Starting after Contract 01, you'll have some free time before driving off to your next assignment. This and three other trophies can be obtained during this time:
Every chance you get, watch the television by interacting with it with X. You'll get bits of news here and there, as well as some sports coverage. Perform this action fifteen times before heading off to your next contract and you should get this before you'd have to restart doing them (there is a point in the game where you won't be able to do these anymore unless you restart from an earlier contract).