The influences on cultural identities are complex and fluid. As more of us reconnect with our ethnic roots, live abroad, or marry interculturally, we no longer see one cultural identity in the mirror but several. Yet society still has a simplistic definition of cultural identity and what our mirror image should look like. It assumes that the culture we were born into determines our lives. Such ‘essentialist’ or categorical thinking fails to appreciate that cultural identity evolves and is constantly reconstructed in response to our life experiences and the meanings we draw from them. In this chapter I will describe how we reconstruct our cultural identities by considering three philosophical positions: existentialism, yin-yang, and wabi sabi. Drawing from cross-cultural research, and my own experiences growing up as a Canadian-Greek-Macedonian and later living abroad, this paper argues that our identities are fluid and constantly reconstructed. Such identities are reconstructed by actively negotiating them, accepting our multiple identities and embracing our imperfections, the transience and incompleteness of our identities. Applying these philosophical reflections can help us achieve greater clarity about our self-concept, and our cultural identities and well-being.