I just turned 39 this past week.
My first "hard time" was 12 years ago -- the first time I seriously contemplated transition. However, I had a wife and children and also had spiritual issues over the entire thing that I was working through. My choice at that time was to work at staying where I was for my family and because I thought it was the right thing to do.
Over the years, I worked through all of my other emotional issues (social anxiety/depression)... and eventually the only issue I had not addressed and worked through was my gender dysphoria. My depression had also gradually been getting worse over time. I did not want to hurt my wife and children by transitioning, but I didn't know how much longer I could survive if I did not do something. I became suicidal and spent every night for months fighting off the urge to kill myself, life and work just became very hard, and I withdrew from everyone.
Finally my wife got a real understanding of how close I was to dying, and told me that she would support whatever I needed to do in order to resolve this. My spiritual beliefs had also shifted somewhat over the years, so I no longer felt that transition was "wrong." So this past May I started electro and seriously pursuing all of this (working on my voice, building a support network IRL, coming out online, etc.)
It's funny. From a practical standpoint, my goal is to transition. My actual goal is to do whatever I need to do in order to become a "real person." What I have noticed in the process of pursuing all of this is that I have had to work through a lot of my anxieties and learn to accept myself and even my body (because it's the only body I have, regardless of its gender). I have had to be brave. I have had to learn to trust people rather than assuming the worst. I have had to plan and organize and schedule and discipline myself (things I am bad at by nature). I have had to stop hiding myself, stop covering myself up in fear of rejection, and be willing to be "out there" and let people think what they want.
Remarkably, this had made me a MUCH happier person to be around. I know wherever I end up, I am going somewhere good and I'm going to finally be "me," at long last. It is not an easy road, and my family is my major concern -- I want my children to still feel loved and safe and cared for.
So I suppose I waited this long partly out of fear of rejection, and partly out of fear of hurting people I cared deeply about, and partly out of fear of making a mistake. It was a dreadful thing to do, but I'm not sure how I would have gotten to where I am now otherwise; you can't move forward until you're ready, and I guess I did need all this time to become ready.
~ Jennifer