Writing can be a profound spiritual practice. In the days of Elul, leading up to the High Holy Days, these questions can help prompt the soul accounting essential to teshuvah.

1. What do you hope for in the New Year?
2. What is forgiveness and how do we forgive?
3. What makes a good apology?
4. What do you regret?
5. What does teshuvah mean to you?
6. Have you ever changed for the better? If so, how?
7. What are your bad habits?
8. What’s one good habit you aspire to embrace? When will you start?
9. Imagine High Holy Days three years into the future … 20 years …
10. Pick your favorite prayer, story, or practice of the season and interpret it.
11. What have you learned since last Rosh Hashanah? About yourself? About the world around you?
12. What sustains you in times of challenge?
13. What does it mean to be good?
14. Which virtue do you value most and why?
15. Who inspires you and why?
16. What is one thing you are ashamed of? One thing you are proud of?
17. If your soul could speak, what would it say?
18. What can you do if your loved ones make a mistake?
19. Who do you yearn to be?
20. What do you need to release or embrace in order to shine more brightly?
21. Who are you remembering this year?
22. What are your mistakes? transgressions? 
23. Write your own eulogy.
24. How are you being called to take responsibility?
25. Where do you need to heal?
26. What are you turning away from and what are you turning toward?
27. What are your strengtths?
28. What activity (or activities) are you currently doing that utilize your strengths?
29. Is there a way to build upon these current strengths and activities? If so, how?
30. Are you interested in putting these strengths into practice with a new initiative/project? If so, how?
31. How do these strengths/activities help your relationship with others?
32. How do these strengths/activities help your relationship with G-d? 
33. Write a letter — perhaps to G-d or perhaps to yourself — about what you would like to get out of life, how you would like G-d’s blessings for yourself and others in the coming year and beyond. 

With thanks to Ritualwell and Chabad.org. For more Elul journaling prompts, check out this blog post on RebekahLowin.com.