When I initially sat with Dr Innette Cambridge for this conversation, I imagined spending about two hours conversing about the evolution of social policy as it intersects with social work as an academic discipline and practice-based profession, with special reference to the policymaking arena in Trinidad and Tobago. Instead, what transpired was a series of in-depth interviews, each spanning approximately two hours in length. We explored history, delved into diverse stories and perspectives with lively analyses of social welfare policies and indigenous practices. We sang classic calypsos and soul music hits from the 1970s. Between each interview session, I dove into texts, articles, and archival materials, burrowing down fascinating rabbit holes. This chapter offers a glimpse into truly indispensable discourse with a stalwart of scholarship and activism at the intersection of Caribbean social work and social policy. It explores women’s work in social work, advocacy, and policymaking. We explore relationships between their lived histories and the principles and objectives underscoring social work, social policy, activism, and policymaking.