Cynicism is characterized by anti-conventionalism and a close connection between theory and praxis. Paradoxically, the emptiness of theory is demonstrated by cynic praxis. The audacious freedom expressed in the life and thought of Diogenes Laertius results from the rejection of common rules of life and replaced it by philosophy as a form or way of life (Hadot 1995). The Cynics develop a spirituality of ethical virtue connected to inner freedom and a realistic perception of (human) nature where paradox plays a key role. Epictetus portrays Diogenes as the ideal philosopher, as a pragmatic practitioner of philosophical life (Schofield 2007). The cynic lifestyle demonstrates a particular understanding of moral truth. It is the Socratic idea of philosophy, pursuing the truth, yet understood as care for the soul. Epictetus sees the cynic as the true practitioner of this ethical ideal, spiritually and physically. Similarly, the early Christian philosophers identify a concrete lifestyle as the path towards truth (Gjermundsen 2023). The scholars known as desert fathers did not shun isolation and anti-conventional lifestyle in order to achieve inner freedom. This is characteristic of Evagrios Pontikos (4th C) who developed a threefold path toward theosis, understood as a way of life: 1. Ethical purification through ascetical practice (praktike) leading to dispassion and inner freedom (apatheia); 2. Contemplative perception of the true nature of created physical reality (theoria physike); 3. ‘Theological’ union with God according to grace (theologia). In my paper, I will emphasize the connection between (i) ascetic practice and freedom as condition for (ii) a pragmatic, and yet contemplative perception of nature as physical reality. I will argue that Evagrios adopts cynical strategies in order to avoid speculation and demonstrate the truth and freedom in a specific praxis or way of life.