When Holly Conroy organised the 2019 Pride Parade in regional New South Wales’ Wagga Wagga, she feared it could be the first and last. The city with a population of just over 60,000 had never hosted such an event, modelled on Sydney’s annual Mardi Gras Festival that is attended by hundreds of thousands.
Now, a year later, the transgender truck driver is planning the area’s own Mardi Gras Festival after the community’s positive reaction to the pride parade. “Last year’s event was just one night. This year I’ve actually put it over three days,” said Conroy. “It’s quite a big deal.”
The Riverina region where Wagga Wagga lies has the country’s highest percentage of people identifying as Christian, so it is a big deal as Conroy leads the charge in changing conservative attitudes towards the queer community.
Her efforts haven’t gone unnoticed. She has been nominated for the NSW Women of the Year Awards, which is “extra special” to her “because I fight to be accepted as a woman and I fight to have trans rights being acknowledged as women’s rights”.
“It really shows all the hard work I’ve put in to creating visibility and trying to gain acceptance to be included as a woman is all paying off. Women are women, whether you’re a cisgender woman or a transgender woman.”
Like Conroy said, it’s been a fight. It’s been a tough fight since childhood, when Holly was Dave and wanted to wear a dress to school.
“From early on as a kid, I knew I was different. I looked at the girls at school and I was jealous,” she said. “When I was about 11, I cut the crotch out of an old pair of shorts to make it a skirt.”
However, “growing up in a small country town and hearing relatives and friends talking really bad about gay and trans people” made it next to impossible to come out at that age.
Fourteen years ago, she tried to come out as a 27-year-old trans woman, but negative reactions from close family and friends forced a return to the closet. A decade later, she came out again, and committed to hormone therapy and gender reassignment surgery.
“I didn’t get the response I wanted,” she said of her initial attempt to come out. “What I got the first time around was, ‘We love you, but you’re going to lose friends, you’re never going to get a job. We’re not going to leave you, but everyone else will.’ They kind of accepted it, but they did nothing but fill my head with negative thoughts.”
Conroy knew that her mental health was suffering as she lost her job and friends.
“It all piled on at once, and I thought, ‘Maybe they’re right. Maybe I’m never going to have any kind of life if I do this.’ It scared me to the point where I went back into the closet.”
“I didn’t get the response I wanted”
Suppressing her true identity, she later married a woman. Their marriage lasted five years, at the end of which she was ready to come out as Holly.
“I left [the relationship] and three weeks later I came out as trans and haven’t looked back,” she said, explaining that self-reflection drove her to make the big decision. “I had no respect for myself, and then I sat down and reflected and thought, ‘You know what, Holly? You need to do something’.”
Choosing to do it her own way now, Holly pursued a very public transition journey, including coming out to friends on social media and then sharing updates.
“It was the best decision I made, to come back out at 37. Once I got good reactions on Facebook about coming out, that was a huge load off my shoulders. I thought, ‘What have I been worried about?’ I think I cried happy tears for at least the next hour after I started getting reactions from people.”
Emotional and teary as she reflected on the affirming reaction, Holly spoke about a man she used to do MMA (mixed martial arts) fighting with.
“The very first comment I got was from one of the guys I fought with before, and it said, ‘We were brothers in the ring, and now we’re brother and sister. If anyone has a problem with you, they’ve got me to deal with.’ I tear up every time I tell this story.”
Holly has felt touched by being able to help change others’ views on trans people through sharing her story. Navigating the workplace has been another example of her challenging the norm.
“When I first started transitioning, I was unemployed. I was looking for a job and I thought, ‘I’m not going to start a job as Dave and then try and explain to them. I would have to come out again’,” she said.
Soon after, she landed a casual contract with a construction company where her role involved driving a delivery truck to work sites.
“I started out as a very camp Dave. The first time I went to work there, I had nail polish on but was wearing high vis,” she explained.
“I thought, I’m just going to deal with the backlash. People will assume because I’m wearing the nail polish. So, I won’t have to portray this masculine fake person. I could still go and be at this stage girly Dave, which was going to make it a lot easier to tell people because they would have already had an inkling because of the nail polish and everything else.”
“I started out as a very camp Dave. The first time I went to work there, I had nail polish on but was wearing high vis.”
Holly eventually confided in a colleague, revealing that she was seeing a doctor in Canberra to start hormone therapy. Word got back to “the big boss”, who called Holly in for a Friday afternoon meeting.
“I thought they’re going to sack me because they don’t want a transgender person working here,” she recalled. “I’ve gone into the office, shaking like a leaf and my boss turned around and said, ‘I hear you’re transitioning’. He’s like, ‘I want you to know I don’t have a problem with it and the company doesn’t have a problem with it. Any time you want to come to work as yourself, feel free, no pressure.’ I turned around and said, ‘She’ll see you Monday’, and that was it. From that time onwards, I was full-time Holly.”
Her contract eventually ended at that company, but two years later Holly continues to be a Wagga Wagga truck driver, and her straight male colleagues attended last year’s pride parade. She’s a few months into a happy relationship, and she hopes her openness will inspire others.
“The whole reason I went public to begin with was to create an environment where people could gain knowledge and open their eyes. Or if a young trans person is sitting in their bedroom, either dressing up or having mental health issues, I would most definitely think I’m trying to help those people by going public and putting my story out there for everybody to see,” she said.
As the festival draws nearer, the trans rights activist recalled the time a young man approached her at the 2019 Wagga Wagga Pride Parade.
“It was about one o’clock in the morning, and I was just about ready to go home to bed, and this young boy came up to me, he would’ve been just 18 or 19. He had tears in his eyes and said, ‘Holly, I’ve been trying to run into you all night. I just wanted you to know that I came out today’.
“And it was because the hometown was so supportive of the Mardi Gras event,” she explained. “So many people embraced it, from young kids to grandparents. I’m pretty sure there were more straight people at the parade last year than there were gay people.”
Will this year’s festival have an even bigger turnout from the community? Holly is as sure of it as she is of her identity as a woman.
This article is part of HuffPost’s Proud Out Loud project, which profiles the next generation of LGBTQI change-makers from around the world.