The Ultimate Questions to Consider Before You Quit Your Job

Be honest.   You are sick and tired of putting in overtime.   You feel undervalued working for your company.   You are at your wits end with work.   You know you can choose to Stay Where You Are. Look For Another Job. Or Be Your Own Boss.   In your heart you probably have an idea of what you want to do but you are just scared and just haven’t had time to really think things through. After all you’ve got bills to pay. It’s not so easy to just say ‘I quit’!   Kinda frustrating right? To help you out, here are the ultimate questions to consider before you quit your job. Let’s start with


Staying where you are


If you are considering this option, chances are there is a benefit you are enjoying at your current job that outweighs the negatives you are experiencing. Or else you’d be eager to make the effort to look for another job or be your own boss.


So find out what is this benefit and how important is it for you?


1. Is your current job a stepping-stone to get you closer to what you want to do?


Make sure the benefits and what you put into your job helps you gain the skills or time you need to progress to where you want to be.

2. Do you believe in the company and the mission of what it is about? Is it in line with your values?


Knowing your values are important. If you value family but have to consistently work overtime then you’ll feel stressed, as your values are in conflict.


Or if you value fun and creativity and the environment you work in is formal and conservative how satisfied will you be with your job? Or maybe your job offers fun and creativity but you have a manager that is serious and lacks imagination.


In these types of situations, understanding your values can help you figure out the next question.


*  If you are not already working at the company, trying to figure out how it really operates and if it lives up to its values is tricky  There are of course exceptions.  Nonetheless you may want to try and speak to employees (or, even better ex-employees who left on their own terms). Start by checking your LinkedIn profile see who you can find to reach out to.

3. What about your current situation frustrates you?


Is it your manager? Your co-workers? Your work hours? The commute time to work? Not being recognized? No room for growth and advancement? Identify what frustrates you so that you can make your decision accordingly to improve your quality of life.

4. What is it you want right now? What would be better than   what you have right now?


After identifying what you don’t want, ask yourself what is it you do want? Is it more time off, more freedom, more pay, less commute time, a nicer boss. How important is it to you to have what you want?


5. Can the company give you want you want?


Have you exhausted all your efforts and taken every action possible to ask for what you need and make your job workable?


6. Is there something left for you to do at work outside of your role?


Say you have exhausted all your options and you have decided to move on. You are currently staying in your job to buy time to bridge you to your next venture.


In your next venture you have this vision of doing something to add more value or meaning to your life and those around you.


Why wait?


Take a look now and see if there’s something left for you to do at work outside of your role that involves lighting up and lifting the mindsets of an individual or the culture of your organization.


Sometimes, we get caught up with the grandiose impact we want to leave, we forget that change starts within you, and that it starts one action at a time. The marks you leave along the way as you make a difference in a colleague’s life, or in an organization is what causes the ripple effect in the world.

Switch Jobs or Career Path?


For those of you who like what you do and is happy with being told what to do. You favor routine and your preference is to receive a steady pay-check along with other benefits but is looking to upgrade your job that is more aligned with your values and what you want then consider these questions.


  1. What are your career non-negotiables?  


This goes back to your values. What will make you content with your work life? Take some time and write it down. It could be money, respect, promotability, flexible schedule, being able to work from home, opportunities to travel. Psychology Today provides a great list to think about.


  1. How long will you need to secure a new job?


Finding a job that meets your non-negotiables is not an overnight process. So given the economy and other environmental factors how long can you stomach working in your current job?


  1. Identify skills and experience gap.


If you are looking to switch career paths or find a similar job but in a different industry, identify what current skills and experience do you already have and what other skills and experience do you need to successfully transition.


  1. What can you do now?


As you plan for your exit, what are things you can do to leverage your time and efforts to prepare you for your new role.


  1. Who can you network with?


Who can you share your decision with to help keep an eye out for you? Perhaps old colleagues who works in the same field, friends, placement agencies. Make a list and reach out!

Start your own Business


You may have started building your passion on the side or perhaps you haven’t started but it has always been on your mind. What is important is you need to be mentally and business ready.




Because starting a business is not for everybody. It takes time, persistency, not being afraid of failure or uncertainty. Being able to roll with the punches. Hard work and self-discipline. You need to hold yourself accountable and be okay with not receiving a steady paycheck. You may also be working more than you use to but the difference is you are in control of when you work, what you want to work on and how much you work.


So let’s do a check in before we go any further.


  • Do you really have a burning desire to start your own business venture?
  • Are you willing and able to forego temporary financial loss, health insurance and other benefits
  • Does pursuing your dream mean more to you than job security?
  • Do you really have what it takes to do whatever it takes to make it work?


If you hesitated in answering yes to the questions you may want to hang tight before jumping into entrepreneurship. If you answered with an emphatic yes to the four questions, keep reading.


So mentally you feel ready, let’s get to the questions that will help lay the foundation for your success.


The smart thing to do before quitting and deciding to start your business on a whim is to keep your day job, stay gainfully employed and do your due diligence first.  Research, network and develop a strategy. As Derek Sivers (Founder of CD Baby) said,Change careers like Tarzan. Don't let go of the old one until the new one is supporting you. And make sure you don't lose momentum.”


1. What is your ideal vision for your business?


Go back to the basics and do a little research. Can this dream of yours pay your bills? Are there other businesses that exist? Network and talk to people about your idea, find out if your passion business idea fulfills a market need? It’s a business you are going to be running after all and you can only be financially successful if it addresses and fulfills your client’s desires.


Once you’ve identified that there is a need for your services and your idea is profitable.


2. Do you believe in yourself and your ideas? This one is from Richard Branson's Entrepreneur Quiz

3. What do you need in place before you feel comfortable and confident to making the leap?

4. How can you maximize the benefits you’ll receive before quitting your job?


You need to create a plan to make your dream a reality.


5. What are your specific goals and targets?

6. What skills (if any) do you need to bridge the gap?

7. What’s your plan to get you to where you need to be?

8. What are your specific action steps?

9. What can you do now while you prepare for your exit?


Looking at your financials


10. How much money do you need to have saved before you can safely quit your job? General rule of thumb is at least 6 months with a 10-20% cushion for emergency related items, plus other costs you expect to incur as you start up your business.

11. What kind of things and expenses are you willing to cut back or forego during transition?

12. How much do you need to cover your monthly expenses?


Create a budget and savings goal to reach this number. Track your progress. Stick to it


13. What is your realistic timeline for these steps?


Pick a date to realistically quit your job. Mark it on your calendar making it real but also know it can be changed at anytime depending on circumstances etc.


14. What does your family think?


If your family and those who matter to you are not fully on board behind your pursuit in your dream, it will strain these relationships.


15. What can you do to make your family be more comfortable and confident during the transition?

16. Who has successfully done what you want to do? Who can you talk to?

Research and start following people on social media who has accomplished what you want to do. Reach out to help you navigate your journey as you create what works for you to succeed.


17. What if things don’t work out, what is your Plan B? What is your back up?


You have got a plan in place. And you have decided to give yourself _____ months to dedicate to your business in hopes you will generate income by month _____, it’s still important to have a contingency plan (just in case something comes up), especially if you decided to quit your job and you need more time.


Often what causes people to give up on their pursuit is seeing their financials dwindle. So if you decided to quit your job to solely focus on building momentum in your business and things are taking longer than you thought, you may have to consider taking on a part-time job to pay the bills. Or think of other creative revenue generating options temporarily, as you keep the momentum going.

Quitting a job to pursue your dream to start your own business is a big decision and is not a breeze.


But you already know this right?


You also know that you’ll likely have to make personal sacrifices in order to ensure your business is a success.


But in the end the hard work you paid upfront to redesign and create a life you want will be worth it.


You were put here for a purpose. The purpose is to be useful, to live well and make a difference in the lives of others. Once you found what you love to do, the purpose is to share it. The world awaits your gift.


So start now. What are you waiting for?



If you enjoyed this article you may also enjoy the What excuses are keeping you stuck at your job?

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  1. Hi Theresa,

    I love this list of questions. I even feel like if you weren’t sure if you want to stay at your job or not and you asked yourself all of these questions, you might end up with more of a solid sense of where you stand.

    I feel like many people are unclear about their own motivations, maybe because of pressure and duty? Not sure. But clarifying questions like these can be a big help.


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