Ask HN: How to help teach a friend advanced python concepts?

I have a friend who is learning python. He is learning fast and getting the basic concepts down. When he looks at higher level code as part of bigger systems he is getting a bit overwhelmed(django source). How can I help this person bridge the gap. I went through this too when I was first learning, the easy stuff online was too easy and the hard stuff online was too hard. I'm trying to ease the transition from being able to write a few scripts to becoming a django contributor