The Biggest Mistakes I’ve Made in My Writing Career (So Far)

Lessons learned and my plans to keep making mistakes

If I know anything about writing, business, and how to actually pay your bills with nothing more than a keyboard and an internet connection, it’s because I’ve screwed up so many times.

My many failures have helped shape my career in ways I could never have anticipated. However, it would’ve been nice to have avoided some of the bigger mistakes. Failure is part of the job description for writers, freelancers, and business people. Because I’m all three of these things, I have more chances to make mistakes. But, like any rational person, I work hard to avoid mistakes and prevent failures.

They say you can learn more from a mistake than you can from any success. However, you don’t have to make all the mistakes yourself. You can learn from the mistakes of others. I hope this will help other writers, freelancers, and solo-business people find a less painful route to success.

I Kept Working for Bad Clients

I’m an evangelist for the idea of firing clients early and often.

I’m so fervent in my belief because I spent the early part of my career working for clients I hated. The work was miserable. I wasn’t being paid enough. I dreaded hearing from them. But, I kept working for some of these clients for years.

I was too scared to fire a client. I was afraid of not being able to find more work.

Eventually, I reached a breaking point and fired a bunch of bad clients. It was incredible. I felt better. I suddenly had more time to find clients I enjoyed working with. I raised my rates, and my career took off.

I Attracted Bad Clients

Another reason I kept working for bad clients is that I was attracting them. Everything from my branding to my pricing to my client management practices sent the message out that I wanted terrible clients. At the same time, I was repelling good clients.

I was desperate for work, and the only clients that wanted to work with me were ones eager to take advantage of desperate writers.

The fix was changing my mindset. I realized two things. One, it was my fault I was attracting bad clients. Two, I was a professional service provider. Clients needed my work. I wasn’t their servant or lackey.

This shift in mindset made it easier for me to raise my prices, set firm limits for clients, and to focus on my services.

Once I started telling bad clients no, I started getting better clients. I also began to love my work. The more I enjoyed my work, the more talented I seemed. My work improved.

I Wasted Time Looking for a Shortcut

I read a lot of books and articles about freelancing. I listened to a ton of podcasts about online business. I told myself I was just trying to learn more. But, at some point, I was hearing the same things over and over again.

I was looking for a shortcut. I wanted an easier way to earn the kind of money I needed. I was a sucker in search of a system. But, nobody else’s system worked for me.

Instead of doing the work of building my business, I was loitering, looking for an easier way.

Once I started to cut my own path, I started having success. There is a lot of great information on the web, but eventually, you have to decide to stop researching and forge ahead. There isn’t an easy way to be successful.

I Cared About What Other People Thought

I spent too long trying to win the approval of people who are never going to understand what I do for a living. Many people in my social circles still think I’m an unemployed bum. I wanted everyone to know I had a real job — that I was taking control of my destiny.

But, what other people think about me is irrelevant. I was making myself miserable trying to prove my worth for people who don’t care about me.

I spent too much mental and emotional energy wishing for acceptance. Gradually, I’ve become more confident in my skills and more comfortable in my own skin. I’m a weirdo, and I’m at my best when I’m not trying to fit in.

Because I’m no longer trying to meet anyone else’s expectations I have the time and energy to create a life that I love.

I Was Afraid of Screwing Up

I became a freelance writer after I had crashed two other businesses. These were spectacular failures that left searing scars on my psyche. I developed a fear of failure.

But, I was too careful. I didn’t take responsible risks. Instead, I tried to play it safe, and I went nowhere. I was afraid that I would ruin my career.

This mistake, like so many of my other ones, has its roots in my living a fear-based life.

The reality is anytime you put yourself out there, you are taking a risk. You could fail. You might make a mistake. I was too afraid to expose myself.

As I overcame my fear in other areas, I gradually opened up to the idea of taking more risks. Most of those risks didn’t pan out.

But, I survived. The way to overcome a fear of failure isn’t to succeed. It’s to fail. I kept learning, and I made fewer mistakes. Some of my risks paid off.

I Will Keep Making Mistakes

I still try hard to avoid making mistakes. But, I’m no longer paralyzed by fear. Most of the posts I write are duds. Most of my pitches are rejected. All of my brilliant ideas for books have failed to work out.

I now know that mistakes won’t kill my career. I learn my lesson and keep pushing forward. The beauty of my path is that nobody else can tell me I have to quit. I don’t need to show a supervisor or a set of investors that I succeed more than I fail. I can fail more than I succeed.

Mistakes are one of the costs of the path I have chosen. But, the cost is worth it. The successes are much sweeter.

I hope you can avoid some of the mistakes I have made. But, you will make your own set of mistakes.

I hope you will be willing to share those failures with me — and all the other writers out there — so we can avoid them.

It’s nice not having to make all the mistakes yourself.

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👽🌊 Amature Human, Haiku Poet, Pocket Story Writer and Essayist. FREE dailyish newsletter

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