In Germany and Denmark, the systems of further education and career guidance are well developed, offering a wide range of services and learning opportunities for targeted, specific and also general skills development. Based on an empirical study with mid-career individuals in both countries, the article investigates how the different systems support individuals to manage a career transition and develop their individual pathways. Mid-career transitions can be considered particularly challenging as they often reflect a more profound crisis and major concerns about future career opportunities. Constraints that prevent individuals in mid-career to fully benefit from the learning and guidance offers available can be identified in both countries. These range from the availability of programmes and accessing funding to getting the 'right' information. These constraints partly derive from adult education and guidance systems presupposing linear careers rather than disruptive trajectories and horizontal mobility.