02/13/2013 10:33 am ET Updated Apr 03, 2015

When To Quit Your Job: Questions To Ask Yourself

By Amy Shearn

So: You've been rehearsing your "You can't fire me -- I quit!" speech in the mirror. But are you sure you want to take it out of the bathroom?

  • 1. Who Else Needs A Vote?
    A friend of mine (whom I'll call Will) once told me a chilling story of how his wife came home from work one day with an air of triumph. "What happened?" Will asked, for obviously something had. "Did you get a promotion?" "No!" she said. "I quit!" He described the feeling of his heart falling to his feet. He worked, too, but she was the breadwinner. P.S. They had three children under the age of three. I don't mean to be a career-change Cassandra here, but I must tell you that soon they were getting divorced. To Will, what stung wasn't that she wanted to change careers -- he swore he would have been supportive of whatever she wanted to do -- it was that she made the decision without him. Following your passion is wonderful. Leaving your family without health insurance is not.
  • 2. How Will You Explain This To Future Bosses?
    Unless your reason for quitting is that you found a huge bag of money somewhere, eventually you're going to be looking for another job. Alison Green, creator of Ask a Manager and columnist for U.S. News & World Report, points out that future employers will want to know whether you had a good reason to leave. They'll also look at how long you were there and how long you stayed at previous jobs. "If you have a pattern of leaving jobs after less than two years," she says, "future employers will worry that you're a job hopper -- and that you'll leave them quickly too. Sometimes it's better for you in the long run to stay a bit longer in a job so that you don't harm your ability to get jobs you want in the future." (Click here to see more of Green's tips for people thinking about quitting their jobs.)
  • 3. Aside From The Paycheck, What Are You Giving Up?
    Whether you're moving on to another opportunity or just can't stand one more day, take a moment to consider the intangibles. What else does this particular job provide? Training in a growing field? Connections to other professionals? Or little joyful things? Boston artist Jasmine Laietmark told me, "When I quit my most recent nonprofit job, what I failed to consider was the other things I'd lose: the exercise that I got on my bike commute, daily visits to my favorite café, people to practice speaking Spanish with, the cash to pay for odd, unexpected expenses like my cat's teeth extractions, and so on." Maybe you have enough in savings to cover your bare-bones expenses, but have you thought about what will happen when the cat has a dental problem?
  • 4. Is What You Really Want A Promotion?
    Go ahead, take one of those pretending-to-go-to-the-bathroom-but-really-walking-by-your-boss walks. Do you wish you were she? Or does she exude a stress that makes your heart palpitate? Macon York, who runs her own letterpress and design business, told me, "I moved to New York City to be a magazine designer, but it hit me that the people above me seemed to be busier, more stressed, and doing more managerial work." She asked herself, "Do I actually want a promotion?" At 25, the answer was yes (she was designing). "I knew that at 40 the answer would be no -- I'd likely be more of a manager," she says. "So I began to move in the direction of working for myself." If it turns out that the next step for you doesn't seem appealing, perhaps a change is in order.
  • 5. Are You Helping Your Bosses To Help You?
    Hmm... now that you think about it, a promotion or a shift in your responsibilities might make you feel less quitty. As management consultant Marcus Buckingham, the best-selling author of Go Put Your Strengths to Work told O, The Oprah Magazine, "One of the most insidious myths people suffer under in the workplace is this idea that we should all be team players and do what the team asks of us. It's a moral myth, but it misunderstands our moral duty. Our real moral duty is to offer our greatest strength to the team -- to give it the opportunity to use us where we're at our strongest." Follow his advice and list 10 things you could do over the next month to gain more opportunities to do the work you actually like. (Click here to get the whole story and more great advice for pinpointing your own strengths.)
  • 6. Does This Job Make The Life You Love Doable?
    I actually know someone who works in the circus. Really. She's an elephant trainer. And she's going to have great stories to tell when she's an old lady. Do you want to run away with the circus? Maybe. Do you have a life that allows for constant travel and lots of spandex? Or, come to think of it, do you need a job that allows for flextime so you can operate a gymnastics-practice car pool (aka your unpaid position as the patron of future circus performers)?
  • 7. Can You Be A Nighttime Baker For A While?
    Before making a big career change, consider what kind of apprenticeship you might be able to engage in without leaving behind that sweet, sweet paycheck. Careerosity, a website dedicated to helping people navigate career change, recently interviewed product manager Emily Johnson, who left behind her freelance writer career. How did she decide to take the leap from writing to being a product manager at a tech company? As she put it: "If you're interested in trying it, I'd recommend starting a mini business of your own. Most of the product managers I know sold pizza on the corner in college, or made jewelry to sell on Etsy, or started a website. These mini businesses failed in many cases, or made just a bit of extra spending money, but thinking about your market, your product, and your delivery will teach you most of what you need to know for a regular product manager job." In other words, if you think you want to be a product manager (or whatever it is you're thinking of), try it out on the side first. Just to make sure.
  • 8. How Will 5 Years As Head Of Household Activities Fit On Your Résumé?
    Here's something that happens in my household with slightly maddening frequency: My husband comes home from a day at the office, and the kids -- who have been literally pulling out my hair -- are so happy to see him that they put on the Adorable and Perfect Show. And he comes out from tucking them in, sighs dreamily and says, "I wish I could be home with them." Right. Because it's always like that. If this scenario sounds familiar, then before you quit to be home with your kids, think five to 10 years down the road: How easy will your re-entry into the workplace be with that gap on your résumé? Do you work in a technology-driven field that will be completely transformed by the time your kids are in kindergarten? Would an occasional day working from home help you to not miss those little rug rats quite so much?
  • 9. Do You Have The Patience Of A Ninja?
    This guy, Izzy, left his job to become a ninja. And all the little boys in the world said in unison, "WHAT?!" But it didn't happen overnight. Izzy told me: "There's a lot of information out there that implies (or directly states) we should drop everything and pursue a dream. Often the pursuit of a dream is seen as this either-or type of thing. But in reality there is a transition period." As he shares on his site and in his TEDx talk, he had a long path between leaving his deadening career behind and realizing his lifelong dream, including, um, a year of living at home with his parents to save up the money for his sojourn to Japan.
  • 10. Do You Have A Brother With A Business Degree?
    Remember Macon York, the designer who struck out on her own? She says that the least fun part of running her own business has been "all the legal stuff: tax IDs, quarterly freelance taxes, copyright stuff, trademarks, registering my business with the state, etc." She goes on: "I'm great at the design part; it's the business end that I'm scared of. But my brother has a business degree, so he's been helping me." If you're thinking of going rogue -- I mean, freelance -- or starting your own business, keep in mind you're going to need to get real cozy with your accountant, keep careful records, learn about some legal stuff and maybe talk to York's brother.
  • 11. Are You Succumbing To The Nostalgia Bug?
    I tend to wax poetic about a barista job my husband tells me I actually hated. So how do you know whether an urge to return to a former field is misplaced nostalgia for a hazily recalled "simpler" time in your life... or everything coming full circle? Noah Pinzur, a Chicago-based finance associate, told me that he was returning to a startup after years at a large bank because he remembered that he "enjoyed working in what was essentially a startup environment in 2003," adding, "l loved that environment." It was the specific job responsibilities and roles that he missed. Going back to a former field can also offer, ironically, a chance to move forward as a person. After working as a medical technician, Deirdre MacNamara left the field to bartend and write. Seventeen years later, she's working as a medical tech again and "determined to make this go-round work better." She said: "Now, having worked in other fields and living through friends' illnesses and seeing my dad through his final days, I'm much clearer on what it is to be a patient or the loved one of a patient. I want to use this opportunity to strengthen my skills and make a living, yeah, but also to test my humanity skills."
  • 12. Are You Paying Attention To Where The Universe Is Nudging You?
    We all love the Following a Dream story. It's a great story. It's exciting to hear about someone quitting a mundane job to become a ninja or to run her own business. But sometimes it's possible that you're following the wrong dream. Photographer Evan Schwartz had a good job as a home stylist in a West Elm furniture store, though he had not expected to be working retail after nearly a decade working for editorial publications. Sometimes, he thought he might want to try something a hundred percent artistic, like going back to photography full-time. But then it happened: He realized he actually really loved his job. He told me he realized how much he loved interior design -- "It took me a year to listen to where the universe was pushing me" -- and he's now taking classes toward certification in the field. Sometimes the dream job turns out to be the one you already have.