Amir Sharif
Weekend hacker.
Self improvement enthusiast.


Questions are useful prompts for the brain. Tim Ferris got me thinking about questions when he shared 10 questions that changed his life (he’s since released 17 more). There are entire sites dedicated to collections of questions. Below are some of the questions that I’ve saved” and I review them time to time.

On Business

The following are from Extreme brainstorming questions to trigger new, better ideas

  1. If you were forced to increase your prices by 10x, what would you have to do to justify it?
  2. If all our customers vanished, and we had to earn our growth and brand from scratch, what would we do?
  3. If you were never allowed to provide tech support, in any form, what would have to change?
  4. What would be the most fun thing to build?
  5. If our biggest competitor copied every feature we have, how would we still win?
  6. What if we are forced to ship a full, completed (at least MVP) new feature, in just two weeks, that would delight and surprise some fraction of our customers.
  7. What if you were forced to charge customers in a completely different manner?
  8. If you were not allowed to have a website, how would you still grow your business?
  9. What if you made your most introverted teammates’ dreams come true: No more synchronous meetings, ever again?
  10. If we could never talk to our customers again, how would we figure out what to build?
  11. What if it didn’t matter how unprofitable you were?
  12. What if you could change anything, regardless of what anyone thinks or feels?
  13. What externality has the potential to kill the entire company?
  14. What if our only goal were to create the most good in the world, personally for our customers?
  15. What if you could only ship one thing this year?

What’s something you’re good at unrelated to business or soft skills?

Did I fulfill my potential with time I was given today?

What did I discover this week?

Where do you get your dopamine?

What is working?

What isn’t working?

What is giving me energy?

What have you said no to? Better question: what were good ideas that you said no to?

What is draining my energy?

What relationships give me genuine pleasure?

What relationships are toxic?

What is surprising me about the present?

Are my current habits aligned with my goals?

Am I happy doing what I am doing right now?

On a scale of 1-10 how happy are you and you can’t use 7. (You can’t use 7 because it’s too easy to be wishy washy and say things are ok.” In my world, it’s either a f*ck yes or a no.)

What would I do if no one was watching and success was inevitable in it?

What would I NOT do if I knew for sure it would fail?

What would I do EVEN if I knew it was going to fail.

What am I doing right now because I think I SHOULD do it?

Looking back at last week, how much of my day was spent doing things I actively enjoyed? How’d that compare to the week before?

How’s the weather in your brain?

How am I being complicit in the behaviors that I’m complaining about?

What are your biggest problems right now?

What’s the most impressive thing you’ve done?

What’s the worst hour of your day and why?

If I keep doing what I am about to do today for the next five years, will I end up with more of what I want or less of what I want?

What would I do if my current time available is slashed by 90%? (source)

What activity if you stopped doing now would you start craving?

How can I improve myself? Root for others but compete with yourself.

Am I working on the right level? Do I need to zoom in or zoom out?

What’s the One Thing I can do such that by doing it, everything else will be easier or unnecessary?

Who am I becoming?

What did I change my mind on this week?

What gave me energy?

What drained my energy?

What did I learn this week?

From I Owe My Success As A Creative Entrepreneur To These 8 Questions I Ask Every Month:

  • Is this actually working?
  • If you had to stop doing 10% of what you’re doing, what would you abandon?
  • What would you do if you had to launch/finish X in Y days?
  • What work did you most enjoy doing recently?
  • What work did you least enjoy doing recently?
  • What have you learned to do well in the past year?
  • What would happen if you raised your prices?
  • What would it look like if it were easy?

When did you have to make a decision to quit or keep going?

A common piece of advice is to focus and concentrate on something before you move on to something else. Describes this as chasing the shiny object of the day.

In the exact same way you can spend too much time on something.

Knowing when to switch seems to be something that everyone has a different opinion on and is context specific. By learning from other people specific stories, it may help with your own scenario.

January 6, 2023