You win the lottery. Which of these activities do you most enjoy?

Take it that you’ve a life-altering sum – say $100 million – in a state requiring that winners accept their fortune publicly; thus everybody and his brother is gonna know. It seems to me that this will allow you to engage in any or all of about seven different categories of activity:

  1. Paying off all your current debts and setting yourself up for lifelong financial security.
  2. Giving gifts to loved ones (which can include paying off THEIR debts as well as giving them cash, buying them houses, etc).
  3. Making public donations to worthy charities.
  4. Making anonymous donations to worthy charities.
  5. Allowing non-worthy charities to solicit you for donations just so you can tell them to fuck off.
  6. Blowing large sums on hookers and blow. Or champagne and caviar. Or vintage cars & comic books. The point is to spend money on stupid crap.
  7. Telling your boss to eat shit and die.

Rank those categories from most to least enjoyable.

1, 2, 6, 4 3, 5, 7

After handling my own stuff would come helping family then extra dumb crap, contributions, etc. I like my job so while I’ll be happy to retire I don’t need to rub my balls on his keyboard or anything.

2, 1, 3, 4.

Since winning the lotto is pretty much my retirement plan, I’ve given this a fair amount of thought.

  1. Paying off all your current debts and setting yourself up for lifelong financial security.
  2. Giving gifts to loved ones (which can include paying off THEIR debts as well as giving them cash, buying them houses, etc).
  3. Making anonymous donations to worthy charities.
  4. Blowing large sums on hookers and blow. Or champagne and caviar. Or vintage cars & comic books. The point is to spend money on stupid crap.
  5. Making public donations to worthy charities.
  6. Allowing non-worthy charities to solicit you for donations just so you can tell them to fuck off.
  7. Telling your boss to eat shit and die.

I have anti-consumerist tendencies, so I have no desire to spend on stupid crap. No, an in-home fully staffed spa is not stupid crap, it’s job creation! :wink:

I happen to really like my boss, and would probably include him in number 2.

My biggest personal expense would be houses, because I’d get one near family and one where I actually want to live (and would spend most of my time in the latter). Ideally, both would be in the 1000 sq ft range.

1,7,2, then the unlisted option of assuming a fake identity and disappearing with the balance of the dough.

Answering ny own question, I rank the fun in this order:

  1. Setting myself up for lifelong financial security.
  2. Giving gifts to loved ones (which can include paying off THEIR debts as well as giving them cash, buying them houses, etc).
  3. Allowing non-worthy charities to solicit me for donations just so I can tell them to fuck off.
  4. Making anonymous donations to worthy charities.
  5. Spending money on stupid crap.
    Making public donations to worthy charities and telling my boss to eat shit are tied for last place; I doubt I’ll do either.

1,4,2, 6, and the rest are tied. I like my boss, so I would never tell him to fuck off even if I quit. I don’t do public donations, for the most part, and I don’t get any particular thrill out of telling the unworthies who call me up to beg to go away now, so meh. Actually I think simply repeating “put us on your Do Not Call List” would get tiresome. I would probably hire an answering service to tell people to go away and not bother me.

Giving gifts to loved ones is nice now, but I worry that even people I like now would treat me as their ATM, and then I would lose friends.

Regards,
Shodan

How about stupidly spending money on the usual stuff? Next time you search for something on Amazon, sort by price from highest to lowest and then buy the first one on the list.

2,1,4,6,3

I wouldn’t take any calls from half-arsed charities that would waste my money and I happen to really like my boss, so wouldn’t tell him off. However…if the CEO of the company would take my call, that’s another subject entirely. He’s a stone cold jerk!.

I"m not talking about doing the unwrothy charity thing over the phone. I mean say, allowing someone from the Family Resource Council to think I’m willing to donate half a million dollars, getting a high-ranking executive to visit me, making said exec explain his opposition to allowing same-sex couples to adopt, and when he’s done saying, “Wow, you’re so full of shit you cannot possibly have an asshole. Get out of my house before I release the hounds.”

1, 2, 6(cars & boats, within the limits of #1), 4.

1, 2, 4, 7.

  1. Paying off all your current debts and setting yourself up for lifelong financial security.
    No debts and already there.
  2. Giving gifts to loved ones (which can include paying off THEIR debts as well as giving them cash, buying them houses, etc).
    Pay off one debt and give equal amount to other kid, but they are both doing fine and don’t need to get into the daddy supports them trap.
  3. Making public donations to worthy charities.
    Only for small amounts to not stand out.
  4. Making anonymous donations to worthy charities.
    For bigger amounts.
  5. Allowing non-worthy charities to solicit you for donations just so you can tell them to fuck off.
    Allow? How you gonna stop them?
  6. Blowing large sums on hookers and blow. Or champagne and caviar. Or vintage cars & comic books. The point is to spend money on stupid crap.
    Have more stuff than time already. Might blow some on first class travel and fancy hotels though.
  7. Telling your boss to eat shit and die.
    Nope. Already have a sweetheart deal at work.

Ranking 2,4,3,6,1,5,7

I’ve never won the lottery, and I already do all those things (with moderation).

1, 2, 6, 4

No desire to tell unworthy charities to fuck off (waste of my time), to make public donations, or to tell my boss off (I like my boss and my job–I’d definitely quit, but with grace).

I understand that, even if the state requires winners to accept publicly, you can have an attorney set up a trust, accept the award on behalf of the trust, and disperse the trust’s assets to you, anonymously.

On the list, in enjoyment order:
4. Making anonymous donations to worthy charities.

  1. Paying off all your current debts and setting yourself up for lifelong financial security.
  2. Giving gifts to loved ones (which can include paying off THEIR debts as well as giving them cash, buying them houses, etc).

Wouldn’t happen, but in order of enjoyment if they had to happen:
3. Making public donations to worthy charities.
6. Blowing large sums on hookers and blow. Or champagne and caviar. Or vintage cars & comic books. The point is to spend money on stupid crap.
5. Allowing non-worthy charities to solicit you for donations just so you can tell them to fuck off.
7. Telling your boss to eat shit and die. [-- I love my boss!]

And your point is…?

You are less petty than I.

1, 2, 6, 4, 3, 7, 5.

Call me selfish, but myself and my loved ones have lived too poor and shitty of lives for me to not immediately make ours, and their, lives better.

I’m also not going to “blow” my money on frivolous things, I’m not going to spend 60,000 on Superman number 1. But spending 80 or 90 on a convertible car to enjoy the Florida sun? Yup. Upgrading my theme park annual passes to the highest one just because I can? Yup.

As for charity, what I would do is walk into a college bar and give them my credit card and say “pay off literally everyone’s tab right now” and then walk out without anyone saying a word. Same for dinner places too. I think it’d really make someone’s day.

My final two numbers are there because I’m just not that mean. I don’t have the time or the energy to pretend I want to do something just to be mean. Most of the time if someone is talking to me on behalf of someone else they are just doing their job and don’t deserve my wrath. I also happened to like my job and my boss. I’ll still (probably) quit, but I’ll turn in my two weeks and train my replacement with a smile.

7- I like my job. I might even stay on in a advisory capacity after I win.
5. This i would hate. the constant begging.