From the Main Stage: A Full-Circle Moment

For years, Out & Equal has been a cornerstone of my journey, a space where professional excellence and personal advocacy intersect. Being invited to the main stage in Seattle for the Storytellers segment on Day 2 of the 2025 Workplace Summit was more than just a speaking engagement; it was a seminal, full-circle moment in my career. Standing before thousands of peers, I felt the collective power of our shared history and the urgent necessity of the stories we carry.

My talk, centered on the courage it takes to lead authentically, was a reflection of my own path—finding the strength not just to occupy a space but to redefine it. It was an honor to share the “Reflections From Both Sides of the Glass Ceiling” that have shaped my life, and to witness how those truths resonated with a community that has supported my growth from the very beginning.

Below is the video of the presentation, along with a gallery of images capturing the energy and emotion of the day. I hope these moments inspire you to lead with your most courageous, real self and to remember that you don’t need to wait for an invitation when you have the power to “become the table” yourself.

Bring This Story to Your Organization

If you are looking to inspire your own team to lead with authenticity and courage, I would love to help you make that happen. Whether it’s a keynote, a workshop, or a leadership session, I am ready to help your organization change hearts and minds. Click here to book me for your next event.

Renewing the Spirit for the Fight Ahead

Full Disclosure: I traveled to Seattle this year with a nearly-empty well. The fight for true workplace equality and the survival of the transgender community in the United States—the constant advocacy, the challenging conversations, the emotional labor required to champion the Cause—is a marathon that demands more than mere resilience; it demands replenishment. I arrived at the Out and Equal Workplace Summit not just seeking reconnection with my colleagues and friends in the Movement and to speak and to teach, but with a deep, personal need for my soul and spirit to be nourished for the next phase of the struggle.

The toll of the work had become evident. In the face of legislative headwinds on the state and federal levels, the energy required to simply show up as my authentic self, let alone lead others, had left me running on fumes. But this depletion is not new. It connects back to a moment that shaped my entire professional life, a moment the collective power of this Summit helped me to fully recharge.

As I had shared when I told my story to this year’s attendees, twenty years ago—almost to the day—I walked into my office for the first time as myself. Before that moment, I spent decades working up to my position as a Vice President at a major insurance company, managing a large team of about fifty, in a culture that was described to me at the time as “classic old boy network.” The stakes were impossibly high: this came at the end of a brutally painful year of divorce, adjusting to life as a single parent, and navigating custody. My job wasn’t just mine to possibly lose; my ten-year-old son was counting on me as well.

The day before my return, I stayed home so my team could have a meeting to “prepare.” While I still don’t know what was said in that room, I do know what I did: I sent an honest, vulnerable email to over a hundred of my colleagues. It explained what I was going through and why now was the time to finally close the painful gap between how they saw me and who I truly was.

Vulnerability didn’t feel optional; I was already losing so much, I asked myself, what else is left but to be real?

And then, something incredible happened. While I was at home, notes started pouring into my inbox—expressions of kindness, support, and gratitude from people I had worked with for years. I cried so much I thought my tears might short-circuit my computer. They didn’t all understand my journey, but what they gave me was even more powerful: their humanity. And they freely gave to me their grace. They gave me the courage to keep going.

That next morning, heart pounding, I walked up the glass staircase that wrapped through the middle of our office building, visible to everyone. It was strangely quiet. I didn’t see a soul. But when I reached my office, a beautiful bouquet of flowers was waiting—a gift from my direct reports. As the morning went on, conversations began. One colleague, nervous but sincere, asked, “So, uh… you’re still… the old you on the inside, right?” I smiled. “Of course, I am. I’m just happier now.” And you know what? He got it. My skills, my leadership, my core—nothing had changed, except how the world saw me.

That long, quiet walk taught me that the journey of claiming our space is full of moments where we stand completely alone, and also moments where the love and support we receive nearly short-circuits a computer. We are worth being real. And two decades later, I can say with full confidence: I didn’t lose myself in the process—I finally found her.

This is why the Out and Equal Summit was such restorative justice for the spirit. The collective energy of EVERYONE there – created an undeniable wave of shared purpose. That unexpected, life-changing humanity I received twenty years ago was amplified in Seattle, replacing the isolation that this work often creates with a sense of collective power and unshakeable hope. The themes of the conference—resilience, community, and the fundamental right to belong—were the fuel I needed.

I left Seattle with my spirit full, my resolve sharpened, and a fierce, renewed determination to dive back into the fight. The spiritual nourishment received connected directly with my soul and provided me with a clearer picture of that beautiful future we are building, and fighting for, together.

The challenge I carry forward is the one I learned on that quiet staircase two decades ago: Don’t wait for permission to be real. Your vulnerability is not a weakness; it is the most powerful asset you have. It opens the door not only for your own liberation but for the humanity of those around you. We all have that feeling of standing alone on that glass staircase, heart pounding. But when we choose to step out—when we show up fully as ourselves—we give others the courage to show up too.

We are in this fight together, committed to tearing down the walls of isolation and creating spaces where every member of our community—the fabulous, unique, and immensely talented individuals that we are—is not just tolerated, but celebrated. And remember, when we show up fully, authentically, and joyfully, we don’t just ask for a seat at the table—we become the table.

TD Bank hosts Stephanie for Pride!

A BIG THANK YOU to Stephanie Eckersley-Ray and Steven Garibell and the entire team at TD Bank for including me in last Thursday’s AMCB Pride event! It was truly a transformative day for me and a real honor to be included in the program. I was so touched by the energy and passion that was in the room – and the commitment to evolving the already inclusive culture that has been built. You and all of your colleagues should be so very proud of all that you have accomplished – not only in making the event happen but for the positive, inclusive impact you have had and no doubt will continue to have on the culture at TD Bank!

A Big THANK YOU to Gina Carriuolo and the entire team at Robinson+Cole! What a wonderful event! It was a pleasure and an honor to share my journey with each of you!

https://www.linkedin.com/feed/update/urn:li:activity:6940389201209171968/

Telling my story.

From a keynote that I delivered at the Museum of Public Relations’ Pride Month event, “The LGBTQ Experience in Public Relations: Visibly Proud.”

That’s how it all began for me after becoming the first transgender person to successfully transition in the 160-year history of New York Life Insurance Company back in 2005.

It is quite simply the through line to everything related to the journey to my authentic self – to the person that I’ve always known myself to be.

In the lead up to my coming out, for every person that I shared my true self with, I did so by telling a story in the hope of making who I am as accessible as I could to their unknowing ears.  I did so somewhat naively, not knowing how it would land, despite my attempts at fashioning it as authentically as I could.

It’s the only way I knew how.

For my entire life, telling a story had always been my default mode of communication.  It’s what I always did – most of the time without even thinking.  It was how I pursued a human connection – how I went about getting people to like me – and hopefully, not see the real me hidden behind the façade of maleness I was desperately trying to keep in place.

Telling my story helped me hide the real me from everyone around me.  All of those stories – mostly real, and some – I must admit – that were fabricated for the time, the place, and the audience – all seemed to work at keeping my deep, dark secret from the world through four-plus decades of shame guilt and denial.

So, it should come as a bit of a surprise that when it came time for me to give back, to pay it forward, I wasn’t sure how to go about it.  While I was quick to point out to the HR VP’s at New York Life that “I may be the first, but I won’t be the last,” I had no idea about how I would go about creating a path for others to follow.

What perhaps I didn’t fully realize in that moment was that I was taking on a responsibility to do everything I could to make it easier for those who were to come after me – whether they be at my company, or at any other.

It would require me to create space on my shoulders for those who would follow me, just as I stood on the shoulders of my trans sisters who came before me.  People like Maggie Stumpp who, as an executive at Prudential, had come out a year or so before I did.  Her story – and how it was spread through the media of that time – gave me the courage I needed to overcome my fears and pursue my dream.  I felt a strong desire within myself to do the same, but I was at a loss as to how.

I struggled with what it was that I could bring to the trans inclusion conversation.  What was my angle, how could I best position myself to be heard amidst what seemed like a cacophony of much more compelling voices.

But then, through perhaps more than a little divine intervention, I received two particularly important pieces of advice that taken together formed a seminal moment for me.

The first came from a friend of mine who at the time was a leader at a national LGBTQ organization.  In responding to my question “but is there room in the sandbox for me?” he said quite pointedly “Stephanie, it’s not a sandbox, it’s more like a beach!”  And the second came from another transwoman who had already achieved some measure of notoriety with a book of her own, who said to me “all you have to do is tell your story.”

These honest and authentic answers instantaneously impacted me.  Suddenly I realized that my own story – however mundane and run-of-the-mill it may have seemed to me, wasn’t mundane or run-of-the mill at all.  And, that there was a place for it in the ever-expanding constellation of voices that were already out there calling for equality and inclusion for all transgender people.

What I have learned every day since is that there is immense power in our stories.

They truly can change hearts and minds.  It is the connective tissue that binds us together as human beings, because they have the unique ability to tap into our shared humanity – and it is precisely this shared humanity that is our greatest common denominator.

But it is not just the stories of other LGBTQ individuals that add to this collective voice, it is also the stories of our allies.  Those that stand in solidarity with us and urge others to join our fight to be heard.  They are equally, if not more important, than our own.  Their stories of love and support for the LGBTQ people in their lives creates space for others to step up and do the same.

For the last seven years I have been privileged to serve on the board of PFLAG National and have witnessed firsthand the incredible power that a parents’ love for their LGBTQ child can create.

It’s as if we were all standing on the shore of a mountain lake . . .

(TELL THE RIPPLES STORY) 

And that’s where each one of you here today come in.  By amplifying our stories – and those of our allies – you are creating even more ripples.  And make no mistake, each one of those ripples contributes to the movement – to the greater good.  By proudly proclaiming your support and allyship you are sending a powerful message to your employees, clients, business partners and customers that equality for all people is a major priority.

But the question I put before you is this:  are you – and the company that you represent – and ally with a capital “A” or an ally with a small “a?”  Capital A allies are visible, engaged in our history and our issues, and embrace teaching moments when they encounter them.  Small a allies just talk a good game and wave their pride flags for the month of June and then put them back in their desk drawer for the other eleven months of the year.  They acquiesce when conflict arises, and they shy away rather than lean into the difficult conversation.

Make no mistake, we are at an inflection point for the LGBTQ community – and in particular the transgender community.  We need all the capital A allies we can get, because we cannot fight this battle for equality and inclusion alone.

Our very authenticity is under attack.  While this has certainly happened before – think North Carolina’s bathroom bill in 2016 – it has now taken on a particularly hate-filled and hurtful turn.  The opposition has taken direct aim on the most vulnerable of my community – trans kids and trans athletes, many of whom are of middle school and high school ages. At last count, some 37 bills have been introduced across 20 state legislatures, and in nine states these have been signed into law banning transgender girls and women from participating in school sports consistent with their gender identity.  The latest happened at the very beginning of Pride Month – on June 1st to be exact – in Florida – and as you all well know that timing was not by accident!

But trans youth are fighting back by living their truth – and telling their stories.  Voices like Stella Keating, who bravely testified before the Senate on behalf of the Equality Act, are sharing their challenges, their hopes, and their fears so that society can get an honest picture of what it is like to be a young trans person in today’s America. They are courageous, they are brave, they are resilient.  They are my heroes.

And that is why, among other things, I decided to write my book. I am proud to share my stories with the world in the hope that it can raise up the many in my community that feel they do not have a voice, for they all have a right and a need to be heard.  And that’s why I think it is right for precisely this moment in time that the transgender community finds itself in.

One of the key post-transition themes that I write about is around my experience with white male privilege.  For 25 years of my corporate life, I had it and didn’t think much of it.  But when I made the decision to embrace my true self and live my life authentically, it vanished in an instant.   All that power that I possessed throughout my climb up the corporate ladder was gone.  And its loss cut like a knife.

Many of you possess great privilege – I’m speaking directly to the straight and gay white males in the room.  How are you going to use this to fight for equality for underrepresented communities like mine?  We need you.  And to be clear, it is not a zero-sum game.  Share your knowledge.  Share your value.  Share your network.  Share your own story.  Because as you lift us up, you elevate the entire LGBTQ community in the process.

In closing, I ask each of you here to consider these questions:

-What is your responsibility as public relations and communications professionals, to amplify these voices and raise up these conversations?

-What will you do to mirror the courageousness of my younger trans siblings in combating the onslaught of misinformation and disinformation designed to eradicate their existence?

-What will you do shape the narrative around equality and inclusion for not just the transgender and non-binary community, but for LGBTQ persons everywhere within your cultures and within your community?

I ask each of you, what will be YOUR story?

 

Thank You Very Much and enjoy the panels!

 

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