Emerging as a futurist and positioning oneself as such is a nuanced and difficult path to navigate. This paper explores our experiences as aspiring foresight professionals through a collaborative autoethnographic approach using our experiences and insights to explore our futures in the field, taking us 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 they 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.