The keys to crossdressing success

One of the common misconception is that transvestism means your life is destined for a hard battle from one failure to the next. Dragging around your shame and guilt it seems as if crossdresser success and life success are mutually exclusive. Yet reality seems balanced on this question. While there may be many in the transgendered community who are struggling to come to terms with their transgendered nature and at the same time live a fruitful life, there are others who manage to do both.

What is crossdresser success?

I think the essence of success is being able to fully accept and live as who you are, while at the same time making a meaningful contribution to your family and society.

Recently on a forum that encourages crossdresser success, tekla made an insightful comment that with her permission I’ve shared:

I see all too often a linking between sex and the rest of the life deal. People can be successful, motivated, achieving people regardless of who they are attracted to. Nor, as a visit to the successful transitions website shows are there any lack of TS persons with PhD, or who are doctors, lawyers, professors and other accomplished careers.

I would speculate that the difference is not in who you are attracted to, or what your GID status is, but rather what you choose to do about it, how you work with it, incorporate it in your life or if you just sit somewhere and obsess about it.

I said somewhere else that most TS don’t need therapy, they need a life – and in the end, that’s all therapy will tell you to do, go out and be the person you think you are, the person that will make yourself (and maybe others) happy.

If you liked driving around to music, and I did, try riding a bike with some iTunes, or my favorite, a skiing soundtrack (Big band and rockabilly and bluegrass do very well) or just walk. You still don’t need a destination, I ride for miles and miles every day with no real point, just for the workout and to be out in the sun, and doing something. I take a camara, so I can take photos of some of the things I see.

I’ve always been ashamed of it like I am taking part in some demonic ritual.
Hopefully you will find a way around that shame, and it can become someother, better type of ritual, one of joy, acceptance, and exploration.

No matter what your looking for, I know that person, or persons are out there. Find out what kind of things such people might enjoy, and get involved in that, join a group or two, volunteer or something.

Well said tekla!

P.S. If you are struggling to find self-acceptance or the acceptance of others I highly recommend reading Helen Boyd’s book My Husband Betty.


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Lynn Jones
Lynn Jones
15 years ago

I think some of it comes from what you as a person want out of life. If you’re happy to dress at home (in secret or otherwise), that’s fine. Likewise, you may enjoy the ‘part time’ going out or even want to live full time. All of these are fine because it’s about your personal wellbeing. What’s right for you may not be right for me and vice versa. Do what you need to to stay level headed. There will be some hard choices along the way and I won’t lie to you saying it’ll be easy…. It’s like a… Read more »

Zosimus the Heathen
Zosimus the Heathen
15 years ago

I’d have to say that I’ve been very lucky in that I’ve always accepted my transgender tendencies. I remember even as a child feeling somewhat “girly", and while I sometimes thought that was a bit odd, I can’t say it ever really bothered me. As a result, I’ve always been very open about this side of me, and I’d have to say that this has yielded positive results far more often than not. The more you like and accept yourself, I’ve found, the more likely other people are to do the same, which in turn tends to make you even… Read more »

15 years ago

Yea, I agree. Get a life. What a person wears is not that big of a deal. It doesn’t change your intrinsic nature.
I dress in various outfits throughout the day depending on the task at hand. Wearing a nice outfit to work if I am doing something involving grunge just does not make sense.
Is that a man dressing as a woman?
Maybe it’s a person with a male body choosing clothing to wear, clothing I like, clothing that feels good, clothing that supports what I am trying to get done.

And halloween is going to be fun!

Zosimus the Heathen
Zosimus the Heathen
15 years ago

I loved your breakdown of four key attributes to have!

Why thank you.

Would love your thoughts, please comment.x
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