If you think for one second you can ask me anything, you’ve got another thing coming. Now, if I can get a word in edgewise or otherwise or not too wise at all, I would like to ask you a few leading questions. If I may, and I may indeed!
- What will be your biggest future regret?
- If you had to move at least 100 miles to live for at least 10 years, where would you go? You don’t get any adjustments to your life (standard of living or otherwise); you are just relocating at your own expense.
- Will any of us travel to outer space (defined as being beyond the Kármán line, 62 miles of altitude)?
- Why and in what ways do you seek the approval of others?
- Would you rather be 10% smarter, 10% healthier, or 10% more athletic?
- What is the most limiting factor in your life?
- If you have one, what is your Sword of Damocles?
- What makes you special?
- What was your “closest call”?
- What do you find to be magical?
- What is the most overrated vacation experience? Why?
- How much more do you expect to learn from here on out?
- What is something I am doing very wrong? In execution or morality/ethics–you decide.
- If you could change or institute a social norm, what would it be?
- Do you laugh enough–have enough laughter in your life? If not, why not? Is it your fault?
- Which do you value more and why: surprise or meeting expectations?
- What is a problem you experience regularly that you have no idea how it could be solved?
- What is a personal setback that has changed you for the better?
- What is a controversial position you confidently hold that is important?
- Suppose I offer this: Pay $20,000 to instantly know any hobby or skill at a near professional level but remain incapable of profitably making it a career while being obsessively devoted to its pursuit…what if anything would you choose?
- At a concert what is the optimal mix of classics/hits to new stuff/obscure songs?
- What are your blind spots (intellectual, emotional, spiritual, etc.)? What are mine and other Fribrarians?
- Kevin, it turns out you have a terminal disease. You have 10 days to live. Also, you have a large financial debt you previously were unaware of. The good news is you will be completely symptom-free before suddenly dropping dead. I have a proposition for you for your last days. Would you rather have an all expenses-paid trip to Vegas (up to $10,000) and I can give you a pill that can cause you to forget knowing the disease diagnosis or would you rather me pay off the debt?
- If you were given the equivalent of having $10 million today in Oklahoma, what foreign country would you choose to spend the rest of your life in?
- What is the probability that intelligent, extraterrestrial life exists currently in our galaxy outside of earth? What is the probability that intelligent, extraterrestrial life has visited earth at any point?
- How many phases have there been in your life–distinctive periods that are meaningfully different than each other in total even if the transition between them was quite blurry?
- What is the least amount of money that if you lost it, you’d still feel sick about it a week later? Is this amount higher or lower than you’d like it to be?
- Who are you resentful of?
- What do you not have that you wish you did?
- What do you want the Fribrary podcast to be including what do you not want it to be?
- Kevin, the war in Afghanistan has finally ended. Having served there in active combat, what are your thoughts?
- Josh, Han shot first—what is your view?
- Lucas, what is the best Pearl Jam lyric?
- Close your eyes. Image for a moment a terrible event: a very small asteroid plummets to Earth striking this bar. All people within 100 yards are killed except for one. Raise your hand if you image yourself as the survivor.
- Kevin, when did boxing peak? Will it ever be as good again?
- Which are there more: wheels or doors? What counts? What does not?