Billie Lee’s Journey: Navigating Transgender Unemployment, Sex Work, and Resilience in a Tough Job Market

Billie Lee’s story hits hard because it shows what it’s really like for transgender people trying to make a living in a world that often shuts them out. She moved to Los Angeles hoping for a new chapter, but her gender identity made finding work a constant battle. Even with years of serving experience from college, she’d get excited calls about her resume, only to be ghosted or rejected after showing up in person. Restaurants, especially the trendy ones, cared more about her “look” than her skills. “They wanted sexy, attractive servers, and I didn’t fit that mold,” she said on the Oldish podcast. This isn’t just Billie’s problem—it’s a pattern. Transgender people face unemployment rates three times higher than the national average, according to a 2015 survey by the National Center for Transgender Equality. For Billie, the job market wasn’t just tough; it was a brick wall.

This kind of discrimination matters because it’s not just about missing a paycheck. No job means no stability, no safety net, and often no way to feel like you’re worth something. For Billie, the rejections piled up, and money ran low. So she turned to sex work in her early 20s. She described it plainly: getting paid for sexual acts. But it wasn’t just a desperate move. “It gave me confidence,” she said. In a society that either ignored her or fetishized her transgender identity, sex work let her take charge. She’s a self-described people pleaser, and the clear, transactional nature of the work—do this, get paid—felt empowering. It was a way to make money while feeling valued, something the job market rarely offered her.

But sex work isn’t a fairy tale. It’s risky, especially for transgender women, who face higher rates of violence than almost any other group. Billie was careful. She checked hotel rooms for hidden cameras, made sure the front desk saw her face, and carried a pocket knife just in case. She was lucky, working mostly in upscale Beverly Hills hotels with clients who treated her respectfully. That’s not the reality for many transgender sex workers, especially those on the streets, who are far more likely to face assault or exploitation. A 2015 report from the National Coalition of Anti-Violence Programs found that 54% of transgender sex workers experienced violence on the job. Billie’s safety habits weren’t just quirks—they were survival strategies.

She doesn’t do sex work anymore. These days, she’s writing books, hosting a podcast, and doing stand-up comedy. But she’s open about how sex work helped her through tough times. “It was a way to survive and feel good about myself,” she said. She’d even notice guys hitting on her in everyday life and think, “I could make money off this.” For her, it wasn’t just about the cash—it was about self-worth. When society made her feel invisible or unsafe, sex work gave her a space to be seen and respected, even if just for a transaction.

Billie’s time on Vanderpump Rules, where she was the first out transgender star on Bravo, showed another side of the challenges transgender people face. The show put her in the spotlight, but it wasn’t always kind. She worked as a hostess, but the role leaned heavily on her appearance, not her skills. Behind the scenes, things got uglier. Some cast members made insensitive comments about her body, and producers pushed her to share personal details about her anatomy on camera. “It felt like they wanted me to be a spectacle,” she said. The show’s environment, while progressive in some ways, often reflected cisgender privilege—a lack of real understanding about what it’s like to be transgender. That toxicity took a toll on her mental health, and after Season 7, she left. “It was hurting me more than helping,” she admitted.

This kind of workplace hostility isn’t unique to reality TV. Transgender people often deal with microaggressions, like coworkers misgendering them or making awkward comments, and bigger issues, like being passed over for promotions. The 2015 NCTE survey found that 23% of transgender workers reported harassment at work, and 12% said they were physically or sexually assaulted because of their gender identity. These aren’t just annoyances—they drive people out of jobs. For Billie, leaving Vanderpump Rules was about protecting herself, but not everyone can walk away from a hostile workplace when it’s their only source of income.

So why does this all happen? A lot of it comes down to stigma. Transgender people are often seen as “other,” and that perception shapes how employers, coworkers, and even clients treat them. In industries like hospitality, where Billie worked, appearance-based hiring is common, and transgender people are frequently judged as not fitting the “right” image. But it’s not just restaurants. Across fields, employers often lack policies to protect transgender workers or training to help staff understand gender identity. The result is a job market that’s harder to navigate for transgender people than almost anyone else.

What happens when the job market fails you? You find other ways to survive. For Billie, sex work was one of those ways. It wasn’t her only survival strategy, though. She also leaned on her resilience—her ability to keep going despite rejection after rejection. Moving to LA, coming out as transgender, and building a career in entertainment took guts. Her story shows how transgender people often have to be tougher than most just to get by. But resilience isn’t a cure-all. It doesn’t fix systemic barriers or make discrimination disappear.

Let’s talk about how sex work fits into this. For many transgender people, it’s not just a fallback—it’s a deliberate choice in a world with limited options. The NCTE survey found that 20% of transgender people had done some form of underground work, like sex work or drug sales, to make ends meet. It’s not always about desperation. For Billie, it was about control and confidence. She could set her own terms, choose her clients, and walk away feeling like she’d accomplished something. That sense of agency is huge when the rest of the world is telling you you don’t belong.

But sex work isn’t safe or sustainable for everyone. The risks—violence, arrest, exploitation—are real. Billie’s safety measures worked for her, but street-based sex workers, who are often transgender women of color, face far worse odds. Mistakes, like not vetting clients carefully or working in unsafe areas, can lead to dangerous situations. And when society stigmatizes sex work, it makes it harder for workers to seek help or report abuse. Decriminalizing sex work, as some advocates argue, could make it safer by giving workers legal protections and access to resources.

Billie’s visibility on Vanderpump Rules also matters because representation shapes perceptions. Seeing a transgender woman on TV, even in a flawed environment, can challenge stereotypes. But it’s a double-edged sword. The show often focused on her identity in ways that felt invasive, reinforcing the idea that transgender people are “different” rather than just people. Good representation means showing transgender characters as complex, not just as tokens or curiosities. Billie’s experience highlights the need for better media portrayals—ones that respect transgender people’s humanity.

So what needs to change? Employers can start with blind hiring to focus on skills, not looks. Clear anti-discrimination policies that include gender identity are a must. Training staff to understand transgender experiences helps too. But it’s not just about workplaces. Society needs to shift how it views transgender people—less stigma, more acceptance. Until that happens, transgender people will keep facing the same barriers Billie did, and survival strategies like sex work will remain a reality for many.

Billie’s journey—from jobless to sex worker to creative professional—shows what resilience looks like. She didn’t just survive; she built a career on her terms. But her story also shows how hard it is to navigate a world that’s not built for you. Transgender people deserve better—jobs that value their skills, workplaces that respect their identities, and a society that sees their worth. Billie’s openness about her life, from the highs of empowerment to the lows of discrimination, pushes us to have that conversation.