In this presentation I will share some of the boundaries crossed and lessons learned in my 20 year psychedelic journey reported in Diamonds from Heaven (forthcoming). Seventy-three high dose LSD sessions conducted between 1979-1999 became the philosophical adventure of a lifetime, but one I had to keep largely hidden from my university colleagues. As psychedelics return to scientific and academic discourse, I am now sharing my experiment in doing philosophy in the psychedelic mode. Categories include: crossing the boundary of birth and death, the ocean of suffering, Deep Time and the soul, the Greater Real of archetypal reality, Oneness and the Primordial Void, the birth of the Future Human, Diamond Luminosity, and coming off the mountain.