Globally, workforce is aging. Workers aged over 50 are becoming an increasingly significant and large component of national workforces. This situation is likely to remain the case for the next few decades. Despite workplaces becoming increasingly reliant on older workers of all kinds generally, the distribution of opportunities for support, professional development and advancement belies that fact. The situation confronting older professionals appears more nuanced and dual. On one hand, many of these workers report little or no age discrimination and high levels of opportunities for advancement, should they wish it. On the other hand, these workers are most likely to retire early and make their own decisions about the duration and intensity of working lives and how they engaged in continuing education programs. They also largely report being active lifelong learners, and whose worklife learning is shaped by work requirements and challenges. Consequently, considerations for ongoing learning for older professional workers are premised on combinations of workplace provisions, personal agency and access to educational programs in ways that are quite distinct from other categories of older workers. The chapter proposes that the ongoing development and employability of older professionals is likely to be central to national economies in decades to come; that it is necessary to have an adequate fit between provisions of formal learning and those afforded in workplaces to support individual skills currency and national innovation capacity, and; that distinctive for older professionals is a high extent of personal choices available for their work and learning, necessitating a concerted public and private effort, in broad cooperation among relevant partners, when seeking solutions for extended job-careers in line with prolonged life-spans.