What Would You Do If You Won $1.9B?
This post may contain affiliate links and Corporette® may earn commissions for purchases made through links in this post. As an Amazon Associate, I earn from qualifying purchases.

So… just in case anyone is having a hard time focusing today (no reason!! no reason at all!!), let's have a fun discussion: What would you do if you won the $1.9B Powerball? (Or, honestly, ANY huge sum of money?) Some questions to focus the discussion:
- Would you give any money to family or friends (and how much, and when)?
- What would you ADD to your life — vacation? private chef? personal assistant?
- What would you TAKE AWAY from your life, e.g., would you quit your job or redirect your time/energy somewhere else?
- What would be the top 3 things you'd CHANGE about your life, e.g., home, locale, something else?
Another few questions: How often do you buy lottery tickets (if ever)? Do you have a strategy (like a betting pool)? In general, how much do you gamble if you're in a place like Las Vegas?
For my $.02, we would give money to family and friends, for sure, but I'm not sure how much. I heard somewhere that 20% of your winnings is a good guideline.
(We'd also give to charities and causes, although I don't have any quick ideas on how much or to which ones — a lot would depend on the status of the world at that moment.)
Assuming we were able to stay anonymous in collecting the winnings, we probably would not tell anyone but parents and siblings how much we'd actually won. We'd also probably wait a bit after news stories (if any) died down about the winnings.
I think a whirlwind vacation would be the first thing on my list to ADD, certainly for the three months of summer vacation, but maybe we'd take the kids out for longer to travel (with private tutors).
Perhaps we'd get a yacht to make travel easier, and so we could bring family along and have easy travel plans for the gang… but we'll see.
A private chef and personal assistant would both be really nice, too! OK, and a daily fitness trainer would also be great. (I saw a meme that said “What I really need is for someone to follow me around and slap food out of my hand,” and, yeah, that too.)
What would I take away? In terms of jobs, I think I'd keep the sites running (although hopefully delegating more than I do right now, ha), and I'd probably expand the idea of it in terms of offerings — maybe a line of Corporette clothes or schmancy retreats or conferences.
(This would be more about hiring the right people to basically do everything. I always imagine the Kardashians basically waltz into the room, look over the products people have designed for them — maybe based on a group brainstorm session — and then waltz out, leaving the experts to actually do the heavy lifting. That would be nice!)
I feel like I spend a lot of time trying to organize my home, so I'd want to take that energy investment away — I'd probably add a household manager (who knows where everything goes and organizes it) to the list.
(We actually talked about this a bit on CorporetteMoms, based on one entrepreneur's description of her $27-an-hour house manager and how she hired her.)
My top three changes would be our home (definitely upgrading) and probably locale, although we'd see in terms of the kids and schools. (We already have our estate stuff set up; if we didn't that would be a top action item also.)
I'm not sure what my third change would be — maybe buying an apartment or home somewhere else with regular plans to spend time there. It's probably silly to think I could set up a PAC or think tank to influence politics, but again — you can hire people who know what they're doing!
In terms of gambling, I am not a big gambler at all. I buy lotto tickets from time to time, but in places like Vegas I'm terribly boring because I give myself $100 to lose. So, I'm done in five minutes! I also can't stand cigarette smoke, so spending time on the casino floor doesn't hold a lot of appeal.
(I haven't been to Vegas in years, but I was surprised how much I enjoyed it despite that — good shopping and restaurants, plus nice pools.)
How about you guys — what are your thoughts? If you won the lottery, what would you add, remove, and change about your life?
Stock photo via Stencil.
I’d switch careers into something that was purely passion-motivated (reporting, journalism, activism/organizing, writing). Maybe go to grad school or get a PHD.
I would buy a ton of cute Alo yoga legging sets and trendy/minimalist outfits.
I would sign up for the E membership at Equinox and spend hours a day in the sauna / steam room + doing yoga. It’s $25k a year instead of a few hundred a month, but you get a bathrobe.
I would maybe buy a house in Tahiti also.
That better be a hell of a bathrobe!
Hahahaha, right?!
I’m in a journalism-adjacent job and while it’s a perfectly fine job as those things go, I can’t imagine anyone who had a billion dollars choosing to work as an underpaid, overworked journalist. The only people I know who wouldn’t quit their jobs with that kind of money are academics, who tend to be extremely passionate about their work.
I would go Full Mackenzie Scott and commence giving it away pronto, after buying a pied a terre in Manhattan, upgrading my house here in So Cal, and setting aside enough to keep Hubby and me in ultra first class travel for life plus make sure my son is secure as well.
We live in a nice city that is near very poor, rural areas. I would set up a foundation to help alleviate the poverty: educational opportunities, health care (medical, dental, mental), grants for community development, even things like trips to DC for kids in school.
Aside from that, I would probably endow a chair at my alma mater, and my husband would do the same at his.
Family and friends? Beyond clearing debts existing at the time of winning (ie not anything racked up later), I see it mostly as ensuring that the wolf stays away from the door and doing things like paying for flights and accommodation on group vacations. Educational trust for kids, definitely – I loved my experience at a private college and would happily give that (and a debt free start to life) to nieces and nephews.
Love your style, Senior Attorney!
Quit my job immediately and spend my time volunteering, pursuing hobbies and exercising.
Give my parents like $50M.
Pay off student loans for any family and friends that still have them. I think most of our circle has paid off their loans though.
Set up trusts for college for my nieces and nephews, my husband’s cousins’ kids, and my close friends’ kids.
Upgrade our cars, but nothing super fancy for me. Maybe a Lexus or Audi. Not sure what DH would want.
Set up significant annual giving to charities I care about.
Do some home upgrades – top priority would be turning our unused back deck into a sunroom or screened in porch. But no new house. I don’t want to move (kids are settled) and we don’t need a bigger, fancier home.
All the travel, of course.
I think this is an unpopular opinion, but I wouldn’t buy a vacation home. Too much work to maintain, and I’d feel obligated to go visit regularly instead of going to fabulous new places. I might get a pied a terre in the big city we live a couple hours away from, but that’s the only property I can see getting used regularly and I’d definitely want it to be an apartment/condo so minimal maintenance.
I also wouldn’t want to fly on private jets because of the safety risks and environmental harm. I’d just fly business class everywhere and stay in really nice hotels.
Lots of yacht rentals too. We rented a (very small) yacht for a week this year and it was by far the best vacation I’ve ever been on. Would love to rent much bigger yachts and invite friends and family to join.
My husband has a huge extended family and although I probably wouldn’t give them a ton of money outright (except kids’ college tuition) I would love to pay for everyone to take a fabulous vacation together once a year.
Would love a personal chef, but I don’t think this really exists in my small city.
I don’t really think there’s much “stuff” I want. I guess if I had that much money I’d buy designer clothes because why not. But it’s not a priority for me.
If I won today, I’d quit my job and buy this cute winery that’s for sale back near where DH and I grew up, hang out in current city long enough to deliver baby with my OB whom I really like, and then move our whole lives to the winery and spend my days doing its books and baking random treats for guests to take home. Have a few more kids and as many dogs as I can keep track of. And one of those infinity pool master spa things and a sauna, so I can swim “laps” in my own backyard and then warm right up.
Off topic, but your OB is rarely the one who actually delivers your child. It’s whoever’s on call when you go into labor.
Finish out this pregnancy, then :)
My OB delivered my son and said that she delivers about 80% of her patients. YMMV.
I think if she really wanted that OB to deliver, with that kind of money she could make it worth their while to be available for her delivery!
There’s that, too!
Right? You could buy the whole practice!
Ha, touche.
Quit my job so fast, give a huge chunk to my parents, and spend the rest of my life giving it away (as well as traveling, buying homes, etc). I would never do laundry or clean my house ever again!
Oh and get a dog!
Go full Peggy Guggenheim and start an amazing art collection, being a patron of up and coming artists.
I’ll also start a foundation to start lobbying against Rupert Murdoch and try to undo all the harm he does in the world.
Plus selfishly, medical research into my post viral neurological disease.
I once told my boss that if I won the lottery, I’d give her at least a month’s notice before I quit to replace me. She said “That’s nice, I wouldn’t.” But yea, definitely quit my job and then hop on a plane to go spend a week in Paris. Then I’d probably take the first six months to do all my hobbies all the time–join the nice gym with the good classes and pool, swim, take the midday yoga class, go horseback riding every day–and figure out what I was doing with all that money. I’d definitely hire a maid and personal chef stat. Once I sorted it all out, probably lots of traveling, buy a beach house for my parents, and give a bunch away to favorite charities (arts and environmental things, probably). I would not work again. I am definitely not one of those people who needs a job. I’ve got plenty of hobbies to fill my time.
As much as I love my job, I would say goodbye to it and travel everywhere I’ve ever dreamed of experiencing.
I would pay off my daughter’s student loans and pay off her mortgage.
Our house is fine, but I’d move us into a ranch-style house in my favorite part of town, with a fenced in back yard for our dog.
I would hire a vegan chef to make us lunch and dinner every day we’re not traveling.
I already donate quite a bit to local and national non-profits whose work I believe in; with the new money, I would increase the size of my gifts.
I’d do my damndest to disappear for at least a year and lay very very very low. I’d pay off my debt and my small family’s debt. Then as anonymously as I could, go MacKenzie Scott while still living a comfortable but not ostentatious life myself.
Pay off house, move to long-desired nearby suburb to house with pool. (not that much $$)
Pay off daughter’s house and set up fund for her and other daughter.
Send enormous fund to veterinary care to Ukraine.
Ditto, domestic animal shelters and pay off some US politicians who will enforce animal rights; dogfighting, puppy mills, etc.
Keep working for a while.
Have another kid, move to San Francisco, hire a nanny or two, go on fabulous trips (bringing the nannies!). Get really into the opera. Take some writing and poetry classes, attend book talks. Learn to cook really fancy things, in my really high end kitchen. Then start a foundation and give the rest, minus a good nest egg and college funds, away.
Basics: housing and educational trusts for my siblings, in-laws, nieces, nephew, kids.
Make substantial donations to the causes I care a lot about: Girl Scouts, public education in my small town, a few arts organizations, access to legal services.
Make strategic political contributions to Democrats.
Buy an apartment in New York City; see a lot of theater.
Keep my job for now. Fund all the next generation’s college for siblings and cousin’s kids and my own. Then fund my friend’s start up, my other friend’s amazing organizing efforts, etc — basically no strings attached funding for women and particularly women of color around the world.
There is not much of my life that I would keep if I won $1.9 billion. My friends, a few pairs of sneakers, my St. John dress, and my dog would certainly come with me. I’d keep my gym membership. And I’d keep my house until I could find the perfect next house within my same neighborhood. I might actually keep the house, pay it off, and effectively give it to my close friend, who is currently (and forever) on welfare. I would definitely quit my job, start traveling, and start collecting art from talented young artists, as well as start a robust philanthropy program mostly supporting organizations with which I already have some affiliation or history. I’d help my friend start the bar he is trying to open. Maybe I’d go back to school and get a therapist’s license and provide reasonably-priced services.
I would take maybe 125 million (being very generous here) to use for myself and my family (outlined below) and become Mackenzie Scott #2 with the remaining 1.75 billion.
Spending for me:
– buy a house in my city (with parking and a roof deck). 2-3 bedrooms. I live alone but I can have a guest room, office or gym.
– buy a new car (probably an Audi)
– buy a beach house ~ 2 hours away from my city. My parents already have a beach house here, so I’m used to going here for most of my PTO, the upkeep (though I’d hire that out). 3-4 bedrooms so I can have guests.
– buy a condo in Florida for several trips during the winter. 3 bedrooms so I can have guests, my parents can winter there
– go on several really fabulous vacations a year, flying first class. At least 1 trip in the winter to the islands to thaw out and lie on a beach, drink umbrella drinks and do nothing else. At least one hiking trip, preferably to a national park I have not yet been to. A one overseas trips, I have a long list of places I’d like to go.
– basically buy myself whatever I want: clear out my wishlists of clothes, jewelry, beauty products, exercise equipment, hobby equipment, etc. Weekly massages and mani/pedis, monthly facials. A personal stylist. House cleaner and chef service?
– I would still work but either something part time or with a very generous leave policy so I have plenty of time to travel and spend time on my many hobbies. Or go to school full time (I’m part time now) but take a lighter course load.
For my family:
– give significant amounts to my parents and brother.
-pay off mortgages and student loans of my immediate extended family.
– set up 529s to completely cover undergrad for my cousin’s kids. Maybe a modest down payment or first car fund for each of them too.
– a very generous gift to my favorite aunt and uncle who are wonderful but have had bad financial luck outside of their control.
– my sister and I are both mid20s without kids, but would eventually fully cover their education/down payments too. Would do trusts for my all of my kids, niblings, grandkids and grand niblings. Trust would be enough that they don’t have to worry, but not so much they don’t have to work. Would likely include stipulations about continuing to work (I know someone who has to have 10 years of FT employment until they can access their trust). I would go back to working in nonprofits (which I did for years and loved, only left because it paid so poorly).
– I went to the same college as my beloved (deceased) grandparents do a nice endowed scholarship in each of their names.
– find a way to give generously to friends without it being weird or being taken advantage of. Unsure how to do this.
Give generously to environmental protection and conservation, anti-hunger, humanitarian aid, global human rights, US voting and abortion rights, and global disaster relief. I live in a poor city and would really focus on local poverty reduction, education, medical access and nutrition.
I would still do some criminal law but only a few cases that I found interesting and would support grants to others to do the same. I would also start a reentry program for newly freed prisoners. I would buy houses for our close relatives near us. Not sure I would stay in Florida. Maybe part time.
Too tired to go deep into this at this time, but one piece of advice I read for people who wins a significant amount of money is to hire someone to be your in-between person with all the people and organizations that will invariably hit you up for $-so that you can respond “please submit your request to _____. my money manager, for consideration.” Or maybe say it nicer, but, you get the idea.
I’ve day-dreamed out it for years.
* Clear my Covid-accumulated debts
* Endow a chair at my alma mater, and establish a few scholarship funds there, too
* Create a scholarship fund in memory of my grandmothers for nation-wide use
* Give a substantial amount to a Classics organization I loved from my high school days
* Donate substantially to every non-profit I’ve ever worked for
* Do some Nouveau Riche spending: house in my current town, pied-à-terre in New York, acreage in PNW, new car, jewelry, furniture, join all the museums, buy season tickets to stuff
* Travel, via Gulfstream of course!
* Continue to work, probably for Médecins sans Frontières
* Buy real estate and invest to generate income; establish FBO trusts for dear friends
Hm, maybe I won’t have time to work.