How to (Finally) Escape a Job You Don’t Like

Monday mornings aren’t your enemy

In 2017, my business failed. We closed the doors and dissolved the corporation — I was heartbroken. In 2018, I started a job in a new industry. My commute was over an hour each way. In 2019, I moved closer to home. My new supervisor and the environment were toxic.

I worked with the same company for four long years. During that time, I constantly tried to get back into my old industry and did more interviews than I could count.

Eventually, I had to accept a hard truth. There was no going back. I had to forge a new path forward. I wish I could say it was a straightforward path, but it wasn’t.

In fact, I didn’t consciously realize the steps I was taking until after. But hindsight is 20/20, and I can clearly see the three big steps I took that put me on a path to escaping a job I did not like.

Without going into details, I want to share three approaches that helped me to make my living without depending on a job that would not give me pleasure and life satisfaction. Hopefully, they can help you do the same.

1 — Uncover Your Natural Interest

Everyone has a clear sense of self when they’re young. In The Laws of Human Nature, Robert Greene talks about how, as kids, we have a visceral connection with our likes and dislikes.

You’re typically drawn to people, places, and activities, even though your young brain can’t explain why. You don’t even stop to think about it. But as you get older, other influences like parents, teachers, and culture guide you away from those initial connections.

You adopt the belief that your dreams are unrealistic. There’s a quote by designer Jessica Hische that I love: “The work you do while you procrastinate is probably the work you should be doing for the rest of your life.” For me, it was writing.

As a kid, I’d staple printer paper together and write a book. As an adult, I’d avoid applying for new jobs that didn’t interest me by working on a novel I’d always wanted to write.

It will probably be something different for you. Here’s a good question to ask yourself. What would your eight-year-old self hope your current self was doing?

Don’t think about it too hard, just go with your initial reaction no matter how outlandish or unpractical it may seem right now.

2 — Invest in What You Love

One of the scariest things you’ll have to do is to spend money on your interest. A financial investment puts you on the hook (psychologically) to get results and take action.

This is often referred to as the “sunk cost fallacy.” It’s when you continue to pour time and energy into something because you’ve already “sunk” money and time into it. Most people only talk about its negative effects. But it's also beneficial if you’ve invested in something positive.

When I decided to take writing seriously, my first investment was on a website for my blog. I spent a couple hundred bucks getting everything set up and ready to take the world by storm with my writing.

Eventually, I learned how difficult it was to get any attention by writing a blog; I started looking for ways to improve my writing. That’s when I began writing on other platforms, which gave me a built-in audience. As I gained traction there, I invested in online courses that helped me learn even more writing skills.

One of those courses helped me land a new job with the company that created the course and became my exit door from the job I did not like.

Even though the initial investments were scary when I made them, I followed through because I was investing in something I already loved. When you invest in learning a skill you are naturally interested in, you’re more likely to stick with it and get results.

You don’t have to start out buying a $5k course. Starting with free resources is okay, like reading a blog or watching YouTube videos. Then you can progress to buying a book, then a course.

As your skills grow, you’ll feel more comfortable making bigger investments.

3 — Stop Trying to Force Change

I mentioned before that I did dozens of interviews trying to get back into my old industry. The more I tried to make it happen, the less success I had.

I’ve learned this usually happens when we really want something. We obsess over getting a specific result or outcome, only to face frustration when it doesn’t work. In desperation, we tell ourselves it will work if we just “keep grinding.”

Know what happens when you grind something? It turns to dust. There’s a concept in Taoism called Wu Wei. It means “effortless action,” which seems like an oxymoron until you think about water flowing in a river.

Water is a powerful element, more powerful even than wind or fire. Given enough time and constant flow, it can erode rock. When it faces an obstacle, it just flows over, under, or around it. Water follows the path of least resistance to get where it wants to go.

You can’t force your way out of a job you hate. The more you try, the more frustration you’ll face.

Instead, look for ways to put that “escape energy” into executing the skills you’re learning. Since you already love doing it, you won’t have to force yourself.

After gaining some success writing stories on Medium, I stopped to spend eighteen months writing a novel — a lifelong dream for me.

During those months, I was working on something I loved but getting little to no feedback or benefits from it. Meanwhile, my mostly dormant Medium account was still getting 6–8k views per month, and I was hardly writing anything!

After I finished my novel, I decided to start putting my energy back into Medium because I was getting tangible results that my novel writing couldn’t match.

When you find something that’s working for you — even if it’s unexpected — put more energy into it. If it’s showing promise, it’s worth your time.

Conclusions and Takeaways

Everyone’s path is unique. Mine has taught me if you dig into your natural interest, invest in building skills you love, and stop trying to force your life to change in your favor, you may find opportunities in places you weren’t expecting.

I can’t guarantee doing these three things will land you your dream job. But even if it doesn’t, you’ll get the innate satisfaction of getting good at something you love. Chances are pretty good that those skills you learn will lead to some new opportunities.

It may not be in the way you expect, but with an open mind, you never know what you’ll find.