The paper investigates topology of uncontrolled dynamic depressive thoughts which is popularly known as “autopilot” in the psychology domain. Persistent homology, a mathematical tool from algebraic topological has been applied on Vector Space representation of tweets generated by users having neurotic personality for determining the topological structure of autopilot thoughts. State-of-the-art machine learning techniques leveraging linguistic resources akin to LIWC, WordNet- Affect and SentiWordNet have been applied for identifying neurotic personality from different Twitter users. An initiative has been taken for empowering Neuro Linguistic Programming (Bandler and Grinder, 1975; Bandler and Grinder, 1979; Bandler and Andreas, 1985) and other psychotherapy techniques using Natural Language Processing in the domain of Mental Health.