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Did I make a mistake? Am I doing the right thing? Is this the path for me? These are questions we usually ask and, if not, should be asking ourselves. Gender transition is not for the faint of heart. Early in my transition from male to female, I gave little thought to those questions. I was very busy buying new clothes, coming out to family and friends, and getting ready to return to work after a lengthy absence.

I was working on name changes, birth records. I was preoccupied early in my transition. There was a lot of ground to cover if I was to come out and be my true self. Endless doctors’ appointments. Sometimes I felt as though I should have had a tube from my arm connected directly to the blood lab. I had more blood drawn from me in my first year of transition than I had in my entire life, and I was under the microscope of psychiatrists, every move scrutinized. Should I sit in the blue chair in the doctor’s office? Should I sit in the pink chair? I felt like I was under constant surveillance, and worried my male side would pop out. It didn’t. I did a very good job at covering the male side of who I was. After a few years of this—the real life test—I received a letter saying that I was eligible for and had met all the criteria to move forward and have gender reassignment surgery. To say I was happy would have been a gross understatement. There it was in my hot little hands, the brass ring! The letter I had been working toward for the last four years.

For a brief moment, I hesitated to pick up the phone to book my surgery date. I read and re-read the letter countless times. Then it went into my file, and I didn’t look at it again for at least three months. Those three or so months were when the questioning began. I tried approaching people in my support system. Each of their answers was almost scripted: “Well, if you have any doubts then you’re not really trans!” I thought to myself that “You’re not really trans” was an odd thing to say. My question was still not being addressed. I had a new brass ring to reach for. “Is there anyone who has any doubts or second thoughts?”

One would think this would be a very easy question to have answered. It was my experience that it was the hardest question that I ever asked to find an answer for. It would appear that by the time I reached that stage in my transition, the medical community felt I was ready to move onto the next stage—surgery. I was supposed to be ready to take the final plunge into the mystery of becoming a woman. Hard as I looked for one person to say, “Yes, I had doubts; yes, I was terrified; and yes, I questioned if I made a mistake,” I never found them. That one person never appeared.

I knew they were out there. They didn’t speak. Now I had a new question. Why weren’t they coming forth with their experience? Shortly after I pulled the letter from my file again, I made the call to the surgeon and booked my flight. I was very excited to be on my way to have this correction taken care of, but that one question still haunted me. What haunted me even more was where were the ones that had gone before me, that were supposed to help guide me through this rocky period. It wasn’t long after I had returned home from the surgery that I found the answers I was looking for. I found where most brothers and sisters had gone; I found the answers to those nagging questions. The real work began upon my return home. The rigid schedule of dilating, the inability to get to the bathroom without assistance, the blood, the pain. I’ll never forget the pain. My hips and halfway up my stomach were yellow and black from the bruising. The simplest act of trying to watch television became agony. The deed had been done; there really was no turning back. I couldn’t go home now .

I was now in this surgically created wonderland that I called my female body, laying awake at night still asking, “Did I make the right choice?” Right choice or not, this was where I was! Life carried on seemingly uneventfully, get-well cards came, flowers arrived, people phoned. It was almost like I had celebrity status, but that was short-lived. Then again I was alone with my thoughts. That one nagging question rang through my head. Did I make a mistake? I felt a bit depressed so I made a couple of phone calls trying to find a counsellor to speak with. Oddly no-one would accept me. I called my old shrink and he said, “Our work was finished. I was only there to help you until you had surgery. You’ll need to find another doctor.” The hunt began for another psychiatrist. I thought it would be easy, but it was not. Depression by this time had taken deep root; eventually I was diagnosed with chronic depression. What followed was not at all what I had expected. I stopped going outside, I quit playing softball, I closed my kickboxing gym. I became a recluse, subjugated in my own home by no one other than myself. My depression deepened. My rigid schedule of postsurgical care went out the window. Then another nail struck into my coffin of depression! My surgical area had grown shut!

I had less than two inches of depth. I was horrified. What had become of that soulful, full-of-life woman that I had known at the beginning of my transition? Where did she go? How could I get her back? The question of whether or not I had made a mistake was secondary at this stage; my priority now was to find the real Carolynn again. This was a daunting task to say the least. I was lucky enough to have been referred to a doctor by a dear friend of mine. He saw me, and I would love to say that we got off to a great start. We didn’t. He called me obese and said I needed to exercise. I didn’t see him again for at least a year. When I finally did return to see him, I was a complete train wreck. I had put on 40 to 50 pounds, and I was depressed. I still had the problem of the surgical area having grown closed. After some time with this doctor, things started to look a little better. Over the next few years things began to change. I felt my old self returning, I re-opened my kickboxing school, and started to socialize again. Then my doctor threw this at me one day in a session. He said, “Carolynn, you know you can go for a surgery revision and get that fixed.” My jaw hit the floor. I was in shock. I thought it was a one-time shot, and if, like me, you screwed it up—well, you were screwed forever after.

I felt this little fire of hope begin to burn in me again. I had purpose in my life again. This time, I wasn’t going to screw it up! I jumped through all the hoops, made all the phone calls, and reattached the tube from my arm to the blood lab. Honestly, I felt happiness shine again in my life. Finally, the day came for me to head off and have my surgery revision. I remember arriving at the recovery house and seeing another group of me’s from six or seven years ago. They were all driven. They were all happy and they all had no clue what was going to happen after.

Not from a place of ego, but rather a place of a caring sister, I took it upon myself to inform the other guests that this was not my first time. I had to go around and return their jaws to the closed position. I became very close with two of the girls there. One very young woman was maybe 17 and there with her mother, and another was my own age and all the way from the U.K. They listened intently as I told them my story and the pitfalls to be aware of. My young friend even went so far as to take notes. Our surgery days came and went. We all returned to the places we respectfully called home. A few days later, I got a phone call from my friend in the U.K. She was in tears and panicking, saying, “I don’t know what I have done.” We talked for what seemed like hours until she said she was feeling better. It’s been some time since I have heard from her. As for my young teenage friend, I got a call from her mother on several different occasions telling me what her daughter was not doing, and how she was feeling depressed. Considering myself somewhat of a hip person, I started to text my young friend. We worked out some things via texting and email. My life continued fairly normally. I was again into my routine of dilating and postsurgical care. Only this time I had a new-found appreciation for what I had been given, and the question had finally been answered.

Did I make a mistake? The answer is No! I did not make a mistake. Do I have regrets? Yes, of course, I have regrets. I do not feel I would be classified as human if I didn’t. Do I miss my old self? Sometimes. The question of whether or not I made a mistake at this stage is irrelevant. The more pressing and more important question is, am I able to be happy living as I am? At time of writing, I have an afternoon appointment coming up with a personal trainer at the gym. Later this evening, I’m going out for dinner with some friends and there is this very handsome man I met who asked me on a date.

The answer is, yes, I am happy and can live this way. The question I had chased and tried to have answered was the wrong question. After a few years of wrestling with it, the question “Did I make a mistake?” became irrelevant. The question I should have been asking myself all along is, “Can I be happy after I have made these final choices?” People have surgery everyday. Most don’t ask themselves, “Did I make a mistake?” If my own personal experience is of any use to anyone, then ask yourself the right questions first. Don’t ask “Did I make a mistake?” or “Am I doing the right thing?” Ask yourself, “Can I live happily once these decisions have been made?” That question is far easier to answer than the others.