75 questions to ask yourself before quitting your job

  1. What is my true opinion of my current job? Am I really unhappy?
  2. What can I do to make my job more enjoyable? What can I do to make my job more enjoyable? 
  3. Are there any other people in my life who need to vote on whether I am going to quit or stay in my current job? 
  4. Do I have a chance of advancing in my current position? 
  5. Do you have any suggestions on how I can explain my decision to my future bosses? 
  6. In addition to a paycheck, what exactly will I have to give up in return? 
  7. Would I be able to provide for myself by doing what I want to be doing instead? 
  8. What I want to do instead of what I am doing right now will I be able to provide for my family? 
  9. Is there a chance that a promotion would keep me at my current job? 
  10. Is my boss helping me to help him? 
  11. Do I do my best to get my bosses to notice me? Am I doing everything I can to get their attention? 
  12. Is my current job a good fit for my strengths? 
  13. What are my weaknesses as far as my current job is concerned? 
  14. Is there anything I can do to improve my weaknesses? 
  15. What can I do to enhance my strengths so that they stand out more? 
  16. Would I be able to live a life that I love if I took this job? 
  17. If I didn’t have my current income, would I still be able to live the life I love? 
  18. Is it possible for me to do something else in the meantime? 
  19. Could you please let me know how my activities fit into my resume if I choose to stay at home? 
  20. What is the frequency with which I decide to change jobs? 
  21. Is it accurate to say that most of the jobs I’ve had are pretty stable overall? 
  22.  Would you consider me to be a very patient person? 
  23.  What is the likelihood that I will have someone in my life who will help me if I want to start my own business? 
  24.  Is it possible that I am reverting to a simpler time in my life? 
  25.  Do you also feel that there is something else going on in my life that I am not in control of? 
  26.  Is it really important for me to pay attention to what the universe around me is telling me? 
  27.  Could you please tell me how my new daily routine will look like? 
  28. Do I have to wait for a long time to become established in a new career? 
  29.  Is there enough time to get established in a new career? Will I have the time to do so? 
  30. Can you tell me some things that I’m really good at? 
  31.  Can you tell me what lessons I have learned from my current job that will be useful for me in the future? 
  32.  I’ve learned that there are some things I’m not so good at and that I need to work on? 
  33.  Could you please tell me who would be my customers if I were to start my own company? 
  34.  Would my competitors be able to compete with me if I were to start my own business? 
  35. Are there any support networks available to me? 
  36. Is there a backup plan in place in case my plan does not work out the way I thought it would? 
  37.  What is the best way for me to leave my current job without burning bridges? 
  38. Do I feel abused in my current work environment? 
  39.  Could my current work environment be exploiting me in some way? 
  40.  Do you have any suggestions on how I could make my current work environment more manageable? 
  41.  Would it be possible for me to make my current work environment more tolerable by making some changes? 
  42. What kind of a plan do I have in place to help me achieve my dream job? 
  43.  In terms of my personal life, what are my ultimate aspirations? 
  44. In terms of my professional life, what are my ultimate goals? 
  45.  What are my chances of being able to live without benefits such as health insurance- at least for a little while? 
  46. Is it possible for me to live without benefits such as a retirement account for a period of time? 
  47. How can I reduce some of my expenses during the time I am between jobs in order to save some money? 
  48. When I’m between jobs, what are some things I can do to earn a little extra money while I’m trying to find a job? 
  49. When is the best time for me to contact you? 
  50. Would my friends and family be supportive of my decision to quit my job? 
  51.  If I quit my job, will I really be happier or will there be something else that needs to be changed? 
  52.   Is it possible for me to pursue another opportunity part-time without leaving my current job? 
  53.  Is there anything that I need to learn in order to be successful in my new endeavor that I am lacking at the present time? 
  54.  Could you tell me if there are any special skills that I need to improve for this new endeavor? 
  55.  Would I have a truly good, original idea to start my own business if I decided to do so? 
  56. Are you sure I have a business plan in place if I decided to start my own business? 
  57. Can I get the funding I need to start my own business – whether through savings or a loan – if I decide to begin my own business? 
  58. Have you ever thought about any potential unforeseen costs which could arise if you decide to start your own business? 
  59. Would I be willing to take on multiple roles until I become established if I had decided to start my own business?  
  60. Would I really be able to be my own boss if I were to decide to start my own business? Would I be able to maintain the discipline I need to succeed? 
  61.  What are the possibilities of maintaining my momentum if things aren’t going so well when I’ve decided to start my own company? 
  62.  Is it possible to make my current job work for me as I begin to make the transition into my new career path? 
  63.  If I were to quit my current job, what would be the best scenario? 
  64. How likely is it that I will be forced to quit my current job in the worst case scenario? 
  65.  If I were to leave my current job, what would be some of the things I would miss the most? 
  66. If I am to leave my current job, what are my plans for continuing to learn? 
  67.  Leaving my current position, what do I plan to do in order to keep growing? 
  68. In the case that I am no longer working for the company I am with now, how am I going to introduce myself? 
  69. The amount of time I have been with the company I currently work for is how long have I been with them? 
  70.  What is the length of time I’ve been working for the company I’m currently working for since I took over my current position there? 
  71. Are my emotions playing a role in my decision to leave my current job? 
  72.  During my previous employment with other companies, how long did I stay with them? 
  73. Can I maintain my current lifestyle while I’m searching for a job if I don’t already have another lined up? Will I be able to maintain my current lifestyle if I don’t have another lined up? 
  74. In the event that I am not already lined up with another job, how long will it take me to find a new one if I don’t have one already? 
  75. Have I discussed what is irritating me with my boss in order to try to find a resolution to this problem? 

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