#71: 3 Failures and the Lessons They Taught Me

On today’s episode, I am sharing three experiences in which I failed and the lessons I learned from those situations. Hopefully, you’ll find a few takeaway lessons here and it will also lead you to analyzing your own failures to see what you can change or learn from moving forward. The idea is not to beat yourself up; we are not perfect, but to learn from our failures and to know that all freelancers make mistakes.

Failure No. 1: I had written two articles for a newsstand magazine that went really well. They didn’t pay as much as my content marketing clients, but I liked the topics and having my stories on newsstands.

The magazine offered me a third article, a feature that was a little controversial. I had not done the type of traditional journalism in which people were skeptical about you since I was a newspaper reporter years ago in Indiana. The story required experience and connections in a type of reporting and in this community that I did not have. And I didn’t really have the time to dive into this story.

My failure started because I let my ego get in the way. I liked this client, and two editors were telling me how great I was and how they really wanted me to do this article. I let their flattery cloud my judgment. I should have trusted my gut.

Instead, I worked on the story and had difficulty finding the right sources, finding sources that would trust me and getting an “official source” to even answer my repeated calls and emails. I did not have the time for this along with all my other work—work that paid much more than this journalism story.

I weakly expressed some concern to my immediate editor, and she gave me a few pointers, but it could not save the story and I did not speak up more at that time. So, I trudged on—not because I was stubborn as much as I did not want to tell my editor I was failing.

A few MONTHS went by, and I finally got so fed up that I wanted to quit. I didn’t even care about getting paid for the work I did because it was unusable at that point. So, I emailed my editor and explained why the story was not working out and that I needed to stop working on it entirely. She was gracious and that was that.

The big lesson here? Do not let a client talk you into a project. Do not let their flattery and your ego get in the way of what you know to be true. You know what you’re good at and what you’re not good at, what you have time and energy for and what you don’t. Listen to that knowledge.

Failure No. 2: I was working directly for a content marketing agency that I had worked with before and really liked. They had a new client. The challenge was that that client wanted me to pitch story ideas, which I rarely do. But I came up with a few ideas and they accepted one. It was clear that my agency contact was more excited about that story than the actual editor was. This should have been a red flag.

But, I found the sources, wrote the article and submitted it. The editor had numerous queries, more so than I’ve received on any article in years. But I addressed the edits and sent back my second draft. Then, I received more edits late on a Friday afternoon, and the editor wanted to call me right then. I relented, only so I wouldn’t stress about it all weekend. She only wanted to go through the edits line by line, which was a complete waste of time. I also recognized that some of her edits were actually questioning the science in the article. That’s when it became clear that she did not respect the basis of the pitch or the research behind the article. She should have either rejected the pitch or put her aside her own feelings instead of continuing to ask me to change the article.

I delivered those edits and cc’ed my agency contact on that email. Then, I emailed the agency person separately to tell them what had happened and that I’d gone above and beyond with multiple rounds of extensive edits and that I was done with the article. My contact was gracious, and the agency paid me the full amount (even though the editor never ran the article).

The lesson here? I should have contacted my agency person sooner. They were my direct client, and I should have let them handle the situation—or at least help me walk through the issues. They also needed to be aware of what was happening.

The overall message here is to speak up sooner rather than later.

Failure No. 3: A new client and I had a misunderstanding over the scope of work. I had emailed a proposal outlining the scope of work that we both agreed on, and we had had multiple phone conversations. I thought we were on the same page, but I then received several assignments that seemed to be outside the scope of work.

Here’s what I did wrong: In the proposal, I was very clear on the scope of work involved in my two primary responsibilities. But the client had mentioned a third service, one that wasn’t my expertise, but I agreed to help with now and then. I thought I was being helpful, but in my proposal I described that third service as “as needed.” That was way too vague and would be defined differently by me and the client.

I reached out to a freelance writer friend, who helped me figure out what to say to the client. I also agreed to a phone conversation with the client to work out our issue. (I sent an initial email so as not to blindside her; then we got on the phone.)

My “tough love” lesson here is do not be wishy-washy in your proposals! In my effort to be helpful, I was vague instead and caused a misunderstanding. Other lessons I learned: Ask for advice from your freelance community and get on the phone to talk through sticky situations. Email was not the answer.

Those were three of my big fails—certainly not the only mistakes I’ve made! It’s important to know what your weaknesses are and figure out how to improve upon them or work around them. It’s also important to learn from your failures. What projects and clients stand out to you that make you a little sick to your stomach? Did you learn anything from them or have you repeated the same mistakes over and over?

Take a few minutes to think about those situations and what you have learned or should have learned from them. Maybe there are a few lessons that you could embrace going forward.

Biz Bite: You are already living your worst-case scenario.

Tip from Gayneté Jones: If you are procrastinating on a new service or something to propel your business forward, you’re getting nowhere by not doing the thing. That’s your worst-case scenario. You can only go up from there.

Gayneté Jones is a millennial mentor and keynote speaker. She is founder of G.A.M.E. Changing Industries and creator of Cubicle Ditch Academy.  

Hear Gayneté Jones in episode 333 of the podcast Online Marketing Made Easy with Amy Porterfield.

The Bookshelf: Recursion” by Blake Crouch


Episode #36 of Deliberate Freelancer: Spotting Red Flags and Scope Creep

Episode #45 of Deliberate Freelancer: You Need to Set Boundaries

Episode #67 of Deliberate Freelancer: How to Fight Imposter Syndrome, with Kristen Hicks

Episode #70 of Deliberate Freelancer: Techniques to Deal with Anxiety from My New Therapist

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