All Kinds of Transgender Dilemma


Image from Karla Hernandez 
on UnSplash

We transgender women and trans men have always encountered plenty of dilemmas as we complete our gender transition, or attempt to. Most of us have friends, family and jobs to consider. Sadly we are considered to be selfish as we pursue our gender goals. Ironically there is truth to the selfish idea because we often need to address our most inner souls to find a path. We found muses were difficult to find.

Dilemmas were everywhere. I know one of my biggest drawbacks to transitioning earlier was trying to figure out how I would support myself. Most certainly I would have had to quit the well paying, hard earned male career I had managed to carve out. None of it seemed fair but who said life had to be fair? As I quote my parents who were fond of telling me just that when I didn't want to do something they wanted me to do.

Another huge dilemma came when I needed to learn the new basics of presenting and appearing realistically as possible in my new chosen gender. The whole process really defined being alone with a terrifying array of cosmetics to deal with. Then there was the problem of what to do about a new wardrobe. Styles and sizes became very important as well as cost. I was in a situation where I needed to hide any feminine expenditures from my wife. I found one big solution by shopping the thrift stores. I could purchase ultra cheap clothes and see if they fit on a very small budget. Plus, I was even able to gather the courage to try an item or two on in the dressing rooms. Finally I was able to dress my way out of my teen girl years and into a reasonable facsimile of what a cis woman my age would wear. Thrift stores not only gave me an excuse to go out shopping, and save money, I could also conquer the appearance dilemma at the same time. 

At the same time, I was ignoring the few friends I had accumulated. Slowly but surely my feminine side was sneaking into the forefront and stealing my life. The more I was in the public's eye, the less male time I wanted. It was working out to be a huge dilemma. The more I accomplished as a transgender woman, the more natural I became and all of a sudden the whole impossible dream of living a feminine life became more achievable. 

My dilemma  of telling friends I wanted to be a woman very much went away when my small circle of close friends passed away close to the time when my wife died. There was no one left to tell. Family, as I have detailed several times, my problems coming out to my family was a different process. Even though my parents had long since passed on, I still had a daughter to tell as well as a younger brother. I had a highly successful experience with my daughter and an equally bad one with my brother who I have not spoken with for nearly a decade now.

My final big dilemma was what to do about my finances. At my age I was getting close to being able to retire on early Social Security. I also owned a house full of antiques and collectibles I could sell to raise money, so I took the early out and retired. All of which of course, did away with me have to worry about job hunting as my new authentic feminine self. With most all of my dilemmas in the past, the door was finally open to complete my gender transition.