First thing I do is go tell my mom I love her. Then I come out to her. Then next time she gets a headache I ask her to get it checked out.

My first date later came out as trans. How unethical would it be to crack the egg if I got sent back in time?

I could honestly write a book at this point about what I would do differently. From taking studies and the idea of a career more seriously, to knowing who I am and having the words to describe it, to making better choices in my relationships with people.

I would change so much if I could. But I can’t, so the next best thing I can do is make the most of my time moving forward.

Since I now know the future, take out DJT before he gets security detail.

I mean, bitcoin obviously. It would be 2008, so a bit late to short the housing market. But all that can come later.

First thing - go through my room and throw out basically everything. I collected so much shit and none of it ever made me very happy. Then establish a good bedtime routine, so I would get 8 hours of sleep every night. Chop off the hair I was growing out long (I look better without it) and get a set of electric beard clippers (way easier than shaving with a razor, so I’d actually do it). Actually get some halfway decent clothes, and ask my folks if I could get lasik. Start lifting in the schools gym after classes, start going to the climbing gym across town on weekends, and cook real food for myself rather than eating the processed crap my folks were serving me. Establish a consistent study schedule for my classes, and maintain a much higher gpa.

Via these things, in about 6 months I’d be way hotter. Proceed to make passes at all my high school crushes.

By the end of high school, get admitted to a top 10 uni. Use the social skills and work ethic I’ve gained since college to work hard and party hard. Get laid a bunch and get hired by a FAANG out of school with a $250k starting salary, probably in SF. Work for 2 years, then pivot to a smaller company with the same salary, but working fully remote. Start digital nomading. Using the money I’m earning, buy some houses at cheap prices in awesome locations (will refi during covid).

And of course, search out all the good friends I have from my current life and re-friend them.

Bitcoin. Thousands of bitcoins.

Be waaaaaay sluttier.

Wait for the late 90s (I would have been in my late 20s) to start buying as much Apple stock as possible when they went almost bankrupt (yep, that Apple) and then retire barely a few years later, after I was able to purchase my own personal remote island with the fortune I would have made by selling those stocks? ;)

Or more realistically: don’t be a dick with that sweet girl I loved so much who loved me too. I was young and very much ignorant but I ended up being a real dick nonetheless and I have always regretted it.

So much more humanities stuff, and just skip drinking and smoking altogether

Come out earlier and be more comfortable in my skin. Live without worrying about others as much. Love myself more.

Don’t start drinking
Don’t start smoking

Actually have some fun in high school, like maybe do theater or something idk.

Well, since you didn’t mention going back in time I’m assuming that I’m still married and have a teenager so things are going to be pretty fucking awkward…

I’m suddenly a 40-year old woman in the body of a sixteen-year old boy. Overnight: the following things are true:

• My English is now good enough to pass as a native speaker with some subtle Japanese biases. Aforementioned English is also spoken very femininely, and child me has no Japanese accent. This alerts my parents, my friends, my teachers, everyone. Trying to do that accent voluntarily feels racist and horrible. I’m immediately caught out and everyone is asking me questions.
• My wife, who I’ve fallen asleep to every night, is now a 19-year old kid in Texas. I will miss her deeply and I cannot even grieve without arousing suspicion. Her existence at this point in her life is miserable. I know what she’s suffering through and which address she’s suffering at. Even if I went to go see her, she wouldn’t know who I am. I don’t look like me. She also hasn’t met me yet.
• I know full well that I’m trans and I know that my mother and father are hostile to such notions, and I know there’s nothing I can even do at that point in time. They will also start questioning how I went from struggling through Goosebumps, to wishing I could read Ryka Aoki one more time. I don’t have access to HRT and will get very depressed very fast.
• Most of my favorite music doesn’t exist yet. I will hum songs by Hitorie, The Beths, South Arcade, Battle Tapes, and Emi Nakamura under my breath decades before they’re written. This is a problem.
• The technology I use to make my art doesn’t exist yet. Digital cameras at the turn of the millennium were ass.
• I’m still 40. I’d look at my friends then, who I don’t talk to at all in the present day, and would abruptly drop them. They’re assholes then, they’re assholes now. I wouldn’t be able to connect with anyone my age cause they’d see a 16-year old boy talking about photography for a style of camera that can’t exist then.
• One of my two strokes gets undone. My body moves somewhat easier. However, I still walk like I had two. This alerts my parents, who have been keeping close tabs on my medical record.
• The house I’m living in now hasn’t been built yet then.

In summary, endless culture shock. I would panic forever. My life would immediately be one of those television shows where suspicion keeps mounting against the main character and there’s jack shit anyone can do to stop it.

I suppose I could tell her that in a month, 9/11 is happening and what transpires, down to Kevin Cosgrove’s phone call. She’d panic and try to contact the feds, and I’d just say that Bush already knows. It’s in the commission report that doesn’t exist yet.

That might actually radicalize them…

Hug my mom. Make sure she checks her cervix every 3 months. Hug my mom again.