Many scholarly analyses of small economies over the past two decades have been premised on the implicit understanding that a state's small population size, compounded by such factors as islandness and remoteness from markets, is to blame for an inherent and unavoidable economic vulnerability. The article critiques the core features of this approach, and proposes in turn to discuss and profile the development trajectories of small economies from the vantage point of the strategic flexibility used by small states (at multiple levels as individuals, household units, corporate entities and complete jurisdictions) in seeking to exploit opportunities and maximize economic gains in a turbulent and dynamic external environment with which they must engage. Keeping alive a portfolio of skills and revenue streams enables these actors to migrate inter-sectorally as well as trans-nationally.