Checking in!
I second MCerberus.
By awakening, do you mean seeing the shadow monsters or realizing they're a real thing and not a dream/hallucination? My backstory for Roland was that he's been seeing the monsters for a while, he just thinks they're hallucinations/dreams.
I don't really have strong feelings either way, but since Roland doesn't have a background in mystical stuff he's probably going to need someone to give him a tap on the shoulder and go, 'Hey, magic exists! And it's affecting the world you live in and your life specifically!'