Kalckstein was the son of Count Albrecht von Kalckstein, a strong critic of Frederick William, Elector and Duke of Brandenburg-Prussia. During his youth Kalckstein had served in the French army under Turenne, but was dismissed as being disorderly. He entered the Polish army in 1654, but fought for Duke Frederick William at the 1656 Battle of Warsaw, for which he was rewarded with a captaincy in the district of Oletzko (Olecko). In 1659 the duke dismissed Kalckstein after the clerk of Oletzko accused the young noble of embezzlement and maltreatment of his subjects.