When to Say ‘I Quit’

UPDATED: August 14, 2018
PUBLISHED: August 16, 2018

I was 35 years old, 11 years into my career with three spent at my current employer, when I realized I hated my job. I still loved magazine writing, but I had started to see colleagues, one by one, cut the corporate umbilical cord (or have it cut by the economy), and float out into freelancing. Meanwhile, I was trapped in my car on my daily commute and drifting off during business meetings—daydreaming about one day walking into my boss’s office, decreeing “I quit,” and doing the slo-mo rockstar strut to the lobby and out into a world where I was my own boss.

Related: What to Do If You Hate Your Job

But in my fantasy, I didn’t know exactly what would be waiting on the other side of those elevator doors. And that uncertainty always kept me anchored to my desk. Leaving your job is not something you want to do on a whim. You have to be sure you’re mentally ready to stray from the herd—and you need to assess the frontier that awaits.

First, interrogate yourself about why you’re unhappy and whether leaving a full-time job will change that. “People get very focused on ‘supposed to’ when thinking about their careers,” says Priscilla Claman, life coach and president of Career Strategies. “I’m supposed to be director now or I’m supposed to be making more money. They forget to ask, Is this right for me? or Is this really what I want? What people should be looking for in a job is a match between the job and their strengths and skills. When that happens, it doesn’t feel like work.”


Leaving your job is not something you want to do on a whim. You have to be sure you’re mentally ready to stray from the herd—and you need to assess the frontier that awaits.

Even though I dreamed of quitting my job, I still liked my co-workers and boss. I believed in the company and its values. It wasn’t about money or my title. I wanted to operate on my own terms, to write about topics I cared about as opposed to what was being assigned. My occupation had come to feel like a job.

Related: Before You Quit Your Job, Try These 3 Things

Next, think of any and all external factors, starting with those closest and moving outward. How was my family going to get money or health insurance? What sort of economy was I venturing into? Did I have any prospective clients lined up? “When you start your own business, there’s a waiting period,” Claman says. “When you start to market your skills, you won’t see a result for a couple of months.” Claman suggests starting with the client who knows you best: Your current employer. Ask if they’ll keep you on part time or as a consultant or contributor. That way you’ll have a base of support to build on.

No matter how much someone prepares, I’m not sure anyone is ever completely ready to jump. In fact, I never got to fulfill my defiant fantasy of quitting—I was gently let go, my discontent having affected my work more than I’d realized. But my boss thought enough of my past performance to offer me a part-time contract. My wife had a corporate job with good benefits to cover us and our two girls. Most important, she had noticed my misery and encouraged me to try the other half of my dream. Three years into full-time freelance writing later, I’m making more money than ever, doing work that I love and am proud of.

And I’m no longer daydreaming about what might be on the other side of the elevator doors.

Related: How to Find Meaning in Your Job


This article originally appeared in the Fall 2018 issue of SUCCESS magazine.