I'm almost 49. I haven't worked since Sept 07. I had 4 job prospects this month, and didn't get any of them. I have a few more weeks of unemployment extensions and little hope left.
I'm writing this more as an exercise in seeing what's really on my mind than hoping somebody will offer useful advice, or wanting a bunch of supporitive answers.
I have a Master's in Library Science, and worked for 15+ years as a librarian. 5 years into my career, I got a very good job as a head childrens' librarian. At that time, I considered myself a hetero-crossdresser, because I was sexually attracted to women. I didn't mind working dressed as a man, with a gender-neutral mindset, in a woman's profession; as long as I could be a woman in private and sometimes when I went out to gay bars. The director who hired me was obviously gay, and he probably looked at my plucked eyebrows and thought I was gay, when he offered me the job. However, some of the mothers took exception to having a queer man in the childrens' room, and they complained to the library board, and I did not pass my probation.
After I lost that job, I couldn't get another job in public libraries; and I wound up as a high school librarian, in a rural area, and I kept my queerness in the closet. I excelled at teaching computer apps and internet research to both students and teachers, and I gained somewhat of a national reputation by posting on librarian listserves. I was recruited by a prestiegous private boarding school, where I acted straight and was a woman when I went on vacation.
A student came out as gay, and the school reevaluated their policies, and I came out to the head of the committee, telling her I was a non-trasitioning transsexual. Kinda like I had a mild case of it, not serious enough to make it worth going through the pain of eloctrolysis or the expense of surgery. The committee head was supportive, and said it would be a plus to have me on staff to help students who were having gender issues. But, I think the upper management felt that gender queer was a step too far. Even though I already had been given a letter of rehire for the next year, with a raise - the Headmaster told me I would not be coming back for the next year. In those days, there were no laws to protect people from discrimination against gays or trans, so they could. They paid for me to go to the librarians' convention, where I could hopefully get another job at the placement center, and promised me good references. But the headmaster made it clear, they would fire me, if it came to that.
I got recruited to be a high school librarian, and moved to Colorado to take the job. Then No Child Left Behind passed, and, without a Teacher's License, I was suddenly unqualified for the job I had been doing so well for 5 years, and lost that job.
Two years later, I got a job as an elementary school librarian, in a two year program to also get my teaching license. There was a budget crunch after the first year, and the principal decided the best way to make his budget was to downgrade the librarian from full teacher to paraprofessional. Because of some union issues, to do this, he had to give me a bad evaluation. Even though I had good evaluations from the teacher education observers, the principal did a hatchet job on my evaluation so he could non-renew me, and make his budget.
I tried substitute teaching, hoping to make a good impression and get hired on the next year. But substitute teaching is hard, they blame the sub when anything goes wrong - so I got fired from that. Plus, it turned out that since I had failed to complete my two year program (being unable to, by rule, without a full-time teaching job), I was not eligible for any kind of elementary school provisional license or licensing program.
Then I got a job at a small for-profit college, as the librarian and teaching some classes. After a couple of years there, I had changed, the medical understanding of transsexualism had changed, and the laws had changed. I came to the understanding that I was trans, and perhaps would want to transition. I started on hormones and went to counseling. When I marched in the Pride Parade, I knew that I would want to eventually transition.
The hormones were showing some effect, I was plucking my eyebrows and removing my body hair, and had come out to some people. Plus, I was seen in the parade. The college figured that, if I transitioned, it would be bad for business. They only had 200 students, many military or ex-military, so any student that dropped out for any reason was a bad thing. If even 10 students dropped because I made them uncomfortable, the school would be in the red. Plus, upper management was very homophobic. They fired me on a pretext of insubordination.
I got a lawyer willing to file a complaint with the state labor board on a contingency-pay basis - but the lawyer was not willing to file a suit. It took a year and a half for the state to rule against me. During that time, I wrote two books and tried to get them published, and applied for numerous jobs. Those prospects kept me hopeful enough to keep going. But I am sure I am getting horrendous job references from my last employer.
Sometimes I applied as a man, and sometimes as a transsexual. I didn't get any interviews except for librarian jobs, probably because people considered me overqualified for regular jobs. Sometimes I wrote a cover letter saying, "I might seem overqualified for this job, but as a transsexual my employment prospects in libraries are pretty dim....". One part time library job in a private prison where I sent my male resume, when they called me for an interview, I told them I was trans, and had been living as a woman since I lost my last job, and wanted to interview as a woman. I told them that I had not been dishonest with the male resume, since I was legally male and my work history was under my male name - but because I was trans, I would be glad to get such a low-paying job as they were offerring, when I might otherwise seem overqualified. The interview seemed to go well, but no job offer.
I have reached sufficient desperation to have applied for library-technician jobs in the state prison system. I tested first place in the state on their objective tests, interviewed (as a male) well, and then flunked what they called the "integrity" interview - because I lost too many jobs in the past.
So, with my checkered work history as a librarian, I don't expect to get any library job in this economy. With my long work history as a librarian, I don't expect to get any job outside of libraries. The way companies do background checks, I don't expect lying about my background to get me a job in this economy. At my age, in this economy, I couldn't even make a living as a prostitute, if I could bring myself to do that. My books were rejected by hundreds of agents.
The most basic thing about being trans is that transition or surgery is considered a medical necessity because the trans-person would rather be dead than continue living in the wrong gender. If I could live in the wrong gender with the hope of transitioning someday, I might be able to make it. But now that I have lived mostly as a woman for years, but can't afford to replace my worn out wig, razor blades not to mention necessary beard cover makeup, or hormones - I've reached the point where I don't care to live any more. When the unemployment runs out, I can't face eviction and giving my dog up for adoption, even if anyone would adopt an 11 year old dog. I owe money on taxes I never paid on unemployment benefits, credit cards now in default. Even if family members could help me financially, they couldn't help me enough to make a difference. My car needs repairs I can't pay for, and next month I won't be able to pay a fine for expired plates. I'm not going to jail as a man, I'm not going to be homeless as a man, I'm not going to be heartbroken as a man. I wrote my suicide letter a year ago, and it's tucked away in my bible. I am going to keep on plugging until I reach the end of my rope, or a more apt metaphor, the end of the gangplank. But I don't have much more hope.
Last night I dreamed that I was singing kareoke, a version of Leaving on a Jetplane, but with my own lyrics. Some of the lyrics are still in my mind:
I'm leaving, for very far away
Don't think that I'll be back again.
So kiss me, and cry with me
Tell me you'll remember me
Hold me like you'll never let me goooooooooo!
I'm leaving, like a jet plane
I know I won't be back again.
Oh how I hate to go.