11 Questions to Ask Yourself Before Quitting Your Job

March 13, 2025

Before quitting your job, it’s important to take some time to really think through your decision. Quitting your job is typically a pretty major choice that can have massive repercussions on your life. At least here in the U.S., our jobs are often tied to expensive benefits like health insurance and retirement accounts. Plus, as a society we often place a ton of pressure on our careers to live up to ‘dream job’ standards- so leaving our jobs behind can feel like a breakup!

11 Questions to Ask Yourself Before Quitting Your Job

If you’re thinking of quitting your job, we want to make sure you’re fully prepared to make that decision. Here are 11 questions you should ask yourself before pulling the trigger and quitting a solid job or occupation altogether.

1. Why do you want to quit?

There are plenty of reasons why you might want to quit your job. For example, quitting your job to pursue something you’re more passionate about, to earn more money, or to find a more pleasant work environment can be a smart move for a lot of folks.

However, quitting for the wrong reasons could leave you just as unhappy at your next employer. 

Before walking out at your current job, ask yourself why you want to quit. Is it because you had an unusually busy week at work or because you had a minor altercation with a coworker? If that’s the case, you might not be in the best frame of mind to make this decision until you take some time to cool off. Making a rash decision based only on your emotions can leave you feeling regretful in a few short days.

That being said, there are lots of really good reasons to quit your job. Here are just a few of them!

  • You can earn higher compensation elsewhere
  • You can get better employee benefits elsewhere
  • Quitting to pursue a different career field
  • Your current work environment is stressful or toxic
  • Your coworkers are regularly making you uncomfortable
  • You feel like you aren’t learning or growing anymore

It’s really important to be honest with yourself when thinking about your “why”. If you find that you’re just running away from your problems, quitting your job usually isn’t a great idea. Instead, find other ways to tackle those problems head on.

2. Should You Consider Staying?

Now that you’ve identified the reasons why you want to leave your current position, ask yourself if it’s worth staying at your current job if some of these issues were addressed.

It’s true that you can often make more money by switching jobs. The average wage jump for switching jobs is close to 15%, as opposed to the average annual employer wage growth of just 5%. But if you love your job but feel you aren’t being paid enough, you could try to negotiate a higher salary with your current employer before leaving. It might even be worth getting another job offer in order to gain some leverage. That might be just the ticket that encourages your employer to give you a more significant raise.  

You could also try negotiating for a better benefits package. Perks like remote work or a four day work week are worth asking for. All of these benefits could greatly improve your relationship to your current employer and the joy you derive from your work. If your employer truly has their hands tied, then at least you’ll know that you’ve fully explored your options.

3. What is your plan after quitting?

Sure, if you’re living at home with your parents, or have tons of cash saved up in your e-fund, you might not need to have another job lined up right away. But if you have bills to pay, it’s important to have a plan for what you’re going to do after you quit. 

Whether you already have a job lined up, are planning on applying for jobs, or are wanting to take your side hustle to the next level, it’s worth jotting down a few notes about what your days will look like after you quit. If you’re planning on quitting to pursue entrepreneurship, take the time to come up with a solid business plan before you put in your notice.

Having a schedule can help to give your days the structure you need to stay productive.

Should you quit your job?

4. Do you have an emergency fund?

If you’re planning on taking some time off after you quit, it’s important to assess the strength of your emergency fund. You’ll definitely want to do this before quitting your job and turning off the income spigot.

Having between 3-6 months of expenses stashed away before you quit can definitely be a good move. You’ll be covered in case it takes you a little longer to find a new position. And better yet, you won’t have to take the first job offer you get, because you have cash in the bank to hold you over.

If you don’t have an emergency fund saved up, we would seriously advise you hold off on quitting your job until you at least have 1-3 months of expenses in your savings account. You can jump start your emergency fund by tackling these 7 tasks that will help you save money this week!

5. What’s your plan for health insurance?

If you’re a part of the 54.4% of Americans who get their health insurance through their employer, you’ll need to figure out a new way to get health insurance. If you already have a job with benefits lined up, you’re all set! But if not, you’ll need to look into other ways to get covered. And news flash, it’s usually not cheap.

It may be tempting to forgo health insurance, as it is notoriously expensive, but that really isn’t a good move. Medical expenses are the number one reason for personal bankruptcy, so you definitely don’t want to skip out on having a plan for how you’re going to handle medical expenses. 

If you’re planning on quitting to become self-employed or to work part-time, you have a few options. If you have a spouse who gets health insurance through their job, you can probably jump onto their plan. But if not, you could try getting insurance through Healthcare.gov, which, thanks to increased government subsidies, has become more affordable for lots of folks.

Another option you can consider is getting a health sharing plan. Health Sharing Plans are organizations where members who share common religious or ethical beliefs all pitch in to share healthcare costs. 

It functions similarly to insurance, although it is technically not insurance. You pay an annual or monthly “share” amount based on factors like age, family size and health, and then your share payments go to help other members pay for their healthcare costs. 

A health sharing plan can be a great option for lots of families, as it’s typically much more affordable than insurance. However, it won’t work for everyone, so be sure to do thorough research on your own before taking the plunge.

6. Have You Worked on Building Your Network?

Having a strong professional network is like having an emergency escape plan. It’s crucial to have it ready before you need it. As our friend Jordan Harbinger says, “dig the well before you’re thirsty.”

Have you been taking the time to strengthen your relationships with the people in your network? Ideally, you’ll want to reach out to your professional contacts before you begin looking for new employment. No one wants to hear from you only when you need something! So treat them like people and stay in touch with them. Ask them how they’re doing and about any cool projects they’ve been working on. 

An easy way to maintain your network is to set a goal to reach out to one person each week, just to check in. That way, once you quit your job, you’ll have a ton of people who you’ve built relationships with who will want to help you. 

Remember that having a network isn’t all about getting something from others. Be sure to pay it forward and help out others in your network whenever you have the opportunity. That reciprocity is what makes it strong and impactful!

7. How are you planning on quitting?

Although in some situations it might be tempting to walk out of your office knocking over furniture and flipping the bird, it’s probably not a good idea to burn bridges. 

Even if you think your new job is your dream job, there’s no guarantee that you’ll be happier there. The grass isn’t always greener. And if you find yourself two weeks into your new job wistfully longing for your old employer, you’ll want to have a good relationship with your previous boss so you can ask for your old job back. 

It seems obvious, but when you quit, be respectful. And I know it’s hard, but don’t slack off during your last few days. Your coworkers will appreciate you setting them up for success after you leave.

8. Can you give more than two weeks notice?

With a new job lined up, sometimes it can be impossible to give a longer notice. But if you can, it can certainly help your coworkers to get organized before you move on from your current position. Especially if you have a good relationship with your coworkers.

Everyone talks about making a good first impression, but making a good last impression is important too. You never know where your old coworkers will end up. And one day they could have new and exciting opportunities to offer you.

9. Can you engineer your own layoff?

If your company is downsizing and you’re looking to move on, there’s a good chance you can engineer your own layoff!

Basically, you get to play martyr for your fellow coworkers by volunteering to get laid off. Your coworkers get to keep their jobs, your boss gets to look good to the higher ups for cutting that salary, and you get a pretty awesome perk– severance pay! 

Then, at your new job, you can even try to negotiate severance up front before you start your new position. That way, if you lose your job (or engineer your own layoff again), you’ll be able to use that lump sum of money to give yourself breathing room as you move on to bigger and better things.

10. Should you improve your skills first?

If you’re hoping to pivot industries, or even just move up within your current job field, it could be a good idea to spend some of your time learning new skills before you jump ship at your current workplace. That way, you can enjoy the perks of steady pay while ‘leveling up’ for your next chapter.

While you could take courses at a university, or participate in paid workshops for programming, remember that you don’t need to spend money to improve your skills. There are so many places to score educational freebies that can help you to learn and grow without spending a dime. Remember that your local library, and websites like YouTube can be a great resource for learning new things!

11. What will you do with your old 401k?

Nabbing a 401k with a company match is a great benefit to take advantage of. But what happens to your old 401k when you leave your current employer?

Leaving your old 401k where it is exposes you to unnecessary account fees. And this can eat away at your retirement earnings over the years. 401k plans also typically have limited investment options. Meaning your money might not be growing as efficiently as it could be!

That’s why we recommend rolling over your 401k to an IRA. Ditching those fees for an IRA with a low-cost brokerage firm can add up to a meaningful difference in your balance at retirement. I’m talking HUNDREDS of thousands of dollars!

We like and recommend Capitalize to help with this task. They are a FREE tool to help with old 401k rollovers. Consolidating all your old retirement accounts is also a good way to not accidentally forget about any savings! You wouldn’t believe how many Americans “forget” about old retirement accounts… It’s a lot!

The Bottom Line:

When done for the right reasons, quitting your job can be one of the more rewarding money moves you can make. It can allow you to chase your biggest career and money goals, and help you along your path to continuous learning and growth.

We hope these questions have helped to guide you to make a well thought out and informed decision! Be sure to check out these related posts for more advice on getting the most from your career.

Related Posts: 

Leave a Reply

Your email address will not be published. Required fields are marked *