How to Tell When it’s the Right Time to Quit Your 9–5 for Freelance Writing

Kristin Beal
3 min readMay 20, 2021

…advice from someone who just quit their 9–5

Photo by Carl Heyerdahl on Unsplash

I’ve recently put in my two-week notice at my desk job at a software company. And by recently, I mean less than an hour ago. Which means that as I type this, I’m still reeling with adrenaline.

I always imagined that when I quit, it would feel like a badass movie sequence. I imagined myself as the heroine, underpaid and under-valued by her corporate overlords, sticking it to the man as she slams both palms down on her desk. “I QUIT!” She would yell, causing a revolution, inspiring those around her to question why they too are still cubicle slaves.

My reality ended up being far different.

My resignation email sat in my drafts all morning. It was short, sweet, and to the point. I was choosing to move on to pursue new opportunities (such as a career in freelance writing!). I thanked my managers. Told them I’d be available for two more weeks.

And then the email sat there. And, boy, did I struggle to hit that tiny little “send” button.

Because as the imminent deadline to actually quitting my 9–5 drew nearer, the more my brain struggled to let me do it. The fantasy of quitting in a John Hughes-esque style movie scene was slowly being replaced with the dread of what was about to happen. My brain was suddenly trying to protect me — to keep me safe — from venturing into this change.

See, the brain likes to keep you comfortable. It doesn’t like when you try to shake things up. And as a response, it will start to present you with all the reasons why your 9–5 really isn’t so bad after all. Yeah, you’re being underpaid, but you’ll be getting paid a whole let less if you quit. Yeah, you’re a young healthy person, but what if you need to visit the ER and don’t have new insurance yet? Yeah, you don’t have much passion for the work you do everyday, but at least you have access to a lunch stipend at the work cafeteria!

Your brain will try every trick in the book to keep you in stasis. Why shake things up when you can be comfortable in your misery?

Well, I refuse to be comfortable in my misery any longer. So I hit that little “send” button on that email and decided to take my life, my career, and my happiness into my own hands.

I know that this course of action is not feasible for everybody. I had to create an action plan before I quit — ways to keep making money in order to keep my head above water. I took a calculated risk by quitting my 9–5, one that I believe will pay off for me because I work hard and am determined to do what I want with this life I’ve been given.

So if you’ve read this far and are still wondering when the right time to quit your toxic 9–5 is, the answer is that it will never feel right. There will always be the nagging doubts inside your brain, the safety mechanism set up to make you question what the hell you’ll do after jumping off that cliff.

But man do I have a strong belief that it will be worth the view.



Kristin Beal

Dynamic young freelance writer, content strategist, and filmmaker. She/Her.