1: Do you have any career “what ifs”? What are they?
2: How many months of financial runway do you think someone should have before quitting a job?
3: How long would you commit to a career pivot before deciding to continue or stop?
4: If your plan failed, how comfortable would you be asking your parents or family for support?
5: Which sacrifices would be hardest for you to accept: less travel, reduced income, or limited free time?
6: How long could you realistically tolerate a pay cut in exchange for long-term career fulfillment?
7: Do you think you’ll be able to pivot your career in a different direction?