top of page

Overconfidence Kills: Why You Need to Stay Humble on Your Writing Journey by Joseph Reilly

I would like to welcome back guest writer, Joseph Reilly. Enjoy!


The scenario: You've been churning away at your writing career for a few years now. You haven't seen much progress. You're really doing a deep dive on some new career tactics. And finally, you see some progress! Maybe you've begun to earn more, you landed some new clients, followers, or you got that all illusive book deal. Congratulations. Now you have to be aware of the proverbial evil elephant in the writer's room: overconfidence. Why? I'll explain.

Work Quality

The second I started to get comfortable in having a big workload via my clients, I started to realize I was taking on more than I could handle because hey, I got some good feedback and figured I could bang out a few deadlines with ease. This was not the case. I encountered my first client who handed me back my work covered in red marks along with a lengthy paragraph on my sub-par work. Overconfidence got me.

Social Media

A few years back I started a faith-oriented blog. And I realized that the audience for this market was pretty passionate. I gained a lot of followers. I was seeing a lot of clicks. So, since my click-bait type headlines were working, I started to push the envelope on my faith-oriented content. This stopped once my very passionate audience became threatening and argumentative. And to be honest, I wasn't an authority on the overconfidence was.

Dry Spells

Dry spells on freelance writing is a guarantee. No matter what, you will have those months where clients just don't need you as much. But, starting out I had a clear streak of months where my income kept increasing. Because if this I started to get a little cocky. I started to spend it all because I figured what the heck, I can just make more! I had this mindset until the month where I only brought in $200. Needless to say, I realized I couldn't just get clients or work whenever I felt like it. I don't have magical freelance powers. Overconfidence made me feel like I did.

Uncle Sam

This next one goes hand in hand with the last, because I was spending so much in my first year, I figured I'd just make a few grand right before tax season came around. That didn't happen. I owed the government money and had to dig into my savings. In my head, I again could just find some new clients to cover the gap. Other expenses came up and I didn't make my own deadline. It was a valuable lesson that I needed. Now I always out roughly 20% to 30% aside for good ol' Uncle Sam.

Overconfidence is definitely something you don't want to have in your writing bag of tricks. It leads you in a very bad direction and places you on a pedestal that will only break over time. Writing is about hard work, line by line quality, never expecting a certain result, and valuing what you get from your written words. Always stay humble or the industry will humble you.



Joseph Reilly is the author of the novel "Vanishing Love" published by Adelaide Books November 2020. He is the current head writer for ShipByMail Services Inc. Joseph’s writing has been published by Ephemeral Elegies, Monologue Blogger,, among others. He has also penned two self- published contemporary romance novels Hearts and Diners, and Better at Friendships on Amazon along with holding a Bachelor’s Degree in Creative Writing from The New School in New York. You can read his work at the website below.



bottom of page