when there is alot of things or people in the way you have move around them, go over things or under things.
person one: How do I get through there if all this stuff in my way
Person two: Dude I guess your going to have to obstacle couse-it
or
Your mom: How do you get to your bed with all this mess in your room
You: I obstacle course-it
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.