Most adults are urged to go through an annual health checkup. We recommend that most mature small businesses perform an annual strategic longevity and health maintenance evaluation as well to ensure their viability. To this end, we provide strategic areas of critical importance to a small business viability and longevity and offer guidelines for small business owners, managers, consultants, and small business/entrepreneurship educators use to help improve performance. We add to the body of literature on small business success and failure factors by emphasizing the need for a closer look at the open systems nature of these businesses and the impact of interaction with the larger external environmental system for viability. We urge small business owners to be more proactive in evaluating the health and viability of their businesses by using systems approach before the emergence of signs of trouble through the use of the Annual Health Maintenance and Viability Evaluation checklist. We recommend the use of the checkup for use by consultants including SBI student consulting projects