This chapter explores strategies for teacher retention in the Australian and Swedish education systems, with a focus on career progression as a critical factor. Through a comparative analysis of Highly Accomplished and Lead Teachers (HALTs) in Australia and the förstelärare (first teacher) reform in Sweden, the study reveals limitations in both approaches to addressing the complex realities of teachers' career trajectories, particularly regarding gender. The Australian HALTs standards have seen limited uptake, while teachers continue to prioritise postgraduate qualifications for career advancement. In Sweden, the förstelärare reform has yielded mixed results in retaining teachers and addressing shortages. The analysis underscores the need for a more nuanced and holistic approach to teacher retention that accounts for gendered career paths and various life stages. This chapter argues for moving beyond policies that solely focus on classroom retention, towards supporting diverse and flexible career pathways that allow for professional growth and changing life circumstances. Strategies such as job-sharing and mentoring are presented as promising, complementary, and easily implementable solutions to retain teachers through different career stages. By examining these two contrasting policy approaches, the chapter provides unique insights into the challenges and opportunities in teacher-retention efforts. It emphasises the importance of creating sustainable and attractive career paths that benefit not only teachers but also the students and communities they serve, ultimately contributing to more sustainable education systems.