50 Questions for Deep Self-Reflection

An open challenge for anyone willing to commit to 50 days of reflection.

Some people have answers, but I, for one, have lots of questions. That inner voice is dying for a dialogue and I have to feed it with some (a lot of, actually) reflection.

Bobby Kountz is right. We need space between the space. We need time between the time. I know I do. I have been neglecting my writing for a long, long time. All focus and energy went into growing the publication and not enough into creating content for me. But now, KTHT is at a level where it is growing naturally, organically and I can become, once again, more invested in my writing.

With that being said, challenges and prompts will continue to be released, but I’ll be taking a break from creating the weekly and weekend masterpieces. I will focus more on reading, as well as on writing for myself. I will also be updating the guidelines soon, as some changes are desperately needed.

For the next 50 days, I’m fully committing myself to a challenge, which means I’ll be writing every day for the next month and a half. The questions in this challenge have been carefully selected — none of them have been included in prompts before, nor in my Shadow Work Journal or any of the Mini Journaling Series I’ve created. They are new, deep, refreshing and nourishing — and they’re here for anyone who wishes to immerse themselves into reflection.

This is a new, exciting chapter and I have to thank Dan Morrissey for his words today that confirmed this is the right decision to take. He said: “Editing was taking me away from the pursuit I love most…writing”. Truth be told, I’ve been feeling that way for a long time now but didn’t know how to go about it.

I will still be editing, but I will work smarter at it, not harder. Meanwhile, I’ll be writing, writing and…oh yeah, writing. I’ll also be investing more energy in my other projects. That’s to make up for all the times I did not.

Here are the 50 questions I’ll be tackling over the next 50 days:

1. How can you have compassion for your own trauma history while also holding yourself accountable for the ways you’re harming yourself/others?

2. How does being endlessly understanding get in the way of true closeness?

3. How can you learn to forgive people for treating you poorly whilst continuing to uphold the boundaries you set in response to their poor treatment?

4. How can you learn to better communicate your needs instead of expecting others to interpret & respond to your mood?

5. How can you handle conflict in such a way that it yields intimacy and helps relationships grow?

6. How can you befriend solitude and learn to self soothe through moments of loneliness?

7. How can you relieve yourself of the burden of trying to problem solve your way into a pain free existence?

8. How can you start choosing your relationships based on their alignment with your needs?

9. How can you pilgrimage your way back into remembrance?

10. How can you revel within each moment of your temporary existence?

11. How can you begin to clearly hear which direction your soul is calling you in and find the courage to trust it?

12. How can you become more mindful of the way you handle composure vs. emotional expression?

13. How can practicing feeling your feelings fully, even when it is deeply uncomfortable, benefit you?

14. How can you actively train your capacity to receive and give love?

15. How can you liberate your fiercest, loving nature?

16. How can you give people space to absorb whatever they’re experiencing without assumption, judgement or projection?

17. How can you wash away the idea that there is a certain standard that you have to exhibit to be enough?

18. How can you harvest love, good energy and meaningful connections?

19. How can you honor a difficult situation before moving on from it?

20. How can you tend to your triggers with love?

21. What is the difference between compromising in a relationship and self abandoning for a relationship?

22. How can you allow yourself to be seen and held in your humanness?

23. How can you use your energy to imagine all the things that can go right instead of everything that might go wrong?

24. How can you escape from the loop of your past?

25. What if the wealthiest thing you can have right now is peace of mind?

26. How can you bring your outer world into alignment with your inner needs?

27. What would it be like to practice giving less and receiving more?

28. How can you learn to stop taking responsibility for alleviating the emotional discomfort of others?

29. In what ways do you allow people in your space to treat you poorly?

30. How can you stop trying to make someone else’s growth happen on your timeline?

31. How can you practice letting yourself find proof that you are lovable?

32. What if no one else knows what they’re doing either?

33. How can you find out if what you’re holding on to is worth the space its taking up?

34. How can you begin to feel the power of your own presence?

35. How does being relentlessly kind to the parts of ourselves that fear being abandoned, betrayed or forgotten impact the way we’ve been wired for disconnection?

36. What if you can care about people without taking on all their problems?

37. How can you exercise your truth speaking muscle?

38. What is the difference between difficult honesty and unkindness?

39. How can you take ownership for your inner saboteur?

40. How can you let the Earth hold you when you feel lost and alone?

41. What if you don’t need to speed up the process of healing?

42. How can you become more willing to be wrong?

43. In what ways is listening a sacred skill?

44. How can you trust your body whilst also challenging your mind?

45. How can you remain connected to yourself whilst being connected to others?

46. How can you move, sway and flow in the way your body wants to move?

47. In what ways is vulnerability the gateway to healing and connection?

48. How can a quiet communion with the nature help you discover deep spiritual truths?

49. How can you avoid becoming addicted to changing yourself?

50. How can you let your heart do the talking in the face of fear?

As I said, feel free to join me. Pick whatever questions resonate and reflect. Write. Do whatever you feel like doing.

There’s no right or wrong — there just is.

Thank you for your time. Love and light!

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