Important Questions You Need to Answer Before You Quit Your Job

Finding a balance between financial wellness and workplace happiness can be tough. Most people spend their lives in an endless search for that career sweet spot. But when our plans aren’t working out, we think of quitting as our go-to option for finding something better.
Before you take the ultimate plunge and quit your job, you must weigh many appropriate scenarios. Some you might have already considered, while others, such as No. 7 on our list, aren’t thought of until you face your boss.
Either way, emotions should only play a partial role in your decision to quit your job. These 16 questions will help ensure you’ve considered all the potentially damaging outcomes before reaching the point of no return.

1. How will I talk about it with my spouse?

woman with head in hand at her desk
Discuss the subject before you quit your job. |

It can be a touchy subject approaching your spouse with the wacky notion to quit your job. Either your partner in crime will be supportive of the endeavor — no one likes to come home to a cranky pants every single day — or worried about what this would do to your overall financial picture. Regardless, quitting and making a massive career pivot is a big deal. Make sure you talk about it beforehand and come to a comfortable mutual agreement. It’s best to discuss this once armed with a proposed new course of action for the future.
Next: What about the finances?

2. Can my family afford to live on 1 income?

family at dinner table
Make sure you can afford to quit you job. |

It might be tempting to throw in that two weeks’ notice without a second thought, but with a family to consider, this would be unwise. Most families rely on two incomes to get by. Your job might have the better benefits package or fund the daily living expenses you count on. Single people don’t need to account for other family members who depend on them, but they do need a steady source of income to survive on their own. Ask yourself whether you can afford to quit. Should you quit without having another job lined up? Don’t resign without knowing the answers to these questions.
Next: See how drafting a pro/con list could help in the decision-making process.

3. What do I like about the job?

good job sign
There have to be some positives to your job, right? |

Can you think of a few things you actually like about your job right now? Is it building relationships with clients or even the benefits package available to you? Be honest and thoughtful here. Try making a pro/con list to see the bigger picture. Answering this question truthfully is quite important, as these will be the qualities you want to replicate in your next venture.
Next: Figuring out what you don’t like about the job is the easy part.

4. What do I dislike about the job?

Tired overworked freelancer working with a laptop
Understanding what you like and don’t like about your job can make the search for a better one easier. |

Figuring out what you like about a position might be daunting, but if asked you probably could fire off about 10 things you can’t stand about your role. That’s the easy part. The harder task comes with figuring out how you’ll take both your likes and dislikes and morph them into a stable career. Many people skip over this step, looking to get to the next position immediately. But without a few clearly defined long-term goals, you’ll just aimlessly wander from position to position with no target in sight.
Next: Are you just giving up?

5. Have I made an effort to remedy any situations clouding my judgment?

sad man in car
Have you wallowed in silence or made an effort to fix the problems at work? | 20th Century Fox

Let’s say you do actually come up with a compelling argument to quit. Your boss has no clue about the definition of a work-life balance, or the possibility of a clearly defined role is merely a pipe dream. Before you quit, ask yourself whether you’ve made any attempts to resolve these issues. Does your boss know about your concerns, or have you simply wallowed in silence? Don’t make a rash decision without trying to repair it first.
Next: Why you should consider your next steps now.

6. What’s my game plan for the future?

sign board saying 'Dream Job This Way'
Have a plan in motion before quitting. |

No, this question is not too obvious. Often in a blind haze, many job searchers forget to actually outline a plan of attack for the future. Maybe you have a solid business plan drafted for your new venture or have already solidified a few contacts in your desired field. If you’re lucky, there’s another position waiting for you should you muster the guts to resign. Either way, a solid game plan moving forward makes everything manageable during such a tumultuous time.
Next: But what if they ask you to stay?

7. Would I accept any likely counteroffers to stay?

Tommy Boy
Would you accept a counteroffer? | Paramount Pictures

In a fit of panic, some bosses will grasp at straws to get you to stay with a seemingly enticing counteroffer. Think long and hard about whether this is something you’d want. If it’s money or some other tangible thing that’s influencing your decision to quit, then accepting this offer might be a good idea. But most of the time, accepting will only put off the inevitable misery you’d feel months later by staying and failing to start something new. Worse, your boss might resent you for forcing his or her hand on such a thing, which is why many experts advise against counteroffers.
Next: Before you actually quit and move forward, you’ll want to consider these common obstacles.

8. How will I explain my resignation to the boss?

Co-workers in The Internship getting laid off
Know what details you will and won’t share with your boss. | 20th Century Fox

Your boss will likely ask why you are quitting. It’s OK to say why — just keep it positive. It’s better to act gracious and be brief in your explanation. Decide ahead of time how you want to play that conversation, so you don’t panic under the pressure. You should also determine whether to divulge what the other company is offering you (because your boss will want to know if planning a counteroffer). If you’re dead set on leaving, know you are under no obligation to report that information.
Next: Avoid the impending media frenzy.

9. Which family members do I tell first?

Three happy friends talking and drinking coffee
Consider nosy family members who could ruin your professional plans. |

The cat’s out of the bag. Whom will you tell first? Surely Mom will worry, and Pops will think you made a rash decision. Your spouse (hopefully) already knows. But it might be best to wait to tell extended family until it’s official. Some family and friends should remain clueless until the deed is done. You don’t want the gossip mill ruining your attempt at professional courtesy.
Next: What does Richard Branson and bridges have to do with anything?

10. How will I avoid office rumors?

man telling secrets
The office rumor mill can get pretty hectic. |

Your curious co-workers will likely fish for details on your departure once they get wind of the news. Just like you handled your boss, you’ll want to practice the same positive and brief responses that will help cut off the rumor mill at the source. But there’s no need to be standoffish in this scenario. Make an effort to keep in touch with co-workers by collecting personal contact information and then actually using it later. Richard Branson advises to build bridges rather than burn them, as we never know what the future holds.
Next: Secure those recommendations before it’s too late.

11. Who will give me the best recommendation?

career coach and job seeker
Recommendations can make or break your career. | Paul J. Richards/AFP/Getty Images

Whether your recommendations are handwritten or posted on LinkedIn for all to see, you want to make sure they speak highly of your qualifications. Who you ask to speak on your behalf is a decision you must not take lightly. Should you even ask for one from this company? Depending on your relationship with your co-workers and superiors, you might want to hold off. Recommendation letters aside, this boss will definitely be contacted from representatives in your next position for a reference, so never leave on a chilly note.
Next: Here’s how not to quit your job.

12. How will I go about actually quitting?

know when to quit
Walk away the right way from a job. |

No matter how much your boss, co-workers, clients, or supervisors deserve rage, always resign with poise and dignity. We suggest no blazes of glory or epic mic drops in this scenario. Yes, it’s tempting to make a grand and dramatic statement upon leaving, but word will get around about your show. And that kind of bad rap will follow you everywhere.
Instead, figure out how you’ll move on with grace and professionalism. That could mean giving more than the standard two weeks, drafting a polite resignation letter, and scheduling an in-person meeting with your senior to discuss your transition. Also, a nice thank-you letter goes a long way, too.
Next: How will you transition out of your position?

13. How can I make the transition easier on the team?

co workers
Figure out how you’ll make a smooth transition from one job to the next. |

Yes, your brain might already be consumed with your next venture, but try to make every conceivable effort to wrap everything up in a tidy bow before leaving for good. Whether it be transferring important files off your work computer (more on that later), training a successor, or tying up any loose ends with your account contacts, a smooth transition will help ensure you leave behind a positive reputation and little semblance of bad blood.
Next: What does your employment contract say?

14. Are there any contractual obligations?

Businessman signing papers
Will contract clauses affect your resignation? |

A fluid resignation could come to a screeching halt if you fail to consider the details presented in your initial employment contract. Before verbally committing to anything, confirm your future plans won’t get derailed from employee-specific clauses in your contract. This could be things, such as a non-compete clause or asking employees to leave immediately without notice (due to competing trade secrets). Prepare yourself for any potential roadblock during this time of transition to make the move as easy as possible.
Next: See how to effectively deal with souring relationships during your last weeks on the job.

15. How will quitting affect my remaining time here?

networking, office, coffee, coworkers, business
Once you quit, you won’t be very popular at the water cooler. | Thinkstock

When your work buddies realize you’re leaving, your relationship with them will change. Your boss might feel surprised and upset, and your co-workers will react with various emotions, from jealousy to bitterness to relief that you’re out of the picture. Before actually quitting your job, think about how you’ll deal with these likely scenarios. You might be excluded from meetings containing confidential company information you were once privy to. When that happens, stay cool. You’re on to bigger and better. Don’t act like a baby for not being in the “cool kids club” anymore.
Next: See one absolutely imperative question people often fail to ask when quitting their job.

16. What information will I need to take with me?

Payroll concept image of a pen
Never leave any money on the table. |

Before you start dreaming of the vacation you’re embarking on in between jobs (which is a good idea, by the way), you’ll want to show your workplace technology and financial accounts some love. Get all those personal files that have found their way into your professional computer before they ask for it back. Note: This is critical to do before they get wind of your pending departure.
Also, consider transferring your money, as well. Figure out how to get your 401(k) contributions and any other payouts before you part ways. Retirement is no joke, so don’t leave any money on the table.
Follow Lauren on Twitter @la_hamer.