This is becoming a great thread. I'd like to comment using my journey as a backdrop for a fairly common trans example of leadership you might expect from my generation.
Based upon my personal experience, culturally we here in the US are pretty individualized, I find that most of the happy and successful trans-women I know well simply became an individualized woman in society: not necessarily a trans-women but simply women. I sort of straddle that fence and being here posting after 15 years since I started my transformation is a testimony to that. Of course, I still like to help and associate with my sisters and brothers because you are so darned cool.
My leadership is largely a product of my background: Transitioned later in life, never saw myself as a troubled of victimized individual (I say that in the face of an attempted suicide and that dissonance is still jarring), but once I embraced my womanhood I began to create a life very different than before but quite similar too: Economically independent, politically active, and willing to publicly advocate for 'my' causes (i.e. children and families, especially LGBTQ impacted). So, I put myself out there knowing I was/am somewhat androgynous and operated in a public way dealing with some headwind at first associated with broad-based community issues. In all this my trans status, which I fully own, but don't pay much attention to was/is an important but not the defining characteristic of who I was/am. Oh, it was for about three years but I am Rachel now and I'm no longer a transsexual; rather, like all natal women in my own way I'm just sexual.
I think in our society it may be a while before a trans-community person stands out nationally as one of our successful leaders. Instead, we'll do what most successful people do here in the US - we'll get on with what's important to us (that individualism again) and make our mark in life after/during the transition kerfuffle we all experience to some degree or another. (Note: for children and young teens I believe after they have transitioned there's little motive to be trans-focused once they are whole, YEA!)
As a leader in the past 15 years I have 'enjoyed" being recognized nationally in a TV special about my transition, have raised hug sums of dollars for LGBTQ children and families and more for straight children and families, have and am helping create better local, state and national policy for children and families, work with large foundations and non-profits to become more effective in today's economy, and so on. To put a phrase to it, "I'm a successful business woman who is a human and social services leader." However, I do none of this as a trans-woman per se, but as Rachel the woman. Me being trans is a footnote, all be it a proud one concerning how I got to womanhood, but not how I live my life, which I live as a 70-something woman who cares and pursues her passions.
I know quite a few very successful trans-women like me and we (mostly boomers) all seem to have taken the same path (self-selection I'm sure). Anyone of these women would make great trans-leaders . . . and maybe one of us should. However, when we passed through our transitions we were filled with a drive to make an impact as successful woman (and men), and we did. I think that's part of growing up with the 'great' post-WW II generation as our role models; they filled us with an un-satiable need to push for the greater good of our fair land and its people. Being trans in this inspired group required a period of transformation for us to fulfill our life's purpose as the real people we were/are. But keep in mind we had latched on to our paradigm for service and leadership pretty early in life. Consequently, by the time I was 30 I was well on my way to becoming a senior exec in a fortune 50. My transition impacted that timeline in my late 50s but only to the extent it took a couple years of adjustment and some refocusing.
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Well, I've written well over 500 words already and I'm not sure I accomplished anything; so I think I'll stop. Let me leave you with there have been many, many brave men and women who made my path so much more manageable and enjoyable. They were leaders, each and every one and I honor them as I do each of you. For I am certain that among you there are our emerging leaders of tomorrow, even today. Your leadership role will be different than that of many of my cohorts and what we saw in our lives; times do change and people respond.
As for Caitlyn, she has a wonderful platform to become a powerful and inspirational leader. Time will tell if she does in spite of the bumps and turbulence she is currently encountering. Well do I remember mine! I wish her well and hope she can be a great trans leader for us all. We shall see.
Rachel