There is increasing rhetoric surrounding the concepts of lifelong learning and the knowledge economy (Peters, 2001); specifically e-learning and web-based learning environments. This paper seeks to explore the journeys of two professionals from two separate disciplines and work environments located in one higher-education institution where there is an increasing push to develop learning materials using online and other e-learning technologies. With the steady shift from traditional learning, online learning is now playing and integral part of course delivery at the Australian regional university where the authors work. A contextual analysis of online learning within the broader views of the institution provides examples of discources relating to online environments, knowledge management, and the professional development of the professionals. This discussion draws on the concepts of lifelong learning (Crowley, 2002; Serim & Murray, 2003) and embeds them within an online learning environment. Exploration of the multiple workplace environments within the institution under review demonstrates one way in which educators can embrace and position themselves as they negotiate changing educational discourses.