The intermediate or mid-career stage, defined in the context of this chapter as between 5 and 12 years of post-PhD experience is a particularly challenge time in a researcher’s career. In this chapter, I provide illustrations of why this is indeed the case, including difficulties arising from a perception of limited opportunities at a time when there is a need to maintain a high level of scientific productivity. I also note the importance of social and political developments that have had the potential to improve and disrupt careers in the Portuguese context. This includes the example of a policy initiative aimed at addressing precarity among postdoctoral researcher that has appears to have had the converse effect, a situation I explain in terms of the ‘cruel optimism’ idea introduced in the work of Lauren Berlant (2011).