There are many stories of obsessiveness, apparent disasters and waking up, mirroring (one version of) the awakening process.
Moby Dick is about one man’s obsessiveness with the white whale (God) which eventually drags him and his ship under (the death of a sense of separate I along with any other belief and identity), leaving only the ocean, the nondual awakening.
The Truman Show is about a man gradually intuiting that his life is a fabrication, the apparent disasters that happens when he attempts to break out (loss of identities and beliefs), and his final breaking out.
The Matrix trilogy is about a man first waking out of the conventional dream, and then through a great deal of struggle finding an awakening that goes beyond and embraces all polarities… Neo and Agent Smith (good and evil, persona and shadow), the machine world and Zion (mind and matter, also in its version of empty luminosity and form), the Matrix and the real world (deluded and awake).