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I argue for a transformative revival or actualization of the very core of an integrative, methodologically secured form of intellect-mystical asceticism. This approach draws on traditional sources that are re-examined from a systematic—synthetic and transcultural—philosophical perspective and in light of the multi-civilizational global environment of the 21st century. The main traditional points of reference in this paper are provided by Nicolaus de Cusa and Ibn Sīnā, and I refer to a few others, such as Attar of Nishapur, in passing. I begin by developing a basic concept of intellect-mystical asceticism. It is distinguished from mystification, science, scientism, and modes of everyday communication and cognition. Then, I make the case for an updated, transcultural approach to intellect-mysticism that can foster the internal (social) and external (environmental) reintegration of the human noosphere and technosphere in future planetary development. In this context, a modern intellect-mystical philosophical notion of “knowing non-knowing” (wissendes Nichtwissen, docta ignorantia) is developed. It is inspired by Nicolaus de Cusa and contextualized from a systematic transcultural angle at the same time. Finally, I discuss the problem of the practical, or rather ascetic, realization of the related possibilities of intellect-mystical self-enfolding. Here, the preceding steps of the reflection are mapped onto an outline regarding distinct developmental stages of such a transformative intellect-mystical practice in Ibn Sīnā’s Remarks and Admonitions (al-Ishārāt wat-Tanbīhāt).