How to Leave Your Boring Job

UPDATED: November 12, 2019
PUBLISHED: January 31, 2017
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How many people love their jobs? The jobs with the way-too-early alarm buzzes, bumper-to-bumper commutes and sack lunches? The jobs with endless emails, pointless meetings and paychecks that don’t even come close to reflecting how much value you’re bringing the company?

How many of us have dreamed, schemed and fantasized about quitting and to do something else? If this is you, abide by these core rules to launch your dream job.

  • Start your new venture first. Gather some momentum and a sense of how much you enjoy the new gig—and its potential.
  • Have a realistic financial plan. New businesses are often rocky on the front end. Understand how you’ll pay your rent and grocery bills, and create a schedule for when you expect revenue.
  • Choose something you love—something you’re absolutely passionate about. Any career takes up so much of your time and energy, and an obsession with the business is key for success.


“Your past isn’t your future, and you can do whatever you want.”


Gregory Nesmith

40; real estate investor, coach and radio personality; New York City

I spent 16 years in corporate marketing. By all outward appearances, it was a glamorous job: global, first-class travel, a high salary and working with some of the world’s most brilliant marketing minds. For many years, I loved what I did. I also loved that I made my friends and family from my working-class community proud. As I approached 40, I kept remembering my childhood dream to be an on-air TV or radio personality. I was also increasingly excited by the portfolio of real estate investments I’d steadily built, and the challenge, risk and thrill of entrepreneurship. Ultimately, I just didn’t care about marketing someone else’s chewing gum.

I quit two years ago, nervous about leaving a comfortable salary and plagued by the doubts and questions of people who lovingly questioned my decision. At the same time, I launched a real estate investment firm with two friends, and I embarked on a new career as a personal-development coach and a media personality. I now host two radio shows.

I’m still often afraid about whether it will all work out, and I’m learning that fear never goes away. But for the first time in years, I no longer let that fear stop me. I now feel the excitement and aliveness that eluded me. As I suspected it would, the money has worked itself out, too.

Jim Wang

36; founder of and; Baltimore

I was a software engineer working for a defense contractor when I quit to work on my first personal-finance blog full time. I loved my staff job and the people I worked with, but the opportunities with the blog were too good to pass up. I was very scared because my job was safe. I had to re-evaluate my identity; my entire academic background pointed to software engineering. I was leaving all of that behind to pursue something that was less predictable and more dangerous.

Regardless, working on the blog energized me and I found I looked forward to the end of my corporate workday so I could go home and work on my side project. The decision was one of the scariest in my life. My blog was very profitable and I sold it for a large sum. The experience also changed my perception of life: Your past isn’t your future, and you can do whatever you want. Hooked, I’ve since launched two new online projects.

Nicole Cogan

27; founder of; Los Angeles

I grew up in a New York City suburb where I was exposed to a career path in finance even though I hated finance and craved a creative life. I graduated from Cornell University in 2011 and worked in equity sales at JPMorgan Chase for three years, launching my gluten-free marketing platform in secret. I didn’t want my boss to know that I would take clients to lunch, and then write about my meal on my platform.

Eventually I was so miserable that I didn’t want to go to bed at night because I didn’t want to wake up in the morning. On a trip to Los Angeles, I found there was more to life than Wall Street and met a bunch of people who had creative, freelance lives and were really happy. I quit my banking job the day I got back from vacation, crafted a 12-page business plan and moved home with my parents to save money for three months.

Even though quitting felt great, it was also terrifying. I was afraid I’d fail or disappoint my family. But my biggest fear, one that is greater now than ever, is that I’d have to get a job again. After a year of no income, I am in my second year of business and earning as much as I did when I left finance. I am also happier than I’ve ever been and determined to never go back. Both are key to my success.

Related: 5 Steps to Turn Your Passion Into Your Profession


This article originally appeared in the February 2017 issue of SUCCESS magazine.

Emma Johnson

Emma Johnson is a business journalist, gender-equality activist, and founder of the world's largest community of single moms, Emma and her best-selling book, The Kickass Single Mom, and her organization, Moms for Shared Parenting, have been featured in hundreds of national and international media outlets.