Is there anyone in your network you wish you could apprentice under for a few weeks?

What is the most impressive thing that you have built or achieved?

What are three things you are currently worried about?

Who is someone you really admire?

If you could pick up a new skill in an instant what would it be?

Is there something you should measure in your life that you currently don’t?

What does your ideal day look like?

In a typical day, what is the activity that makes you feel most energized?

What are you most looking forward to?

What tasks are you procrastinating?

What are habits you wish you had?

Is there any part of your life you wish you had more influence on?

How could you be more useful to those around you?

Imagine you are on your deathbed, what do you wish you did more in your life?

What is something you can apply to your life from the book you are reading now?

A genie appears in front of you and offers you one wish, what would that wish be?

Have you seen something recently and thought to yourself ‘I wish I had done that’?

Are you afraid of anything at work? Why?

When do you feel most productive at work?

What piece of advice would you give to your older self?

Where do you see yourself in 6 months from now?

What's not working in your life right now?

In a typical day, what is the most energy draining activity?

Have you seen someone recently do great work that’s gone unnoticed?

If you were to die tomorrow, who would you spend today with?

If you are the average of the 5 people you spend the most time with, who should be those 5 people?

Who made you smile today?