In today’s rapidly evolving professional landscape, the call for lifelong learning has never been louder. As industries shift and technologies advance, institutions are being asked to equip learners not only with foundational knowledge but also with ongoing opportunities to refine, expand, and adapt their skills. Upskilling learning experiences have emerged as a key component of the response to this demand, offering accessible, targeted ways for individuals to remain agile and relevant in their fields (World Economic Forum, 2025). This Envision piece offers insights to administrators and faculty who are considering whether to integrate upskilling programs into their institution’s broader portfolio of offerings. Additionally, this piece provides recommendations for faculty and staff who are designing and facilitating such learning experiences.