I collect questions Growing towards the direction of our questions

I collect questions. Just like plants grow towards sunlight, questions are my light, the North Star by which I steer. I grow towards the direction of my questions. The kind that is generative, not restrictive. It’s not about being a skeptic or cynic, though. Skeptics and cynics ask questions to refute, to deny, to close off, to pour cold water. I love asking the type of questions that inspire, open up and invite more opportunities, possibilities and directions. A more beautiful question. I find that I love questions more than answers, though truthfully, one cannot do without the other.

“An answer may be right or wrong, but a question is always true. Truth is in the question and not in our answers……in my tradition, we ask questions and we try to find new ones. And if, somehow, we find an answer, we question int immediately. Because our answers confine us to the known, whereas our questions opens us up to infinity.” – Sadhus: Going Beyond The Dreadlocks by Patrick Levy

You might recognize some of the questions here. Some I made up, others I got from books, articles and anything I had came across. The sources vary, and your mileage from these questions too might vary. It’s after all, a very personal list, from my own journey, experiences and reflection. But a close friend showed me the inspiring questions she collected and asked me about mine. So here it is.

So, what are the questions you are collecting?



What is saving your life right now?

Is prayer your steering wheel or your spare tire?

Where is your secret place where you can be quiet and whole without feeling that you need to go somewhere else? Where is this place where you can have peace without fear of being disturbed? Where is this place that inspires, refreshes and nourishes you?

How am I getting in my own way?

How do we know if wanting to grow and change is just a lack of self-acceptance? Pushing past one’s limits and getting uncomfortable is part of the game, but how do I also flow with my own nature? What are my natural dispositions that I can tap on? Is working alone that bad? Do I really need to network like crazy to succeed? How much is too much, when pushing myself to work on a weakness?

How may I push myself out of my comfort zone in a wholesome way? What if (personal) growth at all costs, is not healthy?

What if this time RIGHT NOW, is our good old days? In 20 years time, when we look back, will this be the time we miss the most?

What’s your Massively Transformative Purpose?

What do you imagine that moment will look like when you feel like everything is going to turn out okay?

How do I listen to my body and heed its innate wisdom?

Does my empathy and compassion include myself?



What are the three words you would like people to use to describe you when you’re not in the room?

What’s the best piece of advice you have ever received?

How does it feel like to be seen?

What important truth do very few people agree with you on?

Who can I go to for honesty with compassion for my most vulnerable work?



When was the last time you felt truly light, joyous, and — yes — creative in you own skin?

What does it feel like when an idea comes to you?

Is there anything that I’m even faintly curious about?

How can I game this, for fun?

Would you still do it if someone else had done it before?

Would it discourage or even stop you if your life’s work is arguably useless?

Would I still do it if I didn’t achieve my goals? Would I still do it if no one benefits?

How do I say NO with respect, kindness and clarity?

Instead of “What are you passionate about?”, ask “What are you passionate enough about that you can endure the most disagreeable aspects of the work?”

How can I continue doing what I love without needing it be my job?

How can I stop treating my creativity like it’s a tired, old, unhappy marriage and start regarding it with the fresh eyes of a passionate lover?

Would I still do it if it didn’t bring me any pleasure, only pain?

Instead of asking “What would you do if you knew that you could not fail?”, ask “What would you do even if you knew that you might very well fail? What do you love doing so much that the words failure and success essentially becomes irrelevant? What do you love even more than you love your own ego?

What happens when you made enough for the year?

What if there’s no such thing as a one true calling? What if life didn’t have a singular purpose for it to be meaningful?

What if suffering wasn’t necessary for creative living?

What if passion doesn’t need to be your job?

What if you didn’t need to find your passion to have meaningful and joyful work?

Could working alone instead of being in a team also complete and worthy?

What if money isn’t dirty? What are the more wholesome ways to see money?

How can I find learning from the discomfort of teaching others?

What if I can be myself and still succeed?

How may I work as much with my hands as with my head?

How might a life of grace rather than haste feel like? When was the last time saying no feels as good as saying yes? What if I only did stuff that’s best for me to do, with joy and intention?

If we are going to ask people, in the form of our products, in the form of the things we make, to spend their heartbeats—if we are going to ask them to spend their heartbeats on us, on our ideas, how can we be sure, far more sure than we are now, that they spend those heartbeats wisely?

What valuable company is nobody building?

When a country is founded on the idea of surviving regardless of the cost, what happens when it thrives?

Is the world better with you, or without you?

How can I fight the injustices of this world, without being consumed by hate, anger, bitterness, resentment?

How do I not get carried away and get overwhelmed by the collective energy of hate and anger in the world? How do I protect myself and be a island of inspiration and nourishment instead? How can a doctor ease the suffering of others, if he himself is ill? How does a pine tree help the world?




Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert

Zero To One: Notes On Startups, Or How To Build The Future by Peter Thiel

Sadhus: Going Beyond The Dreadlocks by Patrick Levy

(If you recognize the source of the questions and it’s not credited here, let me know! I forget where I get them sometimes…)

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