If I see things from this perspective, my options are pretty limited...

[Katelyn]

If I see things in terms of what I want to do and be in life, not regarding gender, my options are pretty limited...

I've for a long time wanted to be a businessperson, wanted to be involved in big things, be able to know big people, have lots of connections, etc...

My gender issues had derailed that.  I'm age 32. 

If I see things from that perspective, my options are pretty limited.  Business is one of the more conservative fields.  Your dealing with middle and upper class people, as well as a wide range of other people, and trust and respect are important.  If you appear as weird or strange, it will severely hurt your chances in this field.

Thus seeing it from that perspective, my options are pretty limited.  Either I make it as a woman (even if I have to lie about my past, or my own issues), or I have to stuff it all and pretend to be a regular male (good luck in how long that would last.)

Otherwise I have to live with a life of regret in terms of the stuff that I wanted to do in life. 


This is why I don't believe this BS about being yourself.  You have to make yourself, not be yourself.  Unless you either relegate yourself to the arts or to the more liberal ends of society, or just happen to be a genetic female, you don't really have the choice to live as non-binary IMO. 

Even then, how would cis-women accept you in their circles if you don't firmly say that you identify as a woman, at the least? (once again, exceptions for genetic females.)  And that is if you acknowledge that you are trans.

I don't want to live a life stuck in a minority position.  Why should my life be limited by my gender / expression / sexual orientation?

[VeronicaLynn]

Gender identify is separate from gender expression...Always remember that...you are always you, regardless as to what uniform you wear at work...even if it isn't an official uniform, it still is, even if it is one where you have some choices, like blue or gray pants and what color shirt...

In reality, sexual orientation is a non-issue in the workplace, these days, at least compared to gender issues...I think most people at work think I'm a flaming gay guy...even though that's all wrong, they are right that the LGBT label is something I'm under...

Being a bit mysterious on some of these things also does have some value...

[Julia-Madrid]

Hi Katelyn

There are no easy answers here, and to some extent it is reduced to a cost-benefit analysis where only you can determine which objectives best meet your goals.

If power and ego are your drivers then, sadly, it's pretty clear that, as a woman, you would need to demonstrate characteristics that would permit you to compete in this space with men.  I believe that, while ability is probably still fundamentally appreciated, a strong aggressive and competitive nature is fundamental.  Only you can state whether you are willing to become a woman and expose these characteristics or remain a male and retain what you already have.

Some of us have the ability to defer issues relating to our desired gender and convert the energy and emotional frustration into something more positive and constructive.  I fully knew I was trans at 25 but decided to bury what I saw as destructive and limiting self-realisation in favour of becoming a businessman.  By the time I was your age I had been a core player in two tech startups and was a director of both.  While my co-directors were mostly agreeable men, there were times where I found the aggressiveness to be troublesome on a level that was far more fundamental to me than one of boardroom power.

I fully agree with your comment "This is why I don't believe this BS about being yourself."  My experience is that you're totally correct about making yourself versus being yourself.  But like everything in life,  such an attitude has consequences which may or may not be relevant to your case.  If you hide behind a façade of the strong tough businessman it inevitably means that you lose contact with your true self and, moreover, some people can sense the façade.  One of my co-directors told me he always felt I was hiding. He had insight.  But perhaps you are willing to saccrifice truth for power and effectiveness - heaven knows that in generic terms this is what people have always done.   You may decide that deep interpersonal relationships are not relevant to you, but it would almost certainly have an impact on any intimate life partner relationship you may pursue.

A final observation:  you don't necessarily need to make the choice now.  I chose my moment carefully and transitioned at 45 within a company where my rights and position would be respected.  You could build yourself into a position of power, and a transition from that point would have a reasonable chance of preserving that power.  Success stories of this type do exist - I am sure you know about them - but you will always be known as the woman who used to be a guy.   This may or may not work in your favour.

I do hope you find a path that gives you what you want.  Happy to talk about it more if you wish.

Regards
Julia