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He began his career in education in 1982 in Overton ISD as a teacher and coach. His first administrative position was with the Temple Independent School District in Temple, Texas where he was the Assistant Principal at Temple High School. He later served Rogers ISD as a junior high principal and a high school principal.

In 1993 he was named the Assistant Superintendent of Curriculum and Instruction at Clifton ISD in Clifton, Texas and then accepted his first superintendent position at Thorndale ISD in Thorndale, Texas in 1994. In 1997 he was named the Superintendent of Schools for the China Spring ISD in China Spring, Texas and in 1999 he was named the Superintendent of Schools for Magnolia ISD in Magnolia, Texas. He retired from Magnolia ISD in 2009. During his tenure with Magnolia ISD, the district grew 10 percent annually.

Holland was named the 2002 Region VI Superintendent of the Year, the Magnolia Citizen of the Year in 2009 and was honored by the Magnolia Board of Trustees with the district's natatorium being named after him. His wife, Lori, is a librarian in Magnolia ISD.

Holland received his bachelor's degree in physical education from North Texas State University in Denton, Texas and his Master's degree in Education from Tarleton State University in Stephenville, Texas. He also earned his Mid-Management Certification from Tarleton State University.