November 23, 2025 | Michail Takach

Chasity Jesko: finding her wings in the world

Since embracing her Two Spirit truth, Chasity has soared higher and farther than she ever imagined possible.

Chasity Jesko

"You need to shine brightly in your world -- because the world needs to see you."

For Chasity Jesko, the world was once defined by the quiet highways of Shawano, Wisconsin, and the binding roots of the nearby Menominee reservation in Keshena. It was a place of family and history, but also a landscape of silence where certain truths about herself could not yet take flight.

Today, the world is a different kind of map.

One month she is in Rio de Janeiro, Brazil, feeling the humid air and the pulse of a new city. The next, she’s navigating the ancient beauty of Spain, or planning a trip to Tokyo just to see Lady Gaga. As a flight attendant for a major mainline carrier, Chasity’s office is the sky, and her identity is a vibrant tapestry woven from her Menominee heritage, the sacred role of her Two-Spirit identity, and a ferocious, resilient desire to see and be seen.

Her journey from a queer child stealing her mother’s makeup to a global traveler—a journey that took courage, resilience, and a deep-seated spiritual understanding—is a powerful testament to finding your own destiny, even when the history you need to guide you has been deliberately erased.

Chasity Jesko

Chasity in Chicago

Chasity in Thailand

Quiet revelations

Chasity’s earliest memories in the Shawano-Keshena area, where she grew up surrounded by family, are tinged with a feeling of fundamental difference. Even as a small child, she was drawn to things that were not expected of her assigned gender.

“Even as a kid, I was having the feelings like, oh, I’m definitely different,” she recalls. “My cousin tells me I liked to dress up and have her paint my nails. I was drawn to that existence from a young age.”

This was more than just child’s play: it was a deeply instinctual pull. She remembers vividly some early, clumsy experiments with gender expression.

“I would literally steal my mom’s makeup,” she says, laughing at the memory. “I remember one time she caught me wearing the whitest makeup ever—she’s whiter than me—and she was like, ‘What the heck are you doing?’ That was the first time she caught me.”

Despite her blooming sense of self, the outside world was unforgivingly small-minded. Fifteen years ago, “transgender” and “Two-Spirit” were not part of the common vocabulary in north central Wisconsin. In some circles, transgender might even have been seen as taboo.

“Not many people really talked about trans identity or Two-Spirit,” she explains. The isolation was profound, forcing her to process her identity in a vacuum. “I knew from a young age that there was something different about me, but I didn’t really have words to describe what the difference was.”

Chasity was taking her first steps toward self-acceptance, but the path was far from clear.

A sacred alignment

For Chasity, the question of identity operates on two distinct planes: the mainstream world and the spiritual world of her heritage.

“In the white world, I am a trans woman,” she said, “but in the Indigenous communities, I express myself as Two Spirit.”

While she comfortably uses the term "transgender" to ease conversations in wider society, acknowledging that it’s the term most people understand, her true spiritual and personal alignment is with Two Spirit. This broad term, originating from the Ojibwe language and widely adopted in 1989 to refer to a specific Indigenous cultural role, speaks to a history much older than colonization.

“I do identify and align more as Two Spirit,” said Chasity.. For her, the meaning of Two-Spirit is not a rigid gender definition but a broader, deeply personal embrace of her whole self. “You know, I align more with the female side of myself, but I embrace that I was born male. There is another side of me that – no matter how much I transition – will always be a part of who I am. And I completely respect that.”

This duality, she believes, is a gift, granting her a heightened spiritual perception.

“When you have this female and male vision of yourself, you’re able to see the world in such a broader view than most people can,” she says. “You carry a deeper and more balanced perspective to the conversation.”

It is this broader view that connects her to the revered, ancestral role of Two-Spirit people. She describes this role not in terms of politics, but in terms of healing and comfort.

“Two-Spirit people are healing people. We are a source of safety for our people,” Chasity said.

“A lot of people open up to me, share with me, vent to me, reveal themselves openly to me, and they know they are safe to do that,” said Chasity.

“This is actually an ancestral trait that Two Spirit people were known for. Our ancestors came to their Two Spirits because we were seen as healers, problem-solvers, navigators, and sources of the best possible advice. We were seen as higher spiritual people who held a higher intellectual view of the spiritual world.”

Reconnecting to a hidden heritage

Sadly, this sacred role was rendered nearly invisible in Wisconsin’s Indigenous communities by the impact of white colonization, religious conversion, and attempts to extinguish Native heritage.

“This is a heartbreaking tragedy that nobody really talks about,” said Chasity.

“Two Spirits were among the first targets of the colonizers, because they held so much influence and power among their people. There were extreme efforts to silence and erase the Two Spirit people. As a result, I knew nothing of Two Spirit identity until I was in my 20s.”

It was only six or seven years ago that Chasity even heard the language.

“I didn't know what Two-Spirit was because, to be honest with you, up in Keshena, people don't really talk about that,” she admits. “It’s not taught to us, it’s not discussed in our families, and it’s not part of tribal government. You really have to search for this.”

It wasn’t until she connected with other Indigenous queer individuals, particularly a man named Rico, who was an advocate for Two Spirit history, that the fog lifted.

“He taught me a lot. I would have never known what Two Spirit was if it wasn't for him,” she says, also noting a connection she made much later in Thailand with another Two Spirit person from Vancouver, whom she recognized instantly by their shared reservation slang.

“As I learned more, I realized I needed to speak out more about the erasure of Two Spirit identity,” said Chasity.

She is passionate about sharing an enormous truth: homophobia and transphobia are not Indigenous beliefs; they were imported through colonization.

“This needs to be shared: before Contact, sexual and gender diversity were not a source of embarrassment for Indigenous people,” she said. “Two Spirit people were revered as extraordinary beings for their ability to transcend these human limitations.”

She recounts the brutal harassment she endured as a younger person—being called slurs, having a man aggressively pull her wig at a party—and contrasts it with the contemporary disrespect she sees online, where comments about a murdered trans person's gender identity eclipse any sense of humanity or grief.

“This person just got brutally murdered… and their whole life was taken from them, and you’re more concerned about having to appropriate their gender? That’s your problem?” she said. “People forget they’re human beings. These people have families and they’re watching these comments. That’s heartbreaking.”

This lived experience is precisely what drives her current role as an unofficial mentor and safe place for younger queer and Two-Spirit individuals.

“I always embrace youth and make them feel beautiful,” she said. “I tell them that they’re worth it, because I didn’t always get that from the world when I needed it. I want them to know that I am a safe place where they will not be judged for who they are.”

A legacy of strong women

The bedrock of Chasity’s resilience is her mother. The memory of her mom’s strength is so powerful that it brings Chasity to tears even today, recalling the sacrifices and spirit of the woman who was her protector.

“For me, my mom was my strongest support system,” she says, her voice catching. “She was like both parents sometimes. My mother grew up being abused and being in a really difficult time in her life. She ended up joining the Navy when she was seventeen years old.”

The reservation, Chasity explains, can be a difficult environment where people often feel trapped, believing they will never make it out or succeed beyond its borders. Her mother, however, defied that narrative.

“My mom is a prime example that you absolutely can. She was seventeen years old, and she already knew what she wanted to do with her life. And she left, and she made something of herself,” Chasity says, pausing to gather her composure. “She grew up with a lot of traumas, and she made it through all of it. I’ve seen her do that. It felt like seeing her against the world sometimes. She’s a prime example of who I want to be as a person.”

This inherent fighting spirit, the refusal to surrender to circumstance or trauma, was the first lesson Chasity learned. It informed how she handled the first major rejection in her professional life.

Her childhood dream was interstellar: she wanted to be an astronaut and work at NASA, fascinated by UFOs, aliens, and the supernatural. As she grew older, the desire for travel remained, but the career goal shifted to the practical: a flight attendant.

“I got sick and tired of living in the same place,” she recalls. “I needed an out. I wanted to work in a job where I can travel and get paid for it.”

She applied, went to training with a regional airline called SkyWest, and two weeks later, she was sent home after failing an exam. It was a crushing blow.

“I was devastated. Devastated,” she says.

But she didn't allow herself to wallow. She immediately channeled her mother’s strength.

“The first thing I did was I went, I didn't wallow, I didn't cry, I didn't make any excuses. I was like, you know what, this didn't work out for me. I'm going to keep trying because I want to do this.”

Within a month, she had two new job offers and chose Republic, where she thrived. A year later, she set her sights on the top: United Airlines. She was rejected the first time. Six months later, she applied again, flew out to Houston for the interview, and prepared for whatever fate might bring.

“I was polished from head to toe, and I was like, you know what, I’m just going to show them who I am. I’m going to be myself. I’m going to be comfortable. I’m going to show them why I deserve this job,” she says. The recruiter saw the potential, saw the resilience, and offered her the job.

“It was a reminder that you can transcend any limits in your path.”

The world needs to see you

Four years into her career, Chasity is living the life she once only dreamed of. Her passport is stamped with destinations that were once just words on a map: Iceland, Germany, Paris, South Korea, Thailand.

The most personally satisfying travel moment, however, was fulfilling a childhood promise to herself.

“Even as a kid, I said, I’m going to Hawaii. I’m going to visit Hawaii. And guess what? I made it happen,” she beams. “Within one month of flying for United, I picked up a trip to Maui.”

For Chasity, landing in Maui felt like the ultimate victory. As a small-town kid, often bullied and sidelined, she was now standing on one of the most beautiful islands on Earth, looking out at an ocean that once felt impossibly far away.

Traveling, however, has offered her more than just stunning views; it has provided a glimpse into a world where acceptance is the norm, not the exception. The trip to Thailand was particularly spiritual in this regard.

“I saw so many trans women just walking down the streets confident, and people just were minding their business,” she said.

Chasity at work

Chasity at work

Chasity at work

“These women live openly and without the omnipresent threat of judgment or violence. And that’s how it should be everywhere.”

Chasity now carries that confidence back home and into her work. She doesn’t feel she needs to hide her identity – anywhere.

“I refuse. I come into work. I’m already femme as it is,” she states. “My job is to take care of people, get them to where they need to go, and move on to the next assignment.”

But her biggest mission remains simple and powerful, especially for the young people back in places like Keshena who feel trapped or unseen.

“I just want people whenever they’re reading this, that I want them to know that they’re worth it, and that there’s a whole world out there,” Chasity says. “I want them to be able to travel. I want them to explore their world. I want them to find their place in the world.”

She speaks directly to the version of herself that existed years ago, shy and experimenting with stolen makeup, yearning for a community that she had no idea how to find or connect with.

“If there’s another Chasity out there, I want them to know that, despite what the world may think of them, the world needs to see you. You need to shine brightly in your world. Be a good person, be loving, treat people with kindness. I think that’s my biggest message, honestly, because I think we need more of that right now.”

Chasity Jesko has seen the world, and in doing so, she has found the courage and the kindness to ensure the world now sees her. From the reservation to the runways of the world, her story is an airborne message: be strong, be resilient, and know that no one can ever take your power away.