This article focuses on youth transitions in the specific geo-historical context of post-socialist Poland. While post-socialist 'transition' across Eastern Europe and the former Soviet states has heralded extensive social and economic upheaval in general, different age groups experienced different facets of this change more keenly than others. For those who were teenagers in the 1990s, societal change coincided with their own life-course transitions from youth to adulthood, creating a potentially destabilising 'double transition' for them to negotiate. Based on in-depth, life history interviews with Polish migrants in the UK who were born between 1975 and 1985, this article considers how these changes are represented in their narrative accounts. It concentrates on two narrative strands: the opportunities offered by a liberalising economy and more open borders, and the uncertainties and anxieties that also underpinned their memories and experiences of this time. Ultimately, the article finds that however exciting some of the changes appeared to be in the 1990s, young people had to learn new strategies to navigate the post-socialist worlds, often struggling to find confidence in the new socio-economic environment forming around them.