Update 4/3:
Finally finished. I think I went a little too far with the textures but overall a great experience. I learned a lot.

Here is the process from Illustrator to Photoshop:

I was talking to my mother the other day and she has a way of always putting things into perspective. She said, "Lick your wounds, this too shall pass." Took it to heart this time and figured it was suitable for this project.
I wrote out the phrase and tried a few iterations of it in a blend of styles.

I ended up settling on this sketch and refined it and & it larger.

Here is the final sketch that I will be digitizing.

I'm still open to any suggestions or critiques.