Robin Diane Goldstein’s story is one of resilience, wit, and relentless authenticity. An American transgender rights activist, former talk-radio host, stand-up comedian, and blogger, Robin has gracefully woven together an extraordinary tapestry of life experiences, from law and engineering management to pioneering health projects at Apple Inc., nestled in the vibrant heart of Silicon Valley. Since childhood, Robin knew she was meant to be a woman, even when the world around her had no language or space to understand that truth. Navigating decades before the dawn of broad transgender awareness, her journey was marked by solitude, courage, and a fierce determination to be herself despite the cultural storms of her time. Through it all, she carried a radiant humor and a soulful spirit that have endeared her to friends, family, and countless others.
Robin’s activism is both grand and intimate: a fearless voice on public platforms and a gentle catalyst for change one heart at a time. Her story, shared in The New York Times and echoed through her work at Apple, is a testament to the power of authenticity to transform lives and communities. Beyond her professional accolades and advocacy, Robin is a woman who delights in the small joys, crafting the perfect New York-style cheesecake, strumming the guitar to satisfy her performance spirit, and finding fashion freedom in both funky hoodies and polished blouses. Her vibrant presence is a beautiful reminder that being true to oneself is the greatest success. As Robin approaches her 60th birthday, she continues to explore new passions and reimagine what it means to live fully. Her story is not just about transition, but about transcending, inspiring, and embracing every stage of life with love, humor, and grace.
Monika: Today, I have the pleasure and honor of interviewing Robin Diane Goldstein, a trailblazing American transgender rights activist, former talk-radio host, stand-up comedian, blogger, former Senior Engineering Manager, former Principal Counsel, and currently Senior Manager of Health Special Projects at Apple Inc. in Cupertino, California. Welcome, Robin!
Robin: Hi Monika. Sending warm greetings from the heart of Silicon Valley!
Monika: Robin, your journey spans activism, law, comedy, tech, and beyond. For those who may not know you yet, how would you introduce yourself?
Robin: When I started as a talk radio host, I described myself as a “Straight, White, Buddhist, Vegetarian, Lesbian Fraternity Boy trapped in the body of a Recovering Transexual Woman Patent Attorney with a Bizarre Sense of Humor and a Master’s Degree in City Planning.” Add in the fact that I make a great New York, style cheesecake, and I think you’ve got me pretty much figured out.
Monika: I came across your moving short story in The New York Times series Transgender Today. What inspired you to share your story with such a wide audience?
Robin: I’ve been out from the beginning and, as you kindly note in my introduction, was politically active early on. But as time went on, I recognized that activism can take many forms, sometimes large and public, and sometimes smaller and more intimate. I think every person who finds the courage to express their true self to the world is an activist, and sometimes that’s more effective on a small stage, changing hearts and minds one person at a time. And so that’s what I focused on doing for the last 20 years. Then suddenly trans people were everywhere telling “our” stories, and I thought, “No one can tell my story but me,” so I wrote the short essay for The New York Times.
Robin: I knew I was a ‘boy’ but should have been born a ‘girl’ from around the age of 2. But in the late 1950s and early 1960s, there was no concept of ‘trans.’ There were normal, regular people, there were ‘fags,’ and occasionally you would hear about a ‘sex change/he-she,’ and those folks were clearly considered circus freaks. So what I knew about myself at 2 remained a painful secret until my mid-30s. It was extremely difficult at the time. First, I had to convince myself it was okay to feel the way I did. That took a lot of time (even beyond my transition). The shame and confusion I carried from childhood never really had a space to breathe until much later in life.
Monika: What were some of the challenges you faced once you made the decision to transition?
Robin: Then I had to face family and friends who I assumed would not be supportive. There wasn’t really much of an internet, so it was hard to get information or find a community. The medical field saw themselves as gatekeepers for hormones and surgery. And the whole notion of gender non-binary or fluidity was seen as a pathology. Yes, the earliest days were often tough and lonely. Looking back, I’m amazed I managed to move forward without the resources and role models that exist today.
Monika: Who were some of the people you looked up to during your early transition, and what impact did they have on you?
Robin: Nancy Nangeroni. Kate Bornstein. Riki Anne Wilchins. At the time of my transition, these three women were out, strong, funny, smart, and unwilling to accept somebody else’s definition of normal, including what the trans community deemed normal for a trans person. Their boldness gave me a framework for imagining a more authentic life, even when I wasn’t sure how to live it yet.
Monika: Can you share a specific moment or experience you had with any of them that left a lasting impression?
Robin: I was present for the demonstration at the John Lotter trial (one of the two men convicted of murdering Brandon Teena) as part of the Transexual Menace and spent three days in the company of Nancy, Kate, Riki, and Leslie Feinberg. It was very early in my transition, and I was still very attached to the concept of ‘normative behavior,’ and these four amazing individuals gave me a Ph.D. in post-modern deconstructionist philosophy with respect to gender, identity, and power as we ate fast food and drank warm beer and drove across Kansas and Nebraska. That road trip transformed my understanding of what it meant to be trans and unapologetically human.
Monika: Were there other role models outside of activism who also helped shape your sense of identity?
Robin: I also greatly admire Judge Victoria Kolakowski, the first openly transgender person to serve as a trial judge in California. I met Vicki early in my legal career, long before I transitioned or was able to acknowledge who I was, and her courage was inspiring. Her example stayed with me through the years, showing me that living truthfully was not only possible, it could be powerful and quietly revolutionary.
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| Meet and Greet with the band Cheap Trick in early September 2017. |
Monika: Are there any transgender women today whom you particularly admire or draw inspiration from?
Robin: I work at Apple, where we have a large LGBTQ community. Apple is an extraordinarily supportive place to work and embraces the idea that diversity leads to innovation. And so, as I walk around the campus, I see trans women (and trans men) of every size and shape and color. some who meet gender normative standards and some who don’t. and yet they’re each embraced for who they are and have turned their attention and energy to developing amazing products to enhance and enrich the lives of our customers and maybe change the world. I admire these people. They have found a way to be themselves at the beginning of their lives so they can focus their energy and creativity on doing wonderful things.
Monika: Many transgender women face tremendous challenges, often losing family, friends, jobs, and social standing in the process of living authentically. Did you experience such losses yourself during your transition?
Robin: Professionally, I was very fortunate. I already had an excellent reputation and a small private patent law practice during my transition. One day I had to tell a client I had transitioned and would appear differently the next time they saw me. I sent them an email to advise them and say it was okay if they didn’t want to work together anymore. The president of the company wrote back and said, “It took us a long time to find someone as good as you. Do what you have to, to take care of yourself and then get your ass back to work!” That was amazingly important. That moment gave me a great sense of relief and acceptance in a time when support was rare.
Monika: Aside from your professional life, how did your friends and loved ones react to your coming out?
Robin: I also had a dear friend from university who was like a brother, and he was one of the last people I came out to. He wrote me a handwritten note that said, “We always knew you were strange and that was part of your charm. Now you’re just a lot more charming!” Of course, there were some friends and family who didn’t come along with my new life, and losing them was painful. However, those who stayed became an essential source of strength and love through the process.
Monika: What was the hardest part about coming out and living openly as your true self?
Robin: I know there are jobs I lost out on because of being trans, but to quote the Buddha, “Fuck ‘em if they can’t take a joke!” The hardest part was accepting that not everyone would understand or accept me, and learning to let go of the need for their approval. Ultimately, I had to find strength within myself to keep moving forward despite the setbacks.
Monika: The transgender community is often described as thriving today. As Laverne Cox famously said, “Trans is beautiful.” We see teenage girls becoming models and dancers, talented women succeeding as writers, singers, and actresses, and others making their mark in politics, science, and business. What is your overall perspective on the current status of transgender women in society? Are we just beginning to make progress, or is meaningful change truly underway?
Robin: Change is always happening. Sometimes it’s obvious, sometimes it’s hidden, sometimes it’s welcome, sometimes not… but change is inevitable. I’m thrilled that the generation coming of age now has a much broader range of ‘acceptable’ gender expression. I work with young people in their 20s and 30s, and they couldn’t care less that I’m trans. I’m just me. goofy, loud, smart, and silly. That’s awesome, and ultimately the way I think it should be. It gives me hope that authenticity is becoming the norm rather than the exception.
Monika: Given this progress, do you believe we’re at a tipping point in societal attitudes toward transgender people, or is there still significant resistance to overcome?
Robin: Prejudice and bigotry won’t disappear overnight, but there are inflection points when a large enough part of society says, “We used to care about this, now we realize it doesn’t matter to our lives.” I believe transgender people are at the beginning of one of those inflection points. That’s not to say there won’t be backlash. we’ve seen it. but I bet on smart, kind, and compassionate every time. Ultimately, the momentum toward acceptance and inclusion is growing stronger with each generation.
Monika: The transgender cause is often included under the broader LGBTQ umbrella. As the penultimate letter in this abbreviation, do you think the transgender community is able to effectively promote its own unique issues and identity within the larger LGBTQ group?
Robin: This is a great question. On one hand, being a smaller part of a larger cohort is very powerful. there’s strength in numbers and all that. I’m a big fan of extended families, and the LGBTQ folks I know have been important cousins in my larger queer family. We may not all share the same experiences, but we understand where bigotry and oppression come from and support each other. That solidarity is invaluable, especially during difficult times.
Monika: But do you feel that the transgender community’s specific needs and voices are always fully heard and represented within the broader LGBTQ movement?
Robin: On the other hand, my experience as a trans woman is different than being a gay man or a bi woman, and I wouldn’t want them to speak for me any more than I’d want to speak for them. Ultimately, it’s wonderful to have a community that accepts you for who you are, and the LGBTQ community has been exactly that for me since I transitioned. Still, I think continued awareness and distinct representation of trans issues is essential to true inclusion.
Monika: How do you feel about the way transgender people and stories have been portrayed so far in films, newspapers, or books? Do you think these representations are doing justice to the complexity of trans lives?
Robin: Meh. If the most interesting thing about a person is that they’re transgender, then that’s probably not a very interesting story. Yes, people are still fascinated by folks who transgressively try to redefine gender, but at the end of the day, if they made a movie about my life, I hope the parts about my transgender identity are the moments when people go to get more popcorn or use the bathroom. Those scenes shouldn’t be the focus, but just a small part of a bigger picture.
Monika: So what kinds of stories about transgender people do you think should be told instead?
Robin: I’d rather people hear about how I tried to help beat the world record for most ukulele players playing at the same time, or how, when I was 17, I was a toll collector and took a toll from Art Garfunkel, or how I did stand-up at the Comedy Store in Los Angeles and got so hyper I started improvising by reciting the Torah portion from my Bar Mitzvah. which got a huge laugh. Those are the stories that really tell who we are beyond just being trans. Sharing these stories helps people connect with us as full human beings.
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| "Prejudice and bigotry won’t disappear overnight." |
Monika: Your name appears in the special thanks section on IMDb for the 2016 short film Roxanne, directed by Paul Frankl. Could you tell us how you got involved with this project?
Robin: To quote Spider-Man’s Uncle Ben. or maybe it was Voltaire. “With great power comes great responsibility.” I have been fortunate to be free from hunger and want for a long time, and I always look for ways to give back. The arts are a crucial part of what makes us human, so whenever I can help support an artistic endeavor, I try to do so. I didn’t know much about the film or filmmaker, but crowdfunding caught my eye, and I thought if I could help a bit, I should.
END OF PART 1
All photos: courtesy of Robin Diane Goldstein.
© 2017 - Monika Kowalska
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