Even with those obstacles - not to mention a poor economy - the 26-year-old is pursuing a social work career, and the government's helping her get ready. Williams and 16 other transgender men and women graduated Friday from a month-long, city-funded job training and life skills pilot program in the District of Columbia that aims to find jobs for an often-marginalized population.
"I don't like the stigma that all transgenders are sex workers, and that's all they're good for. I know for myself, I am an intelligent individual and very resourceful to last over 10 years on the streets," said Williams, who was born Terrell Williams and began gender-changing hormone treatments about three months ago. "I just felt that this was the time to be a part of something greater than me."
Washington's program is one of several transgender-oriented career development classes, workshops or job fairs that have sprouted around the country. D.C. officials say theirs is unique because it's organized and fully funded by the city government.
"If we create the employment opportunities that you deserve, class, then you won't have to be out on the streets doing things you don't want to be doing," D.C. Mayor Vincent Gray told graduates Friday, calling the job training program simply the "right thing" to do.
The programs, which teach basics like creating a resume as well as more nuanced workplace skills, reflect a growing appreciation for the workplace obstacles confronting transgender people. Studies show those who identify as transgender routinely endure discrimination, struggle with unemployment, and turn in disproportionate numbers to drug dealing and prostitution to earn money.
"What we see is people who transition, their income rapidly declines. It happens so fast for some people that many folks don't have a safety net, whether that's family to lean on or friends or financial savings," said Gunner Scott, executive director of the Massachusetts Transgender Political Coalition.
Only 15 states plus D.C. have laws banning workplace discrimination based on gender identity, which give workers an avenue to file lawsuits. But even when employers are unfazed by the prospect of hiring transgender workers, other hurdles remain.
Advocates say they regularly encounter transgender job hopefuls who left school early because of bullying and therefore have little formal schooling or work history. Some people change jobs - and their gender and legal name - later in life, which can make it difficult to prove the authenticity of what may be an impressive resume. Then there are workers who get interviews but are rejected after presenting themselves in person as transgender, not to mention workers who select jobs at transgender organizations because they think that's their only option.
A survey of 6,450 transgender people released in February by the National Center for Transgender Equality and the National Gay and Lesbian Task Force found that 90 percent of respondents had reported harassment or discrimination on the job; 15 percent said they left school early because of harassment; and 26 percent said they'd lost a job because they were transgender. D.C. police have also responded to a series of attacks in recent months against transgender people, though there's no indication the incidents are related.
Other cities are trying to address the problem, though typically it's a private organization leading the way.
The San Francisco LGBT Community Center receives roughly $195,000 from the city to provide transgender job services, despite a threatened funding cut last year, said Clair Farley, the center's employment services specialist. She said the center's Transgender Economic Employment Initiative has placed people into more than 300 jobs since its 2007 launch, and the program offers cover letter support, resume-building labs and vocational academies. A local Goodwill Industries thrift store opened last year as a jobs program for transgender workers after partnering with the TEEI.
The Human Rights Campaign hosted a job readiness program for transgender people in Boston last February that drew about 75 people, Scott said. The GLBT Community Center of Colorado in May held a series of preparedness workshops this year, as well as a job fair that drew employers like Kaiser Permanente and Lockheed Martin, said Amy Drayer, vice president for strategic initiatives.
A transgender job training program offered by a nonprofit in Hawaii recently folded after its funding ran out, but is hoping to restart.
Though no one thinks job training alone can undo deep-rooted discrimination, advocates say the programs provide rudimentary skills to get transgender applicants started.
"What we can do is empower the transgender community to feel as confident as possible when they go in," Drayer said.
The D.C. job training is part of Project Empowerment, a government-run program that helps ex-convicts, past drug addicts and others find jobs. Project Empowerment receives $11 million from the city, said director Charles Jones, though he could not say how much money is specifically allotted to the transgender program. That sum includes an $8.25-per-hour subsidized wage the city temporarily pays to the program's graduates, who are linked up with employers in the public, private and nonprofit sectors based on their skills and work experience.
Project Empowerment has been running for about 10 years, but this is the first time a class of strictly transgender students was enrolled.
Of course, the flagging job market - D.C.'s unemployment rate is about 11 percent - affects far more than transgender people, and it may seem a tough time for the city to fund this particular program. But Jones said he's heard no pushback and said the city benefits if transgender residents are gainfully employed.
"If someone doesn't know how to go out for a job interview or dress (for an interview), then I think it's our responsibility to reach them," Jones said.
The program was initially larger, but one student got a job before it was over. Three others failed drug tests and were not allowed to graduate.
Participants learn everything from how to dress for an interview to how to create a resume to how to diffuse conflict. In one recent class, an instructor counseled students about anger management in the workplace "You get too crazy and can't control yourself, what's going to happen?" the instructor asked. "Explode!" came one answer.
Williams, who says she was kicked out of her St. Louis home as a teenager because she was gay but has obtained her GED, hopes to use the training program as a springboard to one day open a senior citizens home for gays, lesbians and transgenders. She says the class helped her adjust to the mundane rituals of a steady job, such as arriving on time - and remembering to pack a lunch.
"We're not looking for a handout, we're looking for a hand," she said. "And we've always just been looking for a hand."