This chapter reflects on my experiences as an early researcher of colour in Dutch academia and in confronting post-graduation challenges. I recount some exclusionary moments that compelled me to realize my own positionality as a ‘strategic outsider’. With the help of previous thinkers who have also felt like outsiders and subsequently theorized ways to navigate ‘outsideness,’ I share examples from my time as a GEMMA student in the Netherlands to illustrate how and why I perceive a need to be constantly alert to exclusionary moments as well as critical of numerous toxicities that any individual in a situation like mine might encounter within and beyond Western academia.