Research has already examined the relationship between planning and success of small firms, but the conclusions drawn are inconsistent. In this study, we argue that the relationship between planning and success is dependent on the cultural context. Planning strategies and their relationship to success were compared in 77 Irish, 102 East German, and 98 West German small-scale enterprises. In Germany, planning had a positive influence on success, while this relationship was negative in Ireland. Moreover, planning strategies were found to mediate the relationship between business owners' achievement orientations and success. This mediating influence was positive in Germany and negative in Ireland. These differences are interpreted to be due to a higher level of uncertainty avoidance in Germany (Hofstede 1991), which makes planning culturally appropriate and successful.