I am going to assume this "money is no object" scenario = ONE BILLION DOLLARS AFTER TAXES.
Instead of spending the next three or four years going through the mechanics of my retirement (so that instead of maybe getting $25,000 for this stuff in bulk and quickly, I can perhaps add a zero to it...as the current situation stands), I would just tell a friend who lives 72 miles from here to just come and "work" the whole thing for me, while I am ELSEWHERE and neither of us are "underfoot" in the way of each other. He would also be allowed to buy my property for $1, with an agreement to make his best effort to eventually sell it, when he no longer needs the facilities, and pay me two-thirds of the proceeds from the sale. (He is also a rather desperate guy who could DEFINITELY use, and be grateful for, the job...and yes, I actually trust he would be "good" for this arrangement, as well as for the commission for selling the other stuff.)
Most likely I would live in downtown Vancouver, as my PRINCIPAL residence. Do what I can to get a DUAL CITIZENSHIP.
Have a second home somewhere in the United States. Boulder? Ann Arbor? Seattle/Portland? Manhattan NYC/Jersey City/Hoboken or...?
More overseas traveling and perhaps, eventually, having a third home in some foreign place that I might really fall in love with.
These homes (probably condos inside high-rises) don't really need to be anything opulent or elaborate, NOT AT ALL - just places where I can be, and be comfortable with amenities such as media that I enjoy, etc. Why would I need more than maybe four or five rooms? Something like Neverland would be entirely irrelevant and rather impractical, even though I'd be able to easily afford it.
If I'm in a relationship, that person would likely live in one of my places, hopefully the Vancouver one.
Take some of this wealth, and give it to some friends I know personally who could definitely make good use of it, not to people who are just going to blow it on frivolous things. (I think I generally can tell the difference.) This would include some people who I know from JUB (perhaps even including some I DON'T know, but I just see in here), a friend in Florida who has been homeless for years and definitely not by choice, a friend in Detroit who is on the verge of homelessness, a friend in Ann Arbor stuck in a hardscrabble part-time-job life with no benefits, etc. Some help for my siblings, but not as urgent because all three of them are in situations which are at least adequate. A widow friend in PA who has no relevant means of support, and both are/were too young for any Social Security to be involved. $20 or $25 million should take care of all this stuff that I'd want to do. Of course this is an incomplete list...
In the world of political donations, emulate Sheldon Adelson - but not catering to "the dark side" as he does.
STILL eat at places like Golden Corral buffets, some chicken restaurants I know, some random Indian restaurant on Devon Avenue in Chicago, a gcreasy spoon diner in central New Jersey, etc. - because I like the food. Still eat bananas, Moser Roth dark chocolate from Aldi, turkey noodle soup made from leftovers, pancakes made from Bette's Oceanview Diner buckwheat pancake mix, Ritz Crackers, steamed vegetables, a Labatt's or a Blue Moon, etc. Still enjoy playing Scrabble in Indianapolis. Still enjoy going to the weekly music parties in Oregon when I have the chance. Still have the great conversations with people like centexfarmer, Sausy, mikeylove, thad1847, swerve, pianist, rationallunacy, GL *and* G-Lexington...as well as many other JUB people current and past (and including some I haven't even talked to much, yet)...I could go on and on.
A billion dollars isn't going to suddenly cause me to enjoy skiing, golf, or polo...or travel to Ibiza and Puerto Vallarta in lieu of more-authentic destinations (such as Montevideo, Croatia, Bangkok, Fortaleza, Cape Town, Rome, Warsaw, Toronto, Sapporo)...or lose my taste for Ritz Crackers, a nice occasional beer, or great chicken-fried steak and replace it with a taste for truffles and for some really ridiculously pricey $300 plate of exotic French food and 1948 vintage wine. That French plate isn't going to suddenly become my favorite food because it's $300. I would probably just rather have my own chili.
Not likely I would suddenly start going around in $3,500 clothes and $2,000 shoes - OK I'd probably buy $100 American shoes instead of the cheap Walmart shit that lasts six months, but I'd still be wearing thrift shop Hawaiian shirts and jeans, etc.
I don't need even CLOSE to $1Bn to accomplish all this.
And...oh yeah...I wouldn't work anymore.
Excuse me? The richer you are the more you get to travel, learn and experience the world and so much of what it has to offer. More money = more opportunities to live life comfortably by having all your basic necessities met and, yes, this enables you to "experience life to the fullest" since you are no longer laboring away to make ends meet. You can afford to branch out and follow your whims and explore.
Yeah. It sounds like something well-off people would romanticize about. How money really doesn't meant all that much, but following your heart will make you "truly rich." Oh please. As if following your heart doesn't require money.
