50 Career Discovery Journal Prompts

I love using journal prompts to explore challenges and things I want to change in more depth, so here are 50 journal prompts that will help you to dig deep and discover what you want and don’t want from your career, what matters to you and generate ideas for moving in the right direction.

Use these questions to empty out all your thoughts and feelings about your career onto paper so you can understand yourself and what you want better.

  1. What does success mean to me?
  2. What would I do if I had no fear?
  3. What would I do if money was no object?
  4. Do I believe I’m on the right path?
  5. Am I doing what matters most to me?
  6. What do I want to do that I’m afraid of?
  7. What is my secret ambition?
  8. What childhood dreams have I neglected?
  9. How did I like to play as a child? What were my hobbies?
  10. My ideal job would be…because…
  11. What one goal would I like to achieve in my career more than anything?
  12. Why does that goal matter to me?
  13. What one thing would take me closer to my goal?
  14. What do I need to learn or do to reach my goal?
  15. What has stopped me achieving my goals in the past?
  16. How would I like things to be different in six months?
  17. How would I like things to be different one year from now?
  18. How would I like things to be different five years from now?
  19. What difference do I want to make in the world?
  20. How do I feel about taking calculated risks?
  21. How do I feel about routine work?
  22. What can I do well?
  23. What have I accomplished, big or small, that I’m proud of?
  24. What are my strengths?
  25. What do I enjoy helping people with?
  26. How do I feel about working alone?
  27. How do I feel about working with a team?
  28. How do I feel about working on something independently?
  29. How do I feel about collaborating with others on a project?
  30. What is my preferred role when I’m working in a group?
  31. What are my ideal working hours?
  32. How much income do I need?
  33. What would my ideal workplace be like?
  34. What would my perfect work day look like?
  35. What kind of people would I prefer to work with?
  36. What values do I think are non-negotiable at work?
  37. What have been my favourite parts of jobs I’ve done?
  38. What have been my least favourite parts of jobs I’ve done?
  39. What skills or traits have people complemented me on?
  40. When do I feel at my best at work? What’s happening at the time?
  41. What interests me the most in work I’ve done?
  42. What do I do – or have done – at work that I find draining?
  43. What skills do I want to get better at?
  44. How could I fill these skills gaps?
  45. What bad habits do I have at work?
  46. What good work habits do I have?
  47. What new good habits would help me at work?
  48. How do I like helping my colleagues or clients?
  49. What are the biggest sources of stress for me at work?
  50. What could I do to reduce stress at work?

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