Richard Rohr’s Falling Upward is a book that speaks to those who sense a hollowness in outward success, whose carefully constructed identities or personas no longer hold the same weight or function as they once did. Rohr offers a language for thinking and talking about this transition, which becomes a descent into a spiritual depth that embraces paradox and uncertainty over self-determined linear progress and achievement in the world. In contrast, there is another path, ancient and austere that can complement Rohr’s presentation: the apophatic tradition. Rooted in the earliest centuries of Christian mysticism, it calls not for building or refining the self, the container we imaginatively construct and fill, but for letting it go entirely. These two approaches, though distinct in their means, converge on the same mystery: union with God.