When is it Time to Quit?


Most of my friends tend to stick with their jobs for many years at a time. I have respect for that, particularly because it’s something I’ve never been able to do. But if you’re satisfied with your job, if you feel like you’re growing and progressing and living the dream, then power to you! Stick to it.

But what about when it’s NOT going so hot? Sure, even the best jobs can have less-than-fulfilling aspects to them. (I imagine even ice cream taste-testers have to fill out paperwork). But when does it cross the line? How do you tell the difference between a necessary evil and a legitimate reason to quit? There’s no universal guide for this because it is a very subjective answer. A dealbreaker for you might be totally fine for someone else. And there can be all kinds of factors mucking up your decision-making process:

What if you have a job that pays really well but is steadily grinding your soul into a fine paste?

What if the country is heading into a recession and you’re afraid you’ll wind up living in a cardboard box?

What if you have a family to support?

Here’s the thing: when you look for them, there are always plenty of reasons to stay put. It’s familiar, it feels “safe” (until you realize that job security is just a quaint relic from a bygone era), and even if you hate your job, staying there can be a lot less scary than jumping off into the unknown. Some people rationalize themselves into dead-end job for years because of this. Decades even!

Perhaps the better question to ask yourself is this: what is keeping you at your job? Actually sit down and write out your reasons– but the twist is that you’re not allowed to write any reason that is fear-based. No scary “what-if’s”. (What if I can’t find anything better, what if nobody wants me, what if I let my family down). If you find yourself unable to come up with anything that passes this test, maybe it is time for a change!

A quick note about “martyr” logic. Some people know they hate their jobs, but they resign themselves to drudgery in the name of supporting a family/spouse. In my humble opinion, this is a crutch. An excuse. I genuinely believe that at the end of the day, you will better serve yourself, your family, and any future employers by pursuing your passions. By doing something you truly care about. By setting a fearless example. Even if you don’t make quite as much money, you’d be teaching your children something far more valuable by taking this path.

Maybe you know in your heart that you need to move on, but you just can’t quite bring yourself to do it yet. You’re waiting for something. Waiting for a sign, waiting for the kids to graduate, waiting to see if that promotion comes six months from now.

Steve Jobs gave a very powerful commencement speech at Stanford in 2005 where he talked about his experience with cancer. (I highly recommend watching the whole thing.) In it he described how all pride, all fear of embarrassment and failure, and all external obligations just fall away in the face of death, leaving only what is truly important. Remembering that you’re going to die is the best way to “avoid the trap of thinking that you have something to lose– you are already naked; there is no reason not to follow your heart.”

Every morning Steve would look in the mirror and ask himself: if today were the last day of my life, would I still want to do what I am about to do? Whenever the answer was a “no” for too many days in a row, he knew it was time for a change. And perhaps this is the most remarkable part: he actually made the change. He did something. He became infamous for cancelling “important” meetings and changing his plans at the last minute– all because he realized how valuable time is, and he refused to spend it on unimportant things. (Keep in mind that this was a common theme throughout his entire life, not just after he became a billionaire celebrity in the tech industry and could “afford” to do it.)

Everyone’s situation is different, but at the end of the day you have to follow your intuition. If your inner voice is yelling that it’s time to move on, have the courage to follow it. It doesn’t mean that you have to burn bridges and go out with a blaze of glory. You can start by quietly looking at options and making a plan. The important thing is that you start! Trust your intuition, and when the time comes to take the plunge, hold your breath and jump in with both feet.


  1. Brianna

    Dan! I’m loving your blog so far, keep up the good work. I particularly liked this post because it describes where I’m at in life to a T. When we started culinary school (can you believe it’s been almost six years since we all awkwardly walked into Chef Al’s class with our measuring cups/cowbells clanging behind us?) I thought that I was going to end up in the restaurant world for the rest of my life. When we finished, though, I discovered that I was damn good at cooking but don’t want to work 70 hours a week in a hot kitchen. After graduation I stumbled into the mortgage industry and discovered that I’m really good at and it’s great money, I thought I was going to make it a career but realized that I don’t want to be another office drone. So, I’m deliberating between going back to school to major in photography or sticking to my current career track. I’m really leaning towards school, photography is something that I’m really good at and it fills my soul but the money isn’t always the greatest. I remember, though, that Clinton Kelly (fabulous fashion guru and TV host who lives in your neck of the woods) said on Facebook that you should pursue your passions and the money will follow. I definitely feel like I’m on the edge of the cliff and just need to take the leap. It’s scary as hell but I’m excited to see where life decides to take me. My biggest hesitation with school is that it’ll take me a full four years to finish but the next four years are going to pass anyway so why not spend the time learning to master something that I love?

    Anyway, this is a super long response, I should probably get back to work. I will say, though, that I’ve always admired how you always tackle your newest idea/dream/passion head on and commit to it 100%, that takes a lot of guts to do.

    • Dan

      Brianna! Thanks so much for the response- it’s good to hear from you. (And sorry it took so long to approve- I need to check my comment logs more often). I feel the same struggle every day, between just chasing money to pay the bills and doing something just for the pure joy of doing it. But at the end of the day I think the latter results in your best work, and can eventually turn into the most rewarding career. (Of course figuring out the specific logistics of that journey is a bit more bumpy, haha). Keep me posted on how things go!!

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