Exploring Aliveness # 6 | The Dao of Working (w/ @dennisxiao )

2 Mar 2026 · 51 min
51:27

In this episode of the Exploring Aliveness podcast, host (Speaker A) and guest Dennis Xiao discuss the nature of work, identity, and aliveness in the age of AI. Dennis traces his personal journey from a high‑paying investment‑banking job, which he found soul‑crushing, to a series of experimental roles—creative production, coaching, AI‑focused side projects (e.g., Homey Calendar), and a current search for a B2B SaaS or operations position. He distinguishes between a "job" (a source of income) and "work" (self‑expression, aliveness). The conversation explores how repeated career experiments have revealed that the specific title or industry matters less than the feeling of being fully oneself at work. Themes of commitment versus attachment, the role of desire and "wants" that generate new possibilities, and the idea that work can be a crucible for inner transformation are examined. Both speakers use musical metaphors (tuning instruments, sound baths, handpan) to illustrate the process of aligning with one’s inner rhythm. They reference Friedrich Weckner’s vocation definition (where deep gladness meets world need), Wu Wei, and the 64‑Door archetype (the Daredevil) as lenses for understanding vocation. The interview also touches on AI as a tool that expands personal dimensionality, allowing one to be a writer, coder, coach, or musician simultaneously. The episode ends with reflections that job‑search interviews themselves become a form of inner work, teaching trust, attunement, and the importance of a "warm, playful, safe" job container that feels like a reciprocal flirtation. The overall message is that authentic self‑expression, rather than external validation or a fixed career identity, is the core of aliveness in work.

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