1. What passions have you developed over time that you didn’t originally know you had?

2. Do you have a career plan? Should you scrap it?

3. For the next steps in your career, what curiosities might you consider following? What are the roles where you think you could learn the most?

4. Have you ever tried quitting on a good day rather than a bad one? What was it like?

5. How do you know what the right time is to leave?

6. What’s the worst career advice you’ve ever received? What conventional wisdom about careers do you think is wrong?

7. Whose career path do you admire most, and why?

8. When you start a new job, how can you make sure you go in with realistic expectations?

9. When you break your job down into different tasks, which ones do you enjoy most and least? Are there adjustments you can make based on that?

10. Do you have any unanswered callings? How have you incorporated them into your job or your leisure time?