Kai Newsome is a blogger and digital creator based in Toronto. Through her personal project, A Blog About a Trans Journey, she documents her experience of transitioning in her 30s, focusing on the thoughts, emotions, and everyday moments that are often difficult to articulate in casual conversation. The blog was created as a space where subjects that might otherwise remain unspoken, because they feel too personal, too complicated, or too emotionally charged, can be explored with honesty and care. Kai’s writing is deeply reflective, offering friends, family, and readers an opportunity to better understand her journey, not as a neatly packaged narrative, but as an evolving process. At the same time, the blog serves as a point of connection for others who may recognize pieces of their own experiences in her words. Whether someone is trans themselves, questioning, or simply trying to understand, Kai aims to make complex and emotional topics approachable without flattening them.
The project originally began as an interactive storytelling experiment. Its first ten entries were written in rapid succession over a single weekend as part of a game jam, using an experimental narrative format to explore themes of identity, transition, and self-discovery. What started as a creative exercise quickly grew into something more enduring, evolving into a long-term documentation of change, growth, and self-reflection. Kai strives to write for a broad audience, including readers who may not be deeply familiar with LGBTQ topics. She approaches her subjects with openness and accessibility, avoiding jargon when possible and grounding her reflections in lived experience. When she is not writing on the blog, she continues to share pieces of her story through Instagram, experimenting with vlogging and short-form content as another way of processing her life in real time and extending her voice beyond the written word. For this interview, I am meeting with Kai to talk through these experiences together, turning her reflections and thoughts into a more conversational space, one where her journey can unfold naturally through dialogue rather than monologue.
Monika: Hello Kai! Welcome to my blog!
Kai: Hi Monika! Thanks for having me.
Monika: Kai, let’s start with content creation, because it really feels like the backbone of how you process your life publicly. You’ve blogged, you’ve vlogged, you’ve experimented a lot. What pushed you toward daily vlogging?
Kai: I decided in November that I wanted to try vlogging every single day. Not just posting Instagram stories here and there, but actually recording myself talking about something, anything, every day. The goal wasn’t to be polished or insightful all the time, it was really about getting more comfortable just putting myself out there. With blogging, I can be very slow and very intentional. I’ve had my blog for a little over a year and a half now, and when I write, I put a lot of pressure on myself. Some articles take me hours and hours spread over several days. I rewrite sentences endlessly, I question whether what I’m saying makes sense, whether it’s phrased perfectly, whether it’s saying too much or not enough.
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| "I work in the software industry, and things are changing very quickly." |
Vlogging felt like a way to break that cycle. I wanted to talk about things as I was feeling them, in the moment, instead of sitting on them until they turned into a “finished” piece. I didn’t want to feel like everything had to be prepared or justified or shaped into something perfect. I just wanted to create and see what happened. I wasn’t even sure if I’d have anything interesting to say every day. Sometimes it really was just me talking about whatever was on my mind that day, and sometimes it felt a bit boring or random, but that was kind of the experiment. I even thought about turning them into reels instead of just stories so they’d exist over time, but I’m still figuring out what format feels right.
Monika: You also completed 30 days of vlogging, which is no small thing. How did that challenge affect you?
Kai: Finishing 30 days of vlogging felt huge. On one hand, it was a lot of fun. On the other hand, it was incredibly exhausting. There were days where I really didn’t feel like doing it, but I showed up anyway, and that alone taught me a lot. The biggest thing it forced me to do was let go of perfectionism. I couldn’t obsess over what I’d already posted, because the next day was always coming. I didn’t have time to spiral over whether something was good enough. I just had to make something and move on.
That constraint actually helped me push my boundaries creatively. I learned so much about making video content for the internet, about pacing, about how much energy it actually takes to show up consistently. I also learned that I’m capable of more than I sometimes give myself credit for. I’m genuinely proud that I stuck with it, because there were moments where it felt very, very draining. And honestly, I couldn’t do 30 days of vlogging without at least one bigger glam moment. That was non-negotiable. So I finally wore the strawberry blonde wig I’d mentioned before and went all in for one look. It felt like a little celebration of making it through.
Monika: Your work life and tech thoughts come up a lot in your content too, especially around AI. How are you experiencing that shift right now?
Kai: I work in the software industry, and things are changing very quickly. AI is hitting us hard. It’s changing how teams are structured, who’s even on those teams, and what kinds of skills are valued. There’s a lot of uncertainty, and a lot of people are anxious. Personally, I don’t feel immediately threatened, mostly because I’m confident in my ability to adapt. I’ve historically been a bit of a workaholic, and while that hasn’t always been healthy, it has put me in a position where I feel relatively secure right now. It’s also allowed me to take care of my transition in ways I’m really grateful for.
That said, this is absolutely not a time to rest on your laurels in tech. You have to stay adaptable. Things are shifting fast, and pretending they’re not is dangerous. More broadly, I don’t think people care enough about the negative implications of AI. I think it’s very similar to what happened with social media and privacy ten or fifteen years ago. We knew platforms like Facebook and Instagram were collecting insane amounts of data about us. We knew they were essentially surveillance machines. And people just accepted it. The operating systems changed just enough to make it feel transparent, permission prompts, little location icons, but the core issue never went away. I think we’re watching the same pattern repeat with AI.
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| "It’s all about finding that balance between comfort and confidence." |
Monika: You’ve also explained why social media is so addictive in a way that really sticks with people.
Kai: There’s this concept called the Hooked model, and once you understand it, you can’t unsee it. It starts with a trigger, usually external. Someone tells you about an app, you hear about it somewhere, you get a notification. Then you take an action in the app, and the app gives you a reward. The really important part is that the reward is variable. You don’t always know what you’re going to get. Maybe it’s likes, maybe it’s attention, maybe it’s validation. That unpredictability keeps you coming back.
Then there’s an investment step. You post something, you follow people, you build a history. That investment makes you more likely to return. And then the loop starts again. Trigger, action, reward, investment. Over and over. It’s not accidental. These systems are deliberately designed that way, and I think that’s something people don’t really sit with enough.
Monika: Let’s shift into appearance, because that’s something you often unpack very openly. You talk through outfits in a very real, unfiltered way.
Kai: Getting dressed is honestly a lot of problem-solving for me. For example, I got this sweater from a clothing exchange that was clearly too short. It was almost like a crop top, and maybe that works for some people, but for me it just made me feel exposed. I didn’t want my stomach out, especially at this time of year, so I started experimenting. A black tank top underneath helped a bit, but it still didn’t feel cohesive. Then I remembered these overalls I was about to put away for the winter. I tried them on, and suddenly the midsection felt more intentional. The colors worked better together.
Even then, it didn’t quite feel finished. Adding a belt was the final piece. That’s often how it goes for me, it’s not about instantly knowing what works, it’s about slowly adjusting until something feels right. Being tall complicates that too. A lot of clothes just aren’t made with tall trans women in mind, so you end up constantly adapting.
Monika: You’ve also been rethinking makeup and color choices.
Kai: Yeah, I saw something on TikTok about choosing colors based on your skin tone, especially if you want to wear less makeup and look more natural. That really stuck with me. It made me realize that I hadn’t always been intentional about color. So now I’m experimenting with darker purples, olive tones, darker reds, colors that actually complement my skin instead of overpowering it. It’s all about finding that balance between comfort and confidence.
Monika: Voice feels like a natural continuation of your journey. How has your relationship with voice feminization evolved?
Kai: Early on, I tried a lot of different things, and most of them didn’t feel right. I really didn’t want to force my pitch up and sound unnatural. I didn’t want to feel like I was playing a character. I recorded myself a lot and listened back, which is uncomfortable but necessary. I was trying to find something that felt sustainable, something I could live with every day. It really came down to one video from Trans Voice Lessons that focuses on reducing the bassiness of the voice rather than chasing pitch. I just focused on that one thing consistently. That approach felt grounded and realistic for me. Lately, I’ve also been thinking more seriously about voice feminization surgery. It’s something that’s been on my mind more and more as I notice what still bothers me.
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| With her best friends. |
Monika: Let’s talk about identity and sexuality. You explained the bi-cycle in a way that resonated with a lot of people.
Kai: The bi-cycle is the idea that attraction fluctuates. As a bisexual person, my attraction to men and women isn’t static. It changes over time. Sometimes I’m really into guys for a while, and then I’ll see a woman and suddenly it flips. Other times, I go through phases where I don’t really feel attracted to anyone in the same way. It can almost feel asexual at times. It’s not always convenient, and it can be confusing, but it’s just part of how my attraction works. It’s not something I think gets talked about enough.
Monika: You once joked that your transition has happened from head to toe, very literally.
Kai: It really has, and it wasn’t planned that way. The first thing I ever did was a hair transplant. Then earlier this year I had facial feminization surgery, which included forehead reconstruction, more hair transplant work, upper and lower blepharoplasty, rhinoplasty, a lip lift, and a trachea shave. So I’ve kind of worked my way downward. And now voice feminization surgery is something I’m thinking about more seriously. I think I’m very focused on what I can control above the neck before moving on to anything else.
Monika: Facial feminization surgery seems to have deeply affected you emotionally.
Kai: It really did. I had it done in April, and going into it I was incredibly anxious. The recovery was intense. Recovering from FFS is a complete mindfuck. You’re adjusting to a new face, a new familiarity, and your brain has to catch up. What surprised me the most was how much it affected my self-worth, especially in relationships. Before surgery, I struggled a lot internally. I didn’t even realize how much that was shaping my behavior. Afterward, I noticed I could communicate more clearly. I went on a brunch date recently where the vibe was off. Instead of spiraling or overthinking, I followed up honestly. We had a perfectly amicable ending. That kind of calm confidence was not something I had before.
Monika: Dating is such a big topic in your content. What feels hardest about it right now?
Kai: There’s a lot. One thing is guys feeling the need to clarify that they’re straight, even when they know I’m trans. As if I’m going to be surprised. There’s also this idea of being “bad at texting.” I don’t believe that’s real, especially early in dating. What it usually means is “I’m not that into you.” When someone tells me that, what I hear is “avoid me.” I want relationships to feel comforting, not like a thrill ride or a guessing game.
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| "I don’t like rewriting the past." |
I’ve also noticed that on apps like Hinge, a lot of dates end up feeling more like friendships. I think many guys are ultimately looking for a cis woman as a primary partner, even if they’re open or curious. I don’t take that personally, but it’s something I’m very aware of. And yes, I like tall men. I hate that it matters to me, but it does. Dating someone significantly shorter than me triggers my dysphoria in a way I can’t ignore.
Monika: Community seems to anchor you through all of this.
Kai: It really does. When I first connected with the local trans community, I had so much imposter syndrome. I genuinely didn’t believe people would accept me or see me as trans enough. I was really humbled by how supportive everyone was. It goes beyond just being trans, it’s about supporting people through self-discovery. I try to host parties when I can and bring new people in. Watching community grow like that has been incredibly meaningful.
Monika: Finally, when you look back, do you mourn not transitioning earlier?
Kai: No, I don’t. I don’t like rewriting the past. Where I am now is the result of everything that came before it, and I’m in a place where my transition is relatively comfortable and supported. What I could do without is second puberty at this age. Teenagers get to be awkward together. When you figure this out later, you’re doing it on your own. But I’m still grateful to be where I am now.
Monika: Kai, thank you so much for sharing your journey and insights.
All the photos: courtesy of Kai Newsome.
© 2025 - Monika Kowalska
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| Kai's blog. |
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