Comment by myth_buster

  Dropping a newbie into Eclipse or MonoDevelop makes them feel like 
  they are walking around in a byzantine museum, afraid to touch 
  things, while DrRacket feels closer to old-school personal computers 
  where you felt like you were in command of the machine. 

I think this is a very important observation. As with most things, it's extremely important to get in during the humble beginning stage and then tracing your way up to grok more complicated systems. Similar to the "first principle" approach.