This chapter sheds light on the often-overlooked segment of mid-to late career professionals, examining the systemic and cultural biases that emerge as early as age 40. Drawing on global data from mandatory retirement policies to performance assumptions linked to age it reveals how ageism operates subtly and overtly in many workplaces. Despite these challenges, this group offers knowledge, serves as cultural stewards, and provides mentorship, yet they are frequently left out of career development initiatives. Drawing from a global coaching program, the chapter illustrates how organizations can better support these professionals through intentional reflection, targeted development, and defining meaningful roles. It introduces a practical coaching practice designed specifically to guide mid-to late career conversations, featuring questions that help individuals clarify what motivates them now, how they want to contribute, and what legacy they hope to leave. At its core, this chapter makes the case for reimagining mid to late career as a time of renewal, contribution, and strategic alignment for both individuals and organizations.