This article examines different orientations to planning in the context of the post-redundancy transition of workers in the Swedish steel industry. The aim of the article is to extend our understanding of the role of planning in careers transitions. Drawing on careers transitions theories, the article explores the qualitative experience of the journey between a redundancy event and the employment situation several years later. Within the careers literature planning is regarded as important to transitions, yet there is a tendency to present planning as an ongoing and lifelong process. By going beyond the prevalent focus within the career literature on managerial, professional or creative industries workers, the article raises the question of whether highly agential, ongoing, lifelong approaches to planning apply to everyone. Data are based on working-life biographical interviews conducted several years after redundancy. The findings show that although some participants resembled assumptions within the careers literature, there are key variations relating to ongoing planning, reflecting differences in the expectations of agency and perceptions of structural constraint. The analysis identifies three orientations to planning – strategic, episodic and truncated – and explores these in relation to both post-redundancy transition outcomes and, crucially, the experience of the transition journey.