In today’s rapidly evolving societies, individuals must possess fundamental life skills in order to effectively navigate the complexities of daily life, cope with frustration, pursue their dreams, foster social connections, and collaborate on a global scale. Schools are ideally placed to support the development of these life skills. Although life skills education is highly recommended by UN organisations and ministries of education worldwide, its implementation varies considerably from country to country. For instance, Namibia has a dedicated Life Skills subject, taught by trained teachers. In contrast, Germany integrates life skills education into some subjects and with the help of external organisations. By adopting a comparative approach and engaging in a dialogue about our experiences, a great deal can be learnt from one another. This is the journey that a group of Namibian and German teacher training students embarked on. This chapter provides insights into what we have learned. After discussing the importance of life skills education, we will explain its theoretical foundations with a particular focus on how it is integrated into the school curricula in Namibia and Baden-Württemberg, Germany. We then share our personal experiences of life skills education in Namibian and German educational institutions as students, graduates, and trainee teachers. Next, the authors present selected results from a workshop, held during the Namibia-Germany Conference in 2022. To provide a comprehensive overview, the workshop discussions are supplemented with new insights gained by both the Namibian and German authors since 2022. Lastly, the authors offer some closing remarks and final reflections.