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Serendipity is where unexpected circumstances and an insightful 'aha' moment result in a valuable outcome. We discuss how interactive systems can support the process of serendipity: from making new connections, to projecting and exploiting their potential value. We focus in particular on how technology can support reflection -- which is an important part of the serendipity process. By considering findings from a set of empirical studies and a set of design principles aimed at encouraging reflection, we present an early stage digital 'Semantic Sketchbook' which was designed with the aim of supporting reflection (as well as other aspects of the process of serendipity). We discuss how our 'Semantic Sketchbook' has the potential to create opportunities for serendipity and the next steps we intend to take in developing it and evaluating its success.