When To Leave Your Job

This is the first part of a two part series. In part 2 I’ll cover ‘How To Leave Your Job.’

Quitting your job can be a very uncomfortable experience. The fear and uncertainty associated with leaving a job is enough to drive people into an anxious frenzy. I should know: I quit my job today.

However, these feelings are completely and utterly misplaced. The moment I decided to quit was an important step in reclaiming my life. I am in control and am no longer a slave to the routine. No matter what your situation (quitting outright to start a business, switching professions, or just changing companies) you should find comfort in “going for it.”


Everyone makes excuses. To quote Timothy Ferris, “The timing is never right. Conditions are never perfect. Someday is a disease that will take your dreams to the grave with you.”

In my case, the timing for my departure is both good and bad. The lease for my apartment is going to expire at the end of the month so I’ll no longer be tied to a large payment each month. This is going to allow me to travel without the guilt of paying for a place I’m not spending any time in. However, I couldn’t have picked a worse time to leave a blossoming company. I am on the ground floor of company that is revolutionizing its industry. The company is being called the new Apple in its particular field. It is currently an indie nipping at the heels of all the majors. I am completely serious when I say this company is amazing. After informing some of my co-workers that I was leaving, they called me Stuart Sutcliffe. Sutcliffe was the guy who left the Beatles in 1961 and then died a year later (good thing for him – the 60’s might have been pretty rough to live through).

Quitting is something I want to do and if I don’t embark on this journey now, I might never. What will more time do for me? If I wait longer some other excuse will pop up.

I’ll just invest in the company when it goes public!


  1. Quit when your job is no longer advantageous to you and your goals.
    Don’t lie to yourself. Why are you really holding this job? Do you just want to pay the rent? Are you looking for a career in this industry? Are you extremely passionate about cleaning toilets?

    The majority of people work strictly because they want more money. They tell themselves otherwise. “I love finance. Doing other people’s taxes is exhillerating!” Yes, you need a certain amount of money to maintain and live. No, it’s not as much as you think. If you want more money, fine. For most that is the determining factor of holding a job. But if your goal is to be a musician, why are you working 40 hours a week in a office? If your goal is to own your own business, why do you continue to work a job that doesn’t lead you in that direction? Figure out what your goals are and work towards them. If a job gets in the way of those goals quit and get a different one.

  2. Quit when you are undervalued.
    You should view yourself as a contract worker for hirer. You only work for someone when you are receiving adequate compensation.

    If you are making $10 bucks an hour then analyze why that is. There is a reason. Maybe you need more education. Maybe your job sucks. Maybe you’re trying too hard at work. Relax a little and work according to how you’re getting compensated.

    It is always good to check out what the competition has to offer. Baseball players jump around to the teams that will pay them more money. Look for opportunities to advance your career (if that’s what you want). You have no obligations to a company. They’re making money off of your work and you’re trying to get paid. It’s a two way street. Companies need to give you incentive to stay.

  3. Quit when your gut tells you it’s time.
    This point is related #1, but it goes a little a deeper. If the job you currently hold seems like it is benefiting your present goals, but you are still unhappy, this means it’s time to go.

    For example: Let us assume that your current goal is becoming CEO of your company. You’re slowly working your way up the corporate ladder. You get promotions and pay raises at the appropriate times. You’re putting in the extra hours. On paper, everything is going great. You’re advancing towards your goal and you’re getting paid what you’re worth. But something is wrong. You’re not enjoying the process. This is a red flag that it’s time to quit or take some time off. From an evolutionary standpoint, human beings weren’t designed to sit in offices and work all day. It’s against our nature. Trust your instinct. If it’s time to move on, it’s time to move on. If you’re in a rut, it might be a sign that your goals are shifting.

In conclusion, a job is not something you’re forced to do. A job is something you choose to do – it’s leverage for obtaining your goals.

Published by

Derek Johanson

The personal blog of Derek Johanson.

3 thoughts on “When To Leave Your Job”

  1. It’s funny you mention Tim Ferris in this post because on his Four Hour Work Week blog today, he has a very similar post about how compounding time is as valuable as compounding interest.

    In other words, the more time you spend at a job that doesn’t get you closer to your goals, the less time you can spend on getting good at the specific tasks that will take you farther in life. Spending 40 hours a week at a job that is not for you is like throwing all your money away on toys and unnecessary items rather than investing it. Those who know how to invest their time wisely now will reap the benefits in the future.

    This all jives exactly with your message here. If your job isn’t for you, then get out and use your time for better things. Enrich your life rather than suffer through it.

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