One of my favorite questions as of late has been: “What is it you do to train that is comparable to a pianist practicing scales?” To me, it is fascinating to deconstruct a practice, or an action, or a set, and just drill on only one element of that practice. Every accomplished musician, athlete, veteran, chef, just to name a few, is uniquely familiar with the concept of repetition and refinement.
For example, part of my job, as now a podcast host, on top of doing research, prepping and making sure the guests are comfortable, getting involved in the editing room, just to name a few, is to ask questions. And because of the way I host Superclusters, my goal is to ask guests questions they’ve never been asked before. Admittedly, tall marching orders to those individuals whose job is to ask questions to get to the bottom of something in ways the recipients of their capital and their network may not expect. But alas I try. That said, I thought, how cool would it be if I could practice asking novel questions to someone who’s seen it all?
Admittedly, there are very few souls out there who would make great sparring partners for this drill. One that’s seen, heard, and thought of almost every known question out there. And even less I have had the chance to personally interact with. Of my limited Rolodex, luckily, the first person I asked was game. And that person happens to be this guy called Kevin Kelly.
The exercise would be, over a 30-day period, for me to ask him one question every day with the hopes that at least half are ones that he’s never been asked before. He then one-upped me and said he’d do the same. As such, it resulted in 60 queries that go beyond the obvious. While I’m not here to share the results of this “question-off”, I wanted to share the below as I hope this inspires you in ways that you might not have considered before. And if nothing else, fun journaling prompts for yourself. As such, I’ve bolded some of my personal favorites.
Kevin’s questions for me:
- What would you do with a billion dollars? (After you gave your family cars, houses, yachts, and vacations, you would still have a billion dollars.)
- Do you see yourself as part of an intellectual heritage? Who is on your tree?
- What is a prediction you made that was very wrong?
- What is the occupation that is the opposite of what you do?
- You get to relive one day of your past life. You could either return it as was at full volume, or you could change it. What day do you choose?
- If your life has a motto five words or less, what would it be?
- What significant law do you think should be changed?
- What do your friends get wrong about you?
- What influential person would you most appreciate a compliment from?
- What is something you can’t do that you’d give up 10% of your current wealth to do exceptionally well?
- What do you know more about than anyone else you have met?
- What is special about the neighborhood you live in?
- What question do you wish people would ask you?
- You get a 2-way ticket in a time machine. Do you go to the past or future? How far?
- What is a rule you gave yourself as a child that you still keep?
- What is the most recent thing you did for the first time?
- Who is a thinker more people should know about?
- What’s the strangest compliment you’ve ever received?
- What widely accepted “fact” do you think will be proven false in the next 50 years?
- What’s the most useless skill you’re proud of?
- What is one non-obvious piece of advice you would give to someone who wanted to get rich?
- They are making a film about you. What should the theme song be?
- What is a famous book you think everyone should read, but for a reason other than the one it’s famous for?
- What is something everyone you know of has done, but you have not?
- What is the most profound thing you’ve learned from a work of fiction?
- What is a popular piece of advice that you think is completely wrong?
- What part of you is a mystery to you, the part of that you least understand?
- What memory do you return to most often?
- What’s the most persistent myth people have about you that you’ve never bothered to correct?
- What’s a small thing you lost that still bothers you?
My questions for Kevin:
- What was your earliest relationship with money?
- Was there any specific groundswell in your early childhood and early life that led to the highest rate of change and growth? Were they largely technological, political or cultural in nature?
- If you had a billion dollars to create a secret society that will last 200 years into the future, how would you go about doing so and what would they be working on?
- As someone who’s used ChatGPT to write a novel you’ll never publish, yet has been an original thinker, thought-provoking writer for decades, what parts of your writing — no matter how far into the future, no matter how good the AI gets — will you never AI touch?
- One of the pieces of advice you once gave was to be able to learn from those you disagree with or offend you. Has there ever been a relationship that has most challenged the grounds of which your ideals stand on? How do situations that have led you to refine your ideals differ from those that reinforce what you believe in?
- If you were the main character of a movie about your life and you had an audience watching said movie, what would the audience be screaming at you to do?
- Kevin, you’re a futurist. You see the world beyond the horizon. But to take a step back, there’s a quote from the show The Office that I really like: “I wish there was a way to know you’re in the good old days before you’ve actually left them.” With all the doom and gloom around us today, what are the reminders you keep close to your heart that today, we’re still in the good old days?
- There’s so much gravitas and leniency given to a founder and their crazy ideas, but I’m curious, in your opinion, what were the greatest innovations at WIRED that weren’t a Kevin idea?
- Has there been a habit or practice you’ve observed from an interviewee of yours that you’ve worked into your own rotation?
- What, if anything, do your peers oversimplify about being a writer? And what, if at all, do they often overcomplicate?
- What was your first failure? How did you know when to quit?
- If you were to put together the perfect interviewer piece by piece Mr. Potato-Head-Style, how would you go about it? Who’s the researcher? Who opens the interview? Who’s the one in charge of going deep in questions? Who closes out the interview? Who’s responsible for the in-person interview setting?
- What is the question that has taken the most mental calories for you to answer? Why?
- You took a variety of roles across your career — some of which you’ve co-created and started, others you joined. Were “what’s best for the company” and “what’s best for Kevin” aligned the whole time?
- When you have time to wonder, what’s the thought of idea you regularly find yourself coming back to because you find it so interesting, but most of the world may not?
- What about your past do you desperately not want your children to know about?
- One of the great Kevin Kelly-isms out there is “Don’t be the best. Be the only.” How much time and discipline do you think is necessary for an individual to fully appreciate that they themselves are the only one doing something? At what point does it become part of their identity?
- As an enthusiast who’s been enamored by photography since you were in high school and took a deep dive into it in 1970, if you had a camera that could only take three photos total starting from today, what three moments would you photograph?
- When was the last time you adopted the habits, wisdom, or advice from someone you disliked or held very little respect for?
- What is an example of a mentorship relationship that you’re particularly proud to have your fingerprints on?
- What’s something others would believe you’d be highly proficient in, but no matter how hard you’ve tried in the past, you’ve found it extremely difficult to raise your skill level at that?
- What is it you do to train that is comparable to a pianist practicing scales?
- If you lived your life 1000 times, would would be true in 999 of them?
- What is the greatest accomplishment that you regret having achieved?
- What was the harshest piece of criticism you gave where you knew that that individual or project was providing more meaningful value to the world than your criticism gave it credit for?
- What coffee table books best encapsulate Kevin’s personality today? And would your coffee table have looked different today than in your 30s?
- If you could only choose 2 personality traits to pass on to your grandchild — 1 strength and 1 weakness, which 2 would you pass on?
- What was one major life decision you’ve made where it was better to not over-intellectualize the decision-making process and shoot from the hip?
- You’ve had a non-traditional path to your life and your career. The stuff that typically goes in movies. And in so much of what you do, you’re a dreamer. You’re a visionary. How much did they first pay you to first give up on your dreams? Why did you say yes or no?
- As someone who’s once recommended people to go to funerals, what is your biggest fear around what someone might say at yours?
Photo by Ahmet Yüksek ✪ on Unsplash