You can only get this trophy during the Introduction day.
You need to beat the Anarchy Man arcade game. This is located in the Facility, in the door to the left of the lift on level 2. The arcade box has a flashing Anarchy sign on it. This is the only time you can complete this game, so if you fail, and it tells you your shift is over, you have to quit to the main menu and then select Resume. This will take you back to the save point where you put your uniform on in your room.