The question of whether early environments provide a challenge or a pressure for young children is being hotly debated, yet there is little empirical research on this topic. This paper presents a subset of data from a two-year comprehensive project designed to examine this question. Parental attitudes and behaviors along with school philosophy and practices comprised the predictor variables used to define academic environments. This study then focused on how these family and school variables related to child outcome measures of competence, creativity, and emotional well-being for 90 prekindergarten children, and a follow-up sample of 56 kindergarten children. The results suggest no advantages for children from highly environments, and potential disadvantages in creative expression (measured as originality) and emotional well-being (measured as test anxiety and attitudes toward school). Possible interpretations and ramifications of these results are discussed.