40 Deep Questions To Get To Know Yourself and Your Life Purpose

Michal Korzonek |

Deep Questions Cover

“Quality questions create a quality life. Successful people ask better questions, and as a result, they get better answers.” – Tony Robbins

The quality of your life is directly connected to the questions you are willing to ask.

Better questions lead to better answers. Better answers lead to better actions. Better actions lead to better outcomes.

The thing is:

We all ask questions to other people pretty much every single day, but how often do we take the time to look within and ask ourselves?

Fortunately, there is a simple way to do it, and the name of this blog probably gave you quite a good hint on what it might be.

You’re right! It’s journaling.

The selection below includes some of my favorite questions for getting to know myself (although you can also ask them to other people). Simply pick the one(s) that resonate with you and answer them in your journal. Profound insights guaranteed.

Note: If you want to learn how to incorporate questions into a powerful journaling practice, here’s an article to read.

Tony Robbins quote

Deep Questions To Ask In Your Journal

  1. What are you most likely very wrong about?
  2. What chapters would you separate your autobiography into?
  3. What are some things you’ve had to unlearn?
  4. What could you give a 40-minute presentation on with absolutely no preparation?
  5. What question would you most like to know the answer to?
  6. If you didn’t have to sleep, what would you do with the extra time?
  7. Why did you decide to do what you are doing now in your life?
  8. What’s the best and worst piece of advice you’ve ever received?
  9. What’s the most impactful ‘no’ you’ve said recently?
  10. What was the most stressful experience of your life?

List of Questions part 2

  1. Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?
  2. What would you like to change about your family?
  3. What was a place or event that transformed your ideas, thinking, perspective, or made you come alive in a new way? What changed?
  4. What one thing you would do if it would be impossible to fail?
  5. What is something you love now, that you never could have imagined you would like in the past?
  6. If you could invite anyone, living or dead to dinner, who would that be and why?
  7. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
  8. What are you addicted to?
  9. What’s the milestone you’re working towards right now in your personal and professional life?
  10. What was the most bizarre encounter you’ve had in your life?

List of Questions part 2

Okay, you’re halfway through! Take a deep breath and let’s take another dive:

  1. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  2. What do you spend too much time doing? What don’t you spend enough time doing?
  3. What makes you feel most alive?
  4. What is something you know you do differently than most people?
  5. What advice would you offer to yourself five years ago? One year ago?
  6. What small gesture from a stranger made a big impact on you?
  7. What are you looking forward to in the coming months?
  8. Did you ever feel lost in your life path? How did you find your way again?
  9. What do you want your epitaph to be?
  10. What do you regret not doing? Why haven’t you done it? List of Questions part 3

  11. What would constitute a perfect day for you?
  12. What’s something you love about yourself?
  13. When do you feel truly alive?
  14. When people come to you for help, what do they usually want help with?
  15. What do you consider as your biggest achievement in the last 5 years?
  16. What is the most challenging part of your job? How do you handle it?
  17. What was a major turning point in your life?
  18. What’s one thing that could happen today that would make it great?
  19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  20. What would you like to ask yourself?

List of Questions part 4

Where to Find Good Questions To Ask?

The list above is by no means comprehensive.

If you’re still hungry for questions, here are some amazing resources I highly recommend:

  1. Conversation Starter World by C.B. Daniels
  2. Big Talk by Kalina Silverman
  3. 36 Questions To Fall In Love With Anyone (based on a study The Experimental Generation of Interpersonal Closeness)
  4. Open Questions by Julia Galef

Can I Ask You a Question?

I bet there were a few times in your life when you were faced with a very good question. You know, the one that made you stop, think, perhaps hesitate for a moment, and then answer.

You see, those are very precious. And that’s where I would love to ask you:

Would you mind sharing it in a comment below or send me a message?

There is nothing quite like learning from other people and their experiences. And I know that you are full of amazing things to share.

The subscribe form is here. If you decide to use it, I'll send you an email (sometimes) and it will have a journaling game in it.