Charles Ostlund graduated from James Madison High School in Vienna, Virginia. He attended Slippery Rock College from 1969-70 before transferring to Madison College, now James Madison University. Ostlund graduated with a degree in economics and went on to earn a master's degree in education from the University Virginia as well as his doctorate of education.

He taught and coached in Fairfax County for 31 years before his retirement in 2004. From 2004–06, Ostlund worked on then-Governor Mark Warner's “Virginia Teacher Retention Initiative.” Since 2006, Ostlund has been a teacher and department chairman at James Monroe High School in Fredericksburg, Virginia.

Ostlund was an assistant coach at Hayfield High School from 1976-80 and head coach at James Madison High School from 1980-8. In 1981, the Northern Virginia Sun newspaper named him Coach of the Year. For the next 10 years Ostlund served as the director of student activities. He served as chairman of the Northern Region Athletic Directors Association from 1995-97, and was a member of the Virginia High School League executive committee from 2002-04.

He was honored by the Vienna Town Council, who declared that October 15, 1995 was “Charlie Ostlund Day.” In 1999, Ostlund was inducted into the James Madison High School Athletic Hall of Fame and received the Lifetime Achievement Award from the VHSL in 2004.

Charles lives in Lake of the Woods, Virginia with his wife of 40 years Penny. He has three sons, Chad, Michael, and Ryan, and as two granddaughters: Maya and Ellie.