In surfing the waves of COVID-19 and the current socio-political culture of alarm, uncertainty, and anxiety, I describe how exploring works by Mark Rothko, the Rolling Stones, and Henri Matisse helped me find grounded experiential footing during the pandemic. Rothko’s multiform and later paintings encouraged exploration of the soul, experiences of the ineffable, of life-and-death. In contrast, the Rolling Stones inspired me to feel my heart, my beat, my connectedness to rhythm and knowledge that presence rests on interpersonal connection. Finally, as seen in The Red Studio, Matisse and his use of color re-vivify the experience of living, and provided a roadmap back to optimism.