I've been down that road.

I see so much of myself in Sterling.  The good and the challenges.
The good news is he will be low key, happy, funny and a good person.
He's all about having fun and having no responsibilities right now.  I understand that.

Like most parents, I worry too much about what will be.
I ask him to clean his room and the response I get is, "now?"
I ask him to find his bike, which he left at a friends, and I get a song and dance.
Be home at 6:45...he makes it back by 7:45.
"Talk to your teacher and figure out where your homework went", I ask...and I get "I forgot".
"Put your dirty clothes away".  "Why do you still have an F and a D...it's been weeks".  "Stop spending so much money at lunch".   
I get tired of asking all the time.  When I continually ask about these things he gets frustrated.  Then, I in turn get frustrated.
see blog post "responsibility 101".
Big picture...he is healthy and a good kid.  We will sit down, I will challenge him and he will step up and do the above mentioned items.  It won't be a happy night...but that's what needs to happen when trying to raise a good person.

I wish he could see himself through my eyes and experiences...It would be alot easier.  But nothing good came out of anything easy.