The digitalization of the retail industry is a disruptive innovation process which endangers the very existence of Local Owner Operated Retail Outlets (LOOROs). Despite the manifold digital options to regain competitive power, LOOROs struggle in their digital transformation and persist often in their traditional business behaviour. As their customers get more and more used to buying via digital channels, they more and more expect the provision of digital services. This paper and the presented survey among 223 LOORO owners from 26 cities in Germany aim to understand why the LOOROs are so hesitant. Our findings show high insecurity among LOOROs about what to do and where to begin the digitalization route. The owners of LOOROs are often decoupled from their near and far business environment. This leads to a wrong self-assessment and implies the risk that the services provided do neither match the competitive environment nor customer expectations.