Online freelancing is small and simple jobs distributed through online platforms to workers for greater cost efficiencies across geographic boundaries. Online freelancing is growing rapidly and gaining popularity within the younger generation. This paper attempts to understand the contributing factors for such growth of online freelancing among younger age groups in Sri Lanka. From a representative survey conducted in 2015 among Sri Lankan population aged 16-40, 11% of the respondents expressed willingness to work on online freelancing jobs. This paper explores the demographic profile and characteristics of those who are willing to work on online freelancing and how they are different to those who are not willing. Using a binary logistic regression model, underlying factors that contribute to the willingness to work on online freelancing were identified while controlling for the differences in various mediating factors such as education, employment status, gender, skills levels and urban rural status etc. The study reveals education, ownership of computer, access to internet, marital status aren’t significantly influencing one’s choice to opt for online work. However, their spontaneous awareness on online freelancing, skills level, gender, age, employment status are significant drivers in terms of determining ones willingness to work on micro-work platforms. After identifying influential factors, this article makes policy recommendations to improve the take-off of online freelancing in Sri Lanka.