Monika: Was there a single moment, or maybe a series of moments, where you truly felt like you had stepped into your most authentic self?
Gwen: Well, growing up with six sisters (and all of their friends), I was constantly surrounded by women. So for me, presenting as a woman came quite naturally. Yes, especially being in public where I regularly meet women and interact with them as a woman, it is indeed very liberating and my authenticity shines through.
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?
Gwen: Yes, the loss of friends and family is inevitable. Fortunately for me, I have kept the majority of my friends, and made many new ones. Initially, the hardest part is revealing your true self, where some people then perceive this as having been lied to all of these years, and there’s a certain amount of guilt that accompanies that. Still, others have an “a-ha moment” where they go “oh, now I get it, that makes sense now,” as they recall all of the subtle signals that may have been there for years. In the latter case, this discovery and realization is followed by acceptance, and this is truly uplifting.
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!”?
Gwen: Sadly, my first experience with anything like that was seeing a bearded man, with makeup and a dress on, walking down the road smoking a cigar. That was clearly NOT me, but it did make an indelible impression. So, for me, I strive to dress and act in the most feminine way I know. This transformation involved studying the female side even more closely, I learned female mannerisms, ways to dress, do my hair, put on makeup, etc. In short, I became more woman than most women, and to this day, when I go out, I routinely dress better than most women and I’m regularly complimented on my appearance by other women. Dress for success, as the saying goes, and I really enjoy being a woman to the nth degree!
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?
Gwen: This can be very difficult for some. There are transgender women who are, shall we say, a work in progress (aren’t we all). Their physical appearance, stature, and male facial features are challenging to overcome. At 6’ 2”, 205 lbs I, as what some nice gentleman remarked to his wife, “man, that’s a big lady!” Well, he got the “lady” part right, so I was tickled pink, LOL! I often remind people that “being transgender is a little bit like being a unicorn, people have heard of a unicorn, but they may not have actually seen one, so they’re sometimes uncertain of what to do with one once they do.”
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| "I often remind people than being transgender is a little bit like being a unicorn." |
I think that it’s important to be mindful that people in general need help with change and new ideas. It behooves us, therefore, to be “ambassadors” for our community and be mindful of just how difficult this may be for others, and therefore, put our best foot forward at all times and show the world what kind and thoughtful people we are, just trying to live our lives like everybody else.
Monika: What are your thoughts on the current situation for transgender women in your country? Do you think we are progressing, or does it feel like we’re moving backward?
Gwen: In Canada, I’d say that we have indeed come a long way. Ten years ago, social media seemed to be just getting going in terms of transgender visibility, now, it’s a lot further developed with more and more women participating in it and discovering that they are not alone.
That said, the political climate in the US is such that there’s a seemingly misguided movement to repeal Diversity, Equity, and Inclusion (DEI) programs both in the federal government and amongst some major corporations. Couple this with executive orders limiting one’s ability to change their gender markers on their passports, and an increase in anti-transgender legislation across many states, and this has caused great concern for the community across North America.
So, on one hand we are indeed moving forward with visibility, participation, and the growth of our community, on the other hand, there are those who would indeed like to turn back the clock. The reality is that “you can’t put the genie back in the bottle” and we as a community aren’t going anywhere but forward!
Monika: Many detransitioners share stories of regret, often feeling that they rushed into transition or were influenced by external pressures, sometimes blaming the medical system for not guiding them more carefully. While their experiences are valid and deserve compassion, it’s also frustrating when their narratives are weaponized against transgender people who are happy with their transition. How do you feel about the way detransitioners are portrayed in public discourse, and do you think their experiences should influence how gender-affirming care is approached?
Gwen: There’s an old saying that “figures can lie, and liars can figure.” I think it’s very important that some would present incidents that, although they do exist, do not represent the whole by any means. Sadly, there are those that often present only a small piece of the story, in this case “detransitioning.” Personally, of the roughly 5,000 “friends” that I have on Facebook (Meta), I’m not aware of a single person that has/is regretting transition. Now I tell you this because this shows that even if “one” person was, this would represent 0.0002% of this group, which anyone who studies statistics knows is not significant enough to draw any conclusions.
That said, there have been numerous documentaries made recently both for and against transitioning, especially children. One such documentary is called Transhood (2020), produced by HBO and is available on Prime. In it, filmed over five years, this documentary follows four kids, beginning at ages 4, 7, 12, and 15, as they redefine "coming of age." It reveals how kids and their families tackle how gender is reshaping “the family next door” and the experiences of both the children and the parents when their identity as transgender families struggle, endure, and overcome. This film was very well done and provides a balanced approach showing both the euphoria of transition at a young age (for two teenagers), to the reversal of a young child (5–6 years old) who changes their mind and decides not to continue down the path of transition.
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| "I’ve always been a bit of a maverick." |
To me, it is a significant reminder that a) everyone and every situation is different and “one size does not fit all,” and b) a significant amount of caution must be used when addressing this life-changing endeavor. Sadly, there are those that choose to re-tell only the part of the story where the child reversed his decision and the unfortunate outcomes for the family unit, versus the pure joy and happiness experienced by the teenagers in this story. So again, one must be cautious about what one reads and hears about these stories, especially when they’re being only “partially relayed” to suit their own desired narrative. Clearly, much more research needs to be done on this subject and I feel that I could write yet another book in this regard.
Monika: I absolutely admire your sense of style, there’s an effortless elegance about you that seems to radiate for miles. How would you describe your personal fashion? Do you follow any specific trends, or are there go-to outfits that make you feel particularly confident and yourself?
Gwen: Awww…thank you, that’s so sweet of you to say. As I said before, I try to look as feminine as possible, and so I spend a great deal of time not only finding outfits that I like, but I also concentrate on coordinating and matching colors. As a “mature” woman, I tend to dress age appropriate, which I’m sure helps me blend in. My go-to outfits typically include either a maxi/midi skirt, with a nice blouse, cardigan sweater, and a complete set of matching accessories (scarves, shoes, purses, handbags/satchels, jackets, and jewelry). That said, I tend to “dress up” to what some would call business attire.
For me, I’ve always admired what I would call “sharp-dressed” women, and so I tend to mirror that style. So much so, that I am routinely stopped by other women who say things like “you look beautiful” or “I love your outfit, shoes, jewelry, etc.” I believe in “dressing for success,” and even with my larger stature, I know that my attention to detail has paid dividends and heightened my acceptance in public, especially among other women, as a result.
Monika: Do you love playing around with makeup, or is it more of a “throw on the basics and go” kind of vibe for you?
Gwen: Well, I’d say that I’m still a bit of “a work in progress,” much like every other woman on the planet, LOL! I am far from a make-up artist, and I lean toward more of a classic/basic look. Being a bit old-school, I do love Classic Red lipstick, and I sometimes wonder why more women don’t spend more time accentuating their lips. To me, nothing is more feminine, and perhaps sexy, as a nice set of lips on display for all to see, as this also helps frame my smile, which I display often and which is mirrored back to me by those I meet. Recently, I’ve started wearing false eyelashes on a regular basis, and this too enhances my feminine appearance (it takes a bit of practice and determination, ladies, but it’s SO worth the effort).
Additionally, I pay a lot of attention to keeping a nice pedicure 24/7 (including several toe rings), as well as a nice manicure, which I do myself, like my mother used to, and change colors depending on what I’m wearing (of course). I have tried false nails, which are lovely, but a bit harsh on my real nails, and so I prefer to take a biotin supplement to help harden my nails, routinely moisturize my nails and hands, and wear gloves to protect my nails anytime I’m doing any kind of manual labor (I just hate breaking a nail, LOL).
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or do you struggle with believing them?
Gwen: I absolutely LOVE being complimented on my looks and my outfits. As you know, I spend a great deal of effort on my appearance, and so I am grateful for the kindness of strangers who recognize that effort. Additionally, I have been blessed with great skin and facial features, which I inherited from my mother. I also ensure that I thank those who have made the kind gesture of complimenting my appearance with a warm smile and a generous “thank you.”
Monika: Did you ever feel pressure to meet a certain ideal of femininity?
Gwen: Well, I’ve always been a bit of a maverick. So, when I dress, I try to portray what “I” feel is the standard for me. While I notice that many women tend to “dress down” when shopping, especially grocery shopping, I “dress up” all the time. I’ve always subscribed to the adage that “it’s better to be overdressed than underdressed.” So, in this way, I don’t actually look like the majority of the women around me, but I feel that I dress better. Yes, this is by design, but I feel that each of us (whether male or female) has to decide on what kind of an image that they want to portray, and then feel good about it.
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| "Personal wellness is not only a choice but a gift that you give yourself." |
For me, my pursuit of being a “sharp-dressed” woman has certainly paid off for some of the reasons I have expressed earlier. However, it comes down to how “I feel” about my presentation, and this is a very personal expression of one’s own tastes, values, and desires. Personally, when I hit the door and head out into the world, I feel REALLY good about myself, as evidenced by the smile on my face that I carry with me everywhere. Again, it comes down to personal choice and each individual’s unique view of themselves in the world.
Monika: Finally, what’s next for Gwen? What dreams and goals are you working toward now?
Gwen: My plan is to continue writing, presenting at conferences, educating other community groups, and advocating for the transgender community as a whole. As I said, this has become a bit of a calling for me, and I feel compelled to continue the work that I have done in the past. Public education continues to be the key in order for society to better understand, and come to grips with, the fact that transgender people, both male and female, have existed for a long, long time and that we’re simply not going to “go away” because of some misguided and potentially harmful populist sentiments.
Further, it is important for people to be aware that, with the advent of the internet, there is a LOT of information available to us at our fingertips. Unfortunately, there is also a great deal of misinformation and disinformation available as well, and one must be diligent in sifting through fact from fiction.
Additionally, as I speak about in my book, personal wellness is not only a choice but a gift that you give yourself. My final message here is for the members of the transgender community to be resolute (admirably purposeful, determined, and unwavering), be brave, and be unapologetic in the pursuit of one’s authentic self while building the very best life possible for yourself!
Monika: Gwen, thank you so much for sharing your journey and insights.
Gwen: Thanks, Monika! I really appreciate the opportunity to share my thoughts with others. I would be remiss if I didn’t encourage people to obtain a copy of my book Transformative Wellness: Change Your Thoughts, Change Your Life!, which is available on Amazon. Thank you to all who have taken the time to listen to this. Sending big hugs to all, and please take every opportunity to “be well!”
END OF PART 2
All photos: courtesy of Gwen Richardson.
© 2025 - Monika Kowalska
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