Engineering educators are drawn from diverse backgrounds. While industry experience and technical expertise are incredibly valuable, they do not necessarily translate into effective pedagogical skills, leading to varying levels of preparedness for teaching and researching engineering education. At the same time, there are evolving visions of the "engineer of the future" emphasizing sustainability, societal considerations, and sociotechnical integration. Together, it becomes crucial to examine how to prepare engineering educators to better educate engineers. This paper adopts a collaborative autoethnographic approach, using reflective writing and thematic coding, to analyze the authors’ personal journeys through engineering education and research. By synthesizing our experiences, we identify key challenges and opportunities in engineering educator development. Our findings contribute to ongoing discussions on pathways into engineering education and offer recommendations for improving engineering educator preparedness to align with the needs of future engineers.