Even though I loved being a high school English teacher, for years I daydreamed about quitting my job to write full time. But I thought it would always be exactly that — a dream.

To be clear, I’d been a full-time writer in the past. Before I started my career in education, I was a staff reporter for a weekly paper in Louisville, Kentucky. But my tenure there just showed me that I wanted to write on my own terms. I wanted to be a full-time freelance writer. But I thought there was no way I could do this unless I was willing to eat PB&J for breakfast, lunch, and dinner every day. I was convinced living a comfortable lifestyle as a full-time freelancer was impossible.

Then one day I decided I was going to give it a shot anyway!

On May 24, 2019, I quit my day job and became a full-time “writerpreneur.”

And I’m so glad I did. I LOVE being a full-time freelancer. (Here are 30 of the many reasons why.)

And it turns out I was wrong about that PB&J thing.

In 2020 — my first full year as a full-time freelancer, which also happened to be the year I was fighting cancer and the world was fighting COVID — I made more money than I ever did when I was juggling teaching full-time with writing part-time.

You may be thinking, “How, Sway?!”

Before you quit your day job, do this…

Here’s what I did to position myself for success as a full-time freelancer:

First, I got out of my head. I know this sounds a bit woo-woo, but before I could be a successful full-time freelancer I had to believe that I could be a successful full-time freelancer. You know how the quote goes: “Whether you think you can, or you think you can’t, you’re right.”

Next, I had to get focused and decide exactly how I was going to make money. Most of my income comes from freelance journalism, but I also do freelance content writing for businesses and organizations, and I make money through courses, coaching, and my membership community. Paid speaking gigs are a nice addition, too.

Networking — whether IRL or online — also needs to be on every freelancer’s agenda. Many of the paid writing opportunities I’ve had landed in my lap because of connections I’ve made.

Along the way, you’ll find you must get organized. You need a system for tracking projects and payments and your time management skills must be on point so you won’t miss any deadlines.

Finally, before you make the leap, you need to do the math. Figure out exactly how much money you need to make to maintain your current lifestyle and be sure you’ve lined up enough steady gigs to make those coins.

If you want to learn more about freelance journalism, check out my digital course See Jane Freelance.