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

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

Who is someone you really admire?

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

What's not working in your life right now?

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

How could you be more useful to those around you?

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

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

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

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

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

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

What are three things you are currently worried about?

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

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

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

What does your ideal day look like?

What are you most looking forward to?

Who made you smile today?

When do you feel most productive at work?

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

What tasks are you procrastinating?

Are you afraid of anything at work? Why?

What are habits you wish you had?

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

Where do you see yourself in 6 months from now?