I assume everything I do in life is gonna be a failure, and then if it turns up roses, then I’m psyched.

Hill frames his working mindset as deliberate pessimism: by expecting failure, he lowers the emotional stakes of any given project and protects himself from disappointment. The payoff is that success feels like an unexpected bonus—“turns up roses”—rather than something owed. Read charitably, it’s a coping strategy for a high-visibility career where outcomes are uncertain and criticism is public; it also echoes a comic sensibility that deflates ego and ambition. At the same time, the line hints at anxiety and self-protective defensiveness: assuming failure can motivate preparation, but it can also become a habit of self-doubt.