1.- Walking urban streets late at night by myself. Not only did I do it, but I was not dressed to NOT attract attention. I am lucky I got by with nothing major happening except paying out a few bucks to pan handlers once. It was back in the day when I used to patronize a couple gay venues. Very unsafe and not recommended- the reason you don't see cis women do it alone.
2.- Driving a couple cars which were very sketchy. They were safe...when they were running. One had an electric fuel pump which sporadically would cut out on it's own and the other a gas gauge which would decide to stick. Both of which caused me immense pain a number of times. Again, late at night.
4.- Clown wigs. I went to a rather lengthy and expensive phase when I thought every time I was busted as a guy, my wig was to blame. Often it was because I was not patient enough to save my money for a good wig and/or listened to a wig salesperson who was just interested in a sale. Notable mistakes were long curly wigs in black, red and blonde. When they brushed out, they resembled Bozo the clown. Another platinum blonde straight wig I had would have looked great on a teen or twenty something, but was totally inappropriate for me. I wore it one day with an extremely short skirt prompting one of my bar tender friends to comment "A little over the top aren't we?"
5.- "Flashing Semi Trucks", or pulling my short skirt up to the maximum height showing as much nylon clad leg as I could as I slowly passed a truck. This could be expanded to just wearing the wrong outfit at the wrong time. A time when I thought being validated as a woman came from looking sexy (trashy) rather than passing from within.
6.- Burning bridges, for the longest time I thought people couldn't recognize me if I was cross dressed which proved to be wrong.
There are so many more mistakes I made, I will have to think of them and write another post someday. But, in the meantime, here is a small list of the stupid things I did...and yes. I mean stupid.
I was fortunate to have been able to get out of the situations I found myself in as I grew to understand my transgender woman status.