My girlfriend and I hosted a tea tasting omakase at our home over the weekend. Three teas and tea pairings across a few hours, with activities mixed in.
Our friends really seemed to like the questions they were asked as part of our icebreaker at the very beginning of the tea tasting experience. So thought that it might be worth sharing for all of you, as, say, introspective queries that you might journal with. Call them journaling prompts. Or 69 questions to fall in love? The number 69 was not intentional, by the way.
The below are just a combinations of questions that I’ve liked over the years, questions I’ve heard from others that I liked, and questions I’ve personally come up with. If you’ve been around here for a while, you might see some familiar lines of queries from the podcast, this blog, and even my question-off with Kevin.
- 528 Hz is the love frequency. The miracle tone. The Solfeggio frequency — that very pitch — that certain songs are tuned to make you feel inspired and emotional. To take a different definition of the word pitch, was there a pitch or story you’ve heard in the past that inspired you to take action for seemingly unexplained reasons?
- If you could open a store and only sell one object that is meaningful to you, what would you sell?
- What’s the closest you came to breaking?
- What’s an adjective you would use to describe your relationship with your mom?
- It’s the last day of kindergarten, and you have the chance to walk home with the child you once were. What would you say to them?
- What is it you do that you use to give you confidence?
- What is a question you feel uncomfortable asking me?
- What’s something difficult you’re going through that people don’t often see?
- Is there a single question or a set of questions that has yielded you outsized returns when it comes to getting to know a person?
- Charlie Chaplin has this great line where he says, “Life is a tragedy when seen in close-up, but comedy in long-shot.” Do you remember a part of your career or life that seemed like a tragedy in the moment, but is something you laugh about now?
- What were some of your come to Jesus moments in the past few decades that your friends may fail to appreciate?
- I’m curious, as you one day age and start to slowly lose your memories, what would be the last memory you would hold dear?
- Has there been a habit or practice you’ve observed from a friend or colleague that you’ve worked into your own rotation?
- What does one need to understand about your childhood and early upbringing to fully appreciate the person you are today?
- If someone were to look at your calendar and only your calendar, what would they say your priorities are? What would you like to say are your priorities?
- If you could pick any of the lessons in your life to canonize in a time capsule, which two would you pick?
- Is there a routine or framework that serves as the scaffolding to how you think about life?
- What, if anything, do your friends/spouse/family often oversimplify about being you? And what, if at all, do they often overcomplicate?
- What’s the worst pain you’ve ever been in that wasn’t physical?
- What’s the one “what if” that keeps you up at night?
- What’s the biggest chance you never took?
- What or who have you given up on?
- Steve Jobs famously said that a typography class he took back in school was one of the most seminal experiences in his life and how he ended up building Apple. I’m curious, for you, was there a moment that you would attribute much, if not most, of how your mind works today?
- What do you think makes your partner so successful?
- In what ways do success fuel ambition and how might success damage ambition and hunger?
- When’s the last time you had a pinch-me moment?
- What talent do you have that you’re not using?
- What is the no or refusal you keep postponing?
- What commitments have you made that you no longer believe in?
- What is the gift you currently hold in exile?
- Is there anything you think the world is too dogmatic on? And in what ways are they too skeptical?
- What in your life before you turned 18 was most formative to the person you are today?
- If today, you could pick the age you’d pass away, assuming you’d be healthy the whole time, what age would it be? And why?
- What’s a system or game you’ve hacked in the past year?
- Can you think of a recent example where you said yes to something you shouldn’t have?
- What was your first failure?
- How did you know when to quit?
- If you were to put together the perfect human being piece by piece Mr. Potato Head-style, how would you go about it?
- 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?
- If all your writing, speaking, and ideas were erased from the internet, and you only had the next 60 seconds to impart your wisdom, what would you say to the world?
- There’s a quote from the show The Office. “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 reminders you keep close to your heart that today, we’re in the good old days?
- What was your earliest relationship with money?
- What is it you do to train that is comparable to a pianist practicing scales? Or a swimmer going to 5AM practice just to practice a single arm stroke?
- Do you see yourself as part of an intellectual heritage? Who is on your tree?
- When you have time to wonder, what’s the thought or idea you regularly find yourself coming back to because you find it so interesting?
- If someone who knows you well were to write a product review of you, what features and bugs would they list out?
- How much of your advice is a function of a glass half full? And how much of it is a function of a glass half empty?
- What is the greatest accomplishment that you regret having achieved?
- What is one major decision you’ve made where it was better to not overintellectualize the decision making process?
- 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 part of you is a mystery to you, the part of you that you least understand?
- What’s the most persistent myth people have about you that you’ve never bothered to correct?
- If you could pay a monthly subscription to be a fly on the wall of the life of one person, who would it be?
- When was the first time you had to be the adult in the room?
- How do you tread the terrain between doing what’s expected and doing the unexpected?
- What is your earliest childhood memory that’s so deeply imprinted in your mind that all else fails to compare?
- Which role have you taken on in your career made you the most nervous as a professional and what felt most immediately like home?
- If someone wanted to do some serious mudslinging, what is the least charitable interpretation of everything you’ve built, of everything you’ve done to date?
- There’s a great line by Soren Kierkegard. “Life is an ironic tragedy, it has to be lived forward but only makes sense in reverse.” For all the events and experiences that serve as building blocks of who you are today, what parts of that lore were more incidental than intentional?
- There’s a scene from the show The West Wing said by the late John Spencer who plays Leo, and the story he shares is: “This guy’s walking down the street when he falls in a hole. The walls are so steep he can’t get out. A doctor passes by and the guy shouts up, Hey you, can you help me out? The doctor writes a prescription, throws it down in the hole, and moves on. A priest comes along and the guy shouts up, ‘Father I’m down in this hole. Can you help me out?’ The priest writes out a prayer, throws it down in the hole, and moves on. Then a friend walks by, ‘Hey Joe, it’s me. Can you help me out?’ And the friend jumps in the hole. Our guy says, ‘Are you stupid? Now we’re both down here.’ The friend says, ‘Yeah, but I’ve been down here before and I know the way out.’ For someone who’s felt the growing pains of life, who were your friends who jumped in the hole with you?
- If you wrote a book where the first and last sentences were the same but had different meanings, what would it be?
- “What most people call authenticity is a costume for childhood beliefs.” I’m curious for you, what are the most seminal experiences you had and remember from your childhood that shape the way you interact with people today?
- There’s an interesting quote by Rishabh Gautam. “Waterfalls wouldn’t sound so melodious if there were no rocks in their way.” You’ve reached heights that most people can only dream of, but I’m curious, what were the rocks that stood in your way?
- What is one thing you believe in that most people would fight you on?
- If you could relive one of your career highlights as a semi-regular recurring dream, which one would it be and why?
- Would you rather relive your childhood or see the lives of one of your parents before you were born?
- There’s a really interesting quote attributed to Voltaire. “Change is annoying, but certainty is absurd.” What are you willing to be absurd about?
- George Bernard Shaw once said: “The single biggest problem in communication is the illusion that it has taken place.” Of all the quiet things that should be said aloud, what were/are your biggest offenders of the illusion of communication?
- What version of yourself do you miss sometimes?
- If your partner asked you, what’s one thing you sacrificed for me that I don’t know about, what would you have told them?
Photo by Michael Sten on Unsplash
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