Monika: And how does that contrast with what you’ve personally experienced in Japan?
Tiffany: Japan, on the other hand, is quite different. While the country has a world-class healthcare system, especially when compared to my home country, the Philippines. It still lacks understanding and support when it comes to transgender health. Even private healthcare in the Philippines can’t match the quality of care Japan offers its general public. But when it comes to us, there are still major gaps, especially in policy, training, and basic human sensitivity.
A personal experience I had in 2023 really highlighted this. Japan offers annual free health checkups through the city, categorized by age, and that year I noticed that a mammogram was included for my age group. Since I have breast implants, I thought it would be wise to take advantage of the service.
Monika: What happened when you tried to access that service?
Tiffany: When I arrived at the clinic and handed over my health insurance card, which still lists my gender as male, everything changed. The nurse at the front desk visibly froze. She went to consult with the doctor, and when she returned, she asked me to wait. Then, in front of the entire waiting room, she came back and announced loudly that they had contacted the city office and, “A male patient cannot have a mammogram.”
It was humiliating. In the past, I might’ve reacted with shame or anger. But this time, I chose to respond calmly. I asked her, “What if I feel there’s something wrong with my breast implants?” She paused and replied, “In that case, we can check you.” So I asked again, “What if it’s too late by then?” She had no answer. That moment was deeply frustrating, but more than that, it made something very clear that it wasn’t just about me. It was about a system that hasn’t been trained to see or support us. That conversation should have happened privately, with care and professionalism but instead, it became a public display of discomfort and ignorance.
Monika: How did you move forward after that experience?
Tiffany: In the end, I booked a private mammogram at a different clinic where I was welcomed as a transgender woman. But I had to pay out of pocket for a service that should have been free through the city’s program. I pay my health insurance just like every other citizen in Japan as I was obligated. But why am I not afforded the same access?
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| "I began studying life coaching, not because I wanted to turn it into a career at first, but because I was searching for tools to better understand and heal myself." |
That experience only strengthened my resolve to speak up. If we don’t share these stories, nothing will change. This is exactly why I created We Exist - to start conversations, to shine a light on these injustices, and to work toward a future where no one has to feel marginalized just for trying to take care of their health.
Monika: Your journey, from nightlife and personal transformation to healing and self-discovery, is incredibly powerful. Was it this path that inspired you to become a transformational lifestyle coach? How did you know it was time to start helping others find their own way?
Tiffany: Thank you so much, Monika. That really means a lot. Yes, my path into transformational coaching came directly from the twists and turns of my own healing journey. For a long time, I navigated life as a transgender woman without fully accepting myself. I lived with fear, shame, and a sense that I had to hide who I was in order to be safe or accepted. After I had my SRS, I thought I could finally live a “normal” life that I could just start fresh and never have to talk about my past again. I even created a different version of myself, one that didn’t need to disclose my gender history. I convinced myself that was the way to truly be seen as a woman.
But deep down, something still didn’t feel whole. I was living as a version of myself, but not in full truth. The real turning point came when I started gaining awareness of these patterns. I realized I hadn’t truly accepted my whole self, my past, my pain, and the resilience that got me here.
Monika: That level of self-awareness is profound. What was the moment you realized you were ready to help others through their own transformation?
Tiffany: I began studying life coaching, not because I wanted to turn it into a career at first, but because I was searching for tools to better understand and heal myself. And then the pandemic hit. Like many of us, I had more time to reflect. I started having conversations, sharing more of my truth, and realizing how much my story resonated with others. That’s when it clicked that I could use everything I had lived through like my struggles, transitions, breakdowns, and breakthroughs to help others find their own way forward. Becoming a transformational coach was my way of turning pain into purpose, and I’m honored every time I get to support someone in stepping into their full, unapologetic self.
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| "After my transition, I thought I could leave the past behind and just blend in." |
Tiffany: Yes, absolutely! I’ve felt that pull many times throughout my life. There was a long period when I truly believed that the only way I could be accepted as a woman was to hide the fact that I was transgender. After my transition, I thought I could leave the past behind and just blend in. That felt like the safest route, especially in a society that often struggles to understand us. There was comfort in being invisible, at least for a while.
But over time, I realized that invisibility came at a cost. By erasing parts of my story, I was also erasing my strength, my journey, and my truth. I started to feel disconnected not just from others, but from myself. And I began to see how damaging that silence can be - not only for me, but for so many others in our community who are still afraid to be seen.
Monika: What helped you move from that place of silence into one of visibility and advocacy?
Tiffany: I made a conscious decision that I would no longer shrink myself to fit into a version of womanhood that denies where I’ve been and who I am. Yes, I am a woman, but I am also a proud transgender woman. And both can exist beautifully together.
Becoming visible, sharing my story, and advocating for our community didn’t come without fear. But I knew that if I wanted to see change, I had to be the change. I want the younger generation to know that they don’t have to hide to be loved or respected. We are worthy exactly as we are.
So now, I stand in my truth not just for myself, but for all those who still feel like they have to live in the shadows. Because the more we’re seen, the more we’re understood and that’s how real transformation begins.
Monika: Choosing a name is such a deeply personal decision, one that can hold layers of significance and meaning. How did you come to choose the name Tiffany? Does it carry a special resonance for you, perhaps representing a part of your journey or embodying a particular feeling or aspiration?
Tiffany: Good question! I actually have been asked this before, and the story always makes me smile. Growing up, I was absolutely fascinated by the idea of the “American dream.” I spent hours watching cable TV, American movies, and reality shows. I was completely hooked! So when it came time to choose a name that felt right for the woman I was becoming, I thought, “Why not go with something that fits that dream?” Tiffany popped into my head, and it just clicked. It sounded glamorous, confident, a little sparkly - everything I aspired to be!
Monika: How did people around you react when you first started using the name?
Tiffany: I tried it out with friends, and the reactions were mixed, to say the least. Some said it was cute and unique, especially for a Filipina. Others teased me, saying it sounded like a stripper or a pornstar name, very provocative! (Which, honestly, just made me love it more. Why not be a little bold?)
In the end, Tiffany became the name I chose for myself. Not something given to me, but something I claimed. And every time I hear it now, it reminds me of the woman I had the courage to become.
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| "I truly believe that what we put out into the universe is what we receive." |
Monika: Transitioning is not just a personal journey; it also reshapes our relationships, especially with those who support us. Have you noticed a shift in how people treat you since your transition?
Tiffany: Always! Every transformational chapter of my life whether it was my gender transition, my healing journey, or stepping into my purpose, has come with shifts in the people around me. Relationships evolve, and that’s something I’ve come to accept with love and grace.
It doesn’t mean I’ve burned bridges with everyone from my past. In fact, I still keep in touch with some of them from time to time. But if someone chooses not to stay in my life, I respect that. I let them go with peace in my heart and wish them well on their journey.
From my own experience, the universe has a way of bringing the right people into my life exactly when I need them. And when certain connections no longer align or resonate, they gently drift away or life takes us in different directions. It’s all part of the flow.
I truly believe that what we put out into the universe is what we receive. When we live authentically and with intention, the energy we attract reflects that. So yes, people have treated me differently since my transition. Some with deep love and acceptance, others with distance but all of it has helped shape the person I’ve become.
Monika: I finally felt free after my transition. How about you? Was there a single moment, or maybe a series of moments, where you truly felt like you had stepped into your most authentic self?
Monika: I finally felt free after my transition. How about you? Was there a single moment, or maybe a series of moments, where you truly felt like you had stepped into your most authentic self?
Tiffany: That’s such a beautiful and powerful feeling, Monika and I resonate with it deeply. For me, it wasn’t just one moment, but rather a series of awakenings that unfolded over time. After my physical transition, I thought I had arrived at freedom. I believed that changing my body and presenting myself in a certain way would be the key to fully living as a woman. And while there was a sense of relief and joy, there was also an unexpected silence inside me. A part that still didn’t feel complete.
The true shift happened later, when I began doing the deeper inner work. It was when I stopped hiding my past. When I stopped trying to fit into society’s definition of womanhood and instead embraced my own. It was when I started speaking my truth openly through coaching, through my podcast, through the We Exist documentary. That’s when I truly felt free.
Authenticity, for me, is about being whole. Owning every part of my story, even the painful chapters. Today, I can say with love and pride that I’ve stepped into my most authentic self. Not because I’ve reached a final destination, but because I continue to choose truth, healing, and visibility every single day.
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| "Authenticity, for me, is about being whole." |
Monika: The journey to being our true selves often comes with a heavy price, losing friends, family, and sometimes even our jobs. What was the hardest part of coming out for you, and how did you navigate it?
Tiffany: That’s such an important question, Monika. For me, one of the challenging moments was when I began openly speaking about my gender identity on social media, especially around the time I launched my podcast, Breakfast With Tiffany Show and stepped fully into advocacy for our community. I had finally found the courage to share my truth publicly, but what followed was eye-opening.
I noticed that many people I had known for years, including several I once called friends, slowly began to distance themselves from me. Some stopped engaging. Others disappeared altogether. I even reached out to most of them, hoping to reconnect or at least hear some words of support, but there was silence.
Monika: That kind of silence and distance can be incredibly painful. How did you come to terms with those losses and find peace in your journey?
Tiffany: It hurt, of course. But over time, I came to understand something deeply that we meet people in different seasons of our lives. Some are only meant to walk with us for a while. And when that season changes, so do the people around us. That doesn’t mean there’s anger or bitterness, just acceptance.
If I ever cross paths with those people again, and they greet me with kindness or respect for the choices I’ve made, I will meet them with the same grace. Because I’ve learned that being true to yourself means choosing peace over people-pleasing. And while it can be painful to lose connections, what we gain self-worth, alignment, and purpose… is so much more powerful.
Monika: Do you remember the first time you saw a trans woman on TV or met one in real life that helped you realize, “That’s me!”?
Tiffany: Yes, I do. Her name was Lea Moreno, and she left such a deep impression on me. She was one of the Filipina transgender women I mentioned earlier, someone I first saw in beauty pageants. She even competed in the very first transgender pageant broadcast on national television in the Philippines. I remember being completely stunned by her beauty! She had this exotic, striking presence with blonde hair and the kind of elegance that turned heads. And when she spoke, she had such a soft, feminine grace. I idolized her, like many other trans in the Philippines at that time.
Then, suddenly, she was gone. People in our community said that she had gone back to Japan to work, and that was all we knew.
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| "I grew up in a culture where beauty was everything." |
Tiffany: Years later, after I had completed my own transition and had started to rebuild my life here in Japan, our paths crossed again. And this time, we became friends. It was surreal to be spending time with someone who once felt like a distant dream. She was so warm, so fun to be around, and incredibly funny. I got to see a side of her that the pageant world never showed… her playful spirit, her kindness, and her vulnerability.
But then, one night, everything changed. I received devastating news that she had been found dead in her apartment. The circumstances were unclear. To this day, there’s still no solid proof or explanation of what really happened to her. It broke my heart.
I dedicated a special podcast episode to her memory on Transgender Day of Remembrance, because her story deserved to be told. She mattered. She inspired me at a time when I needed someone to look up to. And I still carry her spirit with me. I keep the beautiful photos she gave me, and I’ll never forget the way she made me believe, for the first time, that someone like me could exist in this world and shine just like her and all her amazing achievements.
Monika: Many of us feel the pressure to “pass” as women, and even after surgeries, society keeps judging us. How do you personally deal with the outside world’s expectations?
Tiffany: It’s definitely been one of the most challenging parts of my journey. I grew up in a culture where beauty was everything and where being able to “pass” as a cisgender woman was seen not just as a goal, but as a form of survival. In many ways, that pressure shaped me. It’s one of the reasons why I went through multiple surgeries because I thought that if I could just blend in, I’d be safe, accepted, maybe even loved.
END OF PART 2
All photos: courtesy of Tiffany Rossdale.
© 2025 - Monika Kowalska
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