A Practical Guide to Coming Out

Coming out is more than a single announcement—it is a profound, lifelong path. This guide helps you navigate the emotional, personal, and social realities of transitioning with clarity and purpose.

Dealing with friends’ and family’s reactions is just the first step. Then come colleagues, the workplace, and society at large, and it can be overwhelming. You have to juggle that, plus physical, mental, and emotional changes—and figure out how to swim against an ever-raging social current pushing back. So where does one start?

Firstly, you need to determine what coming out means to you.  Are you simply making your crossdressing secret public, or is it a more profound decision to transition? If the latter,  it is much farther-reaching than the former. 

There are serious practical realities to consider when thinking about a 24/7 transition. Do you have children, do you — or are you likely to have — grandchildren? How will they deal or not deal with this? Are you willing to lose your family, friends, and potentially your livelihood — if your job lets you go like they did Danielle?  

These may seem unfair, but they are the realities of transition. These are very real and practical considerations you have to, or should, consider. 

When someone comes out, they do so for varied reasons; some know from the time they are children that they are in the wrong body, or come to that knowledge later in life. Others are on the fence, trying to make heads or tails of feelings they have never quite been able to comprehend or reconcile within themselves, or simply chasing fantasies that have no practical application in real life.

The good news is that no two people are the same. No two situations are the same; you are a unique individual with as much value as anyone else. But understand that the road of your life—the experiences you have, the insight you glean from them, the decisions you make, and the quality of them —is yours alone. Friends can walk with you for a time, but the direction and detours of that ultimate journey are solitary—because you’ll never find your nirvana by simply emulating others’ path.

On the one hand, this trek can be scary; on the other, it can be a surprising experience filled with adventures, insights, and personal growth. Whether it ends up where you first envisioned, the experience itself can give you invaluable insight into yourself. The decision to come out and/or ultimately transition is a BIG one, and should not be taken in haste without a lot of reflection. It requires deep, balanced thought. There are many who “try” hormones to see if they’ll like them without having decided to transition. This is a huge mistake. Many of us are still giddy in the euphoria of short-term experiences, without considering the long-term effects.  

Coming from me, that might seem a bit cautious given my spontaneous and extroverted nature. People have called me impulsive, cavalier, and—sometimes—a bit wild, to be sure. Yet throughout my journey, I’ve always understood that it is full of decisions only I could make, and that I alone had to bear the responsibility and accept the consequences.

If you approach transition — and life — as a victim, you will always be a victim! It’s easy to blame mishaps and unfortunate circumstances on others, but we—all of us—control our own destiny.

My coming out was born of a deep frustration caused by the conflict of a compulsive need to cross-dress in the closet and the havoc that it caused in my day-to-day life. It didn’t matter that, on the outside, I was a good-looking, athletic man and a successful businessman. Always present was that lingering “what’s wrong with me” feeling that raged on deep down within me, causing me to perceive myself as being broken, damaged in some way. Eventually, I felt that I needed to resolve that conflict above all else, or I’d never be able to enjoy the fullness and beauty that life has to offer.

Looking back with the clarity that only time can often provide, I’ve come to recognize what I did right, what I did wrong, and what I still wondered about. I can only hope that by passing that information on, I might help you glean more about the road you’re on… by taking a short stroll along mine.

Many readers are surprised to learn that my motivation for coming out wasn’t to transition. The truth is that it was a commitment to explore the deep, dark hallways of my soul, in an attempt to discover where this “compulsive” cross-dressing behavior in me came from and to “cure” myself. I was determined to confront it, explore it, understand it fully, and then exercise or extricate it from me so I could, once and for all, gain control of my life. I intend to reveal this profound story in the book I’m currently writing, entitled “The Last Woman & Me.”  

I learned that there is no prescription, no set way to do anything: nothing is certain, and everything is subject to change. Our gender journey is not unlike that of any traveler who sets out for places unknown, armed only with a burning desire to explore—a calling for reasons beyond their consciousness. 

We have no idea where we’re going, or what we’ll find when, and if, we arrive. But without that desire for truth above all else, we’re lost, and the current’s rush will disorient us until we forget why we even began the trip. 

The key in any adventure is a willingness to search without fear of what one may find. So at forty-three, I set out with no idea where the trip would take me.

Before the Internet — and all the information it would subsequently make available — mine was dark and narrow, without signposts. Or so I thought. In hindsight, signs are everywhere if you keep your eyes and mind open! While a tourist “looks,” a traveler “sees” and absorbs the world around them. When beginning an exploration of transition, whether it is of gender, career, or life path, one is no longer a casual and occasional tourist; they are a traveler en route to distant and undefined lands, gaining insights into new cultures, people, and an understanding of how it affects them. Therefore, transition isn’t just about you; it’s also about how you impact others, and how they impact you in relation to the world.

The first step on my path was to become mentally strong. This required letting go of what “other people might think” and realizing that “the words of others didn’t define me .” Easy to say, not easy to do. I had to mentally prepare myself every day — usually right after I applied my makeup 🙂 Secondly, and equally important, is recognizing that when I went out into the world as Brianna, I was an anomaly to many in the mainstream—something out of place, something unusual, something they had no reference for except sensationalized headlines, if that. And that’s OK. Don’t be offended that they don’t get you; they’re allowed to have their own initial impressions.

Tolerance should be part of your travel kit.

While I was secure and steadfast in my right to be who I decided to be, I also had to allow others that same right to feel however they did. I had no control over how they perceived me, only control over how I presented and carried myself. 

When I encountered people, my goal was to educate them when I could and move on when I couldn’t. It was never to gain their acceptance or change their minds. What I discovered was that with the absence of intent [to convert them] or to defend myself or their life choice, most people were disarmed, relaxed, and subsequently more willing to “listen.”

I found that when talking with one who doesn’t know about — or understand — what being transgender really means, an aggressive stance by us — whether a defensive posture to withstand their views or an offensive one to convert their views — simply makes them recede into their shell of ignorance, discounting anything we have to say.

Have you ever engaged in a debate about religion, trying to change someone’s beliefs? You can’t change people’s beliefs; you can only provide information that, over time, helps them change their own perceptions based on what you share. 

So, in the words of Lao Tzu, live your religion without the need or intention of converting anyone or convincing them that you’re right.  

To me, this was key to moving through society effortlessly: I never challenged people’s beliefs or sought their acceptance. I simply stated my position, and let them feel however they wanted to about it, with the right to “respectfully” disagree.

I’m not suggesting that you allow people to verbally (or physically) abuse you. If they don’t get what you’re saying, or don’t want to, simply ask why. A question is far more powerful in a discussion than a statement, and it can sometimes open someone’s mind.

And always maintain a sense of humor about the situation and yourself, and be willing to laugh with them, not at them — while getting them to laugh with — not at –you. I explained a real-life experience about this in the essay Candidly Transgender. 

In Part II, I’ll delve into my first days in the workplace, among other things.

Until then, remember to be happy, be safe, love yourself — and always think pretty!