Supported by relevant theories of chaos and dynamic environments, self-efficacy, and outsider assistance, this study analyzes small business owner problems during a dynamic environment created by Hurricane Katrina. While many management theories attempt to explain small business operations, very few studies have been conducted specifically on small business problems following a major disaster. Understanding the needs of small business owners during dynamic environments will assist support organizations in planning for services delivered prior and post future disasters. Second, by offering programs designed to develop business owner self-efficacy, the perceived problems faced during the chaos of disaster recovery may be reduced, thus reducing the length of the economic recovery period. The central question of this study is to determine the problems that delay small business owners during recovery from a major disaster. Analyzing small business owner’s stated problems following a disaster, with respect to the elapsed time from disaster to a request for assistance, provides a glimpse into economic recovery delays. Using controlling variables, it may be further shown how different factors of business may also affect delays in seeking help for recovery. This researcher’s position is that by pre-planning for various disaster scenarios, small business owners will increase their tacit knowledge of potential change during a dynamic environment. With increased knowledge, small business owners will develop a more positive self-efficacy in business operations.