For over nine years, we have been working on Erikson Institute’s Math All Around Me project with caregivers of 0-5 year olds in Chicago’s under-served and under-resourced communities. As each cohort started participating in a series of six to eight learning labs in the MAAM project, many caregivers reported feeling beaten down by the pressure to get 2s, 3s and 4s doing math instead of “playing around.” They were told that the children they worked with were showing “deficiencies” when tested for readiness in preschool, kindergarten, and first grade. Increasing direct instruction in basic skills was the solution to reducing this “achievement gap.” However, drilling counting words and names of shapes did not feel engaging to them or the children. Instead, it brought back the caregivers’ own negative experiences and attitudes about school math. So, what does the research say prepares the ground for the strong number sense that all young children need to be successful, not just in school but in solving the math problems all around us in our real lives?