As the senior living industry prepares to cater to a new generation of residents, there are valuable lessons to be gleaned from large retail organizations like Amazon and Kroger. These companies have expanded their health care offerings in recent years, reflecting the changing landscape of healthcare. With a significant portion of Medicare dollars now going to private health insurance companies, there is a growing opportunity for senior living providers to enhance their involvement in the healthcare space. The blurring of traditional healthcare boundaries means that innovative services, such as those related to food, housing, and social support are increasingly becoming part of the medical care landscape. Retail’s foray into healthcare offers insights into how operators can navigate similar challenges and drive growth. By building strong relationships and aligning with other stakeholders in the healthcare continuum, senior living operators can better meet the evolving needs and demands of their residents. The next few years present a prime opportunity for senior living providers to embrace entrepreneurial initiatives and collaborations, paving the way for a brighter future in the industry.