What Would You Do If You Won the Lottery?

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1. 1) Pay off our mortgage and reno loan

   2) Pay off mom’s mortgage (which I hold, so I’m really doing myself a favor, ha)

   3) Help a dear immigrant family I know get their feet under them

   4) Get mom a new(-er?) car

   I’d probably give up my job if we could afford it long-term. I’d honestly love to be a costumed interpreter at a Revolutionary-era historic site. Husband would keep flying for the airlines because the effort-to-salary ratio is too good not to.

   1. Threadjack, but your husband is a pilot? Can you tell me more about his career path and what his work-life balance looks like. My daughter. She’s only in elementary school now so things could definitely change, but we travel a ton and it’s consistently been her “what do you want to be when you grow up?” answer since she was in preschool.

      1. Sorry posted too soon. I meant to say, my daughter is very interested in becoming a pilot!

         1. Not the OP but most pilots fly first in the military. It is very hard otherwise to get the required hours to be a commercial airline pilot.

            1. +1

            2. My cousin is an AA pilot. He got his hours in working as a flight instructor before starting with AA. So it’s definitely possible.

            3. There are also colleges with professional flight programs that get you the hours required. I work at Purdue and we’re pretty well known for our professional flight program, but other institutions have them too. I know a number of kids from here go straight to commercial airlines after graduation with no military service.

            4. Not true! Most commercial air line pilots graduate from a great university like Embry-Riddle Aeronautical University, build hours flying smaller planes, then upgrade to a major airline as a first officer after a few years

         2. I remember one of my friends getting her license to fly before I had a driver’s license! I’ve met several women who learned to fly and who didn’t end up becoming pilots (or astronauts which was my friend’s ambition), but who still had jobs or careers linked to aviation.

      2. Always happy to talk to aspiring pilots :) My grandfather was a pilot, my dad was a pilot, my mom was a flight attendant, and my husband is a pilot – we are an aviation family for sure!

         HOW TO GET IN
         Traditionally, there have been two ways to get the necessary training: join the military or go to one of the couple colleges that specializes in aviation (Embry-Riddle, North Dakota, there might be others). The colleges and the necessary flight hours are eye-wateringly expensive; 25 years ago, the cost was $100k for the 4 year degree and the flight certificates. For the military, your daughter would do ROTC at any college of her choice (or a service academy, if she’s very athletic). She could go to college for free on an ROTC scholarship, but she won’t know if she got a pilot “slot” until her senior year; she’d have to be ok with any other job in the military in case she isn’t picked for aviation. While the Marines do have some fixed wing ( = airplanes vs rotary wing = helicopters) assets, her options in the military are really the Air Force or the Navy. The Navy is more fighters, while the Air Force has cargo jets, flying gas stations, radar planes, and more in addition to fighters. For the last 20-ish years or so, flying for the military has come with an 8 year obligation that starts after the pilot finishes 1.5-2 year flight school, so basically a 10 year commitment. That big commitment is because the cost is so expensive and they spend so much time training baby pilots.

         I don’t know if you’ve seen headlines about the looming pilot shortage, but because there’s a mandatory federal retirement age for pilots at age 65, the airlines have been trying to get creative with how to fill their ranks. All of the legacy carriers (= United, American, Delta = the big guys that have been around since the beginning of commercial aviation) have now opened their own flight “academies.” You’ll have to research these. I don’t know anything about their requirements (do you need a bachelor’s to enter? what if you have an associate’s and will finish your bachelor’s while there?) or their cost (is there a cost? if not, do you owe a commitment like the military? student loans?) or their target audience (mid-career job changers? 18 year old students?).

         WORK-LIFE
         Most people have no idea what pilot and flight attendant schedules look like. Unless they’re trying to earn extra money, they work typically no more than 15 days per month. A pilot or FA signs up to work a certain number of hours per month. As a baby pilot, she’ll “sit reserve” (on call). Brand new pilots get the super short calls – e.g., be here at the airport in 2 hours. For those calls, you have to be located within X minutes of the airport. When you’ve got a few months under your belt, you get more notice, and can be within X hours of the airport. When you get enough seniority, you’ll get a regular schedule. What’s “enough?” When my dad started flying, the airlines were full of WWII pilots and he had to sit reserve for years, and the pay is pretty crappy. Today, baby pilots are only sitting reserve for 6 months because senior pilots are retiring so rapidly.

         A regular schedule is called a “line.” You hold a line and you bid a line. When enough pilots above you have retired that you graduate off reserve, you’re said to have enough seniority to “hold a line.” Certain lines always go to the seniormost pilots – the ones with a 36 hour layover in Turks & Caicos, for example ;) A baby pilot won’t have the necessary seniority to hold that line; the more senior pilots will snap that one up. A young pilot will be able to hold a crappy line with icky hours and destinations, but it’ll be yours and you can plan around it.

         Pilots and FAs put in their bids every month for the different lines based on what they want to do. Have a dentist appt on the 21st? Great, arrange to be home that day. Recital on the 30th? Ditto. Pilots and FAs always “go out on a trip” for 2-4, rarely 5, days at a time. You, passenger, are only going from hub-to-destination, but your crew has other places to go, so that plane will get freshened up and go out again in 90-ish mins. The crew will do 3-5 “legs” in a domestic day, depending on the length of legs.

         This may vary by airline, but FAs and pilots sign up to fly a number of hours/trips per month.

         Pilots and FAs have federally mandated crew rest requirements, so there’s a limit to how many hours they can work. At the end of day 1, the crew will check and see that they’re staying in the Airport Hilton or whatever tonight, so they’ll call for the airport shuttle, and they’ll pick them up, and each crewmember will check into their own hotel room, all paid, and they’ll meet up in the morning in the lobby and catch the airport van again. The rooms are paid but food is not, but there is a modest per diem. And they’ll do this for 2-4-5 days: fly to 3-5 cities per day, stay at a hotel, go back to the airport and fly to another 3-5 cities… Yes, it’s absolutely exhausting. But you choose your schedule! And say you personally hate the Hilton in Cleveland that the airline has a contract with…well, just don’t bid Cleveland again. And you can choose how many days you’re home between trips.

         My dad died when I was young (car accident, not aviation) and my mom was always able to help out and be as hands-on as she wanted to be (she was an awesome Girl Scout Cookie Mom <3) and she could always make recitals and that sort of thing. But there were plenty of things she wasn't around for because she had literal places to be. The older you get, the better your schedule gets (because it's just you and your friends bidding that Turks & Caicos trip). But when she was home, she was available during the day, which was great for helping out at school.

         DOWNSIDES
         Did I mention this life can be a grind?

         Need I mention winter storms or computer meltdowns?

         The aviation business is cyclical. Is there money to be made for pilots? Yes. Is it guaranteed? Nope. Wait half an hour for some airline to have some crisis. My mom is fully convinced that airlines never actually make money if you balance out the bad years with the good years. And what happens when there's a downturn? Layoffs and furloughs. Which means your income dries up and the only thing you're good at isn't a viable way to make money. For a sample crisis, American Airlines is in a bunch of pain right now because they had ordered a bunch of new Boeings that are years delayed and so AA is flying older planes that aren't as fuel effecient which is decreasing profits – airline execs have to have crystal balls to do their jobs well. AA is hurting so badly they've turned off their pilot hiring, even though they have the oldest pilot workforce in the US.

         Union contracts expire and you'll work years without a contract. Strikes are not uncommon.

         There are other ideas just on the tip of my tongue, but I can't remember them, so this will have to do. Hope this helps!

         1. Thanks so much for all the info! This is super interesting and good to know.

         2. This was FASCINATING!

   2. I’d retire my family and go on a year long round the world trip to include walking trips through Ireland, beach trips to the Riviera, and seeing the Aurora.

2. I’d start by hiring enough people to manage my life (housekeeper, gardener, chef, driver) so I can obtain a childlike lack of responsibility over household maintenance and chores of living.
   I’d probably go live at our vacation house and hire a few tutors for languages and skills I want to learn.

   1. Big Charitable Donation: Planned Parenthood
      Designer: I wouldn’t even know where to start. Probably by hiring a stylist!
      Vacation: Europe for a month straight. One city.
      Home purchase: Hiring an interior decorator and spending ALL the money on home furnishings.

3. $50 million after taxes? I would put $30 million into long term investments (and would hire a fiduciary to advise me there), with the intent of making my children beneficiaries.

   The $20 million left?

   $1 million would pay off all the student loans, mortgages, and miscellaneous debt for my household, our parents, and grandparents, and it would pay for college for all of the children.

   $3 million would go into a variety of semi liquid accounts for health care cost for the grandparents and parents, and general living expenses for each of them.

   $4 million would do the same for us. I would spend from this bucket for any immediate purchases or vacations and invest it in index funds. Our current retirement around are robust, so this would be for ongoing expenses like property taxes and living needs. Probably would splurge on a new EV, a couple of vacations to Iceland and Scotland, a personal trainer, and a personal stylist.

   $2 million would easily buy us a house in our favorite neighborhood, and let us refinish anything we wanted to and still be able to furnish it nicely.

   $10 million would fund a charitable trust or foundation.

   1. Also, I would keep working at my current job.

4. Quit my job ASAP.
   Buy a large home on the coast of Maine and hire the staff to maintain it. My family had a vacation home there for years, but had to sell it due to it falling into disrepair and maintenance costs exceeding rental profits. It was also too small to properly host friends, so I’d want a big enough place where I could host friends and family every summer.
   Take at least one big bucket list vacation – maybe Antarctica
   Get a pied a terre in Chicago – we live a couple of hours away and it would be nice to have a home base in the city with convenient access to ORD
   We already travel a lot, so I don’t think I’d want to up the frequency much, but would definitely upgrade the style (first class tickets, luxury hotels, etc). Would regularly charter yachts and invite friends and family to join us.
   Make sizeable donations to our kids’ former daycare and our public schools
   Offer to help our nieces and nephews with colleeg

   All of that seems like something you could on a post-tax $10M though. $50M is kind of unfathomable to me. I don’t think I’d want my kids to become mega rich so I guess I’d set up low seven figure trusts for them and start the process of giving most of it away.

5. Two words- Lazy River

   1. lol love this

6. I’d give to an autism self help organization (not one trying to cure it through eugenics), and maybe partially fund some experiments in group family living – in my dreams it’s like the Villages with the golf carts and walking but for families with adult autistics living with them.

   Vacation: Italian villa as the home base with lots of side trips to other countries

   First home purchase would be a 4-bedroom apartment in NYC; we used to live there and I miss it so.

   1. I like this. I always daydream about creating a model village with a center square, walkable streets, small but attractive homes, native plants and flower beds, and garden plots.

   2. It makes me think of the legacy of John Langdon Down or Thomas Hopkins Gallaudet and their colleagues and families.

      I keep hoping someone will sponsor some aesthetically beautiful and diversely culturally competent alternatives to PECS (maybe there are obstacles, but PECS always feels like such a “first try” attempt at what it does).

      1. does PECS = picture exchange communication system here? definitely another area that could use improvement!

         1. Yes! The illustrations are sometimes really counterintuitive to me or just kind of weirdly ugly, which I think is not a shallow consideration when something is a big part of your life (especially with especially sensitive people for lack of a better word; I was excruciatingly sensitive to this kind of thing as a child for some reason!).

            1. my son is verbal but I sometimes make our own – he has a choice board for dinner with stock photos of food (or sometimes specific brands like Bagel Dogs), and I used to do a visual schedule with little pictures of his therapists. I’ve always written the words on the pictures since he was an early reader.

            2. I love this, both the visual schedule and the illustrated menu. Something about it just sounds so reassuring.

7. With that amount of money, in the immediate term I’d: 1) pay off our mortgage 2) help our siblings/pay off their mortgages (no debt for our parents). I’d also outsource every bit of household maintenance that we could.

   Medium term: set up charitable trusts for causes important to me (racial justice, womens rights, child welfare domestically and internationally).

   Long term: I’d quit my job in favor of volunteer work, and spend more time traveling domestically and internationally.

8. I’ve already done the spreadsheet. “Hm, how much tax is withheld, okay, then what about paying off CC… fund the IRAs… What’s left.” I have “nouveau riche” spending first, like jewelry, nice clothing and a new car. Then I’d buy some real estate (I rent now) but not go crazy. The kind of house I can age in, since I”m already 55. Then I’d contact my alma mater and ask how much would be needed to fund a $5k scholarship (or $10?) for my major. I’d give to the county animal shelter system. I would set up my investments to generate $100,000 a year income, and I would travel. One of those ride-share but in a private jet kind of travel, because I would want to take my dog. I would buy season tickets to the orchestra in town, and higher level memberships to the local museums. I’d give more to my two volunteer groups. Mostly I’d just sit around the house reading, curled up with my dog.

9. I would 100% quit my job, and take a year off, to just figure out where I want to go next. Even if it wasn’t “stop working forever” money, I really feel like I need a little time just to *think* and figure out where I want my next job to be.

   For just-for-fun purchases, I’d buy a big chunk of land – somewhere with ocean access AND a lake AND some good forests (we’re assuming this is a big lottery I guess). And I’d build basically a mini summer camp on it – some little cabins, lots of rooms for extended family, friends, all their kids, anytime. A big main house with a fireplace, library, and a heated greenhouse (unless we’re in a really hot place I guess). The whole thing is wheel chair accessible. Stock all the water toys you want – some tiny sailboats, surfboards, paddle boards, kayaks, those big floating trampolines. Then I’d spend a while staying there and just building little “secret spots” – a path to the best view with a few hammocks, a hidden photography blind near a pond, little trails to a swing or a tiny garden or other nook, a tree house with an art studio. Invite anyone I know to come build whatever like that on the property as well – I’ll have an Amazon account and a home Depot acct set up to deliver anything you need

   1. I love this! I’ll come and build a secret garden.

   2. +1 sign me up!

10. I would get a financial advisor/tax advisor who specializes in windfalls (or maybe be gauche and try to ask someone in my company C-Suite/leadership for a rec) and figure out a five year plan. I’d keep my job for the time being since insurance is such a perk. I’d plan for how to help out my extended family without it turning into a whole thing, how to diversify and buy property over time, how to set up trusts that would extend wealth across generations without giving any child ruinous amounts of money, and figure out how to give back.

    I would rent a beach house on the other side of town (rent first to see which town we’d really want to live in and to figure out what’s best protected from climate change, falling cliffs, high tide flooding, train infrastructure updates since San Diego didn’t address line routes in a timely manner. Or if we want to be boring and keep kids in the same schools, I’d rent a bigger house with a better yard in our current neighborhood, and rent out the house we own while we figure out our plan.

    Not working sounds nice, but might keep my job anyway without worrying about hustling to the next level. Being a museum docent or delivering science related volunteering sounds fun. Or taking on non profit board positions without layering on top of a job.

11. Purchase outside health insurance, then immediately quit my job once that was in place (ah, America), then decamp to the Caribbean for about a month to figure out what I wanted to do.

12. I’d do all the boring stuff. But in the less boring category:

    I’d buy my mom a beach house in the California beach town she grew up in, where she’s long been priced out.

    I’d hire an amazing landscape designer to overhaul my entire front and back yards and make them magical.

    I’d endow the educational foundation in our town.

    I’d invest in commercial real estate in our downtown strip, convert it all into multiuse retail-housing, and revitalize our downtown.

13. Pay for my niblings higher education. The one who is out of school & married would get a check for what it cost beyond her scholarships, to pay off student loans and help with their house.

    Endow the football program at my alma mater with a fund to replace the artificial turf that causes knee & ankle injuries and put in natural grass. Make sure that they have enough money to maintain it.

    Buy a permanent location for my local farmers market away from the downtown parking lot they currently lease. They have been raising money for 8 years, but their list of requirements means that that there a limited number of properties that fit their needs.

    Create a sustaining endowment for the rescue where we adopted our cats. It is a group of women in their 70’s and 80’s, and they are worried about the sustainability of the rescue as their health declines.

14. Get the actual healthcare tests I need (cries in US, high deductible PPO)

    1. For real

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