…You don’t have to be everything to everyone. It’s okay to focus on what you’re good at and what you want to do, and let the rest sort itself out. I made a lot of mistakes by taking on a lot of other people’s advice without listening to my own instincts. In the early years of Old Pros, we tried to be too many things to too many people. I learned a lot from that experience and cherish those lessons, but that era was rockier than it needed to be. Focusing earlier would have saved us some growing pains, but that’s part of being a young entrepreneur in any field…
We had the pleasure of talking with Kaytlin Bailey. Kaytlin is a leading advocate for sex worker rights, combining her expertise as a comedian, writer, and historian with activism to challenge societal norms and policies affecting sex workers. She is the founder and executive director of Old Pros, a nonprofit media organization dedicated to reshaping the narrative around sex work. Through initiatives like The Oldest Profession Podcast, Bailey sheds light on sex workers’ historical and cultural significance, and with her live show Whore’s Eye View, she guides audiences through 10,000 years of history from a sex worker’s perspective.
Born into a military family in Tacoma, Washington, Bailey’s childhood was defined by frequent moves, including stints in Texas and Germany, before settling in North Carolina when she was ten. This early exposure to diverse environments fostered a curiosity about cultural norms and societal structures. Growing up in the American South during the 1990s and early 2000s, she experienced the constraints of evangelical purity culture, which sparked her interest in stories of defiance, particularly those of women who thrived despite restrictive societal norms.
Bailey’s interest in the stories of historical figures who operated outside traditional roles led her to sex work at various points in her life. Unlike many who enter the profession out of necessity, Bailey’s background was one of economic security; her motivations stemmed from personal curiosity and a fascination with the archetypal “whore.” This experience provided her with firsthand insights into the realities faced by sex workers, fueling her later work in advocacy.
After college, Bailey pursued a career in stand-up comedy in New York, an endeavor she found as financially unsustainable as it was creatively rewarding. Like many artists, she turned to sex work to support herself. Her advocacy took on new urgency following the passage of SESTA/FOSTA in 2018, federal legislation aimed at combating sex trafficking but criticized for endangering sex workers by eliminating the online platforms that facilitated safer working conditions. Witnessing the devastating impact of the law, including the loss of vital resources among her peers, Bailey recognized the need for systemic change.
In response, Bailey took on the role of director of communications for Decriminalize Sex Work, a national advocacy group pushing for state-level policy reform. This position solidified her belief that narrative change must precede legislative action. To that end, she established Old Pros, focusing on storytelling as a means of humanizing sex workers and countering the stigma that often shrouds their experiences. The organization’s work spans podcasts, written content, and social media campaigns, all designed to elevate historical and contemporary perspectives on sex work.
Bailey’s efforts have garnered attention from major media outlets, including The New York Times, Rolling Stone, and The Washington Post, as well as appearances on networks like NBC and Fox Business. She has also penned opinion pieces for the Huffington Post, The Daily Beast and Vice. Her advocacy is aligned with views held by Amnesty International, the World Health Organization, and Human Rights Watch, all of which support decriminalization as a means to reduce violence against sex workers.
Among Bailey’s favorite historical figures is Veronica Franco, a 16th-century Venetian courtesan who leveraged her status to become an influential writer and political intermediary. Another is Ching Shih, a former brothel worker who rose to command the most formidable pirate fleet in history, ultimately negotiating unprecedented terms with the Chinese emperor. These stories, Bailey believes, illustrate the resilience and agency of sex workers throughout time and challenge contemporary stereotypes.
Bailey emphasizes that criminalizing sex work exacerbates risks for those involved, cutting them off from legal protection and recourse. She argues that decriminalization, as adopted in New Zealand, parts of Australia, and most recently Belgium allows sex workers to report violence and exploitation without fear of prosecution. Conversely, laws targeting clients, as seen in the Nordic model, fail to differentiate between respectful patrons and predators, leaving sex workers vulnerable.
Old Pros’ mission extends beyond changing laws; it aims to foster a deeper understanding of sex workers as integral, multifaceted members of society. Bailey’s work underscores that sex work, while stigmatized, has been an enduring part of human history and will continue to be. She advocates for a world where sex workers can openly contribute their talent and wisdom without fear, emphasizing that decriminalization serves the well-being of not only sex workers but broader communities.
Bailey’s vision for Old Pros involves expanding its storytelling reach to include documentaries and other media that preserve sex worker history and inspire future advocates. Her commitment is informed by her belief in storytelling as a potent tool for cultural change, and she continues to build networks among global advocates to strengthen the movement.
In personal reflections, Bailey has noted lessons learned from her years in comedy and activism, emphasizing the importance of trusting one’s instincts and focusing on meaningful work. Her advocacy and storytelling invite a reevaluation of the oldest profession and aim to shift public perception from stigmatization to understanding and respect.
Kaytlin, It’s a delight and an honor to meet you. Before we dive in deep, our readers would love to learn about your personal origin story. Can you share the story of your childhood and how you grew up?
Sure. So I come from a military family, and I’m an only child. I was born in Tacoma, Washington, and before my first birthday, we moved to Texas. Before my second birthday, we moved to Germany. I grew up on American military bases. My father retired when I was 10, and we transitioned out of military culture into civilian life in North Carolina.
I grew up as a curious, provocative kid, having dipped my toe into multiple cultures. I pushed back against the repressive, evangelical purity culture that consumed much of the Bible Belt in the United States, especially in the late ’90s and early 2000s, when I was coming of age under George W. Bush’s abstinence-only education program. I’ve always been drawn to history and women who defied common beliefs — like the idea that women couldn’t do things, go places, start businesses, or have an impact until we won the right to vote.
I would think, “What about all these courtesans who funded entire theaters and art movements, ran businesses, and settled the West, including places like New Orleans?” That’s been a lifelong interest of mine.
I did sex work at different points in my life, first as a young and curious person. I didn’t come from a place of economic necessity. I was born into an upper-middle-class family. I had a generous allowance, and my family supported me through college. But I felt drawn to both the archetype of the “whore” and to the work itself. After college and my first job in politics, I dedicated myself to stand-up comedy in New York and eventually returned to sex work because stand-up comedy is an exploitative industry that pays in alcohol, exposure, and other things people can’t live on. Like many artists throughout history, I subsidized my early career as a performer with sex work.
In 2018, Donald Trump signed SESTA/FOSTA into law. This federal law stands for the Stop Enabling Sex Traffickers and Fight Online Sex Trafficking Act. Like many laws before it, it was sold to the American people as a way to protect vulnerable women and children from violence and exploitation, but it did no such thing. Instead, it erased the platforms my friends and I used to schedule and screen clients and share information. I watched friends lose not just the platforms they advertised on but also their social media accounts, bank accounts, and even their apartments. The consequences of this law were devastating, despite being presented as a form of protection.
As a student of history and someone deeply curious about this work, I recognized this as part of a long-standing pattern. It’s easier for people to see the flaws and failures of past moral panics than to recognize the one we’re currently in. By educating people about the White-Slave Law, the satanic panic, and other sex panics that have come before, I hope to make communities, and especially legislators, a bit more hesitant to take away people’s freedom in the name of protecting them from their own choices.
So let’s back up a little bit. How do you start this organization to advocate for the change you’re looking for?
Sure. In 2017, I started The Oldest Profession podcast, where each episode we do a deep dive on a different sex worker from history. Then, in the immediate aftermath of SESTA/FOSTA, there was a lot of activity in the sex worker rights movement, and I was offered the position of founding director of communications for Decriminalize Sex Work, a national advocacy organization pursuing a state-by-state strategy to decriminalize and end the prohibition of adult consensual prostitution. I spent two years traveling all over the country talking to state legislators about this issue, and it became really clear to me that we are not going to get good laws and policies on this issue until we change the narrative. I understand that history and storytelling are powerful levers, so I started Old Pros to try to go upstream of some of the policy fights that were happening. Old Pros is a non-profit that uses storytelling to advocate for sex worker rights. We do that through the podcast, articles, media appearances, our newsletter, and social media. I also tour all over the world with a live show where I cover 10,000 years of history from a sex worker’s perspective. Everywhere I go, I connect with other sex worker rights advocates doing this work because we have always been a globally connected movement.
That’s amazing. Are there places — I know very little about this, but I know that near Las Vegas and in Nevada there are certain parts where prostitution is legalized. Do you think that’s like a utopia for sex work?
Absolutely not. There are a few rural counties in Nevada that allow for a very specific form of legally licensed and tightly regulated prostitution. What we’ve found is that this legal model really only benefits brothel owners. It is not possible to do sex work legally in Vegas or Reno, where the highest demand is. It is not possible to work as an independent outside the confines — sometimes physical confines — of the brothel. To work legally, you have to register as a licensed prostitute, which comes up not only in child custody cases but also in credit checks and background checks. This means taking on a stigma in a subpoenaable way for the rest of your life. There are many good and reasonable reasons why someone would choose to work outside the legal brothel system, which is why, although Nevada is the only state in the country with legal, regulated prostitution, it has the highest arrest rate per capita for prostitution-related offenses. We do not advocate for legalization or regulation, as seen in Germany, Amsterdam, or Nevada. Instead, we advocate for decriminalization, like in New Zealand. Belgium recently became the first European country to decriminalize sex work, and this is also that in New South Wales, Victoria, and Queensland, Australia.
Okay, amazing. So I think the intellectual framework and the conception that most people come to this discussion with is that the goal is to try to protect women because women who are doing sex work are being coerced into it. It’s seen as a form of coercion, almost like a relative of rape, so to speak. Why is that wrong? How do you argue against that?
Sure. Exploitation is wrong across all labor sectors, whether you’re forcing someone to work in a mine, clean homes, or work in a brothel. It’s the coercion that makes that labor exploitative. But because prostitution has become a symbol of violence against women and exploitation, we end up focusing more resources on trying to eradicate erotic labor rather than addressing the underlying vulnerabilities that lead to exploitation and violence. We do have a real trafficking problem in this country, but people are trafficked into agriculture, domestic work, and the service industry as well. It’s important for legislators, lawmakers, and law enforcement to recognize exploitation in all its forms. People have chosen to participate in the oldest profession for all kinds of reasons, under all kinds of circumstances, for all of human history. There are definitely people who choose to do this work, and none of those people are made less vulnerable by being part of a criminalized class. When you criminalize something, you push it further into the black market, and we know what prohibition does to markets. It doesn’t make them safer.
Okay, very good. So the argument is that if you decriminalize or legalize it, then women will become safer.
If you decriminalize it, you enable sex workers to report violence and abuse committed against them. If we have an abusive manager, client, landlord, or domestic partner, and the work itself is not criminalized, we can report those crimes to law enforcement. We can’t do that as members of a criminalized class.
I never thought about that. That’s a very profound point — that you’re essentially cut out of the justice system. You can’t pursue justice or protection because you’re afraid of scrutiny.
Absolutely. If we fear being arrested or losing our livelihoods, we can’t seek protection. Many well-meaning legislators suggest that instead of criminalizing sex workers, we should criminalize their clients. But this model doesn’t make sex workers safer. There is a significant difference between respectful, well-behaved clients we depend on for our livelihood and predators who pose as clients to exploit or abuse us. Predators’ behavior can and should be prosecuted. But when you conflate paying for advertised sexual services with violent rape, you ironically make it harder to identify and prosecute violent criminals. Most thoughtful people, when they pause to consider it, realize that you can’t criminalize half of a transaction. There’s a big difference between someone coming into a store to buy advertised services or products and someone holding that store up at gunpoint. Pretending those are the same does a disservice to everyone involved, including the sex worker or service provider.
You probably have some unbelievable stories from leading this organization and from your career. Can you share one or two stories that stand out most in your mind, ones that your audience would appreciate?
It is a great privilege of mine, as someone who is out and has lived experience as a sex worker, to share my story around the world. When you come out, others feel encouraged to come out too. One of the best parts of my job is holding space for people who are sharing their stories, sometimes for the very first time. Often, I’ll step off stage and people will come up to me and share their stories. I’ve heard about people coming out to their parents or children for the first time, talking about how they got through graduate school, started their business, or survived a difficult divorce. People share their experiences with sex work, and I’ve found that while everyone’s story is unique, people are eager to share them when they feel safe. That’s what we try to create at Old Pros. By elevating sex workers from history and highlighting the significant contributions of the often brilliant, entrepreneurial people who came before us, we make it a little safer for people to share their own experiences.
Can you share one of your favorite stories from the historical archives?
Sure. I have two favorites that I love to talk about. One is about Veronica Franco, a courtesan in 16th-century Venice. The laws in Venice stated that even the wealthiest wives were not allowed to access the library, as it was believed that promiscuity of the mind would lead to promiscuity of the body. However, courtesans, who were not concerned with protecting their chastity, were allowed to access the library and even become writers. Veronica Franco became a renowned writer, editor, and advocate for women — not in spite of her status as a sex worker, but because of it. She played an essential role as an ambassador to Venice, famously negotiating significant military support from the King of France while working as his entertainment for the evening. She leveraged her position to broker an important alliance in a decisive war (the name of which escapes me at the moment). Her contributions were crucial and were only made possible by the freedom of movement and access to resources she had as a sex worker, which would have been denied to her as a wife trying to protect her reputation.
The second story I love is about Ching Shih, the greatest pirate who ever lived. She started her career in a brothel and caught the attention of a pirate king who asked for her hand in marriage. At just 16 years old, she negotiated a marriage contract that was incredibly progressive for its time, insisting on a 50/50 partnership. They led their notorious pirate crew together for about five years until her husband died during pirate-related activities — an occupational hazard. The crew unanimously decided to keep her as their leader, and she expanded the Red Flag Fleet to such an extent that it bested the Portuguese navy, the British navy, and the Chinese Imperial Navy. She was so successful that the Emperor of China offered her an unprecedented deal: she could keep everything she had stolen, her entire crew would be given positions in the Chinese Imperial Navy, and all she had to do was retire from piracy. She took the deal, making it arguably the best retirement package a pirate has ever received.
It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story of a humorous mistake you made at some point in your career and the lesson you learned from it?
I started my career as a stand-up comic. Stand-up comedy is an incredible craft, but it can be a tricky culture to navigate, especially as a young woman. I wish that my younger self had spent less time in spaces that didn’t value what I was bringing to the table. I think I, like many young people, gave too much of myself trying to prove something. I wish I had trusted that there were other artistic spaces where it would have been easier for me to be seen and heard. I devoted a lot of time and energy to other people’s careers and to institutions that, in the long run, did not have my best interests at heart.
Where do you see yourself both personally and on an organizational level in 10 years?
Old Pros is focused on storytelling, which is a broad and flexible category. Right now, we’re making podcasts and live shows, but I believe we can aspire to create documentaries and content for major streaming services. I also think we can grow into an organization that preserves and elevates sex worker history while cultivating and inspiring the next generation of sex worker storytellers. I don’t know exactly what that will look like yet, but I’m confident we can grow into it.
What are your thoughts about the term sex worker?
The term “sex work” was coined by Carol Leigh in the late 1980s or early 1990s as a way to push back against prohibitionists who were referring to us as “prostituted women.” I think it’s a good, broad umbrella term that encompasses the entire world of erotic laborers working in many different ways. Whether you’re a foot fetish model, a stripper, a porn performer, or a full-service sex worker working on the street or in the most luxurious hotels, we all face stigma. That common stigma unites sex workers of all classes, genders and backgrounds under a shared cause. So, I like the term.
At The Oldest Profession, we often use the phrase “old pros” as a way to avoid internet censorship, which I am against. This helps create language that is harder to censor while still embracing the identity of sex workers. Many people who do this work use other terms and we try to be respectful about how people self identify.
Yeah, so the goal is to destigmatize it by being direct about it. It feels like you don’t see that kind of functional, descriptive term for other industries.
Exactly. It’s a bit like the term “service provider,” which can refer to both busboys and sommeliers. They’re all working within the service industry. I think “sex worker” functions in a similar way.
What’s the origin of the term “oldest profession”? Why do we refer to it that way? I understand that sex work has been around since the beginning of history, but you’d imagine that other professions might have come first.
Sure. There’s a lot of interesting history here. I actually have a line in my show where I say, “Archaeologists will quibble with you about this, but it’s definitely older than money.” We’ve found evidence of animals trading sex for things like nesting material, food, or other resources. While hunting, midwifery, and certain crafts are also older than money, trading sex for something of value predates us as a species and has undoubtedly been present in every civilization throughout human history.
Got it. Okay, great. This is our signature question that we ask all our interviewees. You’ve been blessed with a lot of success now. Looking back to when you first started, can you share five things you know now that you wish someone had told you or that you knew when you first started?
First and foremost, and I hope this doesn’t sound cliché, is that it’s okay to slow down. I made a lot of mistakes driven by what, in retrospect, feels like false urgency. So, remember, it’s okay to slow down.
Second, some version of “You’re on the right track, just keep swimming, keep going. It works out.” I wish I had internalized that sooner.
Third, you can trust your instincts. This is a lesson I thought I learned early on as a sex worker, but I wish I had been able to apply it earlier in my career. Trusting your gut is more important than you think.
Fourth, you don’t have to be everything to everyone. It’s okay to focus on what you’re good at and what you want to do, and let the rest sort itself out. I made a lot of mistakes by taking on a lot of other people’s advice without listening to my own instincts. In the early years of Old Pros, we tried to be too many things to too many people. I learned a lot from that experience and cherish those lessons, but that era was rockier than it needed to be. Focusing earlier would have saved us some growing pains, but that’s part of being a young entrepreneur in any field.
And fifth, work with a fiscal sponsor. Don’t try to immediately create a for-profit or a non-profit from scratch. I could have saved myself years of organizational and tax headaches if I had committed to the non-profit model through a fiscal sponsor earlier. Old Pros is now fiscally sponsored by Social Good Fund, and that structure works for us. It might not be the right model for everyone, which is why it wasn’t an obvious choice in the beginning, but for me, it made all the difference.
Can you share some of the self-care routines you use to help your body, mind, and heart thrive?
Sure. I’m 38 years old, so I’ve committed to a skincare and exercise routine that’s seasonal and works for me. I box and lift weights, I try to focus my energy on getting stronger instead of smaller.
Above my desk, I have a Post-it note that reads, “May I stay hydrated, grateful, confident, and kind.” Hydration is probably the most actionable item on that list, but it serves as a daily reminder.
Yeah. Okay. So, this is our aspirational question. Because of the platform you’ve built and your great work, you’re a person of significant influence. If you could spread an idea or inspire a movement that would bring the most good to the most people, what would that be?
It’s in the mission of the organization I started. I believe that decriminalizing sex work is foundational to the rights of women, queer folks, and over-policed communities, as well as to the lives of sex workers themselves. Participants in the oldest profession have always been and will always be valuable, contributing members of our communities. It is a great tragedy that we cannot freely share our gifts and instead live in fear of persecution. This is something we can change by simply not arresting adults for participating in consensual sex, whether money is exchanged or not.
Wonderful. How can our readers continue to follow your work? How can they support your work in any way?
I encourage folks to stay in the know like an old pro by signing up for our newsletter at oldprosonline.org. If you’re interested in learning more about sex worker history, we have five seasons of The Oldest Profession podcast, and season six on the way. Each episode is a deep dive into a different sex worker from history. You can also see opportunities to see my live show, WhoresEyeView.com.
Kaytlin Bailey Of Old Pros: Five Things I Wish Someone Told Me When I First Started was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.