I’ve been asked “Should I change careers” more in the last two years than in the last 10. The ability to be flexible with career locations, combined with personal job satisfaction has driven many of my friends to walk away from careers, thinking that the next position would fall into their lap.  And that has NOT been the case. This leaves some VERY talented executives on the bench waiting out the next opportunity ……….  Which is fine if you planned for it – but if you didn’t, I’m finding it’s leaving a lot of stress on individuals and families.  So before you pull your best Johnny Paycheck (everyone under 40 can google that) – check out the questions I like to ask over a coffee when meeting with my friends thinking about changing careers. 


Twenty Questions You Should Ask Yourself Before Changing Careers


  1. Am I dissatisfied with my career or only with my job? Could I find satisfaction in a related job within the same profession?
  2. Are the working conditions the motivating factor for a change?
  3. If so, could I change my environment or my attitude toward it, or is the only resolution a career change?
  4. Do I wish to express certain values on the job that can’t in my present occupation?
  5. Do I feel as though I could use more of my abilities and skills in another occupation?
  6. Do I have an understanding of my personality and the type of work environment I’d prefer working in?
  7. Do I know where my interests lie? What do I know about my career Interests?
  8. Have I taken an Inventory of my skills and know what my marketable/ functional skills are?
  9. Have I acquired new skills that I don’t have the opportunity to use in my present occupation even though I’d like to?
  10. Am I willing to make sacrifices to start all over in a new occupation, such as a salary cut? Are the people who are dependent on me also supportive?
  11. Can I enter my newly chosen occupational field/ career without retraining or future education?
  12. Will my functional skills transfer to the occupation I chose, or must I develop new skills?
  13. Do I have alternative plans or have I placed all of my eggs in one basket?
  14. Are there any ways that I can try out a new career without quitting my full-time job?
  15. Exactly what will I be giving up and what will I be gaining by changing careers?
  16. How Important İs my current job seniority, retirement fund, and other benefits to my welfare both in the short term and over the long run? Have I done some pencil and paper figuring or only daydreaming?
  17. Are there resources available in my community to facilitate my career change and to help ensure success?
  18. Do I feel that I have the patience to spend time in an entry-level position to reach my career goal?
  19. What small preparations can I begin today to help with my career change? Do I have a list of small, medium, and big goals?
  20. How willing am I to take risks – the risk of not being happy in my new career? Would I be willing to make another change if that happens?

There are no right or wrong answers. These were some of the pondering thought-provoking questions that I would ask my friends in a coffee meeting to help them think through their decision. I hope this list helped you think through your next big career decision.


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