Today, I have the gentle joy and heartfelt privilege of introducing Cassidy McGuinn, a warm, witty Irish-American blogger from Boston whose musings drift gracefully across topics like love, music, family, running, and baseball, with a healthy sprinkle of humor and heart. Cassidy is the woman behind Cassidy’s Quest, a blog and vlog that have quietly resonated with readers looking for hope, perspective, and a good laugh or two. Whether she’s reminiscing about Del’s frozen lemonade in Newport, cheering on the Red Sox (with some side love for the Blue Jays and Mariners), or sharing vulnerable moments from her transition, Cassidy brings the kind of authenticity that feels like a deep breath on a hard day. Cassidy came out as a transgender woman at 46, in what she describes as a moment of sleepless clarity, honesty, and fierce resolve. Since then, her journey has unfolded with courage, humor, and grace.
Her words have helped others feel seen, understood, and encouraged to walk their own paths, with petticoats, ponytails, or whatever suits them best. From her love of 1950s-inspired fashion to her reflections on self-acceptance, Cassidy radiates kindness and wisdom, often wrapped in the colors of a striped dress or the energy of a runner’s high. In this interview, Cassidy opens her heart to talk about the importance of humor in transition, the ache of family estrangement, the power of finding one’s own love within, and her dreams for a better world, one where a transgender First Lady or President isn’t a fantasy, but a real possibility. She speaks with humility, but her impact is quietly radiant. I invite you to meet Cassidy not only as a blogger or baseball fan, but as a woman who has turned self-discovery into a beautiful act of generosity.
Monika: Today, I have the pleasure and honor of interviewing Cassidy McGuinn , an Irish-American blogger from Boston, Massachusetts, who shares her thoughts on life, love, music, and baseball (not always in that order) through her blog Cassidy’s Quest and her YouTube vlog. Welcome, Cassidy!
Cassidy: Hi, Monika! Thank you so much for the invitation. I’m genuinely honored to be here and flattered by your kind words. It means a lot to be part of this conversation, and I’m really looking forward to it!
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| Which is whiter: my complexion or my jacket? Discuss. |
Cassidy: Let’s see… as you mentioned in your introduction, I’m an Irish-American gal from the Boston area. I’ve also been fortunate enough to live in Seattle and Newport, Rhode Island, two of the most beautiful places in the United States. (For your readers: be sure to try Del’s frozen lemonade if you ever visit Newport. You can thank me later!)
Monika: And what are some of the things that bring you joy or help you unwind?
Cassidy: I am indeed a die-hard baseball fan, not just the Red Sox, the team from Boston, but also the Toronto Blue Jays and Seattle Mariners. To be honest, I’ll watch any baseball game. Hmm… what else? I’ve gotten into running over the past few years and absolutely love it. It’s also very peaceful. I wish I had a dollar for every time I’ve finished a run and realized I had worked out the solution to some issue I’d been wrestling with!
Monika: What inspired you to start documenting your journey through blogging?
Cassidy: Two reasons. First, I wanted to keep a record for myself of what I was experiencing and feeling as my transition progressed. Second, I hoped that others might find something in it that offered some measure of insight, comfort, or hope, the way a handful of blogs did for me when I was starting out. If even one person finds or has found something of value in it, “if she did it, then I can too,”then it will all be worth it.
Monika: The topics you write about most often, transitioning, acceptance, coming out, humor, family, friendship, and personal reflections, seem deeply personal. Would you say they reflect your everyday life?
Cassidy: Interesting question! Yes, I think they do. I would not be at this stage in my transition without all of those things. The support of my sister and nephew, and of my friends, has been invaluable. As for acceptance, that’s really what transitioning is all about: learning to accept ourselves. And humor is absolutely crucial; being able to laugh at myself and find the humor in transitioning is so important. I’m so glad I inherited a sense of humor!
Monika: Do you remember how old you were when you finally decided to transition? What was that moment like for you?
Cassidy: I woke up in the middle of the night on my 46th birthday and finally admitted to myself that I had to transition. I simply could not fight any longer. Up to that point, I had never once uttered the word “transsexual” or allowed myself to do any research about it. I spent the rest of that night on the Internet, during which I found the wonderful therapist with whom I still work, as well as several blogs that proved to be invaluable. I’ve since become friends in real life with several of those blog authors, which has been a wonderful gift.
Monika: When you first came out, did you have any transgender role models or public figures who helped guide or inspire you?
Cassidy: Not at that time, as I hadn’t ever allowed myself to acknowledge that I was, in fact, transsexual. It wasn't until the therapist I had called early the morning of my birthday (who is my therapist to this day) returned my call that I actually said aloud: "I'm a girl. And I want to transition."
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| My moose impersonation. (It's a work in progress.) |
Cassidy: There certainly are. :c) They are far too numerous to list in full, but here’s a representative sample: Kelli (author of The Good, The Bad, and the Blonde blog, and the first person to reach out to me after I started my own blog); Alice (Alice in Wonderland); Halle (Two Spirits – One Halle); Calie (Calie’s Chronicles); Stace (Musings of an IT Girl); Jenna (Jenna’s World); and Nadine (Unordinary Style). And again, there are many more… (I would also like to mention Joey, at Joey’s iPad. I’ve long admired his blog, particularly his sense of humor.
Monika: Coming out as a transgender woman can come at a steep personal cost, many lose relationships, careers, or even their place in their communities. Did you experience any of those losses when you came out?
Cassidy: My brother no longer speaks to me, and hasn’t for the past four years. I haven’t seen either of my nieces in that time (although the oldest found out about me and reached out to me online). I am in touch with my parents, but it’s an evolving discussion. They do the best they can, which I appreciate, even as I wish it could be more.
Monika: That must have been incredibly difficult. What would you say was the most challenging part of your coming out process?
Cassidy: The hardest thing about coming out, though, was the struggle to accept myself. It really didn't happen until nearly a year after I'd gone full-time. In retrospect, I was trying (unconsciously) to still be the person I was before transitioning and my true self. One morning I got up, looked in the mirror, and literally said, "F*** it." And the instant I did, I finally saw myself. Not him. Me. And I haven't looked back since!
Monika: In recent years, we’ve seen a dramatic rise in visibility for transgender women, models, artists, scientists, politicians, you name it. Laverne Cox famously declared, “Trans is beautiful.” Do you think this visibility reflects meaningful progress, or are we still just scratching the surface?
Cassidy: The speed with which awareness of the transgender community has grown is astounding, isn't it? You get some sense of it with the ferocity of the pushback here in the United States, particularly the odious bathroom bills being pushed by the right wing. It's heartbreaking. They aren't going to win, though. They are on the wrong side of history.
Monika: Unfortunately, visibility hasn’t stopped the violence and discrimination. The so-called “restroom wars” rage on, and trans women still face deadly threats. How do you stay hopeful in the face of all this?
Cassidy: I'm reminded of the lyrics to Peter Gabriel's song Biko, about the South African anti-apartheid activist Steven Biko, who was murdered by the pro-apartheid government ruling South Africa at the time: "You can blow out a candle / But you can't blow out a fire / For once the flame begins to catch / The wind will push it higher."
Monika: Within the LGBTQ+ community, do you feel that the "T" is finally finding its own voice? Are we able to advocate effectively for our unique needs and rights?
Cassidy: The transgender cause is really still in its infancy, comparatively speaking, but yes, I think that is increasingly the case.
Monika: What’s your take on how transgender people are portrayed in mainstream media, films, books, or the news? Are we heading in the right direction?
Cassidy: I wish more transgender actors and actresses were actually cast to play transgender characters (which is not to take anything away from what Eddie Redmayne and others bring to those roles). It was so inspiring to watch Jamie Clayton's amazing performance in Sense8; I can't wait until the casting of a trans actor or actress is so commonplace as to be unremarkable.
Monika: Are you personally involved in any activism or political campaigns? And more broadly, do you believe transgender women can shape the political landscape?
Cassidy: I'm active in liberal/progressive causes. I absolutely think transgender women can make a difference, and in fact, already are. Again, it's very inspiring!
Monika: Let’s imagine the future for a moment. Do you believe we’ll live to see a transgender woman become President of the United States, or perhaps even First Lady?
Cassidy: If we can elect Barack Obama as President, twice!, then I think there is a very good chance we’ll see a transgender First Lady and/or President.
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| Red, white, and blue. (Mostly blue.) |
Monika: You strike me as someone who enjoys expressing herself through clothing. How would you describe your fashion sense, and what styles or outfits make you feel most like yourself?
Cassidy: I certainly do!!! lol. I am happy to admit I’m a clothes addict. I love stripes (see the photos for proof), maxi-skirts, and I’m very fond of little black dresses. (I have a short torso but long legs for my height.) I’m always excited to find pieces that flatter my figure while letting me have fun with colors and patterns. Fashion has become one of the most joyful parts of my journey.
Monika: After playing around with different looks, did you settle into a style that truly feels like “you”?
Cassidy: After experimenting, I discovered that I was, well, a girly girl. lol. My favorite brand is Lindy Bop; much to my surprise, I apparently was either a 1950s housewife or a Southern Belle in a previous life.
I own three of their dresses (and counting). I would happily wear petticoats every day if I could. I adore vintage-inspired looks that let me lean into a playful, elegant femininity, even if I’m just headed to the grocery store!
Monika: Your hair color is absolutely stunning, it suits you so well! Have you always been a redhead, or was that a fabulous discovery along the way?
Cassidy: Thank you, Monika! The credit really goes to my hairdresser, she’s the one who discovered my inner redhead! :D I never imagined how much confidence a color change could bring until I saw myself in the mirror that first time.
Monika: Growing your hair out can be quite the journey, especially with curls. What has the process been like for you?
Cassidy: I’ve learned a few things while letting my hair grow over the past three-plus years: a) curly hair takes forever to grow out (sigh); b) curls and humidity do not play well together; and c) scrunchies, barrettes, and ponytails are a running girl’s best friend. ;-p It’s been a mix of frustration and fun, but I’ve really come to embrace the wild personality of my curls.
Monika: It’s interesting to think about how liberation looks different across experiences. Some say cisgender women gained freedom through the contraceptive pill, while transgender women’s liberation is tied to advances in cosmetic surgery, freeing them from the pressures of “passing” or “not passing.” What’s your take on this idea?
Cassidy: Yes, I think that’s true. I’m extremely fortunate in that I seem to pass without any FFS. I would absolutely have done so if needed, though. On the other hand, I will eventually have implants; the “girls” need all the help they can get!
Monika: Switching gears a bit, what’s your opinion on transgender beauty pageants? Do you think they have a positive impact?
Cassidy: If they empower even one person, either participant or viewer, then I am all for them!
Monika: Many transgender women share their journeys through memoirs. Have you ever considered writing a book about your own experience?
Cassidy: I have, actually. I have a series of posts called The Chronicles of Cass that are a sort of autobiography. I still need to write the first section, about reaching puberty and realizing something was terribly wrong, even if I lacked the resources to understand what it was. I’ve shied away from writing it because, frankly, it’s quite painful. But I think I need to write it anyway. Writing the other Chronicles of Cass posts was also quite painful at times, but I invariably felt better after finishing them.
Monika: Love often plays a huge role in personal transformation. How has love influenced your life, especially during and after your transition?
Cassidy: It’s crucial. I was alone for my entire life until about a year after going full-time. It wasn’t for lack of effort; I tried desperately, thinking being loved would save me. As it turns out, I was right, only the person whose love I found was mine. :c) As soon as I accepted myself, things started to change. Go figure.
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| Actually, it *is* easy bein' green! |
Monika: Are you currently working on any new projects? Could you share a bit about them, or are they still under wraps?
Cassidy: I am, with a dear friend, but it’s still in the early stages, so I’m afraid I need to keep it under wraps at the moment. It will be very cool once we launch it, though!
Monika: What advice would you give to transgender girls who are struggling with gender dysphoria?
Cassidy: If you can, do see a therapist specializing in transgender clients. It’s by far the most important aspect of my transition. My therapist has been a godsend. A friend once told me transitioning is 25% physical and 75% mental/emotional (not sure if she heard/read it elsewhere), and that certainly has been true for me. If seeing a therapist isn’t possible, writing out your thoughts can help enormously. Just beginning the process of articulating the tangle of conflicting thoughts and emotions out loud is so incredibly liberating, and empowering.
Monika: My pen friend Gina Grahame once told me that we shouldn’t limit our potential based on how we were born or by what other transgender people do. She said our dreams shouldn’t end on an operating table; that’s actually where they begin. Do you agree with this perspective?
Cassidy: I certainly do. I haven’t had my GCS yet (long story), but that is EXACTLY the way I view it. It’s the beginning of the adventure, not the end, and I cannot wait!!!
Monika: Cassidy, thank you so much for this interview!
Cassidy: Thank you so much, Monika. This was a lot of fun!
All the photos: courtesy of Cassidy McGuinn.
© 2017 - Monika Kowalska
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