Children growing up in low-income households tend to be less academically, socially, and emotionally ready at school entry. Self-regulation has been identified as a key factor underlying children’s academic achievement and social–emotional competence and may be promoted through effective parenting. However, few existing parenting programs that teach behavioral parenting skills simultaneously address parents’ self-regulation skills or promote strategies for coping with income-related stress and adversity. Systematic evaluation of the added benefit of incorporating these practices into parenting programs is needed. We conducted preliminary evaluation of a brief parenting program that aims to promote young children’s self-regulation, social–emotional competence, and academic readiness by enhancing parent mindfulness, self-regulation, and evidence-based parenting practices. Evaluations were conducted in two early learning programs serving low-income families. Staff at the sites received limited training and supervision to deliver the program, to test the feasibility of implementing a program with lower resource demands. Observed and self-reported changes in parenting (increased scaffolding and consistency, decreased rejection and negativity), self-reported changes in parent self-regulation, and observed and mother-reported changes in child adjustment (decreased negative affect, increased social competence and academic readiness) were demonstrated. This pilot yielded promising initial evidence for a two-generation approach to increase both parent and child self-regulation in at-risk families.