Well-managed grasslands provide numerous ecosystem services. Ranchers who employ sustainable grazing practices limit grassland conversion and conserve critical habitats. This phenomenological study explored the grassland management decisions of progressive ranchers in Nebraska. Each individual interviewed for this study is proactive about the state of their grasslands, whether they are motivated by financial or conservation factors. Throughout the evolution of their businesses, these ranchers have taken steps to improve their management techniques and continue to employ new strategies while planning for the long-term productivity of their grasslands. For policy makers and educators seeking to improve grassland management decisions, demonstrating new methods to be economical, promoting stewardship, and allowing for flexible implementation may increase acceptance of recommendations. Because progressive ranchers’ livelihoods are connected to the land, and they are long-term goal oriented, they closely scrutinize, yet are open to advancing grassland management practices that benefit their cash flow, their pastures, their animals, and their families.