This chapter is co-produced to share the lived experience of ‘becoming’ an experienced academic and to share our passion for action learning and insider-research. We have each been employed as Higher Education (HE) lecturers for approximately 15 years and remain passionate about the potential of insider-research to positively impact on individuals and their lives. It is this passion and interest which brought us together as colleagues and co-researchers. We are Michelle (health), Aileen (business) and Deborah (education), co-founders of MAD, an action learning set with a stated aim to raise the profile of insider-research through Mutual Action and Development. Insider-research is a common feature of many postgraduate and doctoral programmes and is undertaken by members of organizational systems and communities in and on their own organizations. This form of research can also be undertaken as collaboration between insiders and outsiders. A key challenge for insider-researchers is to undertake academic research in their own organizations while retaining the choice of remaining employed and employable. It is not unusual for insider-researchers to uncover the darker aspects of organizational life, surfacing ideological dilemmas. We argue that it is the surfacing of ideological dilemmas which opens a discursive space and provides the foundations for emancipatory learning. In co-producing this chapter, we have provided three autoethnography tales of ‘becoming’ experienced academics and analyse our ‘tales’ from a discursive and community of practice perspective. In doing so, we illuminate how the surfacing of ideological dilemmas, within the relatively safe space of our MAD set, has enabled us to cope with the barriers and constraints faced by experienced academics within the current HE system