A gaming device having a plurality of goals, at least one destination goal, a player goal indicator, an award associated with the destination goal which is provided to the player if the player goal indicator reaches the destination goal, a setback condition associated with one of the goals, wherein when the player goal indicator moves to the goal having the associated setback condition, the player goal indicator is relocated to one of the goals further from the destination goal based on the setback condition, an advance condition associated with one of the goals, wherein when the player goal indicator moves to the goal having the advance condition, the player goal indicator is relocated to one of the goals closer to the destination goal based on the advance condition, and a plurality of offers associated with the goals, wherein the player is enabled to accept or reject the offer associated with goal of the player goal indicator.