Many small businesses fail after 5 years, having a negative impact on local and national economies. The purpose of this phenomenological study was to explore small-enterprise leader-operators’ experiences regarding practices that aid sustainability beyond 5 years. Twenty small enterprise leaders in the United States Midwest who were identified as having 5 years of longevity in leading organizations with fewer than 500 employees were invited to participate. These participants shared their lived experiences through semistructured interviews conducted in-person and by telephone. The dynamic theory of leadership development was used to underpin the study. In the central research question for this study, the skills and practices needed by small-business practitioners to ensure success beyond 5 years were addressed. A reduction method was used to reduce data from 11 interview questions in 20 semistructured interviews into common themes. Seven themes emerged as long-term practices used by practitioners. These 7 practices included collaboration and forms of communication, mentoring, people skills, networking, investing in people, setting an example, and planning. The implications for positive social change include the potential to stabilize the economic wellbeing of the small business sector and therefore the community. Small business practitioners may benefit from this research by identifying and improving practices leading to long-term viability.