25 Slightly Scary Deep Questions Worth Asking Yourself

One of my wishes for Profound Journey is that it be a place where we can all experience a sense of community, of connection. To that end, when I started the site last October I published a list of 25 Not-Too-Scary Life Questions Worth Asking Yourself, and I invited you to share your responses on the Tribe Stories section of our site. Susan Millard and Fran Fearnley took me up on the offer. Thanks, ladies! Now I’m hoping to entice a few more of you with some deep questions to ask yourself… and perhaps share your answers with the rest of us!

It’s All About Choice

  1. Choose the questions you want to answer from the Deep Questions list below or from the Not-Too-Scary list. Answer as many or as few as you wish. Or choose to write something that has nothing to do with the questions. That’s what Fran K. did and it was great! Another option is to send me a video, a collage, a poem or a painting. I’ll be happy to post it for you.
  2. Share your written or artistic responses with me. Send toย karen@profoundjourney.com. If you’d rather chat and you live in North America, send me your phone number. I will take your information over the phone and write the responses for you.
  3. Decide how you want to appear on the site. First name only? Full name? A nickname?
  4. I’ll be putting an image with your post. Decide what you’d like to use. A photo of yourself? Something you are interested in? Or leave it to me. I’ll find something perfect.

Why Should You Consider Contributing?

Contributing selected tidbits of your personal story to the Tribe Stories section of this site is an act of clarification, connection, and generosity.

Your own self-realization is the greatest service you can render the world.

Ramana Maharshi

  • Clarify what you believe and what you value in your responses to the questions you choose to answer or the story you choose to tell. Writing for publication encourages you to think more deeply.
  • Connectย with your tribe, giving and receiving support and encouragement through the comments you leave and receive.
  • Recognize that you are generous; that sharing pieces of your story may inspire and sustain someone else.

25 Slightly Scary Deep Questions

Here are the 25 deep questions (well, some of them are deep) to ask yourself. If you prefer, you can download the list here.

  1. What trip have you taken that had a huge impact on you?
  2. Who is your favourite character in fiction? Why?
  3. What would you do if you could not fail?
  4. When did you last laugh so much that it hurt?
  5. What can you never imagine buying? (question from Natalie Goldberg)
  6. If you were writing a book, what would it be about?
  7. What is your body telling you?
  8. If you could be famous, what would you like to be famous for?
  9. What life advice do you give to your friends? (question from Danielle LaPorte)
  10. Who was your favourite teacher? What made him or her so special?
  11. What do you want that you can’t have?
  12. Describe a perfect ‘ordinary’ day.
  13. What song has been significant in your life?
  14. If you could choose to live anywhere in the world, where would it be?
  15. What do you most value in your friends?
  16. Which creative pursuits were encouraged in your childhood? Were any discouraged?
  17. What have you collected?
  18. When are you most yourself?
  19. What is the best thing that has happened to you in the last few days?
  20. What is most important to you at this time in your life?
  21. If you could spend ten minutes with a favourite person, alive or dead, what would you ask them?
  22. What is your happiest childhood memory?
  23. Which culture, other than your own, speaks to you? (question from Julia Cameron)
  24. What smells give you a sense of wellbeing? (question from Julia Cameron)
  25. What dream have you had more than once?

Which question is your favourite? Why?ย 

Join the tribe:


  1. Yay!! More questions! Now I can expand on my tribe story. ๐Ÿ™‚ I find by answering questions it is easier to talk about myself than it is to respond to someone who says “Tell me about yourself?”. These are some great questions, a few of them are deep, that may require some thought for me to put together the answers. I will have to think about that last question too, which is my favorite question and why. Hmmm…

    I will be sending my answers off to your email soon, thanks, Karen. ๐Ÿ˜€

    1. Yay back at you, Susan! I’m delighted to hear that you will be expanding, or doing part 2, to your tribe story.
      I too find it easier to answer questions, and especially to answer them in writing. I find I learn so much by writing.
      Looking forward to seeing your responses in my email inbox when you have the time. Thanks, Susan.

  2. Interesting questions – more soul searching than scary. I think my favourite question is “When did you laugh so much that it hurt?” and I can only say that it wasn’t all that long ago and it had to do with a graveyard. The other questions I’ll have to spend some time on – thanks Karen, you never fail to give me something to think about!

    1. Your graveyard comment made me smile, Anna. Thank you!
      I’m glad you find the questions more soul searching than scary. Perhaps they’re just slightly scary to people who want to post their answers. In October I’ll be doing the last batch of them. They’re labelled “totally terrifying.” We’ll see what you think!

    1. Hi Fran,
      Your story came in about an hour and a half after this message.
      Thank you for writing it. I’ll be happy to post it. I see you have also posted it on your own site. I’m assuming you’re okay with it being double-posted.

  3. Another list of great questions that will need to some time to ponder over and be answered. I love interviews – and inspiring people – and hope to do both one of these days/weeks I find some extra time. Maybe on the train… ๐Ÿ™‚ Is there a deadline?

    1. No deadline at all, Liesbet. I will be so happy to share your responses when you have time to write them. No deadline but I can’t wait! As you say, maybe on the train when you need mini breaks from your memoir.

  4. I’m gonna need a break from life, the way this train “journey” is going! Rerouted on a different train (+ connecting bus) to LA, missing the wonderful coastline all together and sitting on a jam-packed train for eight hours, with no room to move my feet… Hope it improves on the longer stretch!! ๐Ÿ™‚

    PS: I did not get a notification in my inbox about your replies to my comments. Is there a way to mark a notification box that I missed?

    1. Oh no, Liesbet! I just hate being crammed in like a sardine in a can. I will keep my fingers crossed that the upcoming 50 hour train journey is the exact opposite experience to the current one.
      Thanks for letting me know that you didn’t get a notification. I will ask my web guy to look into it and will get back to you directly, via your email, with whatever he finds. It may take a couple of days but I’ll be back just as soon as I can.

      1. Thanks, Karen. The 50-hour train journey was much more comfortable, but turned into a 56-hur one which then caused other difficulties… All the Amtrak stories and rumors are true – we confirmed them. ๐Ÿ™‚ I started on the questions, but was soon too exhausted to do anything. Now, we are faced with a tiring road trip back, but I’ll get them to you as soon as I am able. It is a fun project, after all. ๐Ÿ™‚

        1. Oh Liesbet, I’m so sorry to hear that. Those kinds of delays and frustrations are so deeply exhausting. No worry about the questions. Whenever you get to them is just great.
          Take care. Safe, and hopefully speedy, travels home.

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