In articulating his conception of freedom, Kerouac echoes much of the post World War II boundless energy in American freedom. Sal and Dean jump into the car and drive, and drive, and drive. There is little in terms of exact destination because freedom and individuality are depicted as journeys in their own rights, without a need for a defined end. In so much of the poetry which emerges in America after World War II, there is this desire to break free from conventions and the standard depiction of "what is" and transform it into "what should be." Thinkers like Kerouac and Ginsburg were instrumental in conceiving of individuality as a tool to transform the existing social order and perception of self.
Jack Kerouac in the book "On the Road" attempts to do everything that he can the opposite of societal expectations. He loves to travel, smoke cigarettes, and make love to women. He chooses to live with his friends in an unusual marriage situation. There are two men and one wife. He actually lives for awhile in suburbia in this manner.
For Kerouac living a life free of conventional social rules is the way that he expresses his individuality. When the book came out with all the cursing in it, that in itself, was his method of showing his individuality. He was very much anti-establishment.