The Hermit's Journey Challenge

It’s been almost a year since I created a divination challenge, the last one being the In the Bones Challenge tied to runes and ancestors. Now that I’ve come back to some of my roots after a spiritual journey, it seems fitting to offer a set of reflective questions that might inspire others to deepen their connection to self and spirit. That it arrives in time for Virgo season is no accident, but I’ll be participating September 1–30. It’s the Hermit’s Journey, not the Fool’s Journey after all.


There are thirty “days” of exercises, broken up into four thematic weeks for the journey with rest and reflection encouraged on the final day of the week. At the end are two important questions to help you be a useful Hermit, not a selfish jackass Hermit who hoards wisdom and experience. Share, even if you don’t feel qualified. Qualify your wisdom as your experience, and no one else’s, and you’ll be just fine. No one else can question how well you know your experience.

This is my quick take on the famous Romantic painting of the sublime, Wanderer Above the Sea of Fog by Caspar David Friedrich. I love the original, which shows an aspirational Hermit but one who is ready to come back down the mountain into real life when it’s all said and done. Here, the shape of you is still a work in progress.

This is my quick take on the famous Romantic painting of the sublime, Wanderer Above the Sea of Fog by Caspar David Friedrich. I love the original, which shows an aspirational Hermit but one who is ready to come back down the mountain into real life when it’s all said and done. Here, the shape of you is still a work in progress.

1. What will this journey teach me about myself?

2. Why should I go on this journey?

3. Where is my hermitage?

4. What must I leave behind?

5. What must come with me?

6. How can I best prepare for the weeks ahead?

7. Rest & reflection

8. What will this journey teach me about my spirit?

9. How have I previously rejected spiritual connection?

10. For me, what obstructs spiritual connection?

11. How can I work to remove that obstacle?

12. What past version of myself can I release?

13. What wounds are raw and need tending? 

14. Rest & reflection

15. What will this journey teach me about my world?

16. What in the environment sustains me?

17. What in my world brings me joy?

18. What in my world does more harm than good?

19. How can I use the environment to strengthen me?

20. How can I give thanks to my world?

21. Rest & reflection

22. What will this journey teach me about light and darkness?

23. What part of my shadow do I let sabotage me?

24. What part of darkness tempts me with power?

25. What part of my light would blind me if I let it?

26. What form of brilliance am I ready to embrace?

27. How can I best balance light and darkness?

28. Rest & reflection

29. How can I bring my wisdom back home?

30. How do I stay humble?