Studies show that affordances of social media have not yet been fully exploited in the promotion of authentic e-learning in higher education. The e-Learning of the Future project (2009-2011) has met these challenges through working life mentoring using social media. In this paper, we examine the planning and implementation of social media in nine project courses and how these changes support authentic learning. A further focus of interest is the role of working life mentors in the process. The outcomes indicate that the introduction of social media measures strongly supported the strengthening of authentic learning principles (Herrington & Oliver, 2000) on the courses. Revisions to learning tasks centred on establishing connections to expert communities, the use of blogs, and the compilation of recorded entrepreneurial narratives. Working life mentors brought an up-to-date, work-oriented perspective to the process and highlighted skills required by workplaces of the future. Developing educational tasks that cross traditional boundaries raises issues of operational culture change, the roles of partners and transparency of education, and these implications are discussed in the paper.