My Top 5 Failures In My First Year Of Full-time Freelancing

I’ve been thinking a lot about the importance of failure lately, especially in terms of success.

I got laid off from my journalist job a year ago, and even though it felt like a slap in the face (and is categorized as a failure by most), it was probably one of the best things that ever happened to me.

This week it’s official. I’ve been working as a full-time freelancer and food blogger for a year. Pretty sweet!

Instead of writing a #humblebrag post about highlights from this year, I’d like to share my top five failures.

Have you ever thought about quitting your job and going off on your own? It’s important to get over the failure factor from the get-go.

Fact: If you’re too scared to fail before you even begin, then you’ll never take the first step.

I hope that openly talking about my failures encourages you to JUST DO IT (whatever “it” is) because something not working out the way you planned is pretty much unavoidable.

If you’re scared of failing, the first and only question to ask is “what’s the worst that can happen?”

Here are my top five failures/mistakes I made this year:

1. Accepting a project then dropping it because of scope

One of the biggest struggles of freelancing (especially when you’re starting out) is having to somewhat blindly take jobs because you need money — not because you’re dying to do the project.

In March, (one of my best freelance income months) I totally overloaded myself with work to hit my monthly income goal.

The problem? I took on a few too many projects. There was one in particular that I got paid in advance for, but since I didn’t have time to do the project, I dropped it and completely refunded my client.

It felt terrible. I felt like a failure. That client and I didn’t work together again.

Even though the feeling sucked, it was a great lesson in being realistic with what I can do with my time as a full-time freelancer.

Other than burning a bridge, nothing bad happened. My freelance business didn’t crumble. My other clients remained satisfied with my work and I kept going.

But I’ve never made that same mistake again. Now when my plate is too full, I just say when I’m available to take a new project, even if it’s a month later. And if my client can’t wait, they just have to go to someone else.

2. Making less than $2,000 in July

This one was painful. As I touched on in my Q3 recap, my summer was really tough.

It was crunch time to make that savings goal to move across the country, and I was stuck on three projects that just weren’t moving forward. I wasn’t motivated to search for new clients, and I didn’t like what I was doing.

To make it worse, when my paternal grandfather passed away in the middle of the month, I had to drop all my work and fly to Israel for a few days. Understandably, that caused my work and networking momentum to come to a screeching halt.

The outcome: I came $5,000 short of my savings goal, but I still moved to Colorado.

Making so little was painful and stressful. I hated having to dip into my savings that month, then having to play catch up made me completely transition from copywriting to Instagram. This “failure” forced me to take a hard look at my freelance business and change it.

Since that July, my business has been a lot healthier in all ways. Of course, I have a long way to go and I’m still learning, but every little improvement counts.

3. Getting stuck on never-ending projects

One of the reasons why I made so little in July was that my time was spread thin between three time consuming, but not super high-paying projects. I was on a retainer for a few clients and felt like I didn’t have any time to prospect new ones.

This was a huge mistake for me. I feel like every seasoned entrepreneur says, “get clients on retainer” so you have a steady income. I get it.

But it doesn’t work for me. I got bored. I felt like I was an employee instead of a contractor. And the scope creep came at me from all directions.

So I dropped my retainer clients by giving them a few weeks notice and telling them I was shifting my business away from copywriting.

It was one of the hardest things I had to do because even though the projects felt stale, I loved the relationships I had with them.

Now, I work with each client for a few weeks at a time (no more than three weeks for Instagram projects as of November 2017) and I’m happier because my business is more profitable.

Before, my problem was feeling indifferent toward my retainer work. The new problem is having to get new clients all the time.

I’d rather have that problem any day if I enjoy the work I do.

4. Doing a terrible job on a manuscript editing project

One of the most amazing things about freelancing is being able to get paid to learn new skills.

This year I was paid to learn how to write sales pages, email copy, write a book proposal, edit an entire manuscript and more.

As you can probably guess, most of those projects were not my best work. But one, in particular, was a total flop.

I worked with an awesome editor on a project last year who offered me an opportunity to edit a whole manuscript.

I had edited articles and an interview-based book before, and it was good money. So I took it. She hired me knowing I had never done this before.

It was a grueling job. I won’t say what the book was, but it was pretty boring. Somehow I just didn’t expect that editing a 300-page book would be so hard. I was so wrong. 

In the end, the client was so unhappy with my work that I only got paid half of the full fee. I deserved that. I did a terrible job, but it hurt.

I continue to take projects where I have to learn something new, but only if they’re small.

And if you work with an editor, thank them again. Their job is so much harder than it looks.

5. Trying to do customer service for one of my clients

Like the previous failure on this list, I got stuck doing something I thought I wanted to learn how to do.

I was ecstatic to work with this client. He’s someone I really admired and is a great communicator. He hired me to do email customer service for one of his online services in the PR space (something I thought I’d rock at).

Again, this was a retainer deal and I did it for two months before I quit. I felt like an employee. Even though I know a decent amount about best PR practices, I was not a reliable customer service agent because my schedule is different every day.

The reason why these bad projects made the list is that it doesn’t feel good to get paid for a job you don’t think you did well — no matter how badly you wanted to execute it perfectly.

But the catch 22 of these situations is you have to try and fail (or succeed) before you know if you’re going to be good at it.

What every entrepreneur and freelancer knows:

Failure is a good thing. It’s part of the process.

While this list is just a bunch of things that went south this year, there are so many things I turned out to be great at. I wouldn’t have known about those skills and interests if I hadn’t tried copywriting, ghostwriting, email marketing and social media consulting.

And even though some of the projects and gigs I did last year didn’t pan out, I’m still here freelancing. I’m still earning money. I’m still working so hard for the clients I currently have.

Most importantly, I’m in Colorado, where I wanted to be, which was the reason why I started in the first place.

The “worst” thing that can happen is I don’t make enough money on my own to support myself and I get a job. Oh well. No big deal!

Right now, I’m staring down the pipe of my second year as a freelancer, entrepreneur, Founder — whatever you want to call me.

Even though I’ve learned so much from my screw ups in my first year, I’m still going to make new mistakes.

As an entrepreneur, failure is the only thing I can count on.

In a way, it’s comforting. I’ve gone through a lot. I can handle whatever’s next.


Thanks for reading! If you have any questions or comments, reach out directly:







One thought on “My Top 5 Failures In My First Year Of Full-time Freelancing

  1. Christian Prater says:

    Thank you for sharing your story; I find it very inspiring because I want to become a writer as well once I’m done with my studies. This helps me to know that there are other people out there who face challenges in their writing. Again thank you. : )


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