Better Late Than Never – Part 3

Promises Fulfilled, and My Full Life Finally Begins

I think the planning of this road trip was about more than seeing some great sights and just the adventure of a long drive. I am fortunate that a laptop and internet signal is all I need to work, so I could take my time on the trip and continue to serve my clients as I traveled from place to place. This trip was as much a chance to sight-see as it was an effort of true self-discovery. Somehow, I was going to figure out who I really was — personally, professionally, and everything in between (something I probably should have discovered in my 20s but better late than never). 

And before I even left I had some significant doubts about a key element of self. Was I really going to bring “her” on this trip or leave the femme self at home for 2 months? I was once more allowing fear to dictate terms. I had never been so boldly out in public —in and out of places and interacting with the world as a woman. Any interactions I had were carefully curated to this point so bringing all of me on this trip meant creating an opportunity to experience something far more than ever before. 

The solution came from, of all people, my wife: tolerant and maybe just a wee bit more supportive than either of us believed, made a profound statement. “If you don’t bring this all with you on this journey, you will regret it for the rest of your life. You kind of have to do this, and you know it.”

This was a massive statement from her. She knew more about who I was and how I was feeling perhaps better than I did. I love her for that. Sometimes we need a loved one to just show us a small glimpse of what is possible to get over our own fears and misgivings. She was providing me something I was not necessarily seeking but clearly feeling like I needed it. Right or wrong — I received permission. I needed her to be “okay” with it. 

She was right and even though we both knew I did not need her ‘green light’, it eased my heart considerably. I packed for two people, but kept it to one rather large suitcase, a separate carry-on type of bag, and a backpack for my computer. This allowed me to get in and out of the car and into my hotel rooms in one trip, and simplified my travel — well, as simple as it could be. 

Labor Day came and went, and a few days later, with America’s families back at work, and kids off at school, the drive west began. I figured, there would be fewer people at the tourist sights and I would have a more positive experience as a result. 

Driving across the country is an adventure that fulfilled a long-standing desire for me. I got to see so much over the course of two months; it turns out that living as a nomad is incredibly rewarding. More significant — I found out about myself out there. Packing up and bringing my female attire proved to be the right decision. It was critical to help me discover my complete self. 

It started on the first day. I was hardly over the George Washington Bridge before I found a ‘shady spot’ to change in the car. Finding that shady spot became a modus operandi that continued almost daily. In the hotel rooms all over the country, I presented as I wished which, while not full time, was still the majority of it, and more often than not, I looked for a way to present as female while in the car as well. 

A mix of audio books, music, some news, and conversations on the phone with clients, family and friends filled the drive. Sometimes just the hum of the road and talking things out with myself proved immensely valuable and part of my self-discovery. I was stopping randomly at times as I found interesting little areas to photograph and catalog. I was content to take it all in. I felt vibrant, hopeful, alive — and it was glorious.

It was not until I reached Seattle that I made my first real venture out of the room presenting as female. I made it down to the lobby of the hotel and very casually allowed myself to be ‘seen’.

But it was San Francisco where I had the real crossing of the Rubicon and I considered this a now-or-never moment. I began to search for the justification and the way to do what I knew I had to do. The drive to Monterey, CA. was not too long, and I’d likely be just fine. Before checking into the hotel in Monterey, I would find my shady spot and change out, and remove the makeup I wore.

The thing is that when I got to Monterey, I found myself standing in the hotel office at the front desk and checking in — while still presenting as a woman. By the time I got my room, and brought my things in, I realized I did the thing I had longed to do for years, but was always sought to find a way to avoid it. This time, I was seeking ways to turn it all into a very real presentation.

The woman behind the counter could not have been nicer or more gracious. I got a great room and settled in to do some work. By the time I left, two days later, I had experienced my first taste of life openly presenting as female. I did not present as my assigned-at-birth gender the entire time in Monterey, and it was eye-opening.

Some 40 years in the making, it was not lost on me as I drove to my next stop in San Simeon, CA, all while still presenting as female. I found myself recognizing for the first time, that this was what my life was always supposed to be. Just living my whole self without compartmenting anything, no hiding—just living the best life I could. 

Every facet of my life was touched in these days for the first time. My true gender identity lived openly. A dialogue with someone about history — for which I have a passion. Someone else inquired asked about my drive when they saw my car and license plate from New York. I engaged on the phone with clients about work, and my creativity. I interacted over the phone with my wife as well. It was the “All of me” more than 40 years in the making. The bricks of burden and fear and anxiety laid down and left somewhere in the outskirts of Monterey, California.

Oh I am fairly sure I was fodder here and there for some narrow minded fool, but I just didn’t care — and still don’t. Haters will hate and it doesn’t change who I am and how I feel. Within those California days, I did something most of us struggle with: I took on and faced my fear. I was able to challenge the most important person I could — me! I came face-to-face with the truth of who and what I am and how I feel and simply accepted it wholly.

I felt, and still feel, liberated by the moment! This was a long time coming. This was the true beginning of my complete, fulfilling life. The rest of the drive had its additional moments — all the way back to New York. But those days in California changed my life forever. I have always loved the Pacific Coast for its beauty. Driving that Pacific Coast Highway from Seattle to San Diego should be a bucket list item for anyone. For me it certainly was — but I also found my soul on that highway. I will forever be grateful for that chance. And while it still took another year, that place and moment would lead to another very special place and moment. 

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Andrea Smith

I have been someone who has struggled a very long time with my gender identity and have only recently come to accept my truth. It is liberating and wonderful, and also frightening. I am hoping that as I continue to accept more and deny less, my authentic and more importantly complete self will emerge. I live in the NYC burbs. Enjoy photography, museums, history, old tv shows, movies and cooking.

Latest posts by Andrea Smith (see all)

• Better Late Than Never – Part 4 - May 10, 2025
• Better Late Than Never – Part 3 - May 3, 2025
• Better Late Than Never – Part 2 - April 29, 2025
• Better Late Than Never – Part 1 - April 19, 2025

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