Utilizing sociological and comparative international perspectives, we will look at childhood and education in the US and Russia. The evidence on three main trends will be presented. First, over the last half a century, with the rapid expansion of higher education, we observe a greater emphasis on academic outcomes throughout childhood which, in turn, makes parenting further geared to academic success. Second, profound inequality exists within and between countries that affects children’s everyday experiences, as well as their lifelong chances. Finally, the emerging evidence shows the strengthening children’s agency, observed both in theoretical developments in sociology of education and childhood, and educational practice and parental strategies. The arguments are supported by quantitative analysis of the data drawn from several large datasets, both national and international.