Lifeworld is a multi-dimensional concept and reality in philosophy, social sciences and in our practice of living. The present essay explores its different meanings and interpretations starting from Edmund Husserl to Jurgen Habermas in the European intellectual tradition and Sri Aurobindo, Mahatma Gandhi, J.N. Mohanty and Margaret Chatterjee in the Indic traditions. It rethinks the Habermasian idea of colonisation of the lifeworld and argues how we need Gandhian struggles for overcoming this. It argues how lifeworld is a field of satyagraha as it exists in the midst of Sattva, Rajas and Tamas. It also argues how lifeworld is a field of lokasangraha—a gathering of people which is also related to atmasangraha—a gathering of souls. With and beyond Habermas, it argues that lifeworld is not only a field of reason but also of intuition and striving for the spiritual in the midst of many rational and infra-rational forces at work in self, culture and society. The essay then links the challenges of lifeworlds to the challenge of living words in our lives—words which give birth to new words and worlds going beyond stasis, stagnation and death of language, culture, self and society. Lifeworld is a field and flow of living worlds which have both a pragmatic and a spiritual dimension. The essay explores the border crossing between pragmatism and society and looks at lifeworlds and living words as fields of spiritual pragmatism.