So lately I have been thinking ALOT about just posting a Pic of Jessica up on Social Media with a short comment about "this is me - sometimes"

Some background on this. I saw a post on here quite a long time ago about someone who actually did this, not that I can find that thread now though but anyway...
This stuck with me, as it really appeals to me. I'm super lucky enough to have a super supportive wife, and I'm 'out' to most of my close friends.
I guess I am just over worrying about this side of me & people finding out, as I really don't care anymore. I like to share my hobbies etc on social media and I would LOVE to be able to put up the odd photo of Jessica too. I don't dress that often, maybe once or twice a month. No inclination to go out in public really, maybe a walk round a park to get some photos or something, maybe out for a drink or a meal - but more to conquer that fear rather than anything else. I would like to be able to go to friends for dinner etc as Jessica but I still have this worry about what if people see me.
I have spoken with a few people about this, and most have been really encouraging about it. My wife is on the fence, but only because she has concerns how it could effect her job/career (Early Childhood teacher). There are a few people I know won't like it, my parents being one & also a couple of highly religious friends - but I'm really not too bothered about that if i'm honest. I don't believe it would cause a rift with my parents, just maybe a bit awkward for a bit. But hey if they don't want to see that side of me, they can always unfollow me right.

I really do feel that doing this would take a huge weight off my shoulders, let me be free to express myself openly. My wife & I have had infertility problems & have recently come to terms with the fact we are not having kids (been a long road!) and we both have a new outlook of do what makes you happy - which also leads into being fully open about this side of me and embracing it.
I'm coming up 40 next year & would love to have a big bday bash dressed as Jessica - which would pretty much throw it all out there anyway. I know that doing this could open up other issues - friends / employment etc. But I don't feel it should be an issue, as I have no interest in going to work dressed at all. My current workplace I believe wouldn't have an issue with it - which of course they shouldn't! But I do have in the back of my mind what about future employment - which this could affect.

Has anyone had any experience with this? Am I maybe missing a glaringly obvious pit-fall to doing this?
Any and All advice appreciated here - don't worry about offending me (you won't) I really am looking for honest opinions/advice here!

Cheers,
J