As older workers leave the workforce, they take their human capital and specific skill sets with them. Their retirement will have significantly adverse effects on the numerous sectors that employ older adults, including government, public administration, education, and healthcare. This perspective paper describes some factors that hinder or support continued employment of occupational therapy practitioners over the age of 50 and suggests workplace accommodations and considerations that might allow some to work longer in the field. A literature review shows that flexible scheduling, ergonomic design, assistive technology, mentoring, continued training, and appreciation of diversity can support continued employment. The need for healthcare providers is only expected to grow in the near future. Providing accommodations and anticipating the needs of older workers may allow them to stay in the workforce longer. Supporting generational diversity in the healthcare workforce can benefit consumers, providers, and the system at large.