Finding a job can be especially tough for transgender people, and brings different challenges depending on what stage of transition you are in.
Transitioning early has obvious benefits of enabling you to establish your professional network and plan your career without the messiness of transition. However, it may also mean more difficulty in obtaining a job in the first place, compared to someone who gets established in their career before transitioning – which will also provide a financial safety net should their transition cost them their job.
Finding a job
Companies to work for
One good starting place to look for employers would be among the yearly Pink Dot sponsors, as these have made a public commitment to the LGBT community and are less likely to turn you away solely on the basis of being transgender. Small start-ups run by young entrepreneurs tend to be more LGBT-friendly in general. As usual, however, not all companies that describe themselves as LGBT-friendly are trans-friendly, and attitudes may differ among employees themselves.
Reach out and connect – as you speak with more people, more options will surface. Speak to supportive friends and family to see if there are any job openings that they might be able to recommend you for, in their own companies or otherwise. Some of them may be looking to hire for their businesses, and that sort of personal connection is a solid way of getting a foot in at the door. There are also people who work as life coaches in the LGBT community. You may wish to get in touch with them and see what advice or resources they might be able to point you towards.
Freelance work and other self-employment is also a good option if you have marketable skills. As your own boss, you won't need to risk discrimination when applying for a job, and the lack of official identity-based paperwork means that your transgender status can remain private when dealing with clients, especially if you don't need to meet face-to-face.
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Applying for a job
If you have transitioned but have not yet been able to legally change your sex, your job application will almost definitely out you as transgender. Most if not all job applications require that you put down your sex, and at some point they will likely need a copy of your IC.
Civil service jobs often also ask for your educational history. This will make it clear that you are trans if you attended single-sex schools in the past, even if you have since legally changed your sex, and is one case where having attended prestigious schools like Raffles Institution or Nanyang Girls' High would hurt rather than help your chance at employment.
Much of the time, knowing that you are trans might cause potential employers to discard your application right off the bat. While we cannot prove this for sure, many trans people report a significant drop in interview offers after transitioning compared to before. Unfortunately, there's not much you can do about this.
If your name is unisex or otherwise ambiguous, one option is to let them assume that you are a cis person of your assigned gender, which may help you at least get an interview and have the chance to prove yourself to them (after they overcome the surprise at seeing someone of a different gender than expected). Take it as a challenge! You could even use it as an example of your resourcefulness and creative problem solving.
If you are lucky, you may encounter an employer who doesn't look closely at the application and never comes to realise that you are transgender, even after filing paperwork with a mismatched sex and working there for a while. This has happened at least once. People are not always as attentive as you might assume, especially if you more or less pass as a cis person of your gender.
If you have already legally changed your sex and have sorted out the relevant documents (IC/passport/transcripts), you should let your potential employer know before you sign your contract, preferably at the final interview (as you will know they want you, and by that point it would be difficult for them to justify any rejection as not discriminatory in nature).
Do not make it out to be a big issue – how you react will often inform how they react. You can simply ask if they have any LGBT policies, and share your transgender status. This may have an impact on your insurance coverage at work, depending on the corporate insurer. (This is different from personal insurance, as corporate insurers have customised policies for the company.)
If you are stealth, you may still want to disclose your status to HR or your potential employee, as non-disclosure could be seen as a sign of dishonesty.
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Coming out at the workplace
If you are already working at the point you begin transition, you may need to come out to your colleagues.
In some cases, you may decide to keep your transition private at work. This is easier for those in less prominent positions, especially if you do not work in a role requiring much interaction with your colleagues or clients.
If you decide to come out at work, how you do so will depend on various factors including how long you've been at the company, your position in the company hierarchy, the size of the company, how close you are to your colleagues and bosses, and whether you plan to continue working there for a long time - if you're likely to leave soon, it might not be worth the trouble.
If you work in a multi-national company, check with your HR for official LGBT anti-discrimination policies. Most MNCs will not allow open discrimination, and if you face discriminatory behaviour after coming out, such cases can be reported to HR. If you intend to transition at a workplace with official pro-LGBT policies, you just need to have private conversations with your superiors, and make it clear how you would like to be addressed (pronouns, name).
If you work at a local company, the culture may be more conservative, and they probably will not have an official LGBT policy (or even a HR department). Identify potential allies at your workplace, especially amongst senior management. If being transgender is seen as "ok" with management, you will usually be accepted by other colleagues.
Ensure you have a strong relationship with your bosses before you share this information with them. How much you tell depends on your relationship. If your boss claims not to care or mind what gender you are as long as you do your work well, that would be quite a good situation. In an ideal case, the boss may make an announcement or email to the rest of the team, informing them of your transition and the change of name and pronouns. Support from the top reduces issues at work.
When telling colleagues, be discerning of cliques, and test the ground by talking about social issues that touch on personal moral values. At the beginning, you may want to keep to a "need to know" basis, until you have built up sufficient support. For those who are open, make your choice of pronouns, intention to transition, and change of name clear. For productivity at work, most colleagues just want to know what they should call you and get on with it.
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Disclaimer: Information on this site is for general information only. It does not constitute legal or medical advice and is not a substitute for obtaining advice from a qualified professional. We do not represent or warrant that this information is suitable, reliable, complete, accurate or up-to-date.