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If you’re thinking about leaving your job, ask yourself these questions before quitting.
1. How long you can support yourself without a job?
Before quitting, make sure you can cover your housing and basic needs for three months at the bare minimum, says Ayanna E. Jackson, a Washington, D.C.-based career coach. Not being financially ready for a long job search could create more stress in your life than sticking with your job a bit longer. Talking with a financial advisor could give you some perspective.
2. How much energy do you have to look for another job?
Jackson and other career coaches say it can often take up to six or more months to find a job. A survey of 501 unemployed adults conducted by Insight Global, a global staffing firm, found that 55% of respondents felt “completely burnt out” from searching for a new job. Those respondents had applied to an average of 30 jobs, according to the survey, and received about four responses or callbacks .
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3. Are there comparable jobs available?
Make sure you’re familiar with your industry’s job market before you quit. If you work in a specialized role or industry, research how many open opportunities there are that interest you. If your industry is volatile or undergoing changes, check out relevant job openings, speak with a recruiter or check in with your professional network to get a sense for what the job market is like.
4. What would happen if you walk away from your health insurance?
If you get health insurance through your job, list out what you would lose if those benefits disappeared. Consider whether you could afford to pay for medications, specialized care or a surprise trip to the hospital. Also, are any of your benefits hard to get at a new job?
5. What might you lose from giving up your equity compensation?
If you have unvested stock options or restricted stock units, how do you feel about forfeiting them and any future value they may bring?
6. Will your vacation time change?
How confident are you that other employers could provide you with the same or more time off than you get with your current job?
7. Can the workplace issue be resolved somehow?
Write down everything about your job that makes you want to quit. Then, run through the list and see if any problems can be solved, whether by talking to your boss or to human resources. A conversation could make a major difference. Offer some solutions to the problems you pose.
If you’re dealing with an inappropriate manager, discrimination or unethical or illegal work, you may want to go straight to the human resources department, says Tamiera S. Harris, a life and career coach and founder of Black Career Coach in Philadelphia.
“If there is something serious that you need to point out, you really shouldn’t be talking to your supervisor,” says Harris. “You need to go a step above and talk to HR about it.”
8. Have you started searching for a new job?
Consider applying for other positions while keeping your current role. As a job candidate, you're more attractive to other companies if you’re currently employed, Harris says. Recruiters have an easier time placing candidates while they’re working, as opposed to when they’re unemployed — even if they chose to quit the job.
“You’re more valuable employed,” Harris says.
This is also why it’s wise to avoid quitting your job from a place of reactivity, says Tina Marie St. Cyr, executive career coach and founder of Bonfire Coaching in Houston.
“As professionals, we need to pump our own brakes, and we need to say, ‘OK, let me take a breath and look at this,’” St. Cyr says.
» MORE: How to respond to a job offer
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- 1. Insight Global. Survey: Majority of Unemployed Americans Are Burned Out by Job Hunt. Accessed Oct 17, 2025.
