Emerging as a futurist and positioning oneself as such is a nuanced and difficult path to navigate. In this paper we explore our experiences as aspiring foresight professionals using our experiences and insights through collaborative autoethnography, to explore our collective futures in the field and going through hindsight to foresight. We discuss the challenges pertaining to theorizing in futures studies and foresight; positioning oneself as a researcher or practitioner; and seeking employment. Together these discussions form a narrative of overcoming challenges and deliberating between dilemmas. We hope that the insights shared within this paper can support others on this journey.