Evan, I always felt Free Fallin' in this case, meant leaving your troubles behind and just letting life take you where it takes you. Having no control over what happens in your future.
This is from the Song facts website: "The lyrics deal with Los Angeles culture, mentioning actual places in the area: Reseda, Mulholland and Ventura Boulevard. It implies that the people of LA will casually use others for personal gain, as the singer has just dumped a girl and doesn't even miss her. Petty was born and raised in Gainesville, Florida and moved to LA with The Heartbreakers in 1974. His outsider perspective came in handy in this song."