A 1972 UW-La Crosse graduate, Jim taught all levels of physical education in his hometown, Port Washington, with Lincoln Elementary as his primary school. Jim chaired and participated in a variety of building and district committees and pioneered a district-wide wellness program assisting teachers in healthy, active careers. With his 1993 Masters degree from Concordia University, Jim also served in interim administrative positions within the district, retiring in spring 2011 after a great 39-year career, all in the Port school district.
In 1972, Jim began as freshman coach at Port Washington High School. After 7 seasons, Jim became the assistant varsity coach at Port High, coaching with WFCA Hall of Fame Coach Al Urness. For the next 29 seasons they consistently developed tough, hard-hitting, winning teams. In the years of expanding coaching staffs, Jim remained the lone assistant to Coach Urness - he was the “Pirate” staff” - winning 8 Conference Championships, 9 Conference Runner-ups, 13 WIAA Playoffs, 3 WIAA State final runner-ups, and 1 WIAA State Championship. During that time Jim’s offensive and defensive lineman consistently won All-Conference, All-Area, All-District and All-State honors and appearances in All-Star games. In 2000 Jim was named the North Shore Conference Assistant Coach of the year and WFCA District Assistant Coach of the Year. Jim had the pleasure of coaching both of his sons, Ben and Brian, who both earned all-conference honors.
As head coach at Port in 2001 he compiled a 6 – 4 record and qualified for the state playoffs. In 2002-2003, Jim coached receivers at Wisconsin Lutheran College. As 2004-2005 offensive coordinator at Whitefish Bay HS, he earned a 6 - 6 record and state playoff berth. Jim joined the Homestead HS staff in 2006, compiling a 50 – 4 record, 3 State Final appearances and two State Championships over 4 years. Jim enjoyed assisting his son, Ben Chossek, head coach at Grafton High School in 2010 during Ben’s rebuilding of the Blackhawk football program. Jim retired from coaching after the 2010 season.