New normative ideas about flexibility, employability and lifelong learning are shifting labour market requirements as they induce flexible employment patterns and new skilling needs. While the model of a typical progressive career based on possession of a particular set of (occupational) skills has been largely undermined, employees are increasingly challenged to secure their employability by constantly adjusting their skills profiles and manage their own individualised careers. Such trends increasingly affect workers at all skills levels in both production and service sectors. Several indicators and studies support the hypothesis that a new entrepreneurial type of worker, characterised by individualised sets of skills, internalised control mechanisms and the prioritisation of transferable over technical skills, will gradually become the new prototype highly desired by managers and human resources development experts. Based on findings of the 5th EU framework project "Vocational identity, flexibility and mobility in the European labour market", this paper argues that most employees in Europe at intermediate skills level are lacking the resources and capacities to fulfil the requirements of potentially developing into an entrepreneurial type of employee. The focus of this paper is the extent to which different national and sectoral contexts can create a supportive or an adverse environment for employees to develop the ability to deal with great changes at work. (Contains 2 figures.)