Scholars and practitioners alike celebrate the Apostle Paul as an exemplar of Christian mission. But few emphasize how the ministry and practices of the biblical author developed amid incredible intrareligious conflict and relational wreckage. Embroiled in tension over doctrinal and ritual changes, plagued by vitriolic attacks on his character, and caught up in a web of splintered relationships, Paul offers contemporary people of faith a lesson on unity in diversity for mission in an age of hybridity. Embracing the “terrible and troubled” experience of Paul enables us to bring into relief a transformative hermeneutical strategy for negotiating new forms of religious life and multiplicity in belonging. This article will show how competing cultural and religious codes shaped the Apostle’s symbolic universe, causing violence, tension, conflict, and rejection, before reconciling in an ethic of love in hybridity. After making a case for the reclamation of the troubled textual Pauline experience over an idealized picture of early Christian mission, I will argue for the critical importance of Paul’s Damascus Road experience by narratively resituating it from typological “conversion” story to mystical encounter with the Holy Other that catalyzed a new religious imagination for cultivating a revolutionary egalitarian, inclusive pattern of religious life. Then, I will use Paul’s narrative from Galatians and his treatment of holiness in 1 Corinthians to show how ruptures in the Apostle’s journey led him through fractures and failures into spiritual maturity. By welcoming the gendered, classed, and cultic other into fellowship, Paul also found his quintessential theological insights: the new creation and life in the Spirit. Paul’s response to the invitation of the risen Jesus and his record of the missional life that followed offers missiology a way through monocultural approaches and theological exclusivism into a constructive spirituality that unifies radically different factions into one holy, hybrid body.