Lisa Oakley was born in 1953 in Chicago, Illinois. Growing up, Lisa’s mother wanted Lisa to play sports and have male friends, but Lisa was more interested in playing with dolls and cooking. For as long as she could remember, she felt that she should have been born a girl, and hid a secret stash of lingerie as a teenager. During school, Lisa tried to make friends, but it was difficult when she had no interest in gender roles. She scored a ‘D’ in gym class, as she didn’t want anything to do with asserting herself as male.

Lisa entered into the military at age nineteen for four years, choosing to live off-site rather than risk military staff combing through her possessions and finding her lingerie. Shortly after leaving service, she embarked on a career as a truck driver and married for the first time. While her wife was supportive of her dressing as a woman, the marriage did not last, and Lisa later married for a second time. 

Upon finding her stash of women’s undergarments, Lisa’s second wife nailed them to the wall and invited their friends to come see them, leaving Lisa feeling “embarrassed and horrified.” After their divorce in 1983, Lisa married her third wife, Madge, who was significantly more supportive, helping her to wear women’s clothes for Halloween. Compared to this one night of the year, “the other 364 days felt like a lie.” Lisa and Madge had a happy marriage until Madge’s death in 1996.

Four years later, after spending the previous two years living life as a woman when not at work, Lisa came out as transgender at age 47. She realized she finally wanted to begin hormone therapy to medically transition, and began traveling to California for treatment. 

Lisa had conflicting feelings about her religious upbringing. She decided to return to religion after her third wife’s death, a dedication later reinforced after a near-death, out-of-body experience where Jesus told her she needed to return to Earth to be a teacher. Even though she told Jesus all she had was a high school diploma, Lisa went on to teach, delivering lectures at local colleges about the transgender community.

Lisa suffered with her health for many years. She had to relinquish her 20-year career as a truck driver after damaging her neck. For the next 20 years, she worked as a healthcare worker for disabled people, as well as a pizza delivery driver. 

In the last years of her life, Lisa had five toes amputated due to diabetes and came to use a wheelchair. An October 2020 visit to the emergency room led her to search for a long-term care facility. It was an eight-month process, in which she was rejected from over 60 facilities due to transphobia. Thanks in part to the persistence of hospital care coordinator Cori Martin-Crawford, Lisa eventually landed at the affirming environment of Eagle Ridge of Grand Valley nursing home in Grand Junction, Colorado, where she enjoyed fishing, smoking, and meeting other people in the transgender community. 

In her 2022 OUTWORDS interview, Lisa said she would like to inspire people to be more open to accepting of people who are different. Seven months later, she passed away.