For years I asked my students to write a journal entry to me at the end of the month. Try as I might, what I usually ended up with was a laundry list of "I did this and then this and then this and then this."
This fall, I read "Daring Greatly" by Brene Brown and decided to connect some of the concepts from her book into what i ask of my students each month. For example:
What experience helped to bring purpose and meaning to your life?
At what point were you somewhere where you feel you truly belong?
The six different prompts I created have had a profound positive impact on not only the quality of writing that my students produce, but also my ability to connect with them and their interests.
If you do journaling of any kind in your room, I highly suggest this approach.