As work is shifting and changing, we, CSCW researchers, must consider our role in creating work futures, and what experiences we want to produce through technology design. What qualities are important to consider about the human experience when designing work technologies for the future? Exploring the potentials of artistic practices for epistemological inquiry, we demonstrate Research through Art as a novel futuring approach for CSCW research, leveraging the power of artistic practice for exploring questions of human experience. We engaged with young artists who created art pieces that manifested their hopes, intuitions, and anxieties on the future of work. Our analytical inquiry of these artistic practices allowed us to explore what different futures might be imaginable and what might these futures feel like. We find that futuring entails engaging with ambiguities, which can be a productive resource for design. We identified the ambiguities of time, purpose, body, identity, and agency as foundational for the imaginaries produced by the artists. By intersecting the ambiguities, we can begin to systematically frame novel design questions for CSCW technologies of the future by conceptualizing these ambiguities as multifinalities – single points from which many possibilities emerge.