it is impossible to tell the tone of an email. This was not one of those times. She was frantic. Could I send over whatever work I had already completed?

Sure, no problem. We were on schedule and at that point I had 31 articles completely ready to go for her.

20 were from my writers (which I had paid $1200). 11 were from me. Obviously, I hadn’t paid myself, but I had scaled back significantly on the $15/500 work from my other clients in order to have time for this project.

I was worried. Something was definitely up. So I emailed my writers and told them to send me any other articles they had done and then to hold off on doing any more, just in case. They sent in 6-7 more articles between them, which I promptly edited, paid them for, and sent to Melissa as well.

In total, I had paid writers about $1600 for the articles they sent, which was honestly pretty close to my take-home income per month, after taxes. It was almost all the money I had in savings.

Mistake #6 was spending money I didn’t have to build my business. Remember, I wasn’t making much of an income myself that month because I was devoting so much time to editing and writing articles for this project. I wasn’t able to rely on my savings because I spent it trying to scale my business. I had no place spending that money.

The Exploding Train Wreck of Doom

As you have probably surmised, this story leads to a complete melt-down. It could have been worse, because we were less than half-way through the project when it happened… but it was still pretty bad.

Apparently, the owner of the company had done some more research and had some investments fall through. So he was cutting his losses and scrapping the entire project.

Getting articles from me (and some other writers/writing teams, I think), was Melissa’s attempt at convincing him to change his mind. Look at all this great content coming in! This can be a success!

I think her contract and payment was also tied to the actual launch of these sites and publication of our articles, but I don’t really know.

All I know is that suddenly, we were no longer getting paid. And  Mistake #7  I didn’t have a backup plan. I had spent my entire savings. I had earned less than half of what I typically earned in a month from other clients. I had to tell my writers that they were not going to get paid for any more articles like I promised.

I felt completely numb.

I only received one more email from Melissa before her email address went silent and then started bouncing. All it said was that she was sorry it didn’t work out, and that to note that my contract said that I still retained the rights to the articles, since I wasn’t paid for them. She hoped I could sell them elsewhere, somehow.

Defining Moments

Like I mentioned in the beginning of this post, I was so depressed about this that I almost gave up freelance writing. I did have a boyfriend at the time, but I wasn’t comfortable relying on him for financial support; I did the only thing I could think to do: I rang up bills on my credit card. I was also late paying bills for the first time in my entire life. It got me into a vicious cycle of debt that affected my life for many years.

And it was all my fault.

  • Mistake #1: I ignored my gut telling me that the job was too good to be true. Now, I certainly don’t think that $50/500 words is too good to be true, but the project as a whole was causing warning alarms to go off in my head, and I ignored them.
  • Mistake #2: I took a job working for a client who I believed would fail. You don’t need to know their whole business plan, but if you think the entire idea has no chance of success, you probably aren’t going to be working with that client for very long.
  • Mistake #3: I worked for a ghost. You should be able to find some information about your client online, even if they are starting a brand new company.
  • Mistake #4: I didn’t understand the entire contract. Payment terms are especially important. Don’t be afraid to ask for clarification if you don’t understand something, or to ask for a revised contract if you don’t think the terms are fair.
  • Mistake #5: I agreed to do a huge project with no milestones. At the very least, you should always turn in a small batch of work near the start of the project to make sure the client likes what you are doing. The best way to do it is to have milestones for turning in work and getting paid.
  • Mistake #6: I spent money on my business before taking care of myself. You have to pay yourself first. Do not go into debt because you are trying to scale your business.
  • Mistake #7: I didn’t have a back-up plan. Luckily, I didn’t have all of my eggs in one basket, since I was still doing work for other clients, but I was relying too much on this failed project. Try not to let yourself get into the position that if one of your clients drops you, you can’t pay your bills for the month. If any client drops you for any reason, you should have enough money to survive at least 3-6 months, either from income from other clients or from savings.

I did some soul-searching, and eventually with the emotional support of my friends and family, I decided to keep going with the writing.

The writers I was working with were extremely gracious when I explained what happened. They felt like I did right by them because I paid for the work they had completed, even if they wouldn’t get paid for future work on the project. I was lucky in that respect.

I got into a lot of debt trying to survive… but I ended up landing a new client about 2 weeks later, who ordered a series of ebooks from me and paid in advance. So that helped me financially, and it also helped me regain my confidence.

See, I knew that this was not about my writing skills, but I felt like such a dummy. I felt like I wasn’t good enough or smart enough. That I didn’t deserve to be in business.

And I’ll tell you a secret.

Sometimes I still feel like that.

You are a business owner. I know some freelancers don’t think of themselves as business owners, but you are! And owning a business is hard.

We need to give ourselves a break sometimes.

While I hope you can learn from my biggest freelance writing mistake, I want you to be prepared to make some mistakes of your own. It’s going to happen.

Don’t worry; we are in this together. I’m going to make some more mistakes too.

But I truly do believe what I wrote jokingly above; every failure is a step on the road to success. It is not possible to find success if you haven’t made mistakes along the way. You can ask any successful freelancer out there.

What’s important is that you don’t make any quick decisions. If you’re anything like me, feeling like a failure is devastating, even debilitating. I don’t typically tell people about my mistakes, because I’m too depressed and embarrassed, and this is the first time I’ve ever shared my biggest one publicly!

Don’t quit writing because there’s a bump in the road. I’m so glad I didn’t.

Surround yourself with people who lift you up, and who empathize when you face failure.

You will get through it. I promise.

Veteran writers out there who are reading this, leave a comment below telling us about the biggest mistake in your career and how you got through it!