Hi All,
I am a long time reader, and first time poster. My sincere apologies if I am posting this in the wrong area. It touches on a few topics, and I was just not sure which area it should go.
I have a question (actually a few questions), and would welcome candor from those who have journeyed before me. I am in my early 40s, a very successful businessman in my community, married 12 years with no kids, and well off financially. I have a good overall view on life, and a good sense of self-esteem. Of course, it has not always been an easy road. I have been in therapy for nearly six months to deal with an issue that I think many here can relate. I have known from very early on in life that I identify as a female. Without going into a lot of details, lets just say that until I went to counseling I was afraid to "come out to me."
To that last point, I have lived life as a stereotypical male, meathead, jock type persona. You can say that I have overcompensated for what I am now realizing inside. I don't beat myself up about it, as I just didn't get it completely until six months of intensive counseling. However, now I feel like Columbus when he discovered the New World, and I want to get off of this ship and on to firm ground, and this is where it gets sticky. I have lost several close friends to various diseases over the years, and know how brief life is. I don't want to live a day longer in this body than I have to.
My wife has no clue about why I have been going to counseling. She believes it has to do with parental and anxiety related issues. The latter is partially correct, but for different reasons, as you can imagine. I love her to pieces, and she is a bright star in my life. She has helped me through so many things, and I would not be the success I am without her (nor would I have even started counseling). She is also cisgendered, very straight, and my guess is that we may be friends should I decide to move forward with transitioning, but our marriage will cease to exist. Honestly, my decision to transition is solely and entirely dependent on my love for my wife and fear of loss.
My therapist (who specializes in gender identity counseling) has advised that until I figure out what I want to do, that it is not fair to drag my wife through my exploration process. She has said that I am free to decide what is in my interest, but knowing my wife as she does, that she believes the damage of having my uncertainty around transitioning will harm the relationship more than me just saying "This is what I have decided" and then working together to support each other during the transition. My therapist has also indicated that I need to be really certain about my decision as once I am out, it will be impossible to go back.
So I am stuck. I know the risks, and I know they are very real. Unlike many, I have been blessed to work for an employer that pays for hormones, GRS, and counselling. I could take the next couple of years to slowly transition to the woman I am inside, and align my life in a way it has never been before...and risk losing it all in the process.
So the questions....
...how did you know when you were ready to come out? How do I know if it is right? I hate being in this body, and every day that passes I want to be closer to the me inside. How do I know if the risk of losing my wife is worth the reward (and additional risks) of becoming female? How did you make the decision? How did you know when the time was right, especially if you are/were married?
And...do you have any regrets?
Thank you so much for reading my post. Going back to my Columbus analogy, I guess I am just hoping the land I am stepping onto is not quicksand

This is eating me up inside, and I am searching for solutions from others who have been there.
Thanks,
Toni