She began life in Indianapolis, then went to Miami University of Ohio, where she graduated with a degree in French. She began her career teaching in Wallingford, Connecticut, before marrying college sweetheart Richard Workman, who died in 2019. Together they lived in Victorville, California, Indianapolis, Indiana, and Waynesville, Ohio, before moving in 1973 to Sanibel, Florida, where Richard became the first executive director of the Sanibel-Captiva Conservation Foundation (SCCF).
On Sanibel, Judy was one of the founders of the Children’s Center of the Islands. She also worked on the original committee that helped plan the Sanibel bike paths. She was the second employee hired for the newly formed City of Sanibel in 1974, where she served as secretary to the mayor and the city council. She later served on the Planning Commission for two terms and was elected to the Sanibel City Council in 2000. She was also instrumental in the formation of Community Housing and Resources (CHR) on Sanibel and was a champion for Below Market Rate Housing on the island.
In the early 1980s, as a single mom of two children, Judy bravely decided to go to law school, and in 1984, earned her law degree from Indiana University. She passed the bar in Indiana and in Florida and returned to Sanibel. She was hired with what was then known as Humphrey, Jones and Myers and worked in downtown Fort Myers until she started her own law practice. She practiced on Sanibel until 2008 when she moved herself and her practice to Fort Myers. Judy used her profession to help others, often providing free or greatly discounted legal services to those who otherwise might not be able to afford them.
She was a faithful and dedicated 50-year member of St. Michael and All Angels Episcopal Church where she served on the vestry and was parish chancellor. She believed strongly in the church’s Madden Education Fund and worked on that committee for many years.
For the past 18 years Judy’s most treasured role was that of devoted and loving grandmother to her three grandchildren. She had a unique and special relationship with each of them and often commented on how fortunate she was to be a part of their daily lives. She absolutely adored them, and they her.
In addition to her grandchildren and her children, Judy loved her son’s art and music, her daughter’s writing, native plants (especially Geiger trees), classical music, reading, her “Zoom Girls”, and sitting on her porch looking out at the beautiful courtyard.
Judy was preceded in death by her father, John Weaver Holly; her mother, Mary Holmes Holly; and her sister, Jan Holly. She is survived by her son, Michael Workman (Beth); daughter, Jennifer Lessinger (Ozzie); sister, Susan Holly (Mark Twombly); grandsons, Sam and Gus Lessinger; granddaughter, Sadie Lessinger; and nephew James Twombly Holly.
A memorial service is scheduled for June 4, 2023, at the Saint Michael and All Angel’s temporary location at Peace Lutheran Church, 15840 McGregor Blvd. In lieu of flowers donations can be made to the Madden Education Fund at Saint Michael and All Angel’s Episcopal Church or to Moffitt Cancer Center.