I’ve given myself the last two weeks to focus on introspection. Rediscovering cross sections of my life – crystallizing them in amber – to find where I can improve the most in. And in the process of doing so, I found inspiration in. I’ve known for a long time that I was, by no means, the smartest person out there. Arguably, my best ideas find the roots of their ‘originality’ in insights from others. From…
- Friends
- Founders
- Investors
- Subject-matter experts (SMEs)
- Podcasts
- YouTube videos
- Academic journals
- Blogs
- And, really creative and really, really passionate people, where their passion is contagious.
… just to name a few.
But, that’s the best part!
Though it wasn’t my initial intention to do so, some of my favorite, most curiously introspective, most thought-provoking questions came from my guests during social experiments, particularly those who partook in Brunches with Strangers and Hidden Questions. Frankly, I can’t take credit for any of them. And just as I learned so much about them and myself from each, I hope you’ll be able to do the same. I don’t expect every question to resonate with you, but I suspect at least a small handful will. If so, my only ask is that you pay it forward in your own meaningful way.
Between 120+ guests between the two of the experiments, here are some of my favorite.
On Love and Emotions
- When was the last time you said “I love you”?
- When was the last time you wished you had said “I love you”, but didn’t or couldn’t?
- Who was the last person you lost in your life that hurt you deeply (i.e. breakup, death, loss of friendship, etc.)?
- When was the last time you uncontrollably cried?
- When was the last time you genuinely smiled?
- What emotion have you given an overemphasis on in the past year?
- When was the last time you were disappointed in yourself? Why?
- When was the last time you looked yourself in the mirror and thought “I’m killing it”?What might have sponsored that emotion?
On Lack Thereof
- Is there someone you pretend to like but don’t? If so:
- What is stopping you from sharing your thoughts candidly with them?
- What is stopping you from liking them?
- How many friendships do you regret having broken and never healed? Why?
On Candor to Others and Yourself
- What are 2-3 things you look for in a person/friend before you are comfortable sharing a secret? How would you prioritize those 2-3 traits?
- What are you dishonest to others about?
- Why do you lie to yourself?
- Over the past year, what have you gotten better at saying ‘no’ to?
- What are some contrarian beliefs you hold deeply to be true?
- (Also seen asked as) What is an unpopular opinion you have?
- Who have you told? Or have you told anyone else?
- If you could pass 1 value/trait down to your child(ren), what would it be?
- If there was 1 trait that you could prevent your child(ren) from taking on, what would it be?
- What is an unusual habit, or an absurd thing you love?
- What is the best lie you ever told?
- Do you believe it?
- What is the most hurtful comment you once said, wrote, or expressed to another?
- How often do you log on or log off of social media due to envy?
On Goals
- Do(es) your long-term goal(s) scare you?
- What’s the craziest thing you did for X?
- Let X be any goal you’ve once had (i.e. job, relationship, family, grades, to learn, etc.)
- What is something someone once said to you (good or bad) that keeps you motivated to this day?
- What failure has set you up for success?
- If you could title your own biographical movie, what would it be called? And what will it be called post-mortem?
- What is your 10-year goal?
- What’s stopping you from accomplishing it in 1 year?
- If I held you at gunpoint, and told you that you had to reach this goal in 1 month, what do you have to do, starting from now?
- If you could undo one decision you made in the future, what would that be?
- What would you like to have written/said in your eulogy?
Photo by Nijwam Swargiary on Unsplash
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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