Do you know your true limits and do you kiss them?

Deep questions

In the last few years, I’ve collected many deep questions.

I also tried to avoid traps. Let me give you an example. ‘Am I truly capable of love?’ is a false equivalent of ‘Do I love you or do I lie to avoid being lonely?’ Yet, no one will sell a couple’s game with these questions because breaking couples apart gives bad reviews. Hence, they substitute the most superficial fluff, for example, “Which reality show would you like to be a part of.”

Here’s another problem with most deep questions: they use words they have no clue what they mean or whether they exist: ‘Have you found your soulmate?’ Furthermore, your typical questions include questions that don’t have answers. ‘Have you found your purpose?’ - Do you know how many people have lost their mind trying to answer that question?

Yet, still, if your goal is conversations, these false questions can do wonders. After reading many good questions, I trust you to figure out the traps.

Before you ask any of these questions, remember a few things:

• Now is not forever.
• Answers change.
• Some questions don’t need answers – they must be felt.
• The truth has never hurt anyone – unless you’re with one foot in hell.
• Use if useful.

Finally, if you don’t want to radically improve, ignore these questions. For example, ‘Do I love you or do I lie in order to avoid being lonely,’ would destroy almost all relationships. So, if you want to stay mediocre, you’d only suffer by asking yourself deep questions because you would create desires without the intent to resolve them.

Sacrifice and purpose

• What’s the biggest thing holding you back?
• What’s the biggest thing you said no to recently?
• Which conversation are you avoiding?
• What belief is holding you back?
• What sacrifice are you not making?
• What are you holding for too long? What needs to go but you are scared?
• What opportunity cost do you (gladly) pay?

Leverage and strategy

• What’s the best conceivable move?
• How would you ensure your failure in life?
• How would you make success impossible?
• How do you ensure you’ll definitely miss the adventure of your life?
• Which things will compound in your favor and which against you?
• Do you pay the cost of indecision?
• Do you fall for the sunk-life fallacy?
• What do you gain by waiting?

Return to the grind

• Do you believe you’ve already peaked? How do you ensure it wasn’t a local peak?
• Do you worry about the amount of work before you start doing? Does not taking things one step at time discourage you from starting the adventure?
• Are your goals still based on outcomes rather than on the work you need to put in?
• Do you label yourself stupid to avoid the grind?
• Do you quit the moment things get moderately difficult?
• Do you honour those who go above and beyond?
• How large is the gap between your thoughts and actions?
• What do you wish you will have done in ten years from now?
• How will people summarize your entire life in a sentence? Is your life worth summarizing?
• Can you count your tries in the hundreds?
• Can you do one more step?
• Can you do one more second?

Uncompromising excellence is a true testament to the indomitability of my spirit.

• Would that thing-you are so worried about-still affect you if you saw it ten thousand times?
• What do you fear losing so much when you were born naked?
• Do you allow a bad moment to affect a year?
• In ten years, will this matter?
• What if you could only take in what makes you stronger?
• What if you learned from every single mistake?
• How many of your greatest catastrophes never left your imagination?
• What if your exact life were to repeat indefinitely?
• Do you choose to suffer once, or twice by reliving it in your mind?

Thought experiments and time

• What if you had one more year to live?
• If you were sixty, would you want to be twenty again? How do you ensure you will feel no need to go back?
• What if you were teleported … years back with your current knowledge?
• If you were eighty, what would you sacrifice to be twenty?
• If you had no past, how would you live?
• How would you live if you had ten thousand years?
• How does ‘retrospectively, your twenties are half your life’ make you feel?
• What is it now too late for?

Questions that must be felt, not answered

• Do you live every day as if it’s your last?
• What makes you feel alive?
• What if money and status were no object?
• What would you do if no one was watching?
• What would you do if you felt no fear?
• What would you do if you couldn’t fail?
• Which decision needs to be made?
• What truth are you avoiding?
• What is left unsaid?
• Where you need to make peace?
• Do you have experience letting go?
• Do you give freely?
• Do you let the energy flow freely?
• Do you love passionately?
• Do you live with an open heart?

Campfire and date evening

       Storytime

• Which moment disillusioned you?
• What’s your greatest adventure?
• Which failure are you most grateful for?
• When was the last time you felt genuinely inspired?
• Which small moment will you never forget?
• Have you ever seen a miracle?

       Life lessons

• What’s the hardest lesson so far?
• Can you learn the easy way?
• Which was your best decision?
• What’s the biggest life lesson from school/university/hobby/vacation…?
• What’s your biggest life lesson?
• Where have you learned the wrong lessons?
• When was your intuition exactly wrong?
• What would you tell your past self?

       Living true

• What stops you from completing your bucket list?
• If you woke up with no memories, what would you find strange about your life?

       Loss

• Do you miss …?
• What do you not miss?
• Have you seen death?
• What have you done for the last time, knowingly or unknowingly? How does that make you feel?
• Did heartbreak make you stronger?
• Can despair generate genuine insight?

       Space

• Where do you feel at home?
• What’s your favorite location?

       People

• Can people change?
• Have you tried to save or fix someone?
• When was your first impression exactly wrong?
• What makes you lose respect for someone?
• Which standards have you dropped recently?

       Childhood

• What brought you in the flow as a child?
• What was your favorite object as a child?
• What’s your favorite childhood memory?
• If you don’t have a favorite childhood memory, do you judge yourself for it?

       Growing up

• Who’s the most impactful person outside of family?
• Have you ever said something greater than ‘Thank you very much!’ to someone?
• Have you ever talked to your parents like they are people?
• Do you honour thy father and thy mother enough?
• Did getting older strip you of your passion?
• Do you believe in growing up, that means, do you separate between adult and non-adult?

To ask your hot blonde or cute brunette

Do not ask any of these questions if you ‘got what you could get.’

       To ask yourself

• What if she weren’t hot?
• Would you be friends with her if she was a guy?
• What is she going to be like in a decade?
• Does she change behaviour when you tell her?
• Am I ashamed to be seen with her?
• Did your life get more peaceful with her?
• Did your discipline or ambition grow with her?

       To assess the relationship together

• How can we ruin this relationship as fast as possible and ensure that we do not do so?
• Do you like me or do you just feel less lonely?
• When people say, you’re like me, what’s your first thought?
• Did you peak before we met?
• Do you secretly miss being single?

       To ask her

• How did you try to impress me?
• What was my first impression of you?
• Do you feel like you have grown up?
• What’s underrated about you?
• What’s your biggest contradiction?
• What’s our biggest tension?
• What’s youth for?
• When was the last time you felt genuinely …?
• When was the last time you cried?
• How do you imagine paradise?
• What would we laugh about in twenty years?
• What do you want me to notice more?
• What are you scared to reveal to me?

       Tests to assess her virtue

• How did you celebrate your birthday?
• Who is your favorite philosopher?
• When was the last time you were seeing a guy?
• Craziest date you had?
• Thoughts on marriage?
• Tell me about your friends…
• What lie do you keep from your parents?

Identity and happiness

       Direction in life

• If enlightenment came at the expense of happiness, would you give up happiness?
• Would you give up status or money?
• Would you give up power or freedom?
• Would you give up hedonism or family?

       Readjusting life

• How many ‘unteachable lessons’ have you already rediscovered?
• What do you worship? Who is your implicit god?
• What have you done to prevent life from speeding up?
• What would make this awesome?
• What’s the better story?

       Flow

• How would you live if you had meditated for ten thousand hours?
• Do you view life as moments or changes?
• What gets you in the flow?
• When was the last time you sat in stillness?
• Who can you sit in silence with?

       Insecurity and motivation

• Are you misunderstood and do you secretly find pleasure in that?
• What annoys you and what does that reveal about you?
• Are you still fuelled by pain and do you judge yourself for it?
• Which insecurities have you already dropped?
• Are your insecurities rooted in reality?

       Are you working in tangents?

• Do you keep sacrificing the thing to get the thing?
• Do you want things you have no desire to grind for?
• Are you conflating ‘difficult’ and ‘valuable’?
• Can you imagine dedicating your life to memorizing a phonebook?
• Does living a normal life cause you to go at war with your mind?
• If it was ten times harder, would you keep going?
• If your parents threw you out of the house, would you continue?

       Bliss

• Does your judgment impair your happiness?
• Do you judge yourself for not being happy or grateful enough?
• Is sitting in bliss a waste of time?
• Are you in the stage of life where happiness and purpose do not contradict?
• Why aren’t you the happiest person in the world?
• Would you buy yourself a beer?
• Do you treat yourself like you would treat others?
• Will the golden days not be now in retrospect?
• Do you dedicate time to doing what you want to do?

       Darkness

• Which sin is your weakness?
• Which temptations are you still falling for?
• Are you comfort’s slut?
• Do you bet on developments that haven’t started?
• Are you in touch with your shadow?
• Do you apologize for living your life?

Purpose and vision

       Vision

• What if you could remove one problem from the world?
• What do you know that no one else knows?
• What will future generations disagree with?
• What will not change?

       Truth

• Are you as brave as you are intelligent?
• Are you scared to think free of societal norms? Do you censor your thoughts?
• When was the last time you had an original thought?
• Has telling the truth ever hurt you?
• Has the truth ever hurt you?
• Which belief will you die for?
• Is there a difference between truth and adventure?
• Do you live by the deepest realization?

       Return to purpose

• Where do you keep waiting for things to change?
• Does your living reflect the truth that tasks and duties never end?
• Do you know your true limits and do you kiss them?