Transgender employment: responses and notes

Below are 20th century notes and replies about the article on transgender employment, presented for historical interest.

My work coming-out letter (1998)

Our upper management handled telling co-workers of my transition perfectly. Our department director called a mandatory meeting with my group and asked me not to come. This let people talk freely or express concerns without worrying about offending me. Our department director kept it very upbeat and light, but he basically said, “Here’s the deal. You may or may not like this whole thing. That’s your decision, but this is a work environment and as far as that’s concerned, I expect you to act professionally and respectfully.” Afterwards many people stopped by to tell me how well he’d handled it, and how everyone felt pretty comfortable about the whole thing.

For this meeting, our department director asked me to write a note, which I’ve included below. Please note that some terms and ideas are no longer up to date.

[Trans] fun facts

[Our Executive Creative Director] asked me to write up a little information that addresses common questions I get.

How did you choose your name?

I changed my last name to my first because I wanted some connection to my birth name, but I wanted it to be a little indirect. It’s also the last name of one of my favorite novelists (Henry) as well as that of a notorious outlaw (although I learned from the Brady Bunch not to idolize Jesse).

I chose my first name mainly because it’s common, but not too common, and because I had no major associations with that name. Some rejected names were: Fontasia L’Amour, Anita Drink, Amanda B. Reckonedwith…

Wow, so you wanted to be even trendier than Ellen DeGeneres?

It’s nothing new, but it’s been in the media more lately. Transgenderism appears throughout history and is documented worldwide. Medical advances in this century have made it possible for male-to-female [trans people] to achieve nearly identical physiology as genetic females.

Most people don’t differentiate between sex and gender. Basically, sex is biological, gender is social. There really isn’t much difference between men and women physiologically– just a chromosome and a couple of chemical levels. The bulk of the difference is social. From the earliest age, boys are expected to act this way, and girls are expected to act that way. Because these social pressures are so pervasive, they almost seem natural unless you step back and think about them.

So, this is a sex issue?

Because the word transsexual has the word “sex” in it, people often think it’s mostly about sex. While that’s sometimes part of it, [trans people] are usually more interested in getting their bodies to match their feelings. For me, it’s really about how I am perceived in day-to-day situations.

So, this is a gender issue?

Yep. There are many kinds of transgender people […]. Transgender is a general term for crossdressers, [trans people], female and male impersonators, drag queens/kings, [people with differences of sex development], gender dysphorics, and those for whom other gender labels do not fit. I usually tell people I’m [trans] to be specific, and that I’m part of the transgender community, which encompasses all of us.

I totally understand your situation. After all, I saw “Tootsie.”

No, it’s not like “Tootsie,” or “Some Like It Hot,” or “Bosom Buddies” or “Mrs. Doubtfire.” Comedies like those are funny because the male characters are forced by necessity to dress as women, after which the hilarity and hijinks ensue. The Ladies’ Night guys for Bud Light are funny in the same way, because in the real world they would never pass as women. Let’s hope I’m not humorous for the same reason.

So, more like RuPaul?

Um, no. RuPaul is a drag queen, as is Dolly Parton. They are entertainers who use excessive femininity in their acts. Torch Song Trilogy, La Cage Aux Folles, Priscilla Queen of the Desert, the Birdcage, Paris Is Burning– they’re all about drag queens. In the same vein are female illusionists whose goal is to portray a convincing act of femininity onstage and sometimes off. Maybe you saw The Crying Game or have been to the Baton nightclub. Those would be examples of very good female illusionists (they get touchy about the word “impersonator,” and you don’t want one of them mad at you.

So, more like Marv Albert?

Um, no. Marv had a crossdressing fetish of some sort. Same with Dennis Rodman, J. Edgar Hoover, and a huge list of other rather masculine men. Crossdressers get sexual or emotional satisfaction from touching or wearing women’s clothing. Almost all are straight males. The generally accepted number is around 1 in 50 men. Do the math, and that means there’s about one on every floor at here (except 41, now that [my ex-boss] left).

So, like a hermaphrodite?

I’ve been describing what I’m not to clear that up first. One last thing I’m not is intersexed. An intersexual (hermaphrodite) is a person who is born between (inter) sexes, having partially or fully developed pairs of female and male sex organs. “Intersexual” is usually preferred over the word “Hermaphrodite”. These conditions are genetic and occur about as frequently as twins. And no, I have no inside info on that urban legend about Jamie Lee Curtis being one.

OK, OK, you’re [trans]. What does that mean?

[Trans people] feel their body does not match the way they think and feel, and they seek to remedy this by changing their body to match their mind. There are almost as many female-to-male people as there are male to female. For some reason, FTMs are largely ignored– probably because they almost invariably are indistinguishable from genetic men. The effects of testosterone on females is more dramatic then the effects of estrogen on males (think East German olympic swimmers). Plus, I’ve never met a female-to-male whom I could tell without their outing themselves to me. And no, I have no inside info on that urban legend about one of the Victoria’s Secret models being [trans].

So are you, like, gay or something?

Gender identity and sexual orientation are separate traits, although most people don’t think about them as separate. There are straight and gay [trans people], etc. I haven’t felt like dating much anyway, so it hasn’t been an issue. In other words, there are also loser [trans people].

While [tans people] are different from gays and lesbians, we have many of the same issues, since we are all going against what society has constructed as appropriate gender behavior. The Stonewall Riot that sparked the gay rights movement in this country was instigated by drag queens, which is why they marched first in the Stonewall 25 parade. Several women’s groups have also embraced our issues, most recently the National Organization of Women. NOW has acknowledged that [trans people] totally disrupt gender-based stereotypes by forcing people to think about how much of it is merely social instead of “natural.”

How did you get this way?

Plain truth is, nobody knows what causes this, although theories abound. Many people believe there is a biological component. The most common theory involves hormones affecting fetal brain development. But again, no one knows for sure. Personally, I don’t really care what the cause is, anyway. I’ve felt this way as long as I can remember, and I think it’s better to look forward than backwards.

I don’t think of being [trans] as a blessing or a curse. I just think of it as a trait, like being right-handed or tall. Unfortunately, any trait carries with it certain social stereotypical presumptions. The misconceptions [trans people] have to deal with are that it’s all about sex, or that we’re just gay people who hate being gay. I just find that living and interacting with others as a female feels right.

How did you know?

I knew something was up from earliest memory. I have several specific memories from around age 4 or 5. I was frequently thought to be a girl when I was little, which I didn’t mind at all. By the time I was 8 or 9, I knew what a [trans person] was, well before I even knew the facts of life. I was scared to death to tell my parents how I felt, though. By the time I got to middle school, I was starting to have a lot of problems with classmates because I was effeminate, so I made every effort to act the way boys were expected to. This strategy worked, and I decided that I’d be better off putting all that behind me. Eventually, I decided I could manage my feelings without doing anything about them.

By a few years ago, I started to realize that I was getting more and more unhappy because I wasn’t addressing those feelings. I started therapy and quickly concluded what I suspected early on. I began planning for transition several years ago, getting everything taken care of prior to going full-time. This included telling everyone outside of work, having electrolysis to remove my facial hair (yeouch!), starting hormone therapy, growing my hair, developing a female voice, and some cosmetic surgery. I have also legally changed my name and all documents.

How did you go about this?

The medical community has developed its own standards of conduct regarding sex reassignment surgeries. They were created at a conference in the mid-60’s and were adopted as the world standard for sex reassignment surgeries. My transition has been done according to these standards.

How long have you been doing this?

I got serious about it three years ago, and I’ve been living as female outside of work for over a year. All my friends and family know, and everyone has been great so far. I hope you’ll continue that trend.

Why are you switching at work?

The final stage of the Standards of Care is the Real Life Test (RLT), which involves living as a member of the desired sex for a period of time. This is to help [trans people] determine if surgery is right for him or her. Most psychiatric professionals require a minimum of one year RLT before giving their approval for sex-reassignment surgery. That’s the stage I’m at now, and that’s why I came out at work now.

Sex Reassignment Surgery (SRS) is the final event in the sex-reassignment procedure. Although [trans people] have no reproductive organs (uterus/ovaries) the final result is cosmetically and functionally indistinguishable from that of genetic females. Some decide not to have this surgery, but I currently plan to have it.

What bathroom are you going to use?

I don’t want people to feel uncomfortable about this, so I have volunteered to use the bathroom in the workout room to avoid the issue. I’ve been using women’s restrooms when necessary for over a year without any problems– it’s just a bathroom, after all. If some great need arises, I’ll use one that’s closer, but I’ll do my best to plan ahead.

Are you doing this with insurance?

Our small numbers make [trans people] vulnerable to all sorts of discrimination, notably from insurance companies. They classify [trans health services] as “experimental,” even though the same hormonal therapy is covered for non-[trans people], as is genital surgery using many of the same procedures. The trend today is towards a full denial of benefits for “transsexual surgery and related services.” It’s exclusion #14 on Needham’s CIGNA policy. In other words, if a healthcare provider mentioned I were a [trans person] on an insurance form, my claim would be denied. So I don’t even bother trying to fight them. My transition costs have been out-of-pocket so far, and I don’t expect that to change. I’ve spent about $60,000 to date, with another $20,000 to go.

So, when do you appear on Jerry Springer?

Every group has its share of kooks and idiots. Unfortunately, that’s true of [trans people], too. Problem is, the morons who go on shows like Jerry Springer end up getting more media coverage than the doctors, lawyers, and other professionals I know.

For example, my four closest [trans] friends are: an engineer, a geology professor, an art student, and a computer programmer. They lead very normal lives and seek to blend into society rather than stand out. That is my goal as well.

The other group of [trans people] who get noticed are those who are visibly gender variant. While they should get as much respect as those who are accepted as female, they must deal with additional discrimination and harassment. They also have become the cliché of what a [trans person] is, since those who are accepted as female well do not get noticed.

I’m sure you have encountered several [trans people] without even knowing. I have been fortunate enough to go about my life without getting “read” or “clocked” very often. While I’m not ashamed to be a [trans person], I hope it eventually becomes a very incidental part of my life so I can get on with more important things.

When does your […] porno flick hit the stores?

Another thing that doesn’t help the misconceptions about trans people is the sexualization of our condition by the sex industry. Some people consider [trans people] exotic. Because all of this transition stuff is very expensive, and since a lot of teenage trans people are kicked out of their houses or driven out of school, they have limited financial options. Some turn to sex work to survive. And the porn industry is always ready to exploit fetishes, so it’s a lucrative option for some. I feel they have every right to do what they must to survive. However, it doesn’t help those of us who don’t want to be objectified or considered sexual novelties. Last thing I need is Eddie Murphy offering me rides in exchange for fondling my feet (as is his habit, according to my sources).

What if I call you the wrong name?

I know that’s going to happen. It took my family and friends a while to switch, too. Don’t worry about it. You’ll use the other name, other pronouns etc., even if you’re trying hard. I’m not touchy, and I try to have a very good sense of humor about the whole thing. I know this is prime comedy material, and I can laugh along with good-natured joking. A perfect example is [my boss’s] e-mail he sent me after I told him. THAT cracked me up.

What should I do if I have other questions?

1. Everyone is welcome to stop by and talk with me. I’m happy to answer any questions (well, almost any), and I assure you I will tell no one what you asked me. Obviously, I’m pretty good at keeping things secret.

2. If you don’t feel comfortable talking with me, you may ask [our department manager], who can then get an answer from me and get it back to you anonymously. I have also left with Jan a book that addresses the common questions in greater depth. It’s titled Transsexuals: Candid Answers to Private Questions by Gerald Ramsey. It’s by a therapist, and his emphasis is on therapy matters, but he covers all the big issues. While I don’t agree with the whole book, I think it’s pretty good.

3. If you don’t feel comfortable talking with Jan or me, I’ve listed some books, articles, websites and movies I feel deal with the subject in a good way. I have copies of all in my office, or you should be able to browse or buy most of these in a larger bookstore like Borders or in any of the gay/lesbian bookstores in Chicago:

Transgender Warriors, by Leslie Feinberg. (Beacon Press, 1997) Leslie is a female-to-male, and she’s compiled an excellent historical overview of transgender history.
Sex Changes: The Politics of Transgenderism, by Pat Califia (Cleis Press, 1997) Pat has written an outstanding outline of trans history in the U.S. since the mid-fifties, focusing on contemporary issues.
Conundrum, by Jan Morris (Henry Holt & Co.). Jan is a world-renowned travel writer. She has written a fascinating autobiography recalling her days accompanying the first expedition to scale Mt. Everest, up through her sex change and life after. It’s easily the best-written account.
My Story, by Caroline Cossey (Faber and Faber, 1991). Caroline’s autobiography tells of her sex change and subsequent career as an international model under the name “Tula.” Her appearance in a James Bond movie and growing fame led to her outing by the British tabloids. Maybe you saw her photo in an obnoxious Sauza Tequila ad a couple of years ago that said “she’s a he” across her chest.
“The Third Sex” by John Taylor. Esquire Magazine, April, 1995, pp. 102 ff. This is a very accessible article that should be available in Needham’s Info Center.
The internet has been an excellent resource for [trans people], since we’re scattered all over the country. America Online has the Transgender Community Forum (Keyword: TCF), and the other commercial providers have similar areas. Here are a couple of good websites:
- Diane Wilson is a friend who maintains an updated version of the transgender FAQ (frequently-asked questions) at: http://www.lava.net/~dewilson/gender/sstg.faq/index.html [as of 2015: http://dianewilson.us/gender/index.html]
The best movie on [trans people] that I’ve seen happens to be playing at [a local theatre] this month. It’s a Belgian film called “Ma Vie En Rose” (My Life In Pink). It’s in French, subtitled, and tells the story of a six-year old dealing with [trans] feelings, and how that affects his family and their neighbors. The director was deeply influenced by Tim Burton in his attempt to capture the mindset of a six-year-old. I highly recommend it, not just because of the subject matter. It has a very refreshing tone and look, and was one of the best films I saw last year– very funny, very sad, and very sweet.

I got really great feedback from this letter, because it was the right mix of facts and entertainment for my audience. If yours is right for your audience, it will make a tremendous difference in how smooth your transition is.

My first weeks full-time (1998)

Shortly after I came out at work and passed around the document above, I received notes not only from coworkers, but even partners and spouses of co-workers. One of these responses was from a freelance writer interested in profiling my work transition in the Chicago Reader, a weekly focusing on social and cultural news from a generally liberal viewpoint.

I’ve excerpted the sections that outlined why I was reluctant to do so:

Luckily, I’ve managed to keep this job and its badly-needed income level. I handled things about as well as I could, and I’ve seen an outpouring of support greater than I could possibly have imagined. This may sound silly and clichéd, but it actually restored my faith in humanity. However, I know very well there’s a side at work I don’t see. My work partner is ambivalent at best. For a while he asked to work with someone else, but now we have an uneasy arrangement to continue. Management has been great, but I don’t work with management on a daily basis.

Where you find this all fascinating, a lot of people are deeply disturbed by it and find the whole thing sick and repulsive, especially guys. It’s gotten back to me that some guys at work have expressed their horror “that someone would actually want to cut their dick off.” The fact they reduce the whole thing to that inaccuracy says a lot about how misunderstood I still am despite my best efforts. It also makes me wonder just how many people feel this way about me. A very smart woman said, “Don’t count on people at work for validation,” and I haven’t. But those sorts of comments evoke the bad old days of middle school, or the bad old days in 1996 when I pretty obviously transgender and would get ridiculed if I ventured outside.

As long as I stay at this job, I will always be “the [trans person].” Some people will get past that; most won’t. The only reason I’ve stayed in advertising (or even started, for that matter) is because I need a great deal of money quickly that didn’t require much mental energy. The people here who are disturbed tend to stay far away, but I feel the less attention I draw to myself, the better. The initial buzz is finally dying down now, and I worry an article might stir things back up.

The other problem with an article on me is that I’d basically be exposing myself to the criticism and judgment of an even larger audience at a time I think I’m still too fragile to weather that. I’d also be jeopardizing my precarious work situation. It can throw me into a funk just to have someone at work accidentally say “he” when referring to me. Even though I’m sure a lot of the Reader letters and co-worker interviews would be positive, I’m not sure I’m ready for strangers commenting on my looks or attitude or “lifestyle” with absolute candor.

This whole situation is just barely under my control now. To introduce an element over which I have no control makes me very nervous. I had a similar offer in 1996, when I was approached by Dateline NBC. They were looking for someone articulate to follow during a year of transition. They wanted someone just starting out. I couldn’t come up with a good excuse for having a camera crew following me around work, so I ended up reluctantly turning it down. They ended up profiling a very clever FTM Harvard student named Alex. Since then, he’s been slammed all over the place, including a 10-minute slamfest on Politically Incorrect on 3/19/98. In the case of Dateline, it was mainly timing, but also the privacy/fragility concern. I feel like a wobbly-legged newborn fawn not yet ready to face the jackals. My instinct is to hunker down in the grass till I’m stronger.

The profile that gives me even greater pause is the PBS documentary “Man Into Woman.” In it, a smart, humorous, gentle, and very emotionally delicate woman was kind enough to let a filmmaker follow her. A large part of it was about her work situation– she did graphic design in an open environment. She was able to keep her job, but eventually she left. This happens to almost all trans people. As with your thoughts for a story, they interviewed co-workers about their feelings. They spoke the thoughts I have no doubts are being thought by my co-workers: “I’ll always think of him as a man,” “guy in a dress,” etc. It was a great documentary, but very honest. Brutally so.

So much for what a hothouse flower I am. There’s another important aspect of privacy. While I will always identify as [trans], I want to keep the option of “going stealth.” Being accepted as female without question is a privilege few [trans people] ever enjoy, and those who do usually try move on to a life where no one knows. It’s hard to describe how powerful a draw this has: to be able to live my life in a way that feels right to me, in a situation where no one is able to judge me. The trade-off is you live in fear of being outed. I still have a lot of decisions to make, and I feel the more private I remain, the more options I have. I suspect I’ll end up being pretty public about my identity, but I have to look again at the price I’ll pay for that. In the meantime, I’m savoring the bliss of being accepted as female for a moment.

So, to sum up: I have declined, and it may well stay that way. However, I’d be happy to meet and talk at some point. I appreciate the interest and respect you’ve shown, and I’d be happy to answer any additional questions. I also have a few prurient curiosities of my own about the twisted lifestyle of a freelance writer.

Updates

As with most women who transition, I left the job where I transitioned about a year after I came out. After about a year of freelance, I took a job making about twice what I was making before transition. I am treated differently at my new job, and it’s allowed me to be much more comfortable. I generally recommend switching jobs, transferring, etc. if it’s an option.

Unfortunately, my experience is not typical. In order to have a chance at a smooth transition that does not cause a career setback, it’s vital that you plan very carefully. I can also say with confidence that the primary reason my work transition has gone well is because I pass pretty well. I know that’s sad, unfair, etc., but it’s a simple fact of the world at this time. Someday the world will judge people on their merits rather than their appearance, but most people are not that enlightened yet.

I consider myself very lucky to have avoided many of the pitfalls of work transition. Much of my luck is simply because of my race, income bracket, and level of education. However, maintaining my self-esteem, planning carefully, and focusing on appearance and assimilating into mainstream society allowed me to remain in corporate America. With a little luck and a lot of planning, you too can not only survive, but flourish.

Corporate America served me well as far as a good income during transition, but I am now in the process of moving into entrepreneurial work I couldn’t do during transition. It’s great to be able to take a chance without worrying about losing much-needed transition income. With any luck, this new direction will allow me to focus full-time on creating projects that will help people and make them think, all while earning a living. It’s scary, but exciting. Once you have successfully navigated transition, don’t stop there. you have done something most people could never dream of doing. In fact, you have been able to achieve your childhood dream– how many people can say that?

While you have that confidence and momentum, I urge you to keep pushing and follow your heart with the same energy and conviction ou used to pursue transition. Just imagine what else you can do if you can do that? Challenge yourself again– you know you can do whatever you set your mind to!

A reader’s advice (1999)

Most [trans people] are eventually faced with the same dilemma, take a job to actually finance the transition costs. Social welfare is usually the only choice, that and prostitution.

I have been in this situation, which is NOT enviable in the least, i have learned that there are much better ways to discover one’s sexuality, but I had no choice, it was either that or not be able to eat. I did it for 6 months and it left traces that will be in me for the rest of my life.

How to prevent that one may ask? By finding a job is the first and foremost answer, which is usually replied by: yes but i get refused everywhere i apply for.

Yes, it is true. I am in Computer Programming, my Resume can get me appointments in 24 hours, but when i am forced to give them my actual legal papers, POOF! No news of them and if I push the issue, they give me stupid reasons for not hiring me like: The client took someone from the inside to fill in the post, we are looking for someone that actually currently live in the correct city, no no, if you move it will not do. And tones of stupid things like that. But there IS hope.

First thing you have to do is work out your PHONE VOICE!!!! One thing I learned, voice is feminizable if you really work at it. Tape yourself and listen. One good way is to use answering machines services from your phone provider, you talk over the phone and leave a message. Listen to it and see how you sound over the phone. First time is traumatizing but with practice, you can have a feminine voice, especially over the phone. There are a couple of good voice feminization listed on Anne Lawrence’s web site at: http://www.annelawrence.com/speechindex.html and they do work, i managed to get a 99% pass rate over the phone and 95% pass rate in person… Very rarely, when i am tired or sick, those numbers may go down but with carefulness the voice is ok.

Getting a job:

I have discovered by chance that there is one work area that doesn’t look at what you look but rather at your performance and that is phone surveys and phone sollicitation. In one year, i went from earning around 6000$ Canadian to earning 12000$ canadian per year. Some might say it is not much, but it is still double what you can get from being on social welfare and so twice the amount of money for transitionning.

First thing is to find a place that do things like fund raising for charity organisations, those places will hire ANYONE that wants to work and will give you the chance to start learning the tricks of the trade. Me i spent 6 months there and learned. Then, Find a better place, one that pays a regular salary. Me I now work for a Survey firm in my town, it pays me good money for a steady shift (35 hours a week) and with patience and good work i made it to senior interviewer. I now have an assured job for my transition time. It is not the same as my old salary but it IS a salary.

I hope this info helps someone out there, those firms (survey, charity funding, phone clientele service etc) are ALWAYS looking for someone to hire and will hire ANYONE with good communication skills, no education needed and will accept and usually with a little talking understand what and who you are, me at work for everyone i am a woman even though they all know I am a transexual. On top of earning money I have the satisfaction of being accepted as I am.

J’s guide to work transition (1999)

My friend has written the finest document I’ve read regarding work transition, and she’s been kind enough to let me include it here.

She began her transition at a small company on the west coast, before leaving to pursue her Ph.D..

Thoughts about workplace transition

Before Transition:

Try to be yourself, long before your transition, specifically with regards to your feelings, and ways of relating to people. This doesn’t mean so much trying to display a flamboyant manner, as it means being especially (if not conspicuously) sensitive to people and their feelings. It is definitely possible to do this, while still keeping your ties with the old-boys-club, but people will notice, you will win friends, and those friends will have a much easier time accepting and believing the notion that you are a woman when you make your announcement. Besides this, it should help you to be a happier person, and less stressed out in the time when you know you want to transition, but can’t. It will also make things easier because you won’t feel the need to change your personality and way of relating to people when you transition; that can be really upsetting to an awful lot of people. It is very helpful if you can be like in Virginia Woolf’s Orlando, “Same person, just a different sex”.
Try to be outgoing. Try to be a hero. Never turn down a chance to save the day, even if this means working all night. Do it with a smile on your face. The more visible you are, and the more everyone has come to know they can count on you for work and friendly attitude, the more likely management is to realize that you’re an asset, no matter what your gender. Also, the more likely they are to realize that they’re going to destroy morale if they try to get rid of you.
The closer you get to disclosure, the more you will think that everybody knows. The truth is, you never know what people know until you tell them.
Keep in mind that the time leading up to your transition is far more stressful than the transition itself.
Try to have all the money you need for your transition before you go full time. Not only does this protect you, but it will also keep you more sane (i.e. you won’t be thinking, “Oh my gosh! If I lose my job I won’t be able to pay for surgery!”). You need to be as calm and collected as you can manage.
Be adequately prepared for your transition: facial electrolysis almost completely done, hormones for some time, etc. People really do judge others (especially women) based on their appearance. You will be surprised how much even something as simple as one electrolysis session to clear regrowth will impact how kind and respectful people are of you. Sad but true.
If you’re thinking of leaving a professional position (such as a research, engineering, professional, skilled position), it might be a good idea to wait until after your transition, to know what you’re getting yourself into. You’ll be surprised how badly women are treated in general, and a professional position can have more value than you can imagine. Not only will people accept you because of your skills, but without exception in my experience, acceptance and tolerance is directly proportional to education and status. The most cruel people of all will be people with less status, unskilled labor, and basically anybody who might see themselves as down-trodden. The most accepting people of all are the most advantaged and privileged. This is amazing, and startling, but in my experience it is true. I have never (knock on wood) had so much as a *doubtful glance* from Joe Schmoe, M.D. and Ph.D., straight, white, male, married, 2.5 children, and successful. I imagine it has to do with the fact that people treat others the way they’ve been treated themselves. I should also add that being able to go to work each day and be appreciated for what you do can really help you retain your self esteem if things get tough outside the office.

During Transition:

Make sure you have the personal moral support that you need in case everything goes off the rails.
Whatever you do, don’t just show up one day in a dress; this has to be the quickest way to get fired. Make your announcement through the usual management chain if possible, and be as professional as possible. You want them to know what an important thing this is for you, and that you’ve thought this through very carefully.
By the time you make it to this point, you should be absolutely sure of your decision; whatever you do, don’t oscillate between genders (if you want to be accepted in a conservative environment). Long before my own announcement, I was at a lunch get-together where I heard some of my co-workers talking about another person who had transitioned in another employ of theirs, but had oscillated. The gist of what they were saying was that they could manage the notion of transition, but “make up your mind!”. People in general have a very hard time with any notion other than the usual “two gender system”. A successful transition is going to depend on your understanding and empathizing with other people’s feelings, no matter how fascist you believe them to be.
Go in expecting nothing, because that may be what you end up with, and it won’t hurt as much if you do. Also, it will be ten times more wonderful if people reach out to you with love and open arms.
When negotiating your transition, and afterwards, be *really* over-compliant. Never mention your rights, if you are lucky enough to have them where you live, it will only make them angry and drive a wedge between you and everybody else. Besides, your rights are nothing but a nice thought, anyway. They can get rid of you anytime they want. Go out of your way to express how much you love working with your co-workers. You want them to know you’re one of them, and you want to find a solution everybody is happy with. You have to say that you’ll do whatever they think is right, even if in your heart you believe what they’re doing is wrong.

After Initial Transition:

Dress conservatively, perhaps even a little androgynously. You have a long process to undertake, to discover how you want to present yourself, and what kind of clothes suit you. If you aren’t a frilly person, you aren’t a frilly person, and while you’re trying to figure out if you are, you can’t go wrong with a pair of khakis and a pretty sweater.
If you are well-liked, etc., etc. and luck is on your side, the time to get fired / demoted is not when you transition; it will be a few months to a couple of years after your transition. i.e. when people genuinely start seeing you as a woman. The problem is that a woman has to be 10 times what a man has to be to hold a given position. When people *genuinely* start to see you as a woman, they’re liable to all of a suddenly start thinking, “Wait a minute. How did you get that position? You don’t have what it takes to be there. We need to fire / demote you”. The other problem is that you are going to be going through major personal changes during your transition (including the occasional crisis). They’re going to compare you to the hyper-focused wonderful person you used to be; while they may still see that you’re still a wonderful person, they’ll be very overly-sensitive to any temporary decline. Also, the more you become accepted as a woman, the more you’re going to feel social pressure (like pressure to devote huge amounts of your time to family and friends). As it is for all women, it’s going to become harder and harder to be a work-a-holic. Again, if they knew you in both roles, they’re going to see a decline, which you could avoid by being in a new position where nobody knew you before. There must be people who don’t run into these problems, but I’ve never met one. While in-place transition can be a beautiful experience, the best solutions I’ve heard are to either to change places (in a large company) to somewhere that nobody knows you, or transition in place and then a while later (before the above start to become an issue) find a new position. Assuming you have plans already laid out, you can even tell your present employer as part of your initial transition announcement that you’re going to leave them in a few months. This may even make them more likely to want to keep you in the short term, and having had some experience in your new role will definitely help to make you more comfortable when you begin your new position.
If you transition in a new workplace, absolutely, whatever you do, avoid telling anyone about your situation. You may think everyone reads you, but you may be surprised (see #4). The workplace can be the best gender cue; it can be surprising how much the context of your work will help your acceptance as female. In fact, in addition to this, it’s surprising how much people don’t want to know. They just want to know you for you, and at best (at the very best) they will see what you share as an irrelevant piece of very personal information, and at worst, they will feel angry and betrayed. This includes best friends and significant others (or perhaps this is perhaps most applicable to best friends and significant others). You will also discover that the same people who would have stood by your side, and told you how courageous you were had you told them before your transition, will never speak to you again if you share this news after your transition.
Try to prepare yourself for social ‘oopses’ you will make during the course of your transition; it is going to happen. Just try to see every mistake as a learning experience. Try to prepare yourself emotionally for the possibility that you might lose a position. If it happens, whatever you do don’t take it as a criticism of you or your skills. You are still the same wonderful person you always were, it’s only a symptom of the position and situation you’re in. As you grow and become more comfortable in your new role, things will become more and more comfortable.
Treasure every moment, now and forever, because you’re finally the person you always wanted to be. Look forward to the day that you forget all about your past, and are just living, “life as usual”.

Thanks again to my friend for that excellent overview! I’ll be adding my own thoughts soon, but until then, I’ve added my letter to coworkers below. You’re free to use any or all of it for your own letter. For those who plan to compose their own letter, I’ve included a few tips below.

A lot of people have written fantastic coming-out letters.

Here’s one from a worker whose company is headquartered in an English-speaking country, and her office is in the Middle East:

Coming out in a foreign branch office
https://www.transgendermap.com/reality/workletter.html