Kari Kaaja undertook his military service with the Finnish Defense Forces, with modern pentathlon becoming the sport of choice. Kaaja became proficient in fencing, riding, and shooting, helping him to win dozens of medals at the Finnish Championships in both pentathlon and fencing. He represented Finland at the modern pentathlon World Championships in 1963 and 1967, and competed at the 1964 Tokyo Olympics, finishing seventh in the team event at the latter. He then became a noted coach in the sport, helping Finland to win bronze at the 1972 München Olympics in the team event. Kaaja continued to coach the national pentathlon team at the Olympics in Moskva and Los Angeles, as well as at multiple editions of the World Championships. He later founded the Porvoo Fencing Club and was a board member of the Finnish Pentathlon Association for 14 years.