[1] Through the works and lives of various artists – including H. G. Wells (Mind at the End of Its Tether), Franz Kafka, Albert Camus, Jean-Paul Sartre, T. S. Eliot, Ernest Hemingway, Harley Granville-Barker (The Secret Life), Hermann Hesse, T. E. Lawrence, Vincent van Gogh, Vaslav Nijinsky, George Bernard Shaw, William Blake, Friedrich Nietzsche, Fyodor Dostoyevsky and George Gurdjieff – Wilson explores the psyche of the Outsider, his effect on society, and society's effect on him.

Wilson wrote much of it in the Reading Room of the British Museum, and during this period was, for a time, living in a sleeping bag on Hampstead Heath.

He continued to work on it at a furious pace and: One day I typed out the introduction, and a few pages from the middle, and sent them to Victor Gollancz with a letter giving a synopsis of the book.

Sartre's Nausea is herein the key text – and the moment when the hero listens to a song in a cafe which momentarily lifts his spirits is the outlook on life to be normalized.

Wilson then engages in some detailed case studies of artists who failed in this task and try to understand their weakness – which is either intellectual, of the body or of the emotions.

The final chapter is Wilson's attempt at a "great synthesis" in which he justifies his belief that western philosophy is afflicted with a needless pessimistic fallacy.

Philosopher A. J. Ayer, writing in Encounter magazine in September 1956, argued that Wilson's book failed to define the essential characteristics of "the Outsider", stating that "he gives us various indications which do not make an entirely coherent picture."

This reception – of his first book at the age of 24 – was a high critical watermark for Wilson which he did not achieve again until the publication of The Occult in 1971, after which he enjoyed a long and fruitful career as a writer, philosopher, novelist, lecturer and broadcaster until his death in 2013.