Working for Yourself Sucks Sometimes, but It’s Better Than a Day Job

Let me remind you why you (should) quit

Photo: Quang Anh Ha Nguyen/Pexels

The company I quit eight years ago is doing great.

Like, greater than I ever thought they would be, to be honest.

I still keep in touch with some of my former colleagues, and I know they make great money, enjoy flexible schedules, lots of vacation days, company parties, work trips worldwide, and jealous-worthy social packages.

Sometimes, I miss it all. Freelancing, writing, and even entrepreneurship (with all its communities) can be excruciatingly lonely, depressing, difficult ventures. It can feel like it’s you against the world. Most of the time, it’ll be years before you achieve decent results. Financial insecurity is nerve-racking. Confusion, overwhelm and burnout become daily emotions you should learn to ignore.

When I have a terrible run, I start browsing job websites and consider calling my former boss and begging for my job back.

I see people on Medium writing about this: that they quit, got a taste of the freelancer’s life, and got back to 9–5. And I get it. Some months, it’s all I can think about.

Then I read a few job ads, and it’s like I get teleported to an office. I breathe in the stiff air and feel…