The Best Days of Transition

Stories, Coming Out, Male-To-FemaleNatalie Egan
Image by Rebecca Lieberman

Image by Rebecca Lieberman

By Natalie Egan

We’re trying something new here at a regular column in which we ask trans-identified individuals to reflect on the five most memorable days of their transition. To start us off, here are mine. If you’re interested in contributing to the Fave Five column, please write to us at


There was a TON of emotional angst leading up to my decision to take hormones. When I was ready—like ready-ready—after I had become completely clear that I would be taking hormones to physically transition, I couldn’t get on any doctor’s calendar to save my life. Everyone was completely booked and not taking new appointments for 5-6 months.

On a whim, I went on Zocdoc and searched. It was February 26, 2016—two days until my birthday—and an appointment popped up for the next day as I was looking. I called the office immediately. “Is this appointment real?” I asked. The receptionist explained that Zocdoc gets cancellations before the office does. “Hurry, go!” she advised. “Grab it on Zocdoc before someone else does.” So I did.

But when I arrived at the doctor’s office, they said, “You shouldn’t be here. You don’t have your blood work or your paperwork,” referring to the required note from my therapist. I begged them. “It’s two days until my birthday, please. Please. I need this.” I had gotten lucky: the receptionist felt my struggle, and so she went to get the doctor.

When the doc arrived (but before he even said anything), I piped in: “I’m not leaving without a prescription.” He was generous. “OK, I’ll do this for you, but I have to get your therapist on the phone, and you have to go get your blood work today. When I see the results, then I will activate the prescription.” I couldn’t believe it.

The next day, my prescription was activated, and so on my actual birthday, I began my hormone treatment. At 39, I was “born again,” this time as the person I truly am.


LinkedIn would be first. I had worked at LinkedIn in early days, and so I knew the platform inside and out.

As a CEO of my own company, I had more than 1000 real business connections, including former clients, so I had to move very carefully in my profile reveal. The timing was very important. I would turn off any notification settings first. Then I would change my name. After, I would change my title to CEO of and add my new company information. Finally I changed my picture and updated my privacy settings before posting my coming out letter letting my network and the full public see directly into my life. It was orchestrated perfectly.

The groundswell began just moments after my post. Almost immediately, I had people contacting me, congratulating me, saying the kindest, most inspiring things. Because of the public nature of LinkedIn, people I didn’t know found my letter. I got messages from all over the world. (I still do.) Of course, every once in awhile someone will say some stupid shit, but those few ignorant comments were drowned out by an overwhelming surge of love by colleagues and strangers alike.

Next, I went to Facebook, and because I didn’t understand the intricacy of the controls, I completely blew it. I changed my picture first, which was a HUGE mistake. Panicked, I quickly Googled how to change my name. When I figured it out, Facebook then told the world: Natalie Egan changed his name. Panicked again, sweating bullets, my mind racing, I knew I had to get to it before someone commented or liked it. Finally, deep in the settings I found the gender marker, and changed my pronouns to “she.”

Again, I got the most amazing notes of affirmation. Tons of support for who I really am. It felt so significant. Going to sleep that night, knowing that I had told the world––quite literally, and that I would wake up assuredly a woman the next day.


I’ve always been drawn to women’s hands. Look at a woman’s hands, and you will find her soul more acutely than with her gaze, in my humble opinion. My own hands are actually quite feminine. I could always drift away by staring down, my true femininity in the extension of my hand.

I was 32 years old when I started painting my nails, long before I transitioned. I had just started my own company, and because I wasn’t beholden to a boss any longer, I found the tiniest sliver of liberation in allowing myself to paint my nails on the weekends.

On my way home from work each Friday evening, I would stop at Perfection Nails—always arriving at 6:45pm, right before they closed to ensure that I was the very last appointment, and that the salon would be empty.  My treat at the end of the week. I did it every single weekend. And on my drive back into work on Monday mornings, I would reluctantly remove the nail polish. The last possible moments. My hands smelling like nail polish in our Monday morning executive meetings.

If you’ve never had a gel manicure—and maybe you never have wanted one—gel polish is basically “baked” onto your nails with UV-light. Meaning: you can’t take off easily, and often have to get it removed professionally. For me, getting a gel manicure was symbolic. It was the first day of the rest of my life—a statement of permanence for my femininity. She was here. I was here. The color sparkling in the light, my own private fireworks. The celebration that I would never not be me anymore.


Growing up I hated my hair.  It felt like dirt all over my body. Thick black wires of dirt. And ironically, the only place I wanted hair—which was on my head—was where I was losing it.

I remember shaving my legs for the first time and being thrilled about it. But I was quickly disappointed at how fast it grew back and how it felt like sandpaper. Over the years, I had also tried waxing, which was effective but really painful. And of course, I had tried my fair share of gross chemicals that could melt away your hair. But, no thanks.

You can imagine my delight the first day I started laser hair removal. Again, it was the first day of the rest of my life.

Having smooth skin is a huge boost to my confidence in facing the world each day, and one of the greatest gifts from my transition. We should all give ourselves the gift of being our true selves.


It was Thanksgiving Eve in San Francisco and we were at one of those perfect tiny Italian restaurants right in the middle of the Castro. At first, it was only to be my oldest brother and his wife who were to meet me dressed fully as Natalie for the first time. But when my other brother and sister found out, they insisted on coming too and with their spouses. So at that point we figured we would invite my parents, but they respectfully declined. “Sorry, we love you and support your transition but we are not be ready for this,” to which I replied, “I completely understand.”

I arrived fashionably late by Uber. I walked in and there they were, my whole family was seated––including my parents. I’m tall, but taller in heels. My brother Stouffer, a consummate gentlemen in the world, pulled my chair out for me and gave me a single red rose. And then each person came over to greet me individually––giving me their own personal blessing and unconditional love. There I was and there they were, and it was completely normal—better than normal, it was really fun too.

I bounced around the table to talk to everyone, and at one point I landed next to my mom. She tried to fix my hair. “Come on, let’s go to the ladies room,” she said with a coy smile. Looking into my eyes differently, she pulled out these miniature bobby pins. “You’ve got to use the tiny ones for this,” as she pinned my hair. It was such a sweet private moment, a moment that contains your whole life. My first moment as her daughter.

Of course, now that I am living my life as myself—the person I have always been inside and who I wanted to be outwardly—there are countless moments that feel memorable and meaningful.

These are my favorite days—the moments I put on repeat in my imagination when the going gets tough. What are yours?


Natalie Egan

Natalie Egan

Natalie J. Egan is a serial entrepreneur, trans rights activist, and a committed advocate of tech-based solutions to education. As an early employee of LinkedIn and the former CEO and Founder of software company PeopleLinx, Natalie is passionate about using technology platforms to connect individuals, organizations and companies in order to promote social engagement and learning.