The key is to think outside the box. And that is usually the takeaway from the game. But I push the lesson further and use it to introduce the idea of learning systems (the jail, probation, school, work, etc.) and figuring out how to use that knowledge to win at them, for real, not to just work them.
We talk about how the purpose of a system drives the written and unwritten rules and procedures. We talk about the ways to figure out those rules and procedures by asking, listening, observing, reading the handbook, and learning by experience. We talk about how important it is to use good judgment--you can't trust just anyone. We talk about how to handle it when we're called out for breaking rules we didn't know existed or for not properly following a procedure we're not familiar with. We talk about how systems are created by human beings, who are imperfect, which means the systems themselves are imperfect. We talk about not letting arbitrary things that result from that imperfection throw us off.
And then I go back to the first takeaway and we talk about how important it is for us to think outside the box. We can't forget the unique things we bring to the system and the fact that many of us don't fit neatly inside the dots. In fact, if we try to cram ourselves into the box of dots, we end up banging our heads against the sides of it. We not only risk losing the game when we do that. We may even lose ourselves.
The older I get, it seems the less neatly I fit inside some of the places I'm expected to fit. Maybe the boxes are getting smaller. Or maybe I'm seeing the dots too clearly. Or maybe my bleeding heart is too swollen. Whatever it is, I've got to figure out how to draw my lines before I lose myself.