In a Greek myth, Sisyphus pushes a boulder up a hill only to have it roll to the bottom every time he nears the top. Patients may relate to this feeling of a never-ending struggle to achieve the healthcare that they need, pushing against the barriers of their chronic illness or disability. Personal and supportive factors provide these patients the resilience and strength that they need to push this “boulder” every day. With this metaphor in mind, we surveyed our PIE mentors and other people in our lives living with chronic disease and asked them words they would use to describe their healthcare experiences in regards to (1) their needs and expectations from the healthcare system (2) challenges they have faced in the healthcare system, and (3) factors that give them strength to cope.