The purpose of this study was to examine the challenges faced by secondary technology education (TE) teachers in Illinois. Specifically, the study sought to identify and categorize a list of challenges encountered during their first years in the TE profession as well as challenges that veteran TE teachers are facing in their current teaching assignment. Seventy-three TE teachers completed an online questionnaire. Twenty-six challenges were identified and of the top five challenges, only three, equipment, funding, and understanding what TE is were identified as a continuous challenge at each career stage. Knowing the challenges identified by TE teachers at different career stages can assist school administration and TE professionals in providing specific support to address these problematic areas in efforts to improve retention rates among TE teachers.