About Me
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My Digital Brain/
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Questions Database

Questions Database

❓
Questions Database
Name
Tags
Where would I be if I were 3 times more courageous?
Personal
What are the emotions I’m afraid of feeling?
Personal
If money and status were no object, what would I do?
Personal
If I was less afraid of other people’s opinions, what would I say?
Personal
What is my definition of success if money was taken out of the equation?
Personal
What is the hidden price I’m paying for inaction?
Personal
What did it cost to be you?
Mentor
What is something most people think is important that I can skip entirely?
Mentor
What’s something important in your daily routine you wish you started sooner?
Mentor
What channels led to the development of your highest-quality relationships?
Mentor
What is something you did differently than your peers 5 years ago that led to pushback, but served you in the long run?
Mentor
What can I expect to struggle with along the way?
Mentor
What is something you believed 5 years ago that you had to “unlearn” to take the next step?
Mentor
What’s something you didn’t pay enough attention to early on, then had to learn the hard way?
Mentor
What is something you deeply believe but rarely live out?
Personal
The 4-part career question
Business
What would you do if you had no fear?
Personal
Who is a person I should be thanking/complimenting?
Personal
What is the most destructive habit in my life right now that I’m ignoring? What is the solution?
Personal
How can I be working on something that will last 100 years from now?
Business
Where is the third door that the industry is ignoring?
Personal
What metrics am I not tracking that I should be?
Business
Who/what exists in the shadow of my mind that is silently guiding my decisions?
Personal
Give an example of a time you upheld your integrity under pressure.
Interview
Tell me about the last hard conversation you had and how you handled it.
Interview
Tell me about a time you faced a major challenge and how you handled it.
Interview
What would it take to make this a yes?
Personal
What are you afraid of happening?
Personal
If I had $50M in the bank, how would my day-to-day change?
Personal
What are my 3 rules for success/happiness?
Personal
How will being anxious about this serve me?
Personal
Do I really need to answer this text or email right now?
Personal
Am I really happy? Or am I just really comfortable?
Personal
Am I really trying my best or am I just telling myself I am?
Personal
What is it that I can think of, read, watch, listen and talk about for hours on end without tiring of it?
Personal
If I had to describe who I wanted to be in 3 words, what would those words be?
Personal
What would it take to snap me out of my bad mood immediately?
Personal
What’s the first thing you think of when you wake up most days?
Personal
How do I want my life to be different in one year?
Personal
Is this project making me a better person?
Personal
What is a moment in our relationship that changed how you see me?
Conversation
What are you hesitant to ask me and why?
Conversation
What’s something you stress about but know you shouldn’t?
Conversation
What’s something you’d like to be remembered for?
Personal
Conversation
Do you live more in the present, past, or future?
Personal
Conversation
If you could pause time for one day, what would you do?
Personal
Conversation
What’s the worst software that you use on a regular (at least weekly) basis as part of your job?
Business
Who is the most high energy person you know?
Conversation
Business
If you could pick 1 person and you could have 10% of their future earnings - who would you pick and why? How can you adopt the skills, beliefs, and character traits of the person you picked?
Personal
Business
What do you have “unreasonably” high standards for?
Conversation
Personal
If I do [this], will I respect myself more?
Personal
What was that like for you?
Conversation
What’s interesting to you right now?
Conversation
Is there closure you never got to have?
Conversation
What’s the first thing you think people notice about you?
Conversation
What is the less-stressed version?
Personal
So what do you do with your money?
Conversation
Are you afraid of dying?
Conversation
What title would you give this chapter of your life? Why?
Conversation
What do you miss about your childhood?
Conversation
What movie has had the biggest impact on you?
Conversation
What job would you pick if money didn’t matter?
Conversation
What’s one thing about yourself that you hope never changes?
Conversation
If you are in a bad mood, do you prefer to be alone or be with someone to cheer you up?
Conversation
What one quality in others bothers you the most, and what does that say more about you or them?
Conversation
What is something you could never truly forgive yourself for?
Conversation
Is your perception of self closer to who you are or who you’d like to be?
Conversation
What would you rather change: your past or your future?
Conversation
What’s the biggest difference between who you are and who you pretend to be?
Conversation
How did you two meet?
Conversation
Assume you get paid $1M per year no matter what you do, but you still gotta work 40 hours a week. What would you pick to work on?
Personal
Conversation
When was the last time you had so much fun you lost track of time?
Conversation
What’s the kindest thing someone has ever done for you?
Conversation
What usually takes people a long time to figure out about you?
Conversation
What traits do you share/don’t share with your parents or siblings?
Conversation
What do you mindlessly collect?
Conversation
What outfit would you wear everyday if you knew no one would notice that you repeated it?
Conversation
What’s your fighting style?
Conversation
What would you do if you knew you’d be successful at it?
Conversation
What are you borderline overconfident about?
Conversation
What’s your long-term/end goal?
Conversation
Assume that more than one path exists to achieve your ideal life. What would some of the alternative routes look like?
Personal
Imagine you had a really great day at work and you're telling your partner all about your day. What is it that you're telling them?
Interview
Are you inventing things to do to avoid the important?
Personal
What feedback will I be giving you in your first performance review?
Interview
Tell me about a time that you delivered something that was impactful?
Interview
What’s something everyone believes that you disagree with?
Interview
Tell me about a time something went wrong? What was it and what did you do about it?
Interview
What would your sibling say about you?
Interview
Fast forward 3 years… what’s different about you then?
Interview
Would you rather… A or B? Why?
Conversation
Tell me something you’re really proud of?
Interview
Describe to me a time when you were a part of a controversial decision?
Interview
What’s the hardest thing you’ve ever done?
Interview
To what do you attribute your success? (And you can’t say ‘luck’)
Interview
What’s your strategy for learning?
Interview
Fill in the blanks with the first thing that comes to mind: Life is _____. People are _____. I am _____.
Conversation
Interview
What was the [core metric] when you started and what was it when you ended? What were the 3 things you did that most impacted that?
Interview
Ask a reference: On a scale of 1-10, what would you rate this person? What could they do to get to a 10?
Interview
On a scale of 1-10, how lucky do you think you are? Why?
Interview
Can you just screen share and show me your thinking process?
Interview
What can I do to make your life easier?
Conversation
Business
What is not being said that needs to be said?
Business
Personal
Where am I seeking comforting lies over inconvenient truths?
Personal
If you were writing the autobiography of your life, what would your next decision be?
Personal
What’s interesting to you right now?
Conversation
What’s one big thing you want to change about yourself?
Conversation
What’s something simple that makes you smile?
Conversation
How do I win, even if I lose?
Personal
Business
What am I missing that a more humble person might see?
Personal
How did you prepare for this job interview?
Interview
What’s your worst self sabotaging behavior?
Conversation
What’s something that’s always been different about you?
Conversation
What’s something you’ll never understand?
Conversation
What do you get most jealous about?
Conversation
Where can I reduce the friction?
Personal
How can I use my sawdust more effectively?
Content
What assets should I create this week?
Business
Do I have a skill set that will be useful 5 years from now?
Business
What problem have you solved this week?
Business
If there was one goal to commit yourself entirely to, what would it be?
Personal
Does this take me toward or away from my goal?
Personal
What is the transformation you provide to your audience?
Audience
What story am I telling my audience?
Audience
What core emotion do I want my audience to feel?
Audience
What core benefit am I delivering to my audience?
Audience
Would I genuinely read this or am I chasing the wrong incentive?
Content
What would you do differently if you increased your timeframe?
Business
Where could you work harder not smarter?
Business
Where am I approaching my business through a lens of scarcity?
Business
What non-creative, repetitive tasks are taking up your time (and how can you remove them)?
Business
If you had no fear, what steps would you take differently now?
Business
What is my business optimizing for?
Business
What area of my business is less than excellent right now? What steps can I take to improve it?
Business
What would my favorite entrepreneur(s) tell me to do next?
Business
What would my favorite entrepreneur(s) tell me I’m doing wrong?
Business
If I decided to reinvest my earnings, where are the best leverage points?
Business
What can I do to be different from my compteition?
Business
What is my competition doing that I can do better?
Business
What is my competition not doing and why?
Business
Over the past 2 years, what decisions led to the best results? Can I repeat them?
Business
Over the past 2 years, what decisions led to the worst results? Can I avoid them?
Business
If I could only get paid AFTER I got results... what would I be doing and who would I be doing it for/with?
Business
If I could only learn from 3 books for the rest of my life, what would they be and why?
Personal
What are the opportunity costs behind X decision?
Personal
What are the second and third order consequences of this decision?
Personal
How much time do I spend thinking & learning each day? How can I create more of it?
Personal
What makes me feel anxious? How can I do less of it?
Personal
What are my 5 core values?
Personal
What is my 1 year, 2 year, and 25 year vision?
Personal
If I had all the money in the world, what would I do with my life?
Personal
What gives me the most energy? And how can I do more of it?
Personal
What drains me? And how can I do less of it?
Personal
What actions do I do repeatedly that doesn’t align with the person I want to become?
Personal
How would I like to be spoken about at my funeral?
Personal
How can I complete my 2 year goal in the next 3 months?
Personal
What friendship have I let die due to being “too busy”, and how can I get it back?
Personal
How would my daily schedule change if I did a little more of what I'm great at and a little less of what I'm not great at?
Personal
If you could spend 30 minutes today creating whatever you want, what would you create?
Personal
What has been the best hour of my week? How can I make it easier to have more hours like that?
Personal
What can I do today to improve by 1%?
Personal
Are the results I am expecting aligned with the habits I am following each day?
Personal
How can I make situations more magical for those around me?
Personal
When was a time in the past you successfully adapted and made a change? What is a change you would benefit from making right now?
Personal
What can you do in the next 30 days to build momentum and finish the year on a high note?
Personal
How do I become so good I can’t be ignored?
Business
How can I use the negative experiences in my life to drive me? What fuel can I draw from my failures? What lessons can I take from my grief? What insights can I extract from my embarrassments?
Personal
The question is not, "Will I succeed?" but rather, "What should I attempt?”
Personal
What’s something good to "go a little overboard" on? What's something you could benefit from caring less about?
Personal
What’s true about my life today that would make my 18-year-old self disappointed?
Personal
How can I find the synthesis between education and entertainment?
Content
Are you being too passive or too aggressive right now?
Personal
Is taking things so seriously improving my performance? How can today feel like play?
Personal
What will happen if I don't do this?
Personal
What career would you realistically pursue if you wanted the most money? What career would you realistically pursue if you wanted the biggest impact? What career would you realistically pursue if you wanted to have the most fun? What career offers the best mix?
Personal
When was the last time you felt a sense of wonder and awe? What can that experience teach you about how to spend your time?
Personal
What important truth do very few people agree with you on?
Content
What’s my favorite way to fail? What am I willing to struggle for?
Personal
How can I make this process more enjoyable?
Personal
What am I saying no to by saying yes to this opportunity?
Personal
What do you want? What's the price? Are you willing to pay that price?
Personal
Where am I hunting field mice instead of antelope?
Business
What do you believe stands between you and complete happiness?
Personal
If you could write a note to your younger self of 10 years ago, what topics would you focus on?
Personal
What does a perfect day look like to you?
Personal
What’s something you thought you’d grow out of but haven’t?
Personal
What’s something you’re self-conscious about and how does that affect your life?
Personal
What’s something you’d like to do well, but never have been able to?
Personal
Are you willing to see how the opposite of your story might be just as true?
Personal
What do you love about yourself that has nothing to do with your money or success?
Personal
What’s something controversial today that you don’t think will be tomorrow?
Business
What have you been wrong about lately?
Personal
What are you optimizing your life for at the moment?
Personal
What are you good/bad at saying 'no' to?
Personal
What is no one else making?
Content
What aesthetic is no one capturing?
Content
What small details are up and coming?
Content
What would you be most excited to share?
Content
What are you seeing that no one else is seeing?
Content
What am I actually trying to achieve?
Personal
Does the amount of attention I’m giving this match its true importance?
Personal
Can my current habits carry me to my desired future?
Personal
How can I create an environment that will naturally bring about my desired change?
Personal
What game am I playing? Is it worth the prize?
Personal
How do I want to spend my days?
Personal
What is the work that keeps working for me after I stop working?
Business
What can I do today that will make life easier ten years from now?
Personal
Where am I taking shortcuts that may hurt me in the future?
Personal
How can I 10x the speed of my decisions?
Personal
How can I better listen to the wisdom of my body and emotions?
Personal
Where am I copying others that I don’t want to be or shouldn’t be?
Personal
For the things I want to get better at, have I been deliberately practicing or just going through the motions?
Personal
Am I making space for stillness, silence, and solitude?
Personal
What am I putting off? What would happen if I just did it now?
Personal
Am I sticking to the plan or am I letting life get in the way?
Personal
What’s the real goal here? Is there a better way to approach it?
Personal
Who do I need to connect with to gain access to the opportunities I want?
Personal
What if I did the opposite for 48 hours?
Personal
If I could only work 2 hours per week on my business, what would I do?
Business
Am I doing things just because everyone else is or because it’s the right for me?
Business
What if I created my own real-world personal MBA?
Personal
What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?
Business
What would this look like if it were easy?
Business
What challenge, personally or professionally, are you facing that if I helped you, could change your life?
Conversation
"If you accomplished your biggest goal, would it change your world or the world?"
Business
A chef invents recipes, puts new things together & creates new ideas. A cook follows recipes and does things that have been done before. Are you a cook or a chef?
Content
If you were to die tomorrow, what would be incomplete in your life?
Personal
Who’s playing chess when everyone else is playing checkers?
Business
What’s the most valuable place I can direct this attention?
Audience
If you could set a bootup message for your brain every morning, what would it be?
Conversation
Personal
Who’s having the most fun?
Business
In your professional life, who do you admire most? In your personal life, who do you admire most? How can you surround yourself with them more?
Personal
Business
What are you excessively curious about — curious to a degree that would bore most other people?
Personal
What could you not be paid a billion dollars to stop doing? What would you do if the only reward for doing good work is more work?
Personal
Business
If you could give a TED talk on anything, what would it be?
Conversation
If you crack open your YouTube right now, what are the 20 videos it recommends you watch next?
Conversation
What are you getting most excited about right now?
Conversation
What’s something you’ve changed your mind about?
Conversation
If you win at whatever game you're playing right now, would you be happy?
Personal
How many people do I admire that are actually miserable?
Personal
What would this look like if this was fun?
Personal
What are the hard things you’re avoiding?
Business
Personal
You can only keep 3 employees. Who do you keep?
Business
How is this person going to treat me when they have the opportunity to be selfish?
Personal
If life were a video game, whose stats would be maxed?
Personal
What do I believe is true only because believing it puts me in good standing with my tribe?
Personal
Is this thing I’m worried about actually a problem, or am I looking for problems to worry about because they make me feel in control?
Personal
What do I think is a universal truth but is actually just a norm unique to my own culture?
Personal
What was true a generation ago that no longer is, and who is clinging to that old truth?
Personal
Are there things going well in my life today that I will look back on and wish I had quit while I was ahead?
Personal
If someone could only see my actions and not hear my words, what would they think my priorities are?
Personal