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20 Questions to Answer Honestly


  • Do you earn enough money? (If you answer ‘no’, ask yourself why you need more money. eg Security? To buy more stuff? To impress others? For self-esteem? If you answer ‘yes’, ask yourself why you don’t work fewer hours. eg Peer pressure work ethic? You enjoy your work? To keep your mum happy? It’s what everyone else does? You enjoy having plenty of money?)

  • Do you enjoy your job? (If you answer ‘no’, ask yourself why you are still doing it.)

  • Do you prefer Saturday or Monday? (If you answer ‘Saturday’, ask yourself how you can improve the other days.)

  • What would you like to be doing one year from now? Can you make that happen?

  • What would you like to be doing five years from now? Will you make that happen?

  • What would you do with your life if you were a billionaire? Is it possible to live a modified version of that life anyway?

  • How much could you cut your outgoings by? How much time at work does that equate to?

  • Do you have enough spare time to do the things you really enjoy? If not, why not? What could you squeeze in to the time you do have?

  • What takes up a lot of your time but is neither unavoidable, rewarding nor enjoyable? Why don’t you cut that/them out immediately, or pay somebody to do it for you?

  • What mildly pleasant, but pretty pointless things do you fritter too much time doing? How many times a day do you check your email/Twitter/Facebook? How much TV do you watch?

  • What would you like to do more of?

  • What motivates you to do something well?

  • Who do you envy, and why?

  • If you were 100 and looking back on your life, would you be happy with a life well-lived?

  • What makes you proud, satisfied, and content?

  • What makes you frustrated, bored, and unfulfilled?

  • What would you do if you had more talent?

  • What would you do if you had more guts?

  • What would you do with your life if nobody was watching, judging or commenting?

  • What are you going to do about all this?

I have posted these questions before, but I hope you don’t mind me asking them again. I was thinking them over myself and decided to share them again.


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  1. A rather thought provoking set of questions, Alastair, thank you for posting these again as I missed them last time. I think I have some work to do on the answers…

  2. Bloody good questions! I’ve just about finished your second book about your world ride. Love it. I really love it. Fantastic work. Inspirational. Eye-opening. Thanks so much for writing it and sharing it with us all. 🙂 If you’re ever in South Korea I’d love to show you around town and go for a ride together. 🙂



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