Working holidaymakers have traditionally played an important role in supplying short-term workers for the tourism, hospitality and horticulture industries in both urban and regional settings. Attracting WHMs to destination brings with it significant economic benefits. This study was aimed to examine underlying dimensions of WHM motivations and to conceptualize the motivations in relation to the generic skills developed. Online survey was conducted and results were analyzed in light of push/pull conceptual framework exploring generic skills developed by the working holidaymakers and their travel motivations. Five push factors- escape, relationship, self-development, prestige, self-actualization, and four pull motivation factors- nature attraction, culture and events, humanistic resources, and work conditions were identified from factor analysis. Results show that top five skills perceived by the respondents are adaptability, social-cultural awareness, dealing with changes, planning in order to achieve goals, interpersonal understanding. Segmentation results based on travel motivations can be applied by agencies to promote working holiday schemes.