This article analyzes medieval Sufi psychology with special reference to yaqin (certainty), qana‘a (contentment), rida (satisfaction), itma’nina (tranquility), and tawakkul (trust in God. Special attention will be paid to whether these spiritual states and stations of the Sufi path to God are compatible or incompatible with service to the human community. Can one be both socially active and contemplative? Can these two goals be reconciled in the life and thought of the same ascetic-mystic? Should one tie up one’s proverbial camel, while at the same time putting one’s full trust in God? These Sufi concepts and dilemmas will then be compared to the Stoic and Gnostic notions of apatheia, followed by a discussion of the famed Naqshbandi-Sufi idea and practice known as khalva dar anjuman (being one [with God] in a crowd).