This chapter aims to expand the existing knowledge about cultures, attitudes and opinions of young adults aspiring to work in the knowledge-based, digital economy. Based on findings from a questionnaire administered to 19- to 25-year-old students enrolled in university courses in Milan, we give account of the broad range of expectations and perceptions towards working in this emergent domain by this cohort, exploring notions of flexibility, independence and career aspirations in a context, Italy, that is dominated by high youth unemployment. Results question the often-unchallenged assumption that so-called ‘millennials’ are more interested in the pursuit of independence and flexibility, as opposed to job stability, than previous generations. Independence and flexibility emerge as an important but not discerning aspect in a balance between job security and individual passions. These insights suggest that any generational differences that may exist about cultures of work should be seen as be more nuanced than how these are often portrayed.