The article explores the ‘philosophy of the individual’ of Lionel Trilling. Focusing on his essays on Jane Austen and William Wordsworth, and on his 1972 book Sincerity and Authenticity, the author goes deep in dialectic which, in Trilling's opinion, lays at the ground of both modern literature and modern individual. On the one hand extremely aware of the theatrical essence of life in society, modern individual is on the other hand ashamed of it and lives his spiritual life in search of his ‘own self’. Modern individual lives following the two cognate ideals of sincerity and authenticity. But, Trilling holds a dialectic vision of this two concepts as well: the only way to live an authentic life which is not a parody of itself is to live, as Wordsworth and Austen have sometimes fancied, ‘beyond style’.