It is important for islands to discover their genuine competencies and capabilities in order to find their place in an evolving global economy. Economic self‐discovery, however, is difficult because exploitative mechanisms (investing in old ideas) tend to naturally dominate economic behaviour when compared to exploration mechanisms (investing in new ideas). In this paper, a brand diagnostic tool is used to distinguish islands with unique brand images from islands with relatively common brand images. Through a simulation of the mutual learning processes within the social networks of these islands, this paper shows that economic self‐discovery is facilitated in islands with strong and unique branding strategy, as a strong holistic brand frame exploration activities by reducing ambiguity and confusion. Islands with common brand images fail to strengthen their brands because of the predominance of exploitative mechanisms in their economies and as a result enter a vicious circle where increasing brand dilution and confusion blocks the exploration and discovery of new ideas.