This paper examines two American works of fiction concerning how teenage characters explore and manifest their identity, looking up to transcendentalist ideas, whether consciously or not. The paper puts forth the most individualistic protagonists and investigate their motivation, ways of escaping the society’s expectations and the interaction between them and their environment. The first source analyzed: the film Little Women directed by Gillian Armstrong tells the story of the March family living in the 1860s Concord, influenced by the spirit of transcendentalism. The second source discussed: John Green’s novel Paper Towns employs the notion of a character coming back to transcendentalist values and authors in the 21st century. This paper shows how the teenagers use the transcendentalist ways, whether they are aware of them, and defy the rules of the society frequently represented by the people in their closest environment.