Years removed from principal preparation programs and in the face of inconsistent district leadership support and development, novice principals are often left on their own to overcome their early challenges. This study attempted to illuminate how novice principals, on their own, developed best practices, established routines, coping techniques and established support during their first 2 years on the job as high school principals. Using a phenomenological approach, the main data used in this study were the responses of 17 novice principal interview transcripts. All in all, eight themes emerged and were grouped into three broad categories: challenges, enacted practices, and support. The themes in the challenge category included: their challenges with staff, work-life, and the ubiquity of email communication. Most surprising was the frustration that all participants expressed about email communication and their inability to develop a useful approach. Themes involving best practices enacted included the establishing of early communication with staff, taking advantage of morning time frames before arriving to work, having personal belief systems that allowed participants a framework to approach their work, and establishing either end-of-work times or routines. Novice principals in this study revealed the times of their day (morning) where they had more control of their time and decisions than at other times of the day (afternoon and evening). The last category involved novice principals’ strongest forms of support that revealed that novice principals relied mostly on people who they deeply trusted (professionally) as their strongest form of support.