Pixels of Pleasure: My Career Path from Sex Work to Tech

Anna R.
April 8, 2024

Many people on the internet claim they don’t dream of labor, and that’s fine. But, unfortunately, I do. I love working, I love being able to build things, and  honestly I love the way working makes me feel.In my current job, I have the opportunity to construct and document numerous systems and processes. While I'm deeply proud of my career and am actively working to advance it, it hasn't always been this way. For the longest time, I despised my work and felt deeply ashamed of it. Yet, through extensive therapy, strategic planning, tears, and far too much self-doubt, I managed to transition from sex work to a career in tech.

I hold immense admiration and respect for individuals who choose (and pursue) a career in sex work. I firmly believe it can be fulfilling, empowering, and affirming. However, at some point, sex work ceased to embody these qualities for me. I can't pinpoint exactly when or why, but something shifted. Working full-time as a fat fetish model became draining and transformed me into a version of myself I didn’t particularly like. I hit burnout and  realized I needed a significant career change that would provide a better work-life balance and work I could be proud of. But to initiate this pivot, I first had to dare to dream, to be absolutely batshit delusional. 

I grew up in working-class family that eventually ascended to the middle class as I matured. Most of my family members were involved in various trades, primarily electricians and steelworkers. I've always taken immense pride in my family's labor, as their efforts quite literally helped build Chicago.

I am grateful for my biological family and their sacrifices, but I've learned to love and appreciate them from a distance. As a relatively well-adjusted adult, I now recognize that there were numerous occasions where my family couldn't provide the support or affection I needed, partly due to limited access and partly due to their own emotional struggles. As an adult, I often wish my family had encouraged me to dream, to aspire for something beyond mere survival from one day to the next.

During my childhood, I rarely entertained dreams, except for one oddly specific aspiration: designing figure skating costumes for Michelle Kwan. Being a child of the 90s, I harbored an unmistakable femme4femme crush. Regrettably, I haven't had the opportunity to design competitive garments for Michelle Kwan, but I’ll never stop girlbossing  or dreaming. Regardless, I never envisioned my future career or job, primarily because I never envisioned a future for myself. I lacked the capacity to contemplate life beyond merely making it through to the next day. My mother was an addict, and while she has since become sober, her struggles made it challenging to experience a stable childhood. And so with that turbulence often came a lack of support or ability to encourage me to think about my future. And while I feel how I feel about my mother, I can’t imagine it was possible to encourage your child to dream for something bigger, for a future, when you weren’t quite certain you would make it to the next day. I don’t blame her, I just wish it had been different. 

Photo: Matt Blum

These feelings, and the inability to dream, persisted into my teenage years and subsequently into early adulthood. I attended a small private liberal arts college in Chicago, majoring in sociology and gender studies. Although I obtained my degree, I remained clueless about my career path. Which I don’t think is super uncommon for anyone without their frontal lobe developed. For what it’s worth, I also don’t think universities prepare you particularly well for any type of career that isn’t academic. Near the end of college I started casually getting involved with clip work and other online sex work services. It was casual, a quick way to make money for all the American Apparel disco pants I could dream of. 

I never really took sex work seriously, partly because I was young and partly because it was a different era. You didn't have to take it seriously if you didn't want to. Sex work before FOSTA/SESTA was fucking it. I was taking payments through burner PayPal’s, no goals, just pure vibes. During that time I was also posting on social media for fun, casual outfit pics, with some casual hot takes. Eventually, I got pretty good at social media and was able to get some freelance clients. 

After freelancing for a while, I transitioned into a role at a Queer healthcare nonprofit, managing and producing all their digital content. While the job wasn’t challenging in terms of skill, emotionally, it was draining. Working so closely with content directly tied to my identity proved exhausting and left little room for anything else in my life. Despite the job not providing a livable wage, I chose to walk away from sex work; I couldn't manage to balance the two.

Around this time, I began to take a deeper interest in social media as a product rather than just a marketing tool. I started noticing the impact of FOSTA/SESTA and the Trump presidency on my community. While I understood what I was witnessing, I needed to comprehend why it was happening. So, I started learning more about social media companies and, consequently, the broader tech community through reading books, journals, and other publications. I also started networking with more people in the tech space. But, I never disclosed my background in sex work during these interactions. I couldn’t, I felt I wouldn’t be taken seriously. And truthfully, some people probably wouldn’t have, and probably still don’t. Fortunately, though, I got a lot of insights from these spaces, which I was immensely grateful to carry into my nonprofit job.

However, I eventually parted ways with the organization after a significant disagreement with my director regarding my suitability to represent the company at a tech conference. The argument revolved around my lack of involvement in tech and my inability to represent the organization formally due to being publicly out as a sex worker in some spaces. This sentiment was particularly ironic, considering a significant portion of our clients were sex workers. While I wish I had handled my departure differently, I don’t regret leaving an environment where my skills, aspirations, or fundamental identity weren't viewed as assets.

After leaving, I reluctantly returned to full-time sex work. I wasn’t enthusiastic about the comeback and hadn't intended to pursue it full-time. However, bills needed to be paid, and embarrassingly, I was wounded by my previous employer's actions. I felt as though people only saw me as a sex worker, and that my sole purpose was to gratify others sexually. Over time, sex work became increasingly detrimental to my well-being, distancing me further from any semblance of the career I desired. Things felt so far away, nearly impossible to reach.

Photo: Matt Blum

I don’t know what changed in me but I started to push myself to want more, to think of a future that was bigger than one I could have imagined. I knew I wanted a career in social media, but not from a marketing standpoint. I wanted to be involved in constructing the products I was deeply passionate about. I had been obsessed with social media since I was a weird underage teenager flirting with what I can only presume are grown men on VampireFreaks, an infamous goth social media site. And for the first time I thought I deserved to be in those spaces helping make social media products. I recognized my background in sex work as an asset, one that could perhaps bring a new perspective to those spaces. After years of not giving myself space or permission to dream for more, I finally started. 

But what are dreams without a little bit of delusion and strategic planning? I understood that to achieve the career I wanted, I needed to devise a strategy, knowing it would likely take time. So I began roadmapping my career, looking at what my dream was and then breaking that into smaller, much more attainable goals. To gain insight into my path, I studied the careers of others, learning how they reached their current positions and how they articulated their work. I I started forcing myself to be in more tech spaces, despite how uncomfortable I was in them. I knew that things would never get better if I didn’t change. No one was ever going to hand me the career that I wanted. 

I proceeded to create award-winning campaigns for global clients at a prominent advertising agency. Although I hadn’t intended to work in the ad world, I knew I needed more credibility and leverage in my career before transitioning into tech. My experience at the ad agency taught me to get really good at data analysis, laying a solid foundation for the rest of my career while also providing the credibility associated with working with major brands. While I enjoyed my job, it left me financially strained, and so sex work remained a secondary hustle. I wish I could say that I seamlessly transitioned into tech after leaving the ad agency, but that would be too nice of a story. And so of course, sex work continued to be the unwanted gift that kept giving. 

While I was doing sex work full time I started to get better about my social media skills by getting certifications, continuing to learn, and of course networking with those in tech communities. I knew that if I wanted to get into tech and eventually work at a social media company doing product getting into a startup was probably my best bet. Initially, I had some insecurity about my nontraditional background. However, in hindsight, in 2024, most people in tech have nontraditional backgrounds, and we’re all simply trying to navigate our way through. 

I eventually transitioned into a direct-to-consumer startup, using that title to give the perceived legitimacy I thought I needed to be in tech spaces. I know that there are people in tech spaces who don’t understand why I’m there, presuming that I just make memes all day, and at first, I let those feelings really get to me. But the more I showed up and learned about the industry, the less those concerns mattered to me. One of the biggest influences for me was hearing Angelica Ross speak. While Ross might be best known for her roles on Pose and AHS, she’s also a self-taught programmer who founded TransTech Social, an organization dedicated to empowering the trans community, particularly sex workers in tech. 

She was the first person I ever heard talk about sex work so passionately and profoundly in a tech space. What particularly resonated with me were her thoughts about being the best at what you do. She believed it was important to be the best at something, so be the best engineer, don’t just be the best woman engineer. Be the best there is at your craft, because when you're the best at what you do, they can’t deny your skill, no matter what else they may perceive about your identities. Her words continue to be a source of inspiration for me.

I'm immensely grateful for the experiences and knowledge that sex work has afforded me. It's made me a more observant and passionate person, all of which I bring into my career. I'll never forget the community that believed in me before I believed in myself. With that in mind, I remain dedicated to building more accessible and inclusive tech spaces. I will never forget that part of my identity and all it’s done for me

Although I dream of working for a social media company, I know it will take time, and the strategy to get there is an ongoing process. I'm happy to say that I'm currently at my second startup, one that provides me with the autonomy and legitimacy necessary to propel my career forward. It will give me the ability to pivot where I need to to get to my ultimate goal of moving out of marketing. I want to be known for my thoughts on social media, and truthfully that’s partly why I created this website. I want a place to dream, a place to push for more, and a place to be absolutely batshit delusional. 


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