1. Do you still feel like you’re learning something new every day, or do you feel like your job has just plateaued into a predictable and rigid situation where you do the same exact thing every day?
2. If you are learning something new every day, does that make you happy or are you resistant to it?
3. When people ask you what you do, are you comfortable talking about it (even if work is particularly stressful at that moment) or do you dread answering the question?
4. If your families’ and friends’ opinions about your career were going to be ‘supportive’ and ‘proud’ no matter what you do, would you still stay in this same line of work or would you choose something else?
5. If you’re in a career path now that is way different than the one you always thought you’d end up in – does this piece of knowledge make you happy and grateful or does it make you depressed and disappointed?
6. When you feel anxiety about work, is it a situational anxiety about all the things you have to get done, or is it a more broad anxiety about your overall path that can’t be solved by simply working through a to-do list?
7. What are the three things you most look forward to at work?
8. Are these three things focused on the work itself and particular tasks that you enjoy doing, or are the three things you look forward to solely related to vacation, time off, clocking out each day, etc?
9. If you could be promised another job in an entirely different industry than where you are now, and it paid $5,000 more, would you walk away from your current job?
10. Do you ever have days where you are actually excited to wake up and go in to work, or are you always, always full of dread and misery 5 days a week, 52 weeks a year?
11. If you could give advice to your 5-years-younger self, what sort of advice would it be? Would it be more about preparation and helpful tips for handling the real world, or would it be very specific directions about how to do things completely differently?
12. Do the challenges you experience at work make you feel energized, invigorated, and proud of yourself (even when they’re difficult and overwhelming), or do these challenges only make you feel stressed out, panicked, and constantly on edge?
13. How much does your career affect your physical health? Do you sleep well or are you constantly up at night worrying about your job? Do you try to stay relatively active or do you avoid exercise because you’re simply too burnt out? Do you work hard to put relatively healthy food into your body or do you tend to turn to food as a distraction from your unhappiness and/or stress?
14. Are your recreational activities more focused on trying new things and enjoying yourself outside or work, or are they more about providing you with temporary and pain-numbing distractions until you have to go back into the office?
15. If you could go back to school tomorrow with no financial repercussions, would you choose the same/similar major or something that is entirely unrelated to your current field?
16. Do you try to do things well or do you just try to get them done and out of your way?
17. Does your work ever excite you (even if the work itself is objectively not that interesting) or has it permanently become dull, uninteresting, and colorless to you?
If most of your answers to these questions were the latter option, it might be time to have an honest talk with yourself about your career.