25(ish) questions that might change your life

How’s that for a noncommittal title, eh? Well, hear me out and you be the judge…

It’s been said that the quality of your life can be determined by the quality of your questions. 

For a few years now I’ve “known” this quote but dismissed it as esoteric and somewhat meaningless. 

However, in May I completed the 10th altMBA as a student and more recently was lucky enough to coach the 12th session. Doing so allowed me to see first hand how asking the right questions at the right time can lead to huge shifts in mindset both for the receiver and the asker.

Based on these experiences, as well as some of my favourite books and a few hundred podcast episodes of The Tim Ferriss show I’ve compiled a list of 25(ish) questions that I believe can change the trajectory of your life… Or at least how you think about certain things:

  • What do you believe in, that others think is insane?
  • When’s the last time you changed your mind?
  • What self-imposed, restrictive narrative do you tell yourself?
  • What’s one thing in your life you’d like help with?
  • Why do you get out of bed in the morning?
  • What thoughts keep you up at night?
  • What does success look like for you?
  • What are you afraid of?… What else? (Tell the truth this time)
  • Why are you afraid?
  • How do the five people you spend the most time with add value to your life?
  • What does failure look like to you?
  • Are you focussing on things that you cannot control the outcome of?
  • What gets you excited?
  • Who do you know that can help you solve that problem you’re worried about?
  • In 12 months time, will this situation matter?
  • How is your behaviour irrational and the opposing behaviour rational?
  • What are you most grateful for?
  • What’s this piece of work/email/meeting for? What’s its purpose?
  • Who’s this piece of work/email/meeting for? What’s their worldview?
  • Are you being proactive or reactive?
  • What if the opposite were true?
  • What’s something you do that you believe everybody else should do too?
  • If you had all the time and money in the world would you still do what you’re doing today?
  • What is the opportunity in this difficult situation? Where’s the beautiful constraint?
  • How many roads must a man walk down, before you call him a man?

Note: You can ask these questions of those around you as well as yourself. Except for maybe the last one… Don’t ask anyone that.