It is important that what you decide is the result of conscious thought that takes into consideration all factors; positive and negative. The last thing that someone should experience is being outed. If that happens there may never be a chance to tell your story, your way.
The company that I retired from is quite supportive of the LGBT community. They also had a number of things in place for the trans community, including extending healthcare benefits and supporting transition. However, crossdressers were not really part of the program. If you transitioned, you went forward with it. What wasn’t allowed was crossdressing where you went back and forth.
Many would recommend a good therapist to help you sort out things and work through the process of figuring out what you need to do.