You can just tell your doctor that you are socially transitioned, they won't know. Lying to gatekeeping doctors is morally good, just don't lie about any actual health related things unless you really know what you're doing.

I always tell doctors I'm a trans woman, even though I'm nonbinary, since doctors frequently refuse to give trans healthcare to nonbinary people and my physical transition goals mostly align with trans women's

When I first started changing my presentation, I did feel stupid. Somehow it's easy to get so used to the way things are that changing feels ridiculous. At the end of the day, they're just clothes (or a hairstyle, or finger nails, name, whatever) but it definitely doesn't feel that way. If you find a way to not feel that, let me know.

But I will say: that feeling goes away eventually. If you're drawn to present differently than you do, take small steps to slowly expand your comfort zone. I started by wearing feminine clothes for at-home dates with my partner. One of my female friends asked to paint my nails once and gave me her nail polish to keep--since then my nails have been painted almost 24/7. Eventually I bought women's jeans--no one could tell the difference but I knew and that made me feel better. I wear mascara occasionally. I got my ears pierced and most of the time wear androgynous earrings. I switched out my baggy t-shirts for more form fitting ones. Once I got comfortable wearing dresses at home, I started wearing them to friends' houses. Once I was comfortable there I started wearing them anywhere I felt like. Etc...

Don't overwhelm yourself, take it slow. Push your comfort zone but don't go so far so fast that you feel bad, it should feel okay the whole time. And if it's too much ever, just slow down even more or stop entirely for a bit. No need to rush, just figure it out step by step

When I came out, I worked at a medium size company, kind of late stage startup-ish. I was shocked how accepting it was. The only transphobia I encountered was unfortunately from the head of HR, who made changing my name in the system really difficult. Everyone on my team was really good about my name and pronouns and it wasn't a big deal. Outside the team, some people misgendered me but I didn't really care enough to correct them since I didn't have to work closely with them.

Now I work for a consultancy that has a reputation for promoting diversity, and it's been really great. I'm transfem nonbinary but present very feminine, and my coworkers mostly treat me like a woman which is what I want, when I do get misgendered at work it's usually she/her which is fun since I'm used to people assuming he/him. There are also many other out trans and queer people in the company which is great. Lots of my cis coworkers put their pronouns in their zoom names, email signatures, etc...

There are lots of accepting tech companies out there, just have to avoid tech-bro culture like early startups, and avoid giant enterprise companies where everyone is over 50