Across working life, there are daily and continual challenges for workers to learn to adapt to the changes required in their work. This comprises much of what constitutes learning across their working lives. However, across those lives most adults are confronted with significant transitions that they have to negotiate as their occupations change fundamentally or are rendered redundant, their personal and family circumstances change, either voluntarily or involuntary they have to do change their location. The learning associated with these transitions can extend to needing to learn new languages, but also ways of working and engaging in work settings. So, beyond of the everyday and incremental learning that arises through work, is the need to negotiate these challenges, which can comprise significant chal- lenges for their learning and development. This chapter sets out to illustrate and elaborate how those transitions have impacted and been negotiated by working age Australians, of different kinds (i.e., cultural background, gender and age). Drawing upon the data from the survey of over 600 respondents, the chapter identifies the kind of changes in these respondents’ working life that generated or necessitated these transitions, the impacts and set out the requirements for the kinds of learning they require to negotiate those transitions. In many ways, these set out the goals for what is often referred to as lifelong learning or learning across working life and advances the kinds of policy and practice consideration needed for individuals to achieve the kinds of outcomes that governments, workplaces and working age adults themselves want to achieve. So, this chapter provides a basis for coming to understand what the goals for policy and practice interventions might be to assist realising these outcomes.