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Home > Career Management20 questions that can take you from 'woulda coulda shoulda' to #GoOutAndBe

20 questions that can take you from ‘woulda coulda shoulda’ to #GoOutAndBe

20 Questions that can take you from -woulda coulda shoulda- to GoOutAndBe

Are you grappling with the fact that your professional life isn’t how you want it to be? Whether you’re in the early stages of your career or several years in, it’s not uncommon to feel unenthusiastic and unfulfilled about your chosen career path.

But waiting for someone else to come along and fix things, while you mentally debate what you ‘coulda shoulda woulda‘ done differently, isn’t a useful course of action. Instead, you need to find the motivation to take the lead and #GoOutAndBe the change you wish to see.

A great place to start would be to do some soul searching. Ask yourself some fundamental questions that will help you discover new things about yourself and the direction you want your life to take. Answer them honestly, so that you can objectively assess your situation and devise an actionable plan ahead.



These 20 questions can help you understand where you are in your career versus where you want to be, and identify a strategy to #GoOutAndBe:

  1. Do you have a dream?
  2. Do you believe your dream is realistic?
  3. As a college student, how did you visualise your life and career?
  4. What influenced your choice of career – your parents, society, personal ambitions or money?
  5. Do you want to be like your parents?
  6. Why or why not?
  7. Professionally, whom do you admire most?
  8. Are they passionate about their work?
  9. How important is it for you to love your job?
  10. Is the work you are doing today a reflection of your greatest strength?
  11. What do you want: more happiness or more authority?
  12. What challenge excites you the most in your life right now?
  13. Do you feel successful?
  14. Do you have clarity on what the next level is for you at your place of work?
  15. Is it thrilling for you?
  16. Do you feel confident that you are exceptional at something?
  17. When was the last time you took a risk?
  18. What do you like to learn?
  19. What advice would you give yourself today about where you are in your career versus where you want to be?
  20. What are the hidden insights you have learned about yourself from answering all these questions?

Knowing what matters to you makes it so much simpler to make your way to a job that you love doing. So figure out what you enjoy doing and what is important to you in your work (and life), and #GoOutAndBe a success!

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