We employed an in-depth qualitative research approach to understand the challenges and feelings of self-doubt that first-year teachers face. We also explored approaches new teachers take when trying to overcome challenges in teaching. The study draws upon qualitative data from three semi-structured focus groups conducted with first-year teachers in three teacher education programs at the University of Pennsylvania. A total of 25, first-year teachers participated (44% Female). For our analysis, we used an emergent coding and narrative inquiry approach to identify discursive themes emerging from participants’ stories. Participants shared four common challenges: 1) classroom management, 2) lack of strategies and experience, 3) difficulty finding a teacher identity and, 4) time demands and responsibilities. Teachers also described moments of self-doubt, where they felt inadequate, hopeless or like failures in their teaching. This self-doubt originated from two sources: over-identification with failures and social comparison. Teachers described approaches to overcome challenges and feelings of self-doubt, which showed signs of self-compassion and resilience. In light of these findings, we propose that developing a self-compassionate orientation toward challenges in teaching may help to curb self-doubt, promote resilience and boost motivation to improve in teaching. Implications for the field of teacher education will be discussed.