Digital platform labour is increasingly becoming an attractive option especially in countries in the Global South such as the Philippines where employment conditions are fraught with financial stagnation and socio- economic tensions. This chapter focuses on the rise of ‘skill-makers’, specialist coaches who attract and train Filipino platform workers into this labour market and the ‘skill-making economy’, which is playing a crucial role in the local popularity and viability of platform labour. The chapter shows that it is in presenting their capacity to bridge the difficult realities of platform labour with aspirational narratives that these ‘skill-makers’ create value for themselves and their work. Drawing from an ethnographic inquiry on online freelancing in the Philippines, the chapter argues that monetizing ambiguity as embedded within a specific context of Philippine labour, economy, and society is at the heart of the transactional nature of this emerging labour category.