William Dempsey, a Licensed Clinical Social Workers, is a Boston-based social worker and 2SLGBTQIA+ mental-health advocate. He founded Heads Held High Counselling, a virtual, gender-affirming group practice serving Massachusetts and Illinois, where he and his team support clients navigating anxiety, depression, trauma, ADHD, and gender dysphoria. Clinically, Dempsey integrates Eye Movement Desensitization and Reprocessing, Cognitive Behavioral Therapy, Internal Family Systems, and expressive modalities, with a focus on accessible, equity-minded care. Beyond the clinic, he serves on the board of Drag Story Hour, helping expand inclusive literacy programming and resisting censorship pressures. His public scholarship and media appearances foreground compassionate, evidence-based practice and the lived realities of queer communities across North America.
In this interview, Scott Douglas Jacobsen speaks with William Dempsey about why 2SLGBTQIA+ workers still face career bottlenecks despite qualifications. Dempsey highlights uneven protections across jurisdictions, the use of pretext in hiring or firing, and how conservative workplace cultures can pressure people to remain closeted. He connects employment insecurity to housing instability and higher risks of depression, anxiety, and suicidality, especially for queer youth. Stable work, he argues, restores hope and reduces the mental toll of hiding. He also notes scattered 2SLGBTQIA+ union caucuses but a lack of resourced labour structures, making legislative advocacy and systemic organizing essential.
Scott Douglas Jacobsen: Regarding employment issues, everyone has transition points. Some people have trouble even getting on an on-ramp. Regarding 2SLGBTQIA+ community members who hit a professional barrier or struggle to enter a desired industry—even when they have relevant qualifications—what are some of the common issues that arise in employment? What recommendations do you have for things they can control to overcome those barriers? Moreover, when does policy advocacy or activism become necessary and helpful?
Will Dempsey: I do not have the most up-to-date statistics, so I encourage people to look into them. At least in the United States, not all states have comprehensive employment protections that explicitly cover sexual orientation and gender identity. As is true in other countries, in some jurisdictions, employers can legally deny someone employment or terminate employment following the disclosure of 2SLGBTQIA+ identity. That is where policy intervention—especially legislative protection—becomes critically important. We have come a long way as a global society when viewed through a racial lens, but we are still pushing for comparable protections from a gender and sexuality standpoint.
Another barrier is that a lack of employment can lead to a lack of stable housing. 2SLGBTQIA+ youth are significantly overrepresented among unhoused youth populations. Lack of stable employment also increases the risk of mental health challenges, including higher rates of depression, anxiety, and suicidality.
Jacobsen: What does increased stable employment do for young people?
Dempsey: It instills hope and gives people the ability to live without feeling that they have to hide who they are. When we compare this to the civil rights struggles of the 1950s and 1960s, queer people historically could conceal their sexual orientation or gender identity, whereas race cannot be hidden. That created a different set of risks and dynamics. However, concealment itself carries costs.
Access to stable employment reminds people that they do not have to hide. As I mentioned earlier, hiding significant parts of oneself is associated with increased rates of depression and anxiety because people are constantly living under the threat of being discovered. Employment security gives people the freedom to choose between a dream job and a well-paying job, and to be open about who they are. For queer youth in particular, that sense of possibility is paramount. It helps instill hope that they can move beyond the stuck points they often feel trapped in.
Jacobsen: Are there specific labour unions devoted to sexual and gender minority rights?
Dempsey: Not that I am aware of in a comprehensive or widespread way, especially given the current period of substantial pushback in North America. That said, this may be an area where new organizing could emerge.
I should correct myself slightly. Some unions and labour organizations have 2SLGBTQIA+ caucuses or advocacy arms that support 2SLGBTQIA+ workers. This is different from what is more commonly seen: Small, underfunded community organizations that provide limited guidance, counselling, or mentorship. What is largely missing is a fully developed, well-resourced union structure that brings together workers—and potentially employers—to advocate specifically and systematically around 2SLGBTQIA+ labour rights.
Part of the challenge, at least in the United States—and I am not sure how it compares to Canada—relates to the concept of separation of church and state. Many of the gaps in employment protections, while not always explicitly tied to religion, are often rooted in religious doctrine or in how religious language is interpreted and translated into social and political norms.
That creates an opportunity not only to develop new policy, but also to reassess existing legislation—or the lack of legislation—and the reasoning behind how things are structured.
Jacobsen: Canadians can—not all, but many—marvel at the degree to which the United States formally separates church and state, or religious institutions and the federal government, while at the same time observing the substantial funding and political power exercised by religious institutions in ways that attempt to override that separation. Is this a significant issue? Moreover, relatedly, do queer people often remain quiet about who they are in religious or conservative employment settings simply because they need to work?
Dempsey: I would say so, for sure. This is also part of an ongoing legal and political debate. There is a U.S. Supreme Court ruling that employment discrimination based on sexual orientation or gender identity is prohibited under Title VII of the Civil Rights Act.
However, the United States has a complex federal system in which federal law and state law operate differently. While federal law technically supersedes state law, employers can sometimes rely on indirect or pretextual grounds—for example, claiming that a hiring or firing decision was based on an arbitrary factor rather than sexual orientation or gender identity. In states whose political or cultural climate aligns with those views, employers may feel more emboldened to act this way.
As a result, if queer people live or work in more religiously oriented or socially conservative communities—particularly where state-level laws or norms reinforce those views—they are more likely to remain closeted. This is also a significant reason why we see higher concentrations of queer people in more liberal areas, especially cities. It is not because liberal cities create queer people, but because queer people often migrate to those places for safety, community, and access to employment without fear of discrimination.
Jacobsen: Thank you again, Will. I appreciate it.
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