I don't want to derail what is likely to become another awesome thread, but what Jeanette and Nina and others have expressed has given me pause.
When I quit drinking and partying, I lost a whole lifetime of friends, activities, and associations. When I left university, I lost contact with amazing professors, colleagues, and I lost further educational opportunities, as well as losing social and political opportunities, and contact with many amazingly talented associates, with whom I socialized quite frequently. When I quit my profession to seek my way out of mental illness and my internal conflict, I lost tons of income, amazing relationships with stellar talents, as well as daily purpose and much creative satisfaction. When I announced I was actually a woman, I lost status, my spouse, my privilege, my history, my little empire, my self-concept, most of my remaining friends, and my future financial potential. I have gone through many changes in my life, and suffered huge losses each time, but l always got a fair return in exchange. I lost my ability to give birth to my own children as an infant, so yes, I do know loss. I have not had to face losing contact with my children or grand-kids, but I did lose the ability to be a matriarch. There has been no fair return on that loss. Nope.
Life is predicated on the fact that all we have, all we will ever be, will one day, be dust.
I am so very sorry for each and every sacrifice we face as we become authentic, I truly am.
But what we get in return, is ourselves. Our true selves. Without having that, what do we really actually have, even in a crowded room of people we love, if they don't really love the person we truly are?
Sorry to sidetrack, as this is a super topic, but I kinda thought the OP was intending us to answer about why it was we were transitioning, but that may have just been my take on it.
If it were titled 'what was your biggest transition regret or worry', I would have to say the loss of the love of my life. Hands down. But, what was the number one issue that drove me to transition? I needed peace of mind.
Even after all the losses, I do now have what I never had previously.
I have peace of mind.
I truly hope that when the dust settles in all of your lives, you too shall be rewarded with peace of mind.
I truly do.
Missy