My son, who is 13, and I were driving to soccer practice. We were talking about the team and the season. I think he was playing Clash of Clans on my phone so his contribution to the conversation was pretty much single words. Then he looks up and asks, “What’s it like in university?”.

It’s a reasonable question. But there are many layers to that onion — relationships, education, experimentation, finding limits, mistakes, successes. There is a lot there.

The onion analogy applies to almost any aspect of life, really. Once you start asking questions, like a little kid incessantly asking “Why?” (←warning it’s Louis CK. Bad language. But, funny), you can get pretty deep, pretty quickly.

The 5 Whys is also a successful problem solving technique and part of the Lean Startup methodology, if you are interested.

My son’s question got me thinking about the conversations between parents and children. How much do we really communicate? By “we” I mean me but your experience may be similar.

There are the day-to-day discussions about their school, friends, music etc. Sometimes a situation comes up and we need to talk through how to deal with it, or praise them for how they handled it, or point out how they could have handled it better.

But how much do kids know about us and our story? How did we get to where we are today? What would we do differently in life? What are the most important things we have learned? If you screwed up, then that is a perfect opportunity for a discussion around “I did this. It sucked. I don’t recommend it.”

Most likely they don’t know what questions to ask, or they feel uncomfortable about it if they are thinking it. We will need to be the catalyst and start the discussion.

The 50 things.

I roughly organized them by themes. Obviously, it can’t be exhaustive and not all of these apply to everybody’s situation. Some questions are easy and some are hard. I’m sure you can come up with many more insightful things to talk about. If you want to.

Childhood
1. Who was your best childhood friend and why did you like them so much?
2. What was the most trouble you got into as a kid and why?
3. What is your earliest memory?
4. What kind of relationship did your parents have?
5. How did their breakup affect you? (if they broke up)
6. What childhood moments stand out as the happiest for you?
7. What was your favorite thing to do when you were their age?
8. Were you comfortable or nervous around other people when you were young?
9. What teachers did you like the best and what made them special?
10. Are you in contact with any friends from your childhood?
11. Was high school fun for you?
12. Were you one of the cool kids, or did you feel like an outsider?
13. Did you ever drink or do drugs?
14. Did you ever drink and drive?
15. Did you ever get into a car accident? How did it happen?
16. Did you go to the prom? What are the details?

College
17. What was your first day of college like?
18. Why did you decide to go to that college? Would you recommend it?
19. Did you live on campus or off campus?
20. What did you like / hate about your roommates?
21. What classes did you take?
22. Why did you choose those ones? What were your favorites?
23. Did you ever cheat on an exam or paper?
24. What tips do you have to get the most out of college?
25. Based on your experience, should I even go to college?
26. Other than the classes, what lessons did you learn in college about life?
27. What did you do in college that you are most embarrassed about?

Work
28. Did you have a job when you were younger? What was it like?
29. Did you get along with all your co-workers?
30. Describe what your boss was like?
31. What would change about working when you were younger?
32. What was your first job out of college? Did you like it?
33. What was the best and worst things about it?
34. How did your college degree apply to that job?
35. What other jobs have you had since then?
36. Which ones did you love / hate and why?
37. What have you learned about working with other people?
38. What should I know about being successful in a job?
39. Should I start my own business?
40. What have you learned about being an entrepreneur?

Relationships
41. Who was your biggest crush when you were young? Did they know?
42. Who was the first person you kissed and what was the circumstance?
43. Did you have a real girlfriend / boyfriend in high school?
44. What kind of stuff did you do together?
45. What was the biggest relationship mistake you have made?
46. What have you learned about dating?
47. What do I need to know to have successful relationships with friends?
48. What do I need to know to have a happy marriage or relationship?
49. How did you get along with your parents when you were young? Is it different now?
50. What would you change about your relationship with your son or daughter?

So, how many have come up in conversation? If you are like me, there are many (many) that haven’t. I could blame some of it due to their ages (12 and 13) and some of the topics require a bit more maturity. Mostly, I think it is complacency on my part.

Don’t keep it a secret.

I think we can lose perspective on the breadth and depth of our experiences, and the impacts they had on us. All those failures and triumphs shouldn’t be a secret. They were hard work.

A single golf clap? Or a long standing ovation?

By clapping more or less, you can signal to us which stories really stand out.