At the risk of sounding like a spammer, paying the absurd retail prices for glasses is silly. Take a look at www.zennioptical.com and see what you can get for, say, $10 instead. If you need corrective lenses, it doesn’t make sense to go through life without them.
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Weight loss surgery, and skin removal surgery afterwards if I needed it and a boob lift.
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I’d hire a personal trainer that’s not afraid to bitch at me and my family to get us to work out.
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Quit my job and become a professional student.
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Serious dermatological treatment for my chicken pox and acne scars and also the best high-tech skincare available.
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LOTS of travel.
Definitely teeth, fitness, and a course of improving reading.
In addition I’d spend a lot of money on entertaining, and being entertained. When I consider how my life is now one thing that needs improvement is my social life. I’d host frequent small dinner parties and then host all of my guests at the opera or a theatre production.
I would also build a music room and take piano lessons.
With $50 billion I would make my house into sort of an artists’ colony so that I could take my piano lessons from the live in pianist who is working on a master composition, or read and discuss Shakespeare with someone who’s living in one of the suites while she completes her novel.
Two chicks at the same time.
Oh wait, what was the question?
It would improve my… worldliness, or something like that. Hell, for that much cash I could have a lot more than two!
I’d have lots of plastic surgery done. As it is now, I only need one more scar on my abdomen in order to play tic-tac-toe.
I’d become a professional student, too. There are so many things I’d like to learn about that my head is spinning just considering it.
Ditto establishing an artists’ colony. Throw in a vegetable garden and I don’t know if I’d ever want to leave home. But if I did…
I’d go to England and Ireland, first. Then Florence and Rome. And I hear that New Zealand has some beautiful scenery. Australia, too. Bet that’s a great place to visit.
It wouldn’t take anything close to $50 billion but I’d get intensive tuition in all of the half a dozen or so languages I’d like to be fluent in and spend a few months in places where each of those languages is spoken. I’d also get a personal chef cooking only healthy foods in the right quantity for me, and maybe a personal trainer. I’d do a degree in History. I’d start a symposium where I brought people from all walks of life from all around the world to visit me, to teach me about their lives.
A trainer, a chef, and a nanny. I’d have more kids if I had a nanny to take some of the pressure off… and with a trainer and chef I hope I’d look better at the other end of all that.
I’d probably consider a tummy tuck or something similar after I was done having kids. I had a mild diastasis with the first, and it won’t get better on its own. My boobs are fine. My face is fine. My ass is fine.
I’d go to more expensive doctors, more often. Our so-called insurance is crap and I have a chronic condition that could stand closer monitoring. Ditto for the husband and kids, of course.
More beauty treatments. Pedicures, manicures, waxing, facials, massages. All of that fun day spa stuff.
I’d want a house with a pool so that I could swim for exercise and enjoyment. I LOVE to swim. I bet the kids would, too.
I am through with education. I have a Ph.D. I have two nearly-useless undergraduate degrees that I enjoyed the getting of. I don’t need any more of that. With the leisure that a nanny would provide, though, I’d have the time to do more self-educational reading.
I’d want to get myself in the best shape that I possibly could, realizing that to accomplish what I wanted to do with that kind of an opportunity, that I’d want to put my best foot forward. I’d hire a personal trainer to work with me and give me daily routines tailored to sculpting who I am outside now into something society might deem ‘acceptable’. I’d have a special diet set where I only consumed the specific foods proscribed and in the quantities proscribed until I reached the size/shape/form I needed. I’d weigh the pros & cons of LASIK as well as any minor sculptive surgery that diet & exercise might have issues addressing.
I’d take courses in Public Speaking and Force myself to do it. I might be laughed off the podium the first few times, but eventually I’d be able to confidently present a POV and/or introduce a speaker well.
I’d write and self publish a book. It’d be laughed off the shelves, but I’d pay very close attention to the criticism. Then I’d write a second book, learning from my mistakes… hopefully receive a better reception.
I crack wise occasionally. I’d make myself write 90 minutes of material and then I’d pencil-grind it down to one solid routine. And then I’d try it out in front of drunken people at open-mike night. And I’d get booed off the stage. I’d have what happened film so I could see what went wrong and I’d work on timing, delivery, and facial control until the next open mike night. And I’d keep at it until I could deliver in one night a rock-solid performance that the crowd enjoyed.
I’d be a better father. I’d be there for every concert, every event, and every camping trip. I’d learn what the other parents do and I’d do my best to learn it and possibly improve upon it until every kid and every adult had an amazing time each and every time. Snacks, additional help, and equipment: covered. I’d get a copy of the names, authors, publishers of my kids text books every September…and I’d read review them 2 chapters ahead all school year long just so I could be on point with their homework. (It might remind me of some things I’d forgotten too) At the end of the year, I’d donate those books to the school.
I’d Volunteer at shelters and at charities so I’d be a better person, because helping others does that
I’d take several courses in cooking so people wouldn’t turn up their nose when they heard I cooked dinner.
I’d take a course in massage so I could love better.
I’d take courses in auto-repair so I could be better / more self sufficient with my car on the road.
I’d take a professional driving/racing course so I could so what I’ve been doing wrong (and right) all these years.
I’d re-read Shakespeare’s Works and the NY Times Best Seller’s List for the past 10 years: Every. Damn. One of them.
And once I’d become comfortable enough to think that I could help, I’d lend my support publicly & privately to causes and candidates that I believed in. I’d try to make my ugly mug a rallying point of sorts or an icon or a flag for my POV.
$50 billion wouldn’t be enough.
$50 billion? That would just about fix my teeth. 
What others have said: personal trainer, get in shape, fix my knee, fix my teeth (which would go a long way towards eliminating the need for cosmetic surgery), fix my baldness, and get stylized and new-clothinged. Then learning, learning, learning. Take that French immersion course I can’t afford now. Go back to Japanese immersion. Then maybe Spanish, Ojibwe, Mandarin. Take story writing. Take art, especially figure drawing (if there’s one thing I want to be able to do before I die, it’s draw decent people from scratch, without a model or reference). Learn to drive well. Maybe even learn to fly (if they can cure motion sickness–think $50 billion would do?) Learn to fight–self-defence, situational awareness, martial arts (as much as possible at my age; hopefully more after the trainers get through with me. Oh, and learn to cook!
I’m afraid that kind of money wouldn’t make me a better person at all. I might improve myself cosmetically but if I can’t share it I don’t know how it would improve ME. Sure I’d fix my teeth and get new glasses (not implants, not interested in surgery of any kind!), hire a full-time chef well-versed in Atkins-friendly fare, get myself a personal trainer to help me get into shape, buy myself a house in a much safer area and a car that doesn’t break down . . .and from there who knows!?
But would it improve me? I don’t know.
I know. I’m a mess & way off those marks I set for myself. But just remember 3 things:
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Its hard to achieve anything without goals.
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Its as good a place to start as any.
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Even if I fail, in some small way, I’d have still have had a positive effect on the world.
Travel around kayaking which would keep me in better physical and mental shape.
Build a house with a gym.
Get all my medical and dental issues fixed.
Hire some high end hookers to get my sexual game back up to speed.
Hire a guitar coach.
Donate more to charity.
I forgot to mention getting my private pilot’s license. Ultimately, I’d learn to fly and buy a Gulfstream (or something similar that goes fast, can manage passengers and doesn’t require a co-pilot) so I could zip around as I saw fit.
I liked all of your post, but the part about learning massage so you could love better is just…sweet.
Damn, I hope you two aren’t contract lawyers or accountants… you are amazing enough to class anything as an educational expense.
Full-on overhaul, body and brain. (I’d finish my degree).
Hire a personal chef, a personal concierge to run my errands that I didn’t feel like running, organize my papers, and straighten up the house once a day, shortly after breakfast, and a pilot to be on standby to fly us to wherever we wanted to go in our luxury private plane, anytime we wanted to go there.
The personal chef would enable my family to eat healthier (and would enable my wife and me to have an easier time controlling our weight); the concierge would free up time to spend with the people we love, or reading books, or spending time outdoors, or whatever the hell else we wanted to do. The pilot and the plane would enable us to visit anyone we wanted to, any time we were in the mood to see each other, or travel the world. I’d be a hell of a lot more likely to get to the Taj Mahal or Angkor Wat before I die if I didn’t have to fly commercial.
I’d also do things like pay the lady who cuts our hair to come to our house every couple of weeks and trim us all up, rather than having to go to the salon. Similarly I’d have someone come in every couple of weeks to give massages to my wife and me, and give her a facial, manicure, pedicure, and all that. It might not make us better people, but we’d look and feel better.
Conveniences yes, improvements not so much
I’d have a kick-ass wardrobe.