This chapter considers the interrelated issues of work and education. Studies of pre-prison, prison and post-prison experiences inevitably underscore acute issues of the lack of adequate training and education, and suitable paid work, for people with offending histories (see, for example, Visher et al., 2011; Lockwood et al., 2012). Disadvantage compounds disadvantage as unemployed people commit offences, and ex-prisoners fi nd diffi culties in fi nding employment post-release. There is a close and reciprocal relationship between criminality and unemployment. The chapter provides examples of different ‘skills for change’ including employment and entrepreneurship initiatives, and education and literacy initiatives. A common theme is how individuals need to see value in such activities for themselves, as it is their choice to change.