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.

Be waaaaaay sluttier.

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…

Don’t start drinking
Don’t start smoking

Immediately get really fuckin annoyed that Linux is only in its sixth year of development and I still don’t know enough about programming to start developing for it to speed up the process of getting it to how I am used to it today.

On the other hand, though, start magically knowing a bunch of zero day exploits with zero research because of learning about doing these old ones in cybersecurity classes.

Nah mainly still being annoyed at how much tech has regressed. I’m spoiled by FLAC music and 4K video.

Try not to let the women I loved slip away and then inevitably lose them in entirely new ways I am sure. How do you even try to recreate the original conditions without inevitably changing them?

I’m not sure how badly I want to experience it all again with how bad it’s getting.

Oh and maybe get famous as a mystic who can see the future for things like where Saddam is hiding. And get those Saddam memes started a lot sooner.

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

Get medicated earlier. Throw out those awful Ayn Rand books. Start my favorite hobby earlier so I can have another few decades of it (there’s a good place to do so relatively nearby). Don’t send that email. Go back to Germany. Don’t let her follow me. Set myself up financially, maybe well enough to make a difference. Two years under a religious roof in a small town would be awful, so find peers that make it a little less so.

Life is not a straight path. There have been many times when something happened because things were just so. I used to lament all the imaginary paths I didn’t take; I’d have a hell of a ghost for the real one. I don’t think I could recreate my life in any meaningful way. Trying to remake decisions that I think of as mistakes just wouldn’t work. I know things about myself that might make things easier or harder. I’d get to make a bunch of new mistakes, that’s for sure. Planning anything major just seems impossible.

Buy bitcoin, learn a trade and do some coding on the side.

Retire before 2020 on a nice mansion with a big garden to invite my friends to ride out the plague

Short the housing market crash, buy bitcoin, disappear completely.

After freaking out for a bit, I’m moving away from my parents. I’m gonna do A-levels then do a social work degree I can definitely get work with that.

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

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…

In addition to the normal investment stuff (for me it would probably be Bitcoin, or maybe shorting the market in 2008), here are a few things I’d have to consider:

1. I’m now an atheist in the body of a teenager who is super involved in his church and private religious school. I’ll need to be delicate in navigating this, as I can’t just suddenly turn all those things off.

2. I’m being dropped into one of the toughest years of my life mentally. All the bullying I suffered starting at age 10 is finally manifesting in bouts of anxiety and depression. I’ll be better able to handle it, and even push back at the new round of bullying. I don’t know if I’ll still be friends with the same people.

3. I’m going to get another shot at my relationship failures, starting almost immediately with my high school crush. I know that my wife will be waiting for me sometime in the mid 2010s, but all the very many other chances I had are also in front of me. I’ll have the experience to better handle them, and I’ll won’t have the inhibitions and hangups of my youth (see point #1). The question is what to do if any of them turn serious, as again, it will be another 10 years before I will be able to meet my wife.

4. I’m going to get another chance to consider my career. I don’t think I would change it, as that would mean not meeting my wife. However, I know there are things I could do better that would make the first 10 years of my career more fulfilling.

Bitcoiiiins

Enjoy what’s left of the '90s, pursue emancipation, breeze through the rest of high school, get a job and buy some key stocks, start college, and make sure I’m at the right place at the right time to re-meet my husband ❤️