My life would change, because I have a lot of ideas on how I could put large amounts of money to good use. If my friends wanted to come on board with that, it would probably be OK.
I already have good friendships with people significantly more wealthy than me, and it isn’t ever a problem, so it’s technically possible for such arrangements to work - the only tricky bit is the transition.
I want a flunky. At least for the first couple months.
For some odd reason I feel it would be appropriate to have my phone answered “Moon’s line, Flunky here. How would assisting you please my mistress”
It’s not that winning 20 million isn’t awesome. It’s that the odds of winning are astronomical and the Powerball is ALWAYS at 20 million. I’m just not willing to throw money away twice a week in perpetuity chasing after a longshot.
When the lottery gets to somewhere around 120 million and above, it approaches what’s called +EV. That’s when I’ll consider throwing a dollar or two away on the lottery.
The concept of EV, (IMHO), breaks down when we’re into numbers this large and it’s irrelevant for these discussions. But the benefit of having a hard cutoff of 120 million is that, yes, I’ve determined that anything less isn’t worth it for me to play and it keeps me from throwing bad money after worse week after week after week.
I would take care of student loans and retirement, set aside around 10k so I could bail my family out of one or two emergencies, and donate the rest.
I’m happy with my life and can’t imagine not working. My family is happy. Why shake up a good thing? There are better uses for that money than buying my cousins boats.
I always figured I’d split the Net amount 70-30. Wife and I take 70%, give away 30% to friends and family with the understanding that it’s a one time payment. Give my current house to my Aunt & Uncle. I’d rotate between 3 houses and vacations. After the first few years and the initial couple million, hopefully we’d be all spent out and then we’d figure out how much we need per year, and that’s our salary. Let a money manager take care of the details, we’d get a check every month.
I’m a jackass. I want everyone in town to know so they’ll come to me looking for handouts; that way I will be able to make absolutely clear whom I love and whom I despise.
First Congregational Church? I’m going to pretend to be Christian long enough to tithe 10% of my winnings to that institution, because I’m utterly certain they’ll not only do good with the money in ways I’d approve of, but that they’ll think of a way to do good I wouldn’t have thought of but still thing is a great idea.
Church of God in Christ? I’ll be having someone escort you from the building with orders to be as rude as possible without giving them grounds to sue.
I don’t think it would be a big deal as far as my friends. I already make 2-3 times what most of them do.
The way I’d set myself up is that I can maintain my current salary, pretax, by my post tax income from interest. Which should work out to about 3 mil invested conservatively. The interest from the additional money goes into two funds split equally one would be my hedge against poor investments and inflation and the other would be my stupid rich person fund. So while most of my life wouldn’t change, aside from moving home and quitting my job, occasionally I’d do something outrageous or stupid. From the second fund would come all of my charitable giving as well as helping out my friends or buying a gold plated yacht.
Actually Skald, now that you’re in this thread it occurs to me that you would be the perfect personality for my envisioned two month position as lacky.
Should the worlds ever align so that I’m in a position to offer the job (Lottery win 20million or more), how would you feel about a 2 month sabatical from your job?
I’m willing to pay either a flat rate or some weird scale based on the number of times your abuse of callers makes me laugh.
If I won, I’d want the lawyer and financial planner too. It sucks being broke. I wouldn’t want to go back to that.
I would help my immediate family and some friends. One concern I have is that I would be hearing from a bunch of assholes I went to school with claiming they were my BFFs and constantly begging for $$$. I have this because I am back in my old neighborhood and can be found easily.
Okay, I’ll play! 
The discovery that we had the winning ticket would be followed quickly by some basic planning steps-
Get the team together- our tax attorney, our CPA, our trust attorney. Lay out a basic plan of day-to-day cash, long-term investments, education trusts, other trusts.
Once everything is in place, claim the cash and do not allow our faces or likenesses to be used in any advertisement, promotion or press releases. If our names MUST be released by law, then fine- otherwise hell no.
We treat the lottery win like fight club- we don’t talk about it. Period.
We already work from home and have a lot of financial freedom, so from the outside it would be pretty hard to spot. If it was a “big one” we would buy an small apartment in Manhattan first, after paying off our current SoCal house. We would probably also buy a house down at the beach near my parent’s beach house, just as a vacation place.
We would continue to send our kids to private schools, so no change there. We would get another car, but nothing overly flashy- BMW I am sure, plus I used to drive a Range Rover and I’d probably get another one- neither vehicle gets a second glance in our neighborhood. We are pretty clothes-horsey, but the “average” eye wouldn’t be able to tell how much we paid for our clothes.
We go to Europe at least once a year now, so it wouldn’t seem too out of the ordinary to travel a bit more.
The real fun part- keeping it from our families. It simply wouldn’t be something we want to share with the group. The only exception would be a trust to meet the needs of my nephew who needs a lot of help. Not sure how we’d get that in place without my SIL wondring how it was possible.
The smartest thing to do would be to live our usual lives, but without the most typical day-to-day financial stresses. I figure if we lived on 1-2% of the principle, we should be fine forever. We are smart, well-educated and have access to experts in the financial field. Of course, that means we don’t play the lottery, as it is a tax on people who are bad at math…
I know a guy who played major league baseball and made a lot of money over the years. Everybody touched him up, and because he is a really nice guy, he “invested” in some real shit over the years. You would be shocked at how quickly you can run through $10 million a year if you don’t learn to say “no” or protect yourself with a good money manager.
This would be very easy to accomplish. Find yourself a law firm with a trust attorney and have them approach SIL with the news that a fund had been set up for the nephew by a benefactor who choses to remain anonymous and that she needs to forward all bills for nephew’s treatment to them.
She’ll still wonder, but all you have to do is remain quiet and wonder along with her.
If it was a substantial amount after taxes, at least $5M, I’d quit my job within a month. There is plenty else in this world I want to do that would easily fill my time.
Depending on the amount, on the low end, I’d maintain my current lifestyle, perhaps pay off my mortgage, perhaps move to a cheaper area, but either way, I’d vastly ramp up the amount of travel I do. A two month circle tour of Australia–possible. Visits to Tristan da Cunha and Nauru–done. Socotra. Yep. Etc. etc. I could go everywhere and would take advantage of that opportunity.
If the amount I won was really high, I’d take a portion of it and play angel investor in a couple of tech fields that I feel strongly about.
Alas, I don’t play the lottery and I can fantasize about what I’d do even without playing.
To me people overthink such things.
It’s really quite simple - it’s more “fun” to imagine winning the big one than to imagine winning a “normal” one.
Like a movie - am I willing to pay $10 to watch a made for TV Tuesday special? Probably not. Am I willing to pay $10 to watch Harry Potter play with his elder wand - yep 
For me it’s a pretty easy question.
I grew up in a rural area, where life is pretty simply, but for the last decade or so have been living as an expat out of my “growing up” circle. So I could just “go home” having made my money.
A couple of cars, a nice house, regular holidays - good enough for me. Doesn’t need to be anything lavish. Nobody would be any the wiser between “comfortable” andd “insanely wealthy”
Moirai, I remember hearing something form ESPN about broke athletes, so I could see it happening. I think an unlisted number, a PO box and a cellular phone would help.
I think it should be easy to tell people to fuck off but if we should sell the house we have now, I wouldn’t want the next people who live here to be harassed by money-grubbers.
I know I don’t need much but it would be nice to be able to afford some things. I’ve got one sister who needs surgery and a father in the nursing home. And I’d like to travel.