The digital content industries in many countries have seen significant growth over the past decade. This knowledge-intensive sector relies on highly skilled human capital but is often challenged by skills and labour shortages, in turn exacerbated by a lack of high quality industry-ready graduates. This presentation first foregrounds some of the key challenges associated with education-to-work transitions encountered by emerging creative graduates in the digital content industries. It then proceeds to document the design and implementation of an innovative Web 2.0 creative ecology known as ‘60sox’. The potential and challenges of the '60sox' virtual community of practice for enhancing social capital and enabling successful education-to-work transitions among emerging creatives in the digital content industries are highlighted and discussed.