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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.

Don't start drinking
Don't start smoking

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…

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.

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

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

Bitcoin. Thousands of bitcoins.

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.

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.

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.

Not interested. I ain't perfect. But i like me. The past, including the fucking crap I did and the crap done to me has made me who I am.

I'm not rich or even cozy, but I'm a fortunate husband and grandfather. Blessed, really.

Bitcoiiiins

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

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 ❤️

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

Go "WTF, this can't be real" for a couple of weeks, probably. Wonder if this is one of those Groundhog Day things where the loop resets automatically.

My life got fucked up in my early 20s for health reasons beyond my control. Not sure what I could be doing about that. Try to remember some stocks or crypto that went through the roof, hope they'll still do that in this timeline, drop out of school to work early to have enough money to buy those? I actually wonder what the most effective job would be for that, I was never good at physical stuff but I wouldn't have much time to learn something that pays well before my body starts saying "fuck you".

I'll also crack a DAW and spent a lot of time on making music. It took me forever to figure out the tech/methods/music theory, and nowadays I don't really have the energy for it.

Edit: I just remembered that I did learn coding to a professional level. Shouldn't be too hard to find well-paying work with that back then, even without any official certification.

I'd be internally berating myself for not knowing any of the future lotto winning numbers.

Enjoy my late teenage years and early twenties without crippling self-doubts and lack of confidence. God, those years could have been so damn great if I hadn't stood in my own way so much. To have thirties' confidence with teenage and twenties' opportunities and freedoms...

1. Immediately get assessed for autism.
2. Learn to manage and make decisions.
3. I can now not fuck up with The Girl in a couple of years. (We're still friends today however if I knew why I was the way I was I'd be better able to steer the course).
4. Buy all the stocks dude. (not really)
5. Due to knowing why I am the way I am (see 1.), I'd be able to better deal with all The Stuff and make better decisions, or rather actually make decisions.
6. Play the sports with more application.

Immediately emancipate myself out of my abusive household, drop out of the born again Christian school that discriminated against me, work on getting a GED, and attempt to start a business after saving up.

Make the same mistakes and then get angry over it - I'm stubborn

Like here and now? I'm going to revel in the joy of my healthy body. Then figure out how the fuck to look like my driver's license picture and keep my head down while doing my best to enjoy life until I'm old enough looking to do something more significant.

Going back in time?

That's a nightmare. At least at 16, I would stand a chance of shifting my choices just enough to end up in roughly the same current life, but with better options. But the chance of that is low as hell for anyone. Like, for all the bad shit I've dealt with, without it I would have never met my wife, or met some of the animal companions I've had the great luck to share my life with when I encountered them as strays.

The only thing I'd be willing to sacrifice all that for is trying to prevent one of my best friends from killing himself about three years later.

And that would be worth it, but I'd be losing a lot in the process. Life isn't magic, where a do-over automatically means things are better. It's just different. Like, the fantasy is that you'll use your future knowledge to get rich and avoid all the bad things.

But the more you change your past, the more of the good you prevent along with the bad. And the ugly truth is that you still remember every fucking second of the bad. You don't leave it behind, you're still the same set of memories. Yeah, you'll be building new ones, but there's always going to be ghosts of your past casting shadows over your new present. And those new ones aren't going to be like they would have if you'd taken that path when you were actually that old.

It's still old you inside, so all the freshness of youth is missing.

Do-overs are terrifying, and the younger you'd be when you went back, the more horrific they get.

Earn insane wealth, fuck up other billionaires.

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

The stock manulplation is a must. Remembering volatile stocks like HMNY, crypto, shorting housing market, more importantly actually buying house post crash and before covid. Investing in apple and Amazon would lead to major returns even with a part time job.

Actively be more fit and eat healthier. I Did all the distractions and junk food the 1st play through I can skip them this time.

The next part is how I follow my post HS life. Do I go back to the same path that led me to my SO or do I choose a new life? Probably follow same path. I cant do it again without someone I trusted for decades especially now that I can be a better partner from the start, avoid the childish crap, and ill have the $$$ make up for the last timeline.
spend more time with my aunt. Tell my dad off sooner to help my sister avoid the years of therapy. Tell her im on her side (dad told her I hated her for decades).

Post locking down SO is where playthrough changes and ill play by ear.

Pre transition, in a small country town, decades before transition care is available... My child, unborn, and the only way to bring them in to the world is to suck up the dysphoria for decades (again) and not transition until late in life, and then re-marry someone that I had a really toxic relationship with. And my younger brother would be about to come in to the last years of his life as his mental health declines, before he takes his own life.

I honestly don't know that I could go through all of that again.

Travel to my wife's home town and find her.

Easy question. I'd skip all the small and bigger personal mistakes in my life. I'd also invest money into all the exploding tech companies and mine Bitcoin early on. And then see if being rich and "perfect" changes me or makes me happier or something. And since I can carry my wisdom over and don't need to study the same things again (from grounds up at least), I might be able to spend some extra time, train for another job, learn 2 more languages and a bunch of musical instruments.

Though from what I've learned from watching way to many science ficion movies, I'd probably end up making different mistakes. Or find out I didn't learn 5 languages because of a lack of time, but due to my character traits... And then somehow the movie ends with a confusing scene on how I might not have been born.

Go to a different highschool. Don't let them railroad me into remedial classes.

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.

Work out how to circumvent ID verification online.

No thanks.

I'd have to figure out how to reconnect with my Ex in order to create my son. Fuck that noise.

Look to see about graduating a year early. Go to community college for three years picking up as much math, computer science, finance as I can and maybe grab electrician or hvac if I can. As a matter of fact see if I can pick up some shop classes in high school before I graduate. Look into any programs to go to college in toronto or ireland or free rides in the us. Start an investment account at a deep discount broker and minimalize my possesions.

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

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.

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