International organizations, such as the Organisation for Economic Co-operation and Development (OECD), as well as governments in OECD member countries are implementing policies aimed at increasing secondary school completion rates. Some decades ago, the senior secondary years were an exclusive option for an elite minority. Now, a common expectation is that they will cater to 90% or so of young people. However, too often the practices in contemporary schooling contexts have not kept up with this change. In particular, there is extensive evidence that concerning numbers of socially and educationally marginalized students are rejected by, and themselves reject, mainstream schooling. As a result, in many jurisdictions alternative educational provision has been central to re-engaging young people and enabling their secondary school completion. Such provision includes “flexible,” “second-chance,” or “alternative” schools that, although not all the same, often have in common an inclusive and democratic approach to educating young people who have not been well served in mainstream schools. Rather than such alternative schools being seen only as a useful “stop-gap” measure for marginalized students, they offer a valuable opportunity to re-imagine education. Such sites demonstrate structural, relational, and curricular changes that enable a range of education and learning options. First, in terms of structures, practical support and wraparound services are central to removing or alleviating structural barriers and clearing a path for learning. Second, supportive relationships are significant in enhancing the quality of young people’s educational experiences and outcomes. In particular, connectedness and partnerships are key factors. Finally, a diverse curriculum is needed to facilitate an education that is meaningful and authentic, and builds the capabilities young people need in the 21st century. Initiatives aimed at speaking more meaningfully to young people who have traditionally been poorly served by schooling are at the core of many alternative schools, but they are also present in outstanding mainstream schools. These innovations offer inspiration for reform across all schools, for all students. Embedding such reform through broad systemic change in mainstream schooling is necessary to facilitate an education for all young people that is: meaningful in holistic ways, democratic and respectful, supportive and enabling, and equips them with the skills and knowledge to progress their hopes, dreams, and imagined futures.