The Outrageous Decision To Begin

The Freelance Writer’s Journey, Prologue Part 1

In June of 2020, I decided to do something really dumb.

Well, to be honest, it was a combination of two things. I decided on June 26 that I was going to accept a doctoral candidacy at Northwest University. This meant that come September,  just about everything in my life was going to change. The next day, I decided that I was going to leave my job and attempt to “make it” as a freelance writer once school started.


This means that I’m going to start grad school and a new business at the same time. Dumb. At the same time that I’m saying “hello” to the largest financial commitment I’ve ever made, I’m saying goodbye to guaranteed income.

Most people advised me to take it a little bit slower than that, to maybe look for a more stable job. Something a bit safer and more predictable. In fact, an offer to work for guaranteed income did come, but I decided to decline that offer. What was I thinking?

I was thinking that maybe, just maybe, I had what it takes to succeed as a freelance writer, copy editor, and proofreader. There was certainly one way to find out. Sure, I had done paid writing and editing work off and on for years, even writing a book myself and serving on the editorial board of a newspaper. However, it was never my primary source of income. This was taking things to a new level. A new level of excitement, and a new level of fear.

Steven Pressfield wrote a book called Turning Pro in which he describes the difference between an “amateur” and a “professional,” especially in terms of artists and creatives. It’s a fantastic read which I highly recommend. However, what stood out to me about that book was the one thing that amateurs and professionals have in common: Both are extremely terrified.

See, the amatuer in Pressfield’s book is afraid of failure, afraid of success, afraid of risk, afraid of showing their true selves to the world. What do they do with that fear? They avoid risk, they avoid putting themselves out there, they avoid hard work, and they make any excuse not to go after their dream. They go after distractions and addictions. 

The pro is afraid of all of the same things, but what they do with their fear is a little bit different. Rather than running away from their fears, they face them. They master their fears. They make the decision every day to push through, to work hard, and to become the absolute best version of themselves.

I want that to be my story. That’s why I said “no” to guaranteed income, while at the same time saying “yes” to bigger bills than ever before. Because this is quite possibly the best opportunity in my life to try something like this, and I want to see if I can pull it off. If I fail, I want to fail knowing that I did not throw away my shot, but I did everything I could–and discovered that a full-time freelance writer is something I’m not. However, I want to succeed. I want to win at this. 

And that is partly why I started this blog, to help keep me sane during the process. I am going to be chronicling the practical steps I take as well as my thoughts and emotions during the process. Maybe it will inspire you to start and finish that project you have been putting off. Maybe it will just add some entertainment to your day. Maybe, just maybe, I’ll make it in this field and other aspiring freelancers can use it as a guide. Who knows? Crazier things have happened.

In the next post I’ll be talking about the baby steps I took at the very beginning, and some of the resources that I used. Stay tuned!

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