Okolski began skating at age eight and began pairs at twelve with his sister, Colleen. He teamed up with Brooke Castile after the 2002 U.S. Championships. They won two bronze medals on the ISU Junior Grand Prix series. They placed 7th at their first Four Continents in 2005. Following the 2006 U.S. Championships, Castile and Okolski changed coaches to Johnny Johns and Marina Zueva at the Arctic Figure Skating Club in Canton, Michigan. They won the 2007 U.S. Championships, earning them the right to compete at 2007 Four Continents, where they were 5th, and then to make their World debut, where they finished 12th.