18 Introspective Questions for Every Entrepreneur

18 questions to help you learn more about yourself

Everyone, you included, should take the time to interview themselves.

As we meet the demands of our busy day, it is easy to get unfocused and distracted as to what’s important to us.

You may think I sound crazy, but it’s the truth.

Asking yourself the right kind of questions can bring you closer to who you are now, and who you want to be.

Think of it as a mirror into your innermost desires, goals and hopes.

The ones you didn’t even know you had.

There are no rules, just a few guidelines:

Interpret each question however you want.

Think fast.

Go with your gut feeling and answer quickly without self-editing.

This interview is meant to be cathartic.


Your answers may surprise you…

  1. What motivates you more: failure or success?
  2. You can ask anyone in the world a question. Who and what would it be?
  3. If you could say one thing to your 85 year old self, what would it be?
  4. If you could say one thing to your 15 year old self, what would it be?
  5. Imagine money is no longer a thing. How would you spend your time?
  6. If you stripped away all the layers of other people’s expectations and desires for you, what would you want for yourself?
  7. What’s one thing you’ve been putting off doing?
  8. What headline would you like to read in tomorrow’s newspaper?
  9. What do you want written on your gravestone?
  10. What is a perfect day to you? Truly?
  11. What do you find annoying in this great charade we call “modern life”?
  12. What are you most looking forward to, in life?
  13. If you could change just one thing in your past, what would it be? (And no, “nothing” is notan answer)
  14. Would you want to be your own friend?
  15. Describe the last five years of your life in one sentence? And the next five years?
  16. When did you last do something for the first time?
  17. How many hours a week do you watch TV? And browse the internet? If you added them up, how much time would you have to create something of your own, per week?
  18. If I gave you 10k to start a business, what would you do with it?

Answering these questions will help give you focus and align yourself to your goals.

Try it!

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