Chris Schembra: What were you taught as a child about gender and relationships?

Natalie Egan: The first time I recall being aware of my gender, I was doing something that girls do and I remember being corrected harshly. I had 2 older brothers that taught me everything I needed to know about being a boy. You can’t do this or that because you’re a boy and that sort of set the trajectory of my life. From the time I was 5 onward, my gender identity was put on autopilot. It seemed to me that everything I was taught from the time I was born is part of an artificial construct. We create labels to help us identify what’s what in the world; I understand labels are helpful, but I found them to be damaging. I was assigned male at birth and from the moment you are born, and someone announces, “it’s boy!” or “it’s a girl!”, gender becomes this habitual grooming through traditional gender roles. Its reinforced by everything from our language to what we are allowed or expected to experience. When the child is born we don’t just announce, “it’s a soccer player” or “it’s a ballerina”. It sounds crazy to assign an entire identity to someone based on the observation of genitalia. Your gender expression is so much more complex than that. I lived my life based on expectations of what people said I should do or who I should be, and that’s unfortunate.  I was so unhealthy because I was doing what everybody wanted me to do instead of just being who I was.

Chris: From the outside, everything looked fine: you went to a prestigious college, founded a successful company, but as you put it so painfully, you were hiding in plain sight. What gave you the courage to change the narrative and start living your freedom?

Natalie: It was a total breakdown; my failure of the experience I felt like I was supposed to have. I architected this narrative of a person that everybody wanted me to be. I did that well for 40 years until it eventually became unsustainable. I learned that building a sky scraper without a foundation means it’s going to come crashing down. Despite my best efforts. I just couldn’t do it anymore. Everything was breaking apart. My entire life came crashing down so It wasn’t voluntary; it wasn’t like a choice so to speak. I remember people telling how brave it was. Brave to me is like choosing to jump off a diving board, like a high dive or like you’ve chosen to jump out of the plane, but I felt like was pushed out of the plane. Does that make me brave?

It was not about bravery for me; it was about survival. There is no other way. I had concluded that I was going to kill myself or I was going to survive the jump.

I had come within a week or two of feeling completely hopeless and had devised a plan to end my life. I didn’t want to burden the people I loved with my crisis. Luckily, I found my way through that and survived the jump after all.

Chris: You mention that you were about one or two weeks from ending your life. What saved you?

Natalie: I would like to first acknowledge that I’m very privileged overall. I mean I must acknowledge my privilege to give credence to what I experienced as a trans person; a marginalized experienced like I had can often times change perspective. Many trans people -specifically trans people of color do not have a support system. My fear was that I didn’t think I would have that either. I believed that there was no way that my parents, my brothers, my then wife, my kids, my coworkers, my employees could accept what I was experiencing. For me the turning point came through a meeting with an old friend. Some people come into our lives and completely change our trajectory like a gift from the universe and that’s what he was to me.

I happened to be in New York city, waiting for coffee in a bodega in mid-town, and standing in front of me was my best friend from high school. I hadn’t seen him in years and there he was. We started chatting and he immediately recognized that something deeper was going on and I needed to talk. I ended up confiding about what I’d been wrestling with, which was a total Hail Mary throw for me. I had no idea how he would react. This friend of mine was an Alpha male so telling him was going to be my litmus for how I expected people to react. He looked at me straight in the eye and said you have to be you. I was absolutely shocked at how simple and straight forward he made it seem. All this time I was so afraid and here was someone I hadn’t seen in years who embodied all the male stereotypes that I had tried to live up to and society would have me believe would be predisposed to judge me or ostracize me and instead he just accepted what I had to say and validated that I just simply had to be myself.

That moment saved my life; he saved my life. I tell that story because you never know when you’re going to be someone’s ally; you never really know what someone is going through and if you every find yourself in a chance meeting in the middle of the day, this could be the day you save someone else from the isolation of fear. He gave me courage to be able to start the journey.

Chris: That’s an incredible story. Thank you for sharing it with me…and now after all this time, you are Natalie. What has that been like for you?

Natalie: I think it’s amazing; wildly liberating if I’m being honest. Although there’s a common theme I think for people suffering on the other side that it’s going to be all happiness all the time. It’s not all the time. Life is still life. There’s no magic pill for happiness; I’m a human being just like everyone else, facing challenges, overcoming obstacles and finding my way. What I can say for certain is that for the first time in my life, I am satisfied. I’m no longer searching or rushing to fill a void with a new career goal or a new accomplishment.

Nothing ever seemed good enough because I was desperately trying to fill the void of identity with successes and achievements.

After making peace with my identity, I can look in the mirror and instead of seeing a fraud or a failure, I see who I really am. Instead of seeing that reflection with hatred, I see it with love. I get to say I honestly love myself and that’s the coolest feeling.

Chris: You mention business exposure and success. After identifying as your true self, you dedicated your work to creating a company that focuses on diversity inclusion. What can companies do to help their employees work together to overcome the things you faced?

Natalie: I think the important piece of this company, is to help others realize this is a journey; it’s a process that we all go through one way or another and having empathy for someone going through a process of their own is what it’s all about. All processes take time. Helping each other along the way through empathy and understanding is what we strive to achieve. Having vision for who and what we could be if we operated under those terms is how we are trying to change the culture in companies throughout the country. We do this in a number of different ways. One way is by hosting workshops that feature playbooks to help employees understand how to go through an experience of someone else’s process. An example would be how to respond if a coworker comes out as transgender and you as an employee are on the other side of reconciling that reality to yourself, your fellow co-workers, clients, etc. There is a healthy and productive way to experience that and that’s what we want everyone to learn.

Chris: What is a piece of advice you would you give to someone who may be feeling what you felt; before you ran into your friend, when you felt alone?

Natalie: The first thing they need to know is that no matter what you think society is telling you or what your own mind is telling you, you are not alone. I lived my whole life thinking I was alone and I was the only one going through this. I grew up in a world before the internet. There was no website, no support group, no pamphlet with encouraging information. Today we live in a world that connects us to each other constantly, through social media and the internet. It can be a double-edged sword, there’s no denying that, but the access to other people provides unprecedented relief from the isolation of fear. Reach out to the people who may be in similar circumstances. Your circumstances don’t define you or your approach to handling your own process. It can be as simple and arbitrary as finding a hashtag you identify with that opens a whole world of people who think and feel and look just like you or who you want to be. Don’t let the lie of believing your alone prevent you from going on the journey.

Be strong and stay optimistic. Don’t go backward. I truly believe that this will lead to much better reality for all of us. Life is hard and we’re going to hurt and suffer and lose people along the way, but never ever go backward.

Chris: Wow…Natalie, thank you for all of this so much. 

Natalie J. Egan (she / her / hers) is an openly transgender B2B software entrepreneur. She founded Translator in 2016 based on her experience coming out as a transgender woman and experiencing bias, discrimination, and hatred for the first time.

As the CEO of the company, she leads a quickly growing team into the uncharted waters of building enterprise Diversity & Inclusion software. Natalie has over 20 years of experience driving digital change, developing high performing teams, building complex products, and selling B2B technology solutions. Prior to founding Translator in 2016 – and prior to her transition – Natalie was CEO and founder of PeopleLinx, a venture capital backed social selling technology solution that was recently acquired by a leading sales acceleration company.

In addition to her entrepreneurial pursuits, Natalie has also worked in leadership positions at LinkedIn, Autonomy, and Ecolab. Based in New York City, she spends her free time with her three children or mentoring female entrepreneurs and LGBTQ youth. Natalie earned her undergraduate degree in business from The Hotel School at Cornell University, received her MBA from The Villanova School of Business, and is currently writing her first book about transitioning from a male to female CEO in corporate America.