1. What obstacle is your character facing?
My character is asking his parents for money to help with rent, and realizing he either needs to get a higher paying job, or move out of the city if he wants to be able to stop asking them for help.
2. What will be the consequence if your character does not get what they want? What is at stake?
If my character doesn't get money from his parents, he will have to start selling whatever items he can, and start looking for a second or higher paying job.
Very clear and very straight forward. I think it is also important to remember his pride is on the line. Shame and Guilt can be big obstacles. Wanting to be seen as a success can also be an obstacle in dealing with his parents. Being a musician is such a precarious thing, as I know you know. It takes a lot courage and faith in oneself, but there is also a lot of rejection to face down. I know your final monologue will have all of these woven into it. I can't wait to see it.