The Courage to Be Vulnerable

By Melissa Lowery

When I sat down to talk with Schuyler Bailar in mid-August, it was with the intention of finding out what this talented young man would do next. At just 25 years old, his list of accomplishments is impressive – he is a Harvard graduate, a champion swimmer who competed in the Junior Olympics and made history as the first transgender athlete to compete in any sport on an NCAA Division 1 men’s team. He is an advocate for trans rights as well as those of other marginalized communities, a diversity, equity and inclusion consultant, a mentor, a public speaker and an educator. In September, he added “published novelist” to his CV.

When I ask him about future plans, both short- and long-term, he is brutally honest. “I don’t have an answer,” he says, calmly. At first, I am surprised, given how well he has branded himself and his work so far. Bailar’s expression is serious, professional on the other end of the Zoom connection. He seems like someone who would have a step-by-step plan to reach specific goals and milestones. It’s easy to forget that I’m talking to someone in his mid-20s, expecting him to have his life figured out. Is it weird to have people asking about your long-term plans when you’re only 25?

“Yeah, it is,” he replies. “In the past when people asked me that, I would have this rush of emotion where I’m like, ‘Oh my God, I should know and I don’t. I don’t have a five-year plan or a 10-year plan. I’m failing as a business owner.’”

So why does he seem okay with answering “I don’t know” when I ask him now?

“The reason I’m answering this question — and I haven’t actually shared this publicly before — is that I don’t have an answer and I think that’s okay. I think that a lot of people don’t have answers to what they want to do next year, in five years or tomorrow,” he says.

Bailar’s origin story is well-documented. He started swimming before he would walk, began competing at the age of 7 and by age 10 he was competing in the Junior Olympics. By 13, he qualified for national level competition, and less than two years later was ranked one of the top 20 15-year-old breast-stroke swimmers in the United States.

He competed in U.S Nationals, qualified as an All-American in the 100-yard breaststroke and set a national age group record in the 400-yard medley
relay at the U.S. Winter National Championships in 2013. Among his teammates was future Olympic gold medalist Katie Ledecky.

After struggling with body image and self esteem throughout his middle and high school years, Bailar took a gap year after high school to deal with those issues. In the process, he realized that he was transgender. Blessed with supportive parents who embraced their son, his main concern was whether he would be able to swim competitively if he transitioned. In high school, he was recruited by most of the Ivy League universities and eventually committed to Harvard. When he realized he was trans, Bailar thought he would have to choose between swimming for the Harvard women’s team or living authentically. Instead, men’s swimming coach Kevin Tyrell offered Bailar a place on his team, leaving the decision with the incoming freshman. Bailar chose to be his true self and joined the men’s team, securing himself a place in history in the process.

After graduating from Harvard with a degree in Cognitive Neuroscience and Evolutionary Psychology in 2019, Bailar briefly worked for a private firm, teaching emotional intelligence skills at a finance company.

“In theory, the job was great,” he says. “It just wasn’t feeding my current passion.”

Schuyler Bailar | Credit: Beth Barbis

He pivoted to building his own company, pinkmantaray, through which he offers his services as a diversity, equity and inclusion consultant, life coach, mentor, advocate and public speaker. He holds ongoing advisory roles with Monte Nido & Affiliates (the leading eating disorder treatment provider), Plume Healthcare (the first trans-specific healthcare provider) and American Eagle Outfitters (the AExME advisory council) and is a research assistant at Harvard University.

We talk about his consulting work and going into different companies to talk about gender identity and inclusivity. I ask if he has identified a common information gap or area where companies can do better. He immediately shifts into educator mode.

“I think the main thing companies miss when they’re planning these events, and then realize after they’ve done the training, is that gender inclusivity affects everyone,” he says. “Often people will come up to me after a training or a speech and say, ‘Wow, this all applies to me. I’m not trans and I learned something from this, it resonated with me.’ Everybody has a gender identity, everybody has interfaced with gender their entire lives. Everybody has intimate experience with gender; whether or not it’s important to them is another story.”

Bailar’s personal brand is as a tireless advocate for inclusion. He is best known for speaking out on transgender issues, but he has also been advocating for the Black and Asian-American Pacific Islander communities.

“I’m always educating myself on how to be anti-racist and how I can support my Black trans siblings,” he says, unknowingly foreshadowing an upcoming growth opportunity. “Beyond that, I was just talking with my girlfriend about how I need to learn more about climate change. It’s all intersectional, all these things overlap.”

Bailar’s brand is most visible on social media. At press time, he had more than 328,000 Instagram followers who he addresses regularly through posts and stories. Recent topics of discussion include the U.S. withdrawal from Afghanistan, voter suppression, abortion rights and, always, trans rights. He has been open and transparent about his transition from the beginning, frequently sharing photos of himself shirtless, mastectomy scars exposed. Educating people is an important part of Bailar’s life and work. But lately, he’s been wrestling with questions about establishing boundaries and knowing when to stop working.

He unintentionally took a month-long sabbatical from Instagram in July. Initially, it was because he and his girlfriend were moving to a new city together. They also adopted a puppy who requires a lot of attention. When he returned to social media in August, his first post was about boundaries and what creators owe their audiences.

“My paid work is educating,” he wrote. “Because I provide free education on IG, people often assume I should always answer questions and engage in dialogue about my content. Many will even get angry or hostile when I do not answer. Folks fail to recognize this is demanding my free educational [and] emotional labor.”

I ask him about this in our interview, what prompted this post. It was that accidental break from social media that got him thinking about boundaries and what he “owes” his followers.

“Just because I’m trans doesn’t mean I have to educate people on transness,” he says. “I mean, I am transgender 100% of the time and I am advocating for myself and my safety 120% of the time, but I can’t work 100% of the time. So how do I set those boundaries? It’s been difficult to conceptualize boundaries because I’m not in a physical space, like if I worked a 9-to-5 job in an office. This is my apartment. I live here, I breathe here, I work here, I do everything here. So there’s not a physical separation of my work and my life.”

We spend a few minutes talking about the challenges of being knowledge workers, where what we produce comes from our lived experiences. In Bailar’s case, so much of what he creates is steeped in vulnerability, self-awareness and a sense of responsibility that even a whiff of inauthenticity can dilute the message.

“If I don’t live my life, then I don’t have anything to write about,” he says. “But if I’m writing, I’m not living my life. So where is that boundary? This is the age-old conundrum as an artist, and Instagram is art. It is creation and creativity.”
We eventually agree that boundaries shift, and that’s okay, too.

In September, Penguin Random House published Bailar’s first novel, Obie is Man Enough. The novel, written for middle-grade readers, follows 13-year-old Obie as he navigates middle school. Obie Chang is transgender, a swimmer and a Korean-American, all of which sound familiar. But Bailar asserts that although he and Obie share several identities, Obie is his own (fictional) person.

“I will say that I poured a lot of myself into the book,” he says. “It is absolutely my heart and soul in a fictionalized novel.”

The book begins after Obie has come out and while he does experience some transphobia (Bailar included a trigger warning at the beginning of the novel), the story is more about a kid who aspires to compete in the Junior Olympics, who falls in love for the first time and who wants to connect with his heritage through his Korean grandmother.

“I really wanted to write a book about a kid who happens to be transgender, not about a transgender kid,” he says. “So there’s lots more to Obie than his transness. He’s an athlete, he’s a nerd, he’s a loyal friend. He’s navigating middle school and middle school sucks and is wonderful at the same time.”

About a week after we spoke, Bailar caused a stir when he called out Lil’ Nas X for posing with a fake pregnant belly on his new album cover. In his Instagram post, Bailar objected to what he felt was transphobic, insensitive imagery from the artist. Fans immediately questioned Bailar about why he did not post similar objections when YouTube creator James Charles posed for photos with a fake pregnancy belly. He explained that he had not seen the photo of Charles but as the conversation continued, Bailar was challenged to consider that calling out Lil’ Nas X was rooted in anti-Blackness.

Over the next few days, Bailar engaged in education and dialogue both privately and publicly. He hosted an IG Live with Kayden Coleman, a Black transgender man who has given birth to two children, and spoke with other members of the Black transgender community. In a follow-up post, Bailar shared what he learned from those conversations, holding himself accountable for his mistakes. It’s an example of the transparency and accountability he wants to see from the rest of the world. There is no escaping Bailar’s willingness to be vulnerable, keenly self-aware and responsible for his actions—a demonstration of leadership at its best.

It also reinforces what Bailar told me when I asked why he chose to write a novel for middle school readers rather than a memoir, as many expected.
“Because I’m 25,” he says. “I have a lot more life to live and a lot more lessons to learn, so I don’t think my story is ready to be written.”

Learn more about Schuyler Bailar’s work at pinkmantaray.com and follow him on Instagram @pinkmantaray.

Melissa Lowery (she/her) is the Editor of BEQ Pride Magazine and a contributor to other publications focused on economic equality. A native of Kansas, she enjoys subverting stereotypes and is determined to maintain her status as World’s Greatest Aunt to her 13 nieces and nephews.