Go For It!

From BoardGameGeek:

Compete to collect Status Cards in four different categories: House 'n Home, Wheels, Feelin' Good, and Goin' Places. Players take turns moving the shared "timepiece" pawn around the board, which represents a calendar year. Labor Day serves as an annual pay day. On certain spaces, a player has the opportunity to buy or sell Status Cards. He may also risk a Status Card on a roll of the dice in an effort to upgrade to a more expensive card. News cards add additional random events, such as gaining or losing Status Cards. To win, you must declare on Labor Day that you are "going for it". By the following Labor Day, you must have at least 3 differently valued Status Cards in each of the four categories to win.