Serious leisure (SL) is an extensively research area in literature. However, pilots performing in airshows remains an under-researched line of inquiry. This (in-progress) study examines the motivations of a niche cohort: pilots. Stebbins SL attributes (perseverance, significant personal efforts, career, durable benefits, strong identify, and unique ethos) are used to determine if they are evident in the flying/performing hobby of the pilots. Additionally, this study offers insights on how performing in airshows can contribute to overall well-being. A mix of content analysis and semiotic analysis is employed. Data include narration content (e.g., reviews, journal writings) and visual content (e.g., photos, signs), collected from online platforms and event sites (such as airshow sites). Findings confirm that pilots flying/performing in airshows is a SL activity and is influenced by social factors and the influence of media. Based on the results, several strategic implications are offered from airshow marketing and event management standpoints.