Career & Money

7 Questions to Ask Yourself Before Quitting Your Job

It was as if I was floating above myself watching in disbelief

When I was 27 and working as a journalist at a news website in my hometown of Sydney, Australia, I was offered a promotion to the most senior role—and the highest salary—of my career. Instead, I turned it down and quit.

Somewhere, my high school career advisor banged her head against a wall.

I told my boss I was planning to take a grown-up gap year, and as I said it, it felt as if I were floating above myself, watching in disbelief. I’d worked so hard. Was I throwing it all away?

But five years later, my leap of faith has paid off. After six months backpacking around Central and South America, I moved to New York and started writing freelance. I’ve hit career highs I doubt I would have if I had stayed at my job in Australia, and work-wise, I’ve never been so fulfilled. It was all so easy, and I never once questioned my decision.

Ha! Obviously, I’m joking.

I mean, some of it’s true, but for at least the first year of being a full-time freelance writer in a new country, I was constantly anxious and plagued with doubt. I second-guessed my choice every time my credit card declined, every time a pitch went unanswered, every time an old colleague back home announced they’d moved up another rung on the corporate ladder. Some of that’s just part of making a big life change, but diving in blindly the way I did, and white-knuckling it through the freak outs and uncertainty, led to so much unnecessary stress.

As it turns out, there’s a smarter, more thoughtful way to quit your job—even if you don’t have another one lined up. And career coach Foram Sheth knows what it is. Sheth is the co-founder of Chicago-based career coaching company Ama La Vida, and below she shared the seven questions to ask yourself before you quit your job. Whether you’re considering a leap or just took it, asking yourself the following questions will help you plan your next move.

1. What would it take for me to be happy at my current job?

Before you quit, Sheth suggests you write down what would have to be different at work to make you want to stay. These changes might be impossible or outlandish, but getting them on paper can serve an important purpose. “If you don’t take a moment to reflect on what you need and want to avoid,” Sheth explains, “you might find yourself in the same circumstances, just at a different job.”

2. Am I running away from something or toward something?

Wanting to escape a shitty work situation is understandable, but Sheth says that if that’s your only motivation for leaving, you may find yourself in a difficult spot. “When we run from something instead of to something, we are just avoiding,” she says. “If we only avoid, we will always feel like something is missing.” She suggests you spend some time thinking about what you genuinely want to pursue before you make a move, otherwise you might leave only to run in circles.

3. What problems do I expect quitting my job to solve?

“It’s important to ask yourself if you’re unhappy in your job because of other things happening in your life, and not the work itself,” Sheth says. “You might be frustrated with something in your personal life that you haven’t yet been able to identify.” Set aside time to do some self-reflection, she says, perhaps by journaling or taking a long walk. It’s a little woo-woo, but the book The Artist’s Way or a self-discovery journal like this one can be an effective tool to cut through all the noise and get honest with yourself.

Questions to ask yourself before quitting your job


4. Can I defend my choice to leave, even if others disagree with it?

Talk it over with your significant other, parents, friends and/or your doorman if you want. But picture the decision like a set of concentric circles, with your beliefs at the center and the advice of others on the outside. Since others’ opinions may change, or be rooted in their own fears and insecurities, you need your own unwavering support. “Women especially tend to make decisions about themselves to please others,” Sheth says. “Ask yourself, ‘Am I doing this for me, or seeking the approval of someone else?’”

5. Can I financially afford to quit?

Only you can decide if you are financially stable enough to leave your job, but Sheth says considering a few different figures might help you feel more confident in your answer. “Ask yourself, ‘If I quit my job without a new one to go to, how can I budget for a six- or even 12-month safety net? What expenses can I cut temporarily knowing I can get them back once I have a new job?” she says. “At what point will I no longer be able to sustain myself? If that happens, how will I gain financial security?”

6. What’s my plan for day one after leaving?

It’s normal to experience anxiety for the first day (or week, or month) after leaving your job, but Sheth says the right preparation can help. This includes writing a list of the reasons you’re quitting to read in moments of doubt; compiling a document of positive feedback you’ve received, at work or in your personal life, for when you need a confidence boost; making a realistic daily routine that involves your preferred forms of self-care (yoga/meditation/breathing/exercise) to ground you while you job hunt or start out in self-employment; generally caring for your well-being by getting enough sleep and eating well; and seeking out some non-career related sources of self-esteem, like learning a new language or volunteering.

Sheth also advises doing a “pre-mortem.” Write down all the things that could go wrong and come up with an action plan for each scenario. There might not be a solution—the plan could be, “take a walk, wait two hours before sending a response.” But this process can quell the anxiety that things might go wrong (because even if they do, you’ll be ready).

7. Am I scared?

If your answer is yes, that’s okay. According to Sheth, being nervous about quitting is a good thing. “If you don’t feel nervous, you most likely haven’t thought it through properly. [Fear is] a normal response that makes you focus and consider consequences. It shows maturity.” But too much fear can also cloud your judgement. Sheth says it can help to imagine you’ve quit and visualize yourself 9 days, nine weeks, and nine months later.

“Sometimes we shy away from quitting a job because we worry we’ll regret it. But nine months later, it’s unlikely you’ll still be wishing you stayed. And if you do regret it, that’s okay. Rarely is a decision permanent or irreversible. It’s not uncommon for people to leave and then boomerang back to an organization, perhaps with some new skills and life experience. That’s why I always tell people to never burn their bridges.”

What other questions would you ask yourself in this situation?

Graphic by Maggie Hoyle

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