The music video for “Live Your Life” was filmed in October 2008 in Los Angeles and was directed by Anthony Mandler. The video, using the radio edit of the song, stars T.I. and Rihanna. It plays backwards, starting with the end of T.I.’s day. In the opening scene T.I. is shown walking with bloody wounds culminating in the song beginning. It then goes from a series of underground shots of him with interspersed scenes of Rihanna in a dressing room. T.I. is then shown being thrown out of a car, being kicked by a large man. The video then cuts again to the day with T.I. wearing the same suit seen earlier in the video, but undamaged. He then encounters a group of thugs whom he brawls with.
The video then begins a different story arc, showing T.I. before he made his fortune, singing in a recording studio and in front of a house playing dice and dominoes with friends. This portion of the video is interspersed with clips of the other story arc, such as showing T.I. with a briefcase full of money. He is then shown in the bathroom of a bar, before walking out into the bar passing Rihanna who has exited her dressing room. Rihanna performs on stage with a microphone while T.I. talks to a man saying “[he] want[s] out.”; the man replies by explaining that there is no getting out, not for him nor for the character that Rihanna plays. T.I slams the money briefcase down on the table and shows it to the man saying that “I’m done. I got myself here, I’ll get myself out”. Then he is seen walking into that same bar, in a flashback, with a CD in his hand. The man that T.I. spoke to earlier calls him over. This is a flashback showing T.I. trying to get a record deal.
The last shot of the video takes place at around the same time as the first shot of the video. T.I. is walking down the L.A. River, raising his hands triumphantly in the air with a bloodied and scarred face. The song’s producer, Just Blaze, is briefly seen playing pool in the bar during the second verse and final chorus.