Obsessing about obsessing or “OCD about OCD” is all too common. Many individuals who experience this OCD presentation find themselves tormented by unanswerable questions and unattainable goals regarding their OCD’s existence, symptoms, and treatment. Individuals may find themselves seeking perfection in their treatment, therapy, or a desired sense of feeling cured. While self-help can be incredibly powerful in the treatment of OCD, obsessing about obsessing may lead to self-help which goes beyond what is helpful and becomes a compulsion. Collecting self-help books and spending hours on OCD-related content on YouTube or Reddit may be indicators that self-help seeking has gone beyond what is helpful and moved into a relief-seeking compulsion. In this article, the author describes his own experience going down the OCD rabbit hole and obsessing about obsessing.