1. What’s one thing you thought you would never get over – like a breakup, or a job loss, or a hard move – that you rarely think about anymore?
2. What’s one thing you have now that you never could have dreamed of having even a year ago?
3. What was your greatest ambition 3 years ago?
4. What was your greatest ambition 5 years ago?
5. What is one professional accomplishment you’ve already achieved that you used to think would be so great, you wouldn’t even think to wish for it?
6. What were the most worn pieces of clothing in your closet 5 years ago?
7. What did you think was a lot of money 5 years ago?
8. Where is one place you have traveled that you never thought you would?
9. What is the most significant piece of wisdom you’ve gained over the past few years that has changed the way you live?
10. In what ways are you embarrassed by how you behaved a few years ago?
11. In what ways have you changed to no longer act like that?
12. What everyday convenience do you have now that used to be a struggle 5 years ago?
13. Do you remember when you thought it was a big, spectacular deal just to live in your own space?
14. Or to be out of school and finally have a job?
15. Do you remember what it felt like when you first got the jobs, relationships, and advancements that you now have in your life – before they became normal?
16. Can you recall a few people whose opinions you used to worry about constantly, but don’t seem to really think about at all anymore?
17. If you could go back in time, what would be the one piece of advice you’d give yourself?
18. Would it be something along the lines of worry less, but keep going?
19. Yep, I figured. So why are you worried now?