This paper draws on a naturalistic research study into the experiences of six adults with dyslexia, to examine issues arising from their past transitions from the context of compulsory and post-16 education to the world of work and within their career trajectories. A discussion of literature and documentation in relation to dyslexia in adults is discussed, to place the findings in a theoretical background. The emerging themes discussed in this paper were extracted from the analysis of transcripts from in-depth interviews, which illuminated the experiences of these individuals. The traditional English board game ‘Snakes and Ladders’ is proposed as a metaphor to illustrate how dyslexia has affected employment stability in the lives of these individuals and their employers. The implications of these findings are discussed, and recommendations made, which inform stakeholders and policy-makers in the inclusion and employment of adults with disabilities.