An award as principal investigator (PI) is an aspiration for many post-PhD researchers. However, we know little of the actual journey from PhD graduation to achieving this goal. Using a qualitative narrative approach, this study explored how eight science, technology, engineering, mathematics and medicine post-PhD researchers (on contracts and fellowships) achieved PI-ship, specifically, how they learned to use and navigate the funding systems within their working contexts to achieve grant success. They were in two European Union (EU) universities, one in the UK and the other in the Netherlands. The analysis draws principally on their high and low grant-funding experiences. The results show the interaction between individual goals and intentions and the social and structuring elements of their local and extended workspaces--institutional, national and EU. For instance, the funding systems on offer were designed to invest in promising early career researchers, so while these awards provided a research career structure, this was only for a limited number of post- PhD researchers. While the eight were ultimately successful in this competitive environment, their journeys were still challenging. They succeeded by using failure in positive ways, that is, investing in specific learning in respect to different failures. There was a chronology of learning, with immediate past experiences influencing where they invested their learning efforts in order to navigate the funding system successfully. The implications for institutional support are explored.