Guest #1 | Wendy Cole. Authenticity.

Written By Ray Doustdar

Becoming Who You Truly Are.
In this deeply personal debut episode, Wendy Cole opens up about her path of self-discovery, gender transition, and the emotional strength it takes to live authentically. It's a conversation about identity, courage, and the freedom that comes with finally being seen..

🎙️ DSD INTERVIEW #1 | Wendy Cole's Journey of Self-Discovery and Transition.

🌈 Trans at 67 | Wendy Cole on Reinvention, Resilience & Radical Truth

Episode Description: In our very first guest interview, Ray Doustdar speaks with Wendy Cole, a 67-year-old transgender woman who transitioned later in life after decades of suppression, secrecy, and survival. Wendy’s story is a powerful testimony to truth, courage, and the idea that it’s never too late to live authentically.

Can You Live a Lie for 60 Years—And Then Come Back to Life?

For the debut interview of Deep Shallow Dive, host Ray Doustdar welcomes Wendy Cole, a trailblazing transgender woman who transitioned at 67 years old. Raised in the 1950s, Wendy spent a lifetime hiding her identity—from repressing her femininity as a child to conforming through marriage, parenthood, and a tech career. But after decades of anxiety and suicidal thoughts, she finally embraced her truth—and became the woman she always was.

In this raw, emotional episode, Wendy breaks down the difference between being transgender and gay, what it was like growing up in a time with no language or visibility, and how she navigated the long road to self-acceptance. She also walks us through the details of gender-affirming surgery, hormone therapy, and how her physical and mental health radically improved once she began living authentically.

This episode isn't just about gender—it's about courage, healing, and the power of becoming who you truly are, no matter how long it takes.

👤 Who Is Wendy Cole?

Wendy Cole is a transgender woman, speaker, and life coach who transitioned at age 67 after living most of her life as a closeted man. Now, she helps others navigate their own path of gender identity and self-acceptance through coaching and advocacy. Wendy is a former tech professional, a mother, and a fierce believer in late-life reinvention.

🔥 Key Topics in This Episode

  • What it was like growing up transgender in the 1950s

  • The difference between transvestite, crossdresser, and transgender

  • Suppressing identity for decades through marriage, career, and fatherhood

  • Why she nearly ended her life before learning the diagnosis had changed

  • How her 2017 gender-affirming surgery at NYU transformed her health

  • Why transitioning was about survival—not vanity

  • Helping others through “mental work” coaching and visibility

  • The emotional and physical liberation of finally becoming herself

🧠 What You'll Learn

  • The internal cost of repression—and the physical toll it can take

  • That it's never too late to transition, heal, or reinvent your life

  • How hormones, therapy, and mindset shift the entire body

  • That gender identity and sexual orientation are not the same

  • Why many transgender people live decades in hiding due to fear

  • What gender-affirming surgery really entails (and how far it's come)

🗣️ Wendy’s Most Powerful Quotes

“I was a cult survivor—Zionism was my cult.”
“The diagnosis changed. And that changed everything.”
“I lost 70 pounds. I reversed diabetes. All from being happy.”
“It’s not who you love. It’s who you are.”

🧩 Top Themes Covered

  • Wendy Cole Deep Shallow Dive

  • late life gender transition

  • transgender woman age 67

  • trans journey and self-discovery

  • gender identity vs sexual orientation

  • LGBTQ+ spectrum explained

  • crossdresser vs transsexual vs transgender

  • gender-affirming surgery explained

  • NYU transgender surgery experience

  • mental health and suicidal ideation

  • transgender seniors and aging

  • self-awareness and resilience podcast

  • empathy for parents of trans kids

  • 1950s repression and gender roles

  • World Professional Association for Transgender Health (WPATH)

  • transitioning later in life

  • hormone therapy for transgender women

  • redefining family and motherhood

  • closet trauma and coaching

  • trans speaker and advocate

  • reinvention after 60

  • authentic living transformation

  • body and mind wellness after transition

  • Deep Shallow Dive episode 1

  • male privilege and crossdressing

  • transgender medical care in America

🧭 Final Takeaway: It’s Never Too Late to Be Yourself

Wendy Cole waited 67 years to live her truth. In doing so, she became not just herself—but an example of radical resilience. Whether you're facing your identity, a major life change, or your own fear, this episode proves: it’s never too late to start over.

🎧 Listen & Share

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Ray Doustdar

Adding a new chapter to his diverse career, Ray now steps into the world of literature as an author, presenting his debut work, 'Deep Shallow Dive into You.' This book is a testament to his commitment to fostering personal growth and self-awareness.

Ray's venture into authorship extends his passion for meaningful communication and impact into writing, offering readers a transformative journey designed to cultivate a more authentic relationship with themselves.

Ray aims to connect with readers profoundly through his writing, sharing insights and strategies to help them uncover their true selves and live with unwavering authenticity and intention.

https://www.deepshallowdive.com
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Guest #2 | Jonathan Bogner. Resilience.