Asymmetry occupies a remarkable position in the depth-psychology corpus: it functions simultaneously as a neurobiological datum, a cosmological principle, and a generative philosophical category. The dominant voice is Iain McGilchrist, whose treatment across both The Master and His Emissary and The Matter with Things elevates asymmetry from a mere structural feature of the divided brain to nothing less than the condition of possibility for novelty, life, and becoming itself. For McGilchrist, symmetry is sterile — an operation that leaves things unchanged — while asymmetry is generative, coupling disparate elements to produce something genuinely new. Crucially, the relationship between symmetry and asymmetry is itself asymmetrical, demanding both in dynamic conjunction rather than the dominance of either. The neurobiological literature represented by A.D. Bud Craig and Daniel Siegel grounds this philosophical argument in empirical detail: insular cortex lateralization, differential autonomic activation, and the presence of 30–50% more von Economo neurons on the right side of the frontoinsular cortex all speak to functional asymmetry as a constitutive feature of feeling, consciousness, and self-regulation. Siegel situates brain asymmetry within developmental relational frameworks, noting that its basis is laid in fetal stages. Across these voices a productive tension persists: is asymmetry primarily a structural brain fact, a cosmic generative principle, or the ontological ground of differentiation as such?