Sherry Wing Olsen

Sherry Wing Olsen, born July 3, 1949, in Mason, Michigan, passed away peacefully after a difficult battle with cancer. Throughout her journey, she was surrounded by the love and support of her husband, family, and the many friends whose lives she touched so deeply.
Sherry grew up in Dansville, Michigan, the oldest of four children born to Rolland “Rollie” and Patricia “Pat” Wing. She was preceded in death by her parents and, most recently, her beloved sister, Mary Babcock (Steve), who passed away in June 2026. She is survived by her brothers, Larry Wing (Julie) and Ron Wing (Lisa).
After moving to Bartlett, Illinois, Sherry made the community her home for 48 years, living in the same house and building a life filled with family, friendships, service, and love. Although she had no immediate family nearby, she created a close community around herself and developed friendships that became like family.
Sherry was a teacher by nature and by heart. She taught second grade for 36 years, spending the majority of her career at Lords Park Elementary School in Elgin. She had a natural gift with children and seemed to have always known she wanted to be a teacher. But for Sherry, teaching was never simply about academics. She cared deeply for her students, particularly children who came from difficult circumstances. She wanted them to feel loved, valued, and capable of succeeding.
Later in her teaching career, Sherry established a book swap where children could receive books for free. She believed that the path to learning could begin with the simple joy of having a book of their own. It was one of many ways she found to give children something they might not otherwise have had.
That instinct - to care for people and give of herself - continued long after she retired. Sherry devoted much of her time to caring for her closest friends. She drove them to appointments, met them for lunch, helped meet their needs, and was there whenever someone needed her. She had a remarkable ability to take on other people's burdens. She was a rock to many.
Sherry was married to Joseph “Joe” Olsen for more 53 years. They met through a mutual college friend while attending different colleges and built a life together that lasted more than five decades. Sherry spent much of that life caring for and supporting Joe, and during the last year, when she needed more care herself, Joe was there for her. He loved her unconditionally.
Together, they enjoyed experiences that became treasured memories. Joe's love of sweepstakes brought them opportunities to travel and experience things they might not otherwise have been able to do. For their 50th anniversary, they celebrated with a two-week cruise between Australia and New Zealand. She went on a tented safari in Kenya and brought back to her classroom that experience including wearing native dress in her classroom when she taught her classes about that experience. Sherry also enjoyed cruises through the Panama Canal and Alaska with Joe and her son, Drew. She loved watching the people around her and taking in the scenery.
Sherry found joy in the simple things. She took great pride in keeping a tidy home and creating a beautiful yard. She loved gardening, observing nature, volunteering, and supporting her church, Journey of Hope (formerly Good Shephard United Methodist Church), where she was an active part of the community for more than 40 years.
Sherry was also a devoted Chicago sports fan. She followed the Chicago Bears, Chicago Bulls, Chicago White Sox and Chicago Cubs, and especially enjoyed attending games in person. She attended many Chicago Bulls games during the team's remarkable run in the 1990s and, after retirement, she and Joe attended as many as a dozen Chicago White Sox games each season. She threw out a first pitch at a White Sox game, presented a starting lineup card at a Cubs game and attended White Sox spring training with return flight on the team plane. She also followed college basketball and football, particularly cheering for her alma mater, Michigan State University. A baseball game was often playing in the background while she sat in her living room or worked in the garden. Sports were simply part of the rhythm of her life, something she enjoyed following and sharing with those around her.
But above all, Sherry was a person who loved people.
She was a devoted mother to her only child, Andrew “Drew” Olsen, and a loving mother-in-law to Jamie. Drew's children, Benjamin “Benji” and Bowen, brought her tremendous joy and proudly called her Nana. She was thrilled by their births and treasured every moment she had with them.
She read to them, cuddled with them on the couch, baked holiday cookies, and loved their FaceTime calls. Sometimes she was simply “silly Nana,” making them laugh hysterically. She asked about their lives, listened to their answers, and loved them with the same wholehearted love she had always given her son.
For Drew, Sherry was more than a mother. She was his friend and the person he relied on throughout his life. She gave him a love and a sense of being cared for that he now carries forward into his own marriage and family. The love she gave him is something he will continue to share with Jamie, Benji, and Bowen for the rest of his life.
Those who knew Sherry will remember her generosity, her devotion to others, her strength, and her willingness to carry someone else's burden. Her family will remember much more: her voice, her touch, her smile, and simply her presence.
She spent her life making other people feel cared for. Her greatest legacy is the love she gave - and the love she taught others how to give in return.
Sherry will be deeply missed and forever loved.
She is survived by her husband, Joseph “Joe” Olsen; her son, Andrew “Drew” Olsen and his wife, Jamie; her grandchildren, Benjamin “Benji” and Bowen; and her brothers, Larry and Ron.
A Memorial Service celebrating Sherry’s life will be held on October 10, 2026 at Journey of Hope, 751 W. Army Trail Rd., Bartlett, IL. Visitation with family and friends: 11 AM, Memorial Service: 12 noon followed by a luncheon.