Jeilanna Josii of Milwaukee is a showgirl, princess, and rising queen amongst trans women and drag queens, and like many who have come before her, she has had to fight through transphobia, homophobia, an unsettled family life, and poverty to reach where she is today. Jeilanna was born in Milwaukee but raised in Manteca, California, a small town less than 100 miles from queer haven San Francisco.

Facing racism, homophobia, and transphobia as a youth 

Despite the proximity to San Francisco, she faced extreme racism in her community and extreme homophobia and transphobia from her religious family. She’s grateful for her time in California, however, because, despite encountering more racism than in segregated Milwaukee, people there were more accepting of her sexual and gender identities, and she was able to play around with different characters while trying to settle into who she was as a Black, trans girl. She could be open in school and work, effectively becoming two different people: The silly feminine princess to her friends, and the person who was assigned male at birth and who pretended to be who her grandparents and family wanted her to be.

Being rejected by family 

Unfortunately, Jeilanna slipped up on Instagram while her family was away on vacation, showing herself playing with her friend’s makeup and wigs. Her cousin saw the post and outed her to her family, with her mom even calling her at work. When she admitted to being queer and wanting to be a girl, her mother had such a negative reaction that Jeilanna was afraid to be honest with her grandparents, with whom she lived. She trusted another family member with the truth, and was subsequently outed to her grandmother, too, at the age of 16. Her family life disintegrated from there. From ages 16 to 18, Jeilanna emotionally detached from her California family, and worked all the time, not wanting to come home and not feeling like she was wanted there. She ran away a few times.

Finding her place in community and on stage

Once she graduated high school and was 18, she left California and returned to her birthplace, Milwaukee, to live with another grandmother. Once back in Wisconsin, she attended Milwaukee PrideFest and saw her future in the women and drag queens performing on stage. She talked to them and did more research, attending shows at the now-closed Hamburger Mary’s and making friends with the queens there. She knew what she wanted to do and started practicing any time she could, buying and learning about makeup, making videos to post on social media, and getting a job at Hamburger Mary’s—where she had to walk an hour to and from work because she didn’t have a car. She played around with different personas onstage and off, playing with gender roles and who she wanted to be. She has settled now on a princess persona, one she says is a combination of her “old school era” and “glamor era,” and has been able to build on that to become something that she is proud of. Despite the rejections and strain, she still has a connection to her family, and especially her mother, using her as an inspiration for her drag personas, and wants to leave the door open for future reconciliation.

Making a living through entertainment 

Now, through dogged determination, good looks, media savvy, and a sparkling personality, Jeilanna has achieved more than she dreamed possible, working with Red Bull to represent the LGBTQ+ community in front of 60,000 people, and with Chappell Roan, helping the rising super star and being a part of her platform in the mainstream. Jeilanna now makes a living through her entertainment, and, in a country where racism and transphobia are still as rampant as ever, she makes herself visible and succeeds in communities where she and others like her have not traditionally been accepted. She got there through significant sacrifice, and “overcoming excuses that I was using to hold me back,” she said. She doesn’t have a car, so when she started booking gigs further afield than her home base of Milwaukee, she took the Greyhound bus there, doing her makeup in the two-person seats on her way.

Reflecting on her path to happiness 

Jeilanna is nothing if not an optimist, and her belief that she has something to offer people, and something to say, has driven her through even the darkest times. When asked what she would tell that scared 16-year-old in California who had just been outed and was terrified of what was coming, she said she would tell herself to be patient, take your time, and to live your own truth over making other people happy. “Choose joy,” she would say. “Know that it is possible to be happy, which is not an easy task, by constantly working toward it, moving closer and closer to the light.” And these are not the words of a naive girl; Jeilanna fully knows just how hard this path is. That’s why she wants to be a teacher eventually, to teach kids who, like her, have had to fight through poverty, racism, and homophobia. She wants to tell them to never give up or let others extinguish their light.

Accepting every part of herself 

Growing up, Jeilanna always aspired toward greatness and ending the suffering of others—even while her family talked about her and others like her as if they were objects, separate from themselves. She knew this wasn’t true, but the deeply sensitive person she is was wounded by the hatefulness she witnessed, and says that it “almost prevented me from making my own future.” She compares herself to a Kintsugi vase, one which has been broken, but then glued back together in gold to create a whole new form. “I’ve always felt broken,” she said, “but I’ve learned to love and accept those parts of myself, too.”