After the war, Smalling finished out his tour of duty and received his discharge in February 1946. In November of the same year, Winston married and started a family that eventually grew to include three sons and a daughter. In the beginning he was self-employed as an independent trucker. Later he went to college and became an electrical engineer at General Dynamics. He soon became superintendent of it's nuclear Research Facility in Fort Worth, Texas and became involved in the work that led to the first moon shot.

In addition to his successful career, Winston was active in his church and its Missionary Support Program. In 1965, his intensive interest in this work compelled him, his wife (a nurse) and his children to pack their bags and go to a hospital in the wilds of Africa.