I got fired from two jobs due to transitioning, after having only been out of college for 2 years. So I basically did have to start at square one all over again, and I hadn't had any surgeries whatsoever at the time when I was looking for my first ever post-transition job, so I feel qualified to say something.
First of all, change your legal documents. Usually it's not that hard, doesn't take much money (like maybe a couple hundred dollars in court costs at the most,) and it makes EVERYTHING that much easier afterward, because you're no longer under any legal obligation to ANYONE to disclose your past once your name and gender are legally changed. The only person you usually have to tell at work is HR, so that they can do a background check.
Second of all, be persistent. It took me 4 job interviews before I was finally hired for one. Keep trying. Never give up, and don't let yourself fall into a "this will never work" depression. Just keep applying, keep interviewing, and eventually something will come through.
Thirdly, be confident. This can be VERY hard for someone who is newly post-transition and not very confident about their passability. That's where I was at while I was applying for jobs. People called me "she," and I seemed to pass most of the time, but I was still getting stared at, still had like no makeup skills, no female socialization, I was nervous as hell, and I spent the entire first 3 months or so fending off panic attacks because I was so worried about whether people knew, whether they were judging me behind my back, whether I was just kidding myself by trying to be seen as female by them.
Here's another thing, though... these feelings only faded with time. They didn't fade because I somehow magically became more passable and more cislike, they faded because finally, after 4-5 months on the job, I finally started internalizing that people didn't care. That they were accepting me exactly as I was. And slowly, life returned to just being life. The fears faded, and it stopped being "oh my God, here I go in front of all of these people again, I hope I pass today," it just became my normal routine... just a normal person going to work for a normal day. The only way that this will happen is with time. With slowly getting used to your routine, and slowly gaining confidence as a result. Keep moving forward, and eventually you'll wonder what you were ever worried about.
Finally getting a job as myself, and being accepted as that self, was the biggest improvement to my self-esteem of anything that I've done in all of transition.
