Winning the lottery. Having a long-lost relative put you in their will. Selling your TV show. For our Money issue, we interviewed 15 people—and asked writer Ijeoma Oluo to contribute an essay—on the subject of windfalls. How they got their money, and what they did with it, was both as intensely personal, and shaped by cultural expectations, as anything else.

THE TRUST FUNDER: Maddy Shaw

Spanish interpreter and vegetable farmer in Minneapolis, Minnesota (which Shaw prefers to describe as "occupied Dakota homeland and Anishinaabe territory")

AMOUNT: Close to $250,000 HOW: Inherited money upon turning 18 SPENT ON: $25,000 on college, $160,000 on philanthropy

Most of the money was put aside by my great-grandparents, who were Jews who had fled Poland shortly before the Nazi occupation. It was money invested for me to go to college. I think they wanted to give me the best shot that they could at being safe and secure. It was something that was very important to them, given where they came from.

I became aware of the money around the time I was in late middle school or early high school. My mom told me I didn’t have to worry about paying for college and showed me where in our house to find the file folder with some of the different accounts. She told me this information in a really matter-of-fact way, as though everyone’s family put aside college money for them.

When I turned 18, I assumed control of the accounts the money was in. There were a couple different accounts; some were to be used only for higher education. I did go to college for one year. I was in a class called “Race and Racism,” and we did some activities where I was seeing, “Oh, it’s these histories of how my ancestors became white and became upwardly mobile that led to me being here.” I don’t think it’s uncommon for people like me to learn about racial economic justice in a really prestigious higher-education institution. So then the question was, “Why am I here? Am I doing this because it’s what I actually want, or am I doing this because it’s what I’m supposed to do?” I ended up dropping out at the end of that year, partly because I fell in love with farming, which is something I don’t feel I need a degree for.

A lot of the emotional work I’ve done is trying to distinguish myself from this money.

It was within the next couple of years that I found out about Resource Generation, a multiracial organization of young people with wealth and class privilege who are organizing for the equitable redistribution of wealth and power.

One of the main principles of Resource Generation is to give that money away and to reinvest it in the communities that it was taken from. In my mind, the money I inherited, especially because a lot of it gained value in the stock market, was made at the expense of poor and working people, and using land stolen from indigenous people and resources extracted from that land. I think I went from not thinking about it at all to it being very clear to me that this money was not mine. It was legally in my name, but I didn’t feel any ownership of it. And so I started to think about how I was going to give it away.

Most of the money I’ve given to small, grassroots organizations led primarily by poor and working-class people and people of color who are doing community organizing for social and economic justice. And some of the money has been given to GoFundMe pages for activists in my local community who need support. And there have been times when I’ve had to bail out friends in need.

At first, I was afraid to tell my family how much money I was giving away because I was worried they would be upset with me. A lot of the emotional work I’ve done is trying to distinguish myself from this money. We live in a culture that makes us personally identify with any money we have, and we believe our money is us and we are our money. It’s put a lot of work in my lap in terms of figuring out the responsible thing to do with it.

There have been quite a few people, mostly older adults, who have told me that I should save the money for myself, that I should save it to buy a farm. I take it into account, but I also know that I want to try something different than what the generation before me has primarily done in my socioeconomic group. I’m still figuring out what financial security looks like for myself. But so far it’s meant working, and it’s also meant building relationships, because to me relationships have a lot more security than wealth.

There’s been, to be honest, a lot of days when I don’t like being a gatekeeper. I don’t like being in the position of power, of deciding where this wealth goes. Because I think that it’s a very old story for wealthy white people to be deciding where wealth goes. When you look at the statistics for philanthropy, the people who are controlling where the wealth goes tend to be wealthy, tend to be white. For me, a lot of my work has been figuring out how I am breaking out of that. Figuring out how to stand up for the fact that I value things besides money, but also knowing that I live in the reality of capitalism and need to make money in order to survive.

—As told to Andy Wright


THE GAME SHOW WINNER: Tony Hightower

Executive director and host of TriviaNYC in New York City AMOUNT: $250,000 HOW: On Who Wants to Be a Millionaire? in 2015 SPENT ON: Building a trivia company, retirement fund In 2011, while I was running a small trivia business in New York City, I qualified to get on Jeopardy! and won $23,000. Now, there are not many people who’ve won big on Jeopardy!, so suddenly my phone started ringing. There’s a Jeopardy! community, a small but fervent group of people who have been on and done well, and at a certain point, Ken Jennings, who holds the longest winning streak on Jeopardy!, called me and told me he’d been invited on Who Wants to Be a Millionaire? It’d been a long time since they had somebody win the grand prize of $1 million, and the producers figured he had a fighting chance. Ken asked if I wanted to be his Lifeline, which was an honor. I was petrified.

I went up to Connecticut, where they shot the show, and hung out with Ken all day in the green room. There was a long time to wait, so I was hanging out, chatting with Ken and the producers of Millionaire. I was just trying to stay peppy. At a certain point, one of the producers turned to me and said, “You should be on this show yourself.” That turned out to be my audition to get on it.

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Ken walked away with $100,000 that night. The producers called me back, and 18 months later, I went on the show myself. Who Wants to Be a Millionaire? moves quickly enough that you don’t have any sense of time. It feels like anaerobic exercise, intense and hyper-focused. I ended up winning $250,000 dollars. It was the single biggest payday of my life. Me, my wife, and my friends took the train back to New York, got out at Grand Central Station, and went to a martini bar and drank martinis the rest of the night. I was vibrating with excitement. Oh, my God, I just won all that money. I’ve got to figure out what to do with it.

I get flown out for corporate events all over the country. I’ve got a CFO. Who the hell am I to have a CFO?

The producers mailed me a check via regular mail that had my name on it, no money taken out of it. Literally, it read “To Tony Hightower. The amount of 2-5-0-0-0-0.” I brought it into the bank, and I just showed it to the teller and was like, “What do I do with this?” The teller freaked out. “This is the biggest check I’ve ever seen in my life! You must be so blessed to have gotten this.” “I’m not blessed,” I said. “I worked for this. I answered 12 trivia questions.” Twelve trivia questions, $28,300 per question.

At the time, I was running a small trivia business in NYC, hosting one trivia night a week a bar, which paid in cash and drinks. I was doing fine, but it was one of these things where I was living month to month, and I couldn’t afford to expand. (My wife was working toward her PhD at the time.) When I won $23,000 dollars on Jeopardy!, it was enough for me to buy a really nice lounge chair, a couple of toys, a month in Paris, and that was it. Two hundred and fifty thousand dollars felt like I should do something meaningful with it, because I didn’t want to wake up one morning and have it be gone.

I put it into my company. I hired a couple of people and set myself up with a retirement account—something I never thought I’d have. I was in my late ’40s, and I had never been anything other than a subsistence worker my entire life. I have a management team now. We run a few dozen nights around the city. I get flown out for corporate events all over the country. I’ve got a CFO. Who the hell am I to have a CFO?

The trivia company is bigger than it’s ever been. We’re doing far more business now than we ever have. I feel like the early days of me scraping and struggling every minute are now over. It’s nice to be able to have a mattress under you, some padding.

I’ve always lived as if I were two bad weeks away from sleeping in a cardboard box. This is the very first time in my life where I feel like that might not be the case.

—As told to Andy Wright

THE INSURED PATIENT: Sean Strub

Writer and activist living in Milford, Pennsylvania AMOUNT: Around $500,000 HOW: Three viatical life-insurance policies SPENT ON: Creating a magazine for people living with HIV I was diagnosed with AIDS in 1985, and a year later, I was declining rapidly. I was familiar with the viatical-settlement industry because I had been reading about it in the gay press and had seen ads. [Viatical life insurance is a practice in which the policy holder—whose death appears imminent—names a third party as the beneficiary, in order to receive a lump sum worth less than the eventual payout. During the AIDS crisis, viatical settlements were advertised heavily to the gay community.] I had three of these insurance policies and had been aware that they could be sold and I could get a lot of cash.

I decided to start Poz magazine, and I wouldn’t have been able to do it the way I did it without liquidating those policies. At the time, there were people, including in my family, who were concerned about my mental health, about me putting all my resources—not just the money I got from the viatication but also my savings—into starting a magazine that had a very uncertain future.

I did not expect to ever live to see it become profitable. I hoped that would happen, but at the time we started it, not many people would’ve given me a life expectancy of more than a couple years.

I wanted to do the magazine at a very professional level, with great photography. I was tired of the information provided to people living with HIV that was invariably cheaply printed on newsprint, not in color. The only places doing slick stuff were drug companies. I was writing about my friends and people I knew, and the community that I felt such a strong part of. I wanted it to be done beautifully. There was probably also some vanity involved, because I saw this as a legacy project since I didn’t expect to be around much longer. When we first started, we published every other month, and our circulation eventually grew to about 90,000.

Spending money when you think you’re going to die, it’s a little bit liberating, right? You’re not worrying about your old age, you’re not thinking long-term about your financial security. I didn’t have people I felt directly responsible for supporting.

By 2000, I was no longer thinking I might die in the next year or two. And by 2004, I was back to thinking more long-term about my life.

It felt like a little victory. I’d gotten one over on the system. At that time, people with AIDS were feeling so horribly treated by every kind of institution—whether it was the government, or the drug companies, or the insurance industry, or the health-care system. Everywhere you turned, you were being exploited or manipulated for political or other agendas, or you were seen as a market opportunity. And I knew I was not as close to death as they were predicting.

Not that I wasn’t sick. I was sick—I was covered in Kaposi sarcoma lesions all over my face. I’m six foot one and my weight was down to 124 pounds. I looked skeletal. I was very sick, but I wasn’t as sick as they thought I was. I felt like I was on the winning side of a battle.

When combination therapy came out in 1996 and I started to get better, my planning window started to expand, but it expanded slowly because I didn’t trust that these drugs would continue to work. So by 1997, I realized, “Hey, I’m around for a few years, who knows how long it’s going to last.” I had just turned 40, I had worked very hard, been an entrepreneur, but didn’t have a nest egg. I didn’t have an IRA. I was solvent, but I realized I needed to think about retirement again. By 2000, I was no longer thinking I might die in the next year or two. And by 2004, I was back to thinking more long-term about my life. [In 2004, Strub sold Poz to CDM Publishing; the magazine still publishes today, eight times a year, and has a circulation of around 125,000.]

The money enabled me to create a very highly visible media product that was profoundly meaningful for people with HIV, and still is. It made me a much more public person because of my role as the publisher and editor. I became visible in ways I hadn’t been before.

I was really proud to spend all this money. And had I not been so ill, I’m not sure I would’ve been so altruistic. It’d be nice to have it now, but I don’t. But I don’t regret doing what I did with it, because it’s just so satisfying and important to me.

—As told to Andy Wright

THE TV WRITER: Danielle Henderson

Writer living in Los Angeles

AMOUNT: $27,000 script fee HOW: working on the Netflix show Maniac SPENT ON: Living between New York and Los Angeles, saving a year’s rent, help for aunt and grandmother

There are different tiers to writing television shows: you start as a staff writer, and each time you move up the ladder—to story editor, executive story editor, coproducer, producer, supervision producer, executive producer—you get a minimum payment from the Writers Guild.

When I moved up from staff writer to story editor for Maniac, I got my first script fee, which was around $27,000. For most of my adult life, this was equivalent to an annual salary. At the time, I was living between New York and Los Angeles, and that one script really allowed me to pursue my career in both places. I was able to have a friend stay in my apartment in New York and take care of my cat. I still paid rent there. I was also able to rent a place in L.A. for the few months that I was working. The money made my career possible.

I think a lot of people get into this industry and they have help from parents. You start as an intern because your parents are paying your way, and then you become a writer’s assistant because somebody is supporting you on the back end. But I did not have that luxury.

I cannot understand how a single person can have a million dollars in this world and feel like they need it all for themselves.

I grew up poor, and my mom was a single mom on welfare; I was also older when I started writing. Most of my life, I’ve lived very close to the bone. I’ve been independent since I was 17 years old, and even now, having some financial security and comfort, I don’t quite trust it.

I have a manager and agent, and I’ve asked them about what I should do. They were the ones who pointed out: “You are building a career, and you’re getting hired all the time. This is going to become more common for you.” I asked them for advice on good accountants, and how you trust one. I grew up in the age of MC Hammer, so I’m just not gonna give all my money to somebody. That’s never going to happen.

I was able to rent an apartment in Los Angeles that I like that was within my means. I immediately saved a year’s rent in my bank account, so that if things slowed down or I didn’t get hired, I wouldn’t have to worry.

More than anything, I love that I can help my friends and family. My aunt was diagnosed with stage IV breast cancer, and I was able to get her comfortable for the process of chemotherapy. My grandma’s getting older—she’s 86—and she’s starting to exhibit signs of dementia, and I’m able to send groceries and not think about it. I’m able to send her a little bit of extra money so that she’s not stressed out about paying for things. I set up automatic payments for a lot of her accounts through my accounts.

That’s the best feeling of all. It is kind of nice to be able to go to Trader Joe’s and just go HAM on snacks and not worry about it. But more than anything, I feel better about my life and my career when I’m able to give that back to other people. I cannot understand how a single person can have a million dollars in this world and feel like they need it all for themselves. I also think that says something about the gender dynamics of finances. The fact that it feels built into my DNA that it’s my responsibility to give back is something I don’t hear from a lot of men.

The only directive I’ve ever given my agent, my manager, anyone on my team, is to make sure I get paid like a white man. I do not want to get any offers that are lower than average because I’m a woman or I’m black. I’m not out here demanding a quadrillion dollars, but if I see that somebody’s sold a project for a certain amount and my project is in a similar vein, I’m not settling for less than that.

—As told to Andy Wright

THE HURRICANE SURVIVOR: Millie Cruz

Construction worker and resident of Leguísamo Barrio, Puerto Rico

AMOUNT: $1,701 from FEMA, $6,771 from a local relief organization HOW: Applying for emergency relief SPENT ON: Materials to rebuild her family’s house after Hurricane Maria; estimates she would’ve needed $20,000 more to complete the house.

My husband, three children, and I spent Hurricane Maria at my aunt’s cement house in Liceo; it’s the only family house that is secure. Because the roads were completely blocked [by debris], it was three weeks before we got back to our own home.

We lost absolutely everything. Almost the entire roof was gone. It went piece by piece. One zinc panel even fell on my car; it broke part of the windshield. We had secured everything in one room—the mattresses, the refrigerator, the washer, everything. But that part of the roof was gone, too. There had been a lot more rain after the hurricane, and the house was made of wood; the panels and floor were deteriorating.

We applied for FEMA aid. Meanwhile, we replaced some of the roof with zinc panels from the [surrounding] mountain, where the hurricane wind had scattered them. We slept underneath that area, but once we had to get up at 4 a.m. because it started to rain and the drops were falling on us; we had to move our mattresses.

In December, someone from FEMA came—it took them two months to get here. They would only include the damage they saw: a smaller hole over one of the rooms. We had needed to replace part of the roof while we waited for them to come investigate, so we could stay there. We tried to give them photos [of the previous damage], but they wouldn’t hear us. They took photos, measured the hole, and said, “Sign this paper,” and that they’d send a letter. And then they left.

In January, we got a check for $1,701, and that was it. It would have cost more than $20,000 to reconstruct the house.

I can’t explain it. It was all backwards: neighbors who lost a lot didn't get much, and the neighbors who didn't lose much got a lot. We know someone who lost a few zinc panels, and FEMA gave them $17,000. And we lost everything, but they approved only that small amount.

Anything beyond that $1,701 from FEMA would have been a loan from them, which we can’t entertain. We work in construction by contract, and we don’t have work right now because we are too busy repairing the house ourselves. How would we pay it back? Then [a local relief organization called] Brigada Solidaria del Oeste came and asked us what we needed. We had already been building another house, a cement house, on the property, little by little for more than five years—so it was easier and less costly for them to put a roof on that than to rebuild a house from scratch.

The Brigada approved $6,771 of aid. Instead of giving us a check, they buy and bring materials while we do the construction ourselves, sometimes with help from the Brigada or friends. We tell the Brigada what we need, and they quickly help us. They’re available anytime; they never say no.

They took photos, measured the hole, and said, “Sign this paper,” and that they’d send a letter. And then they left.

We had used some of the FEMA money to replace broken wood in the old house, so that we could have a temporary roof. We replaced the kids’ mattresses, too. With what was left, we bought rods to start the process of raising the new roof for the cement house. The Brigada paid for the windows, the doors, electricity cables, kitchen sink, the toilet, and bathroom sink. Next, we have to seal the holes around windows, then get everything that goes inside. My husband and I need a bed, because right now, staying in the new house while it’s being constructed, we sleep on an air mattress.

My youngest son, who’s six, was diagnosed with muscular dystrophy in March 2018, a few months after the hurricane. Right now, he’s like a normal boy, running and jumping, but there will come a time when he can't walk, God be with me. I can't wait until the moment comes to make changes, so we had to construct his room to be close to the bathroom. It's a long process, but it's going to come, and you have to prepare yourself for that.

It's just us here; most of our relatives are older and can’t help us with construction. But the Brigada have become like family. They gave me more than money—they gave us a home. If not for them, we wouldn't be standing on this concrete. They paid for all of this. It's a beautiful thing, and we're grateful.

—As told to Jhoni Jackson

THE RAFFLE WINNER: Lily Gontard

Author living in Whitehorse, Yukon, Canada

AMOUNT: $45,555 CAD ($34,440) HOW: From a raffle at a Vancouver Canucks hockey game. SPENT ON: Down payment for a house

In 2012, I was working full-time in a government job, making what I’d call an average wage for Whitehorse, Yukon, where I live. A friend of mine had group tickets for a Vancouver Canucks hockey game. I happened to be flying out to work a trade show in Vancouver that same weekend, so I decided to buy into my friend's group tickets for the hockey game. I had just started dating Ken two weeks earlier, and I said to him, “Hey, let's go down to Vancouver together. We can go to the hockey game, it will be fun.”

We were late showing up, and as we were walking in, this woman came up and she said, “Do you want to buy a 50/50 ticket? The money raised goes to the Canucks for Kids Fund in Vancouver.” Fifty-fifty tickets are fundraisers at sports events where you buy a ticket and then half of the earnings from all the tickets goes to the winner who's drawn at the end of the game. I gave her 20 bucks.

Ken had a 50/50 ticket, too, and he told me that he would give me 50 percent if he won. I felt like I'd better reciprocate that offer, you know? So I told him if I won, I’d give him 50 percent, too.

At the very end of the game, they had a big screen in the middle of the ice rink, high up, and they announced the 50/50 draw was $90,000, and then they announced the number, and I took my ticket out and I looked up at the numbers on the screen. I folded up my ticket, put it into my wallet, and I leaned over to Ken and I said to him, “I think I won.”

We went down to the area where you claim your prize. They give away what I would call pretty dorky prizes throughout the whole hockey game. The couple ahead of us had won this giant basket full of canned beef soup. They were super stoked.

I was next up, and I said to the guys, “I think I won, can you check my numbers?” And then he looked down at the numbers and he said, “Congratulations.” I didn't really believe it until the check showed up in the mail.

At the time, I was living in a house with five other people, and we were all in our 30s and 40s and had good jobs and were living like college roommates. Housing in Whitehorse is really hard to get [due to a boom in the local mining industry]. The median house cost is around $400,000, and we're a town of 25,000 people. It's quite hard to get a rental.

Don't lose hope—you never know what's going to happen from day to day, so you can take a little chance.

Ken had asked me what I would do with the money if I won, and I said I’d like to put a mortgage down on a house. He also said he’d like to buy a house. When I won, I was like, “I guess we’re buying a house together.”

We'd both been married and divorced before, so we decided that if we found a house and things didn’t work out with us, we’d be civil and split everything evenly. For us, it didn't seem like a risk, really. We bought a house six months later, and we're still living in that house, and we have a dog now. It's a 900-square-feet, two-bedroom bungalow within walking distance to downtown. It's got a nice yard with deciduous trees. We’re going to celebrate our seventh anniversary on Valentine’s Day this year, so it’s worked out pretty good for us.

I buy 50/50 tickets all the time now. It's ten bucks here, it's five bucks there, whatever. You might win something, but the money goes to a charity or an organization that needs it, that's how I look at it. Don't lose hope—you never know what's going to happen from day to day, so you can take a little chance. It might work out. —As told to Andy Wright

THE GAMBLER: Maria Konnikova

Contributing writer for The New Yorker, professional poker player in New York City

AMOUNT: $84,600 for a single tournament, $270,000 overall winnings HOW: Winning poker games SPENT ON: More poker games, taxes

In 2017, I started playing poker professionally as research for a book about luck and decision. I went into this project knowing nothing about poker, nothing about my abilities. It was all meant to be part of this journey into looking at poker as a life metaphor to explore the nature of chance versus skill. Poker’s a nice environment where you can test out a lot of theories about luck, and also try to improve your game. I had no idea if I was going to be good at it.

My coach, Erik Seidel, is a legend, and one of the first things he taught me was that if I was going to do this right, I should approach it the way any professional poker player would. The number one rule is good bankroll management: Don’t play in any events that are above what you can afford to lose, and always have a lot of money in advance.

The first time I went out to Las Vegas, Erik wouldn’t let me play in any event that was more than $60, so the first game I won was a daily tournament at Planet Hollywood. I won close to a thousand dollars, and I was absolutely ecstatic.

The way Erik and I approached the project was my winnings would be put back into poker—that would now be my poker bankroll. So then I was able to play tournaments that were a little bit more expensive. I ended up coming in second in a slightly bigger tournament—I think it was like a $120 tournament, and I won, I think, over $2,000.

But I remember that feeling of winning the 900 some-odd dollars and saying, “Holy shit, this is so cool. I can’t believe this. I can’t believe I did that.”

I had no idea, really, how much money you could make playing poker. I actually thought that I’d be losing a lot of money, but I was willing to sacrifice a chunk of my book advance in order to make this happen.

Poker and tournament poker are insanely expensive. In order to be a full-time poker player, you basically are constantly paying airfare, hotels, food on the road. It all adds up really quickly, and then there are the tournament buy-ins, the amount you pay up front to enter. And because the variants are so incredibly high, you often go for multiple tournaments without cashing in anything.

The only thing that I might spend my winnings on if I do really well is I might treat myself and my husband to a nice dinner or something, but that’s about it. It’s actually not that much money when you think about it, because that’s my income right now. Normally, I would have a very steady income from the New Yorker, but because I’m on leave, I don’t have the usual income stream that I would rely on.

My biggest win was $84,600. That felt insane. Surreal is the best word, because that’s higher than any salary I’d ever had. I only worked a full-time job the first few years I was out of college, and my lowest salary was $23,000. And now I’m about to play in a tournament in two days that’s a $25,000 buy-in.

So I’m playing in a tournament that costs more to enter than my starting salary out of college, and the highest salary I think I ever had was $65,000. So yeah, it’s crazy. And it’s very easy to think, “Oh, my God, I’m so rich now. I can buy anything.”

My family came to the United States when I was four from the Soviet Union. We really had nothing. So I grew up in an environment where I was always very conscious of budgeting, of never going into debt. That’s the mindset that I’ve always had, and when I was out of college my first priority was paying off my student debt, and I never had credit card debt. So when I won that amazing amount of money, I was very happy, and the first few days I was kind of on this cloud.

It’s very easy to think, Oh, my God, I’m so rich now. I can buy anything.

And then I was like, “OK, how much am I going to have to pay in taxes?” It was early January. I was like, let’s imagine I don’t win anything else for the rest of the year. This is actually not that much money to live on for an entire year. And so I quickly came back down to earth. In New York poker taxes are really high; it’s considered gambling, and so when you live here, you end up paying almost 60 percent in taxes on all your winnings, which is really unfortunate.

There’s a saying in poker—and it’s a total cliché—but I think it’s actually so true: “Poker is a hard way to make an easy living.” It’s incredibly, incredibly difficult, and you sometimes go for months just spending money and not saving anything. For instance, I just came back from Prague, and I think I’m down $15,000 on that trip. That happens, and you need to be OK with that and you need to plan for it.

If the poker continues to go well, I think it can be very liberating in terms of allowing me to not take on any assignments that I don’t want. I’ve had a pretty lucky career in that normally I’ve been able to make good choices, at least for the past five years. But I don’t love writing shorter things as much, so it will be nice to actually have a little bit more freedom in what and when I choose to write.

—As told to Andy Wright

THE ASTROPHYSICIST: Sara Seager

Astrophysicist and planetary scientist at MIT, in Cambridge, Massachusetts

AMOUNT: $625,000 HOW: A winner of the MacArthur “Genius” grant in 2013 SPENT ON: Childcare, household help

I had a major tragedy in my family in 2011, when my first husband died of cancer. So I’m a single mom, and I’m working 60 hours a week. I’m out of the house quite a lot, plus I travel for work a lot. I spent through all my savings just so I could work.

When I got my MacArthur award in 2013, they asked, “What are you going to spend the money on?” I said, “I’m going to spend it all on household help so I can spend more time with my kids and more time on my job.”

If you have kids, or a person who relies solely on you, not only do you have to take care of them and want to spend time with them, but you have to make their breakfast and their lunch, if they’re really little. And then clean up after them. There’s this endless series of chores. I got tons of responses from people saying, “I can’t believe you said that,” because people won’t admit that. People don’t want to admit the price you pay for working.

In the first two years, I was just spending it. It may be inconceivable to spend that much money, but think about it: I’m going away on trips quite a lot; I’m paying my babysitters, who are very good family friends, to cover 24-7 when I’m gone; or I’m taking the family with me for a conference, and then we might tack on a few days for vacation. It’s a lot of money. That’s where it went, most of it.

Without the MacArthur money, all my time was spent thinking about household problems.

Once I became widowed, I was burning through cash like there was no tomorrow. Because I was having to get up and go to my job and be at work, get my work done, and come home. You can’t have the job I have as a single mom without a lot of extra support. Maybe you have your parents living with you, or you happen to have extended family who live on your street, but you just cannot do this alone. [The MacArthur grant] didn’t change my life, it allowed me to keep doing what I was doing.

Without the MacArthur money, all my time was spent thinking about household problems, things I had to do. When you’re driving in your car, or you’re walking outside, or taking some time off, what are you thinking about? “I’ve got to get the laundry done.” Or, “I’ve got to get groceries.”

For most of the chemistry problems I work on, there’s no replacement for hard work, but moments of inspiration can come at the oddest times. They’ll come when I’m at the park watching the kids play, and my mind’s wandering and I solve a problem. The MacArthur didn’t just free me from worrying about money, it allowed me to free up my time to dream, just to think.

—As told to Andy Wright

THE INHERITANCE: Jenny Wiegley

Employment lawyer in San Jose, California

AMOUNT: Nearly $500,000 HOW: Mother’s estate SPENT ON: Down payment on a house, funding husband’s business

Financially, I was not really in a good place in 2008. I was in my final year of graduate school. I had student loans for living expenses, but I was in Los Angeles, which is not a cheap place to live.

I was married, but my husband wasn’t making a ton, and we had a fair amount of expenses. Our rent was pretty high; we had car payments; we just always seemed to get ourselves into credit card debt because it always cost more to live than we were bringing in. We definitely had no savings of any kind. We each had a 401(k), but with very little in either of them. I was 28 and he was 29. I had also just had a baby.

My mom was a very, very frugal person her whole life. She was really maniacal about preparing for her retirement, which was ironic because she never got to retire. She got sick when she was 56, I think, and by the time they figured out that she had cancer, it was too late. There was no way she could be cured; it was mostly just treatment.

She was in treatment for just under three years. When she died, her estate was divided between my two brothers and me. But she had given me extra money because I had just enrolled in Cornell Law School, and we were preparing to move when she was diagnosed. I rerouted my life so I could help her and take care of her, and that’s why we were in L.A. I was at every doctor’s appointment; my brothers were off doing their own lives, and they weren’t involved.

My mom wanted to give me, before the estate was divided, a lump sum that would pay off my law-school tuition, which was around $168,000 at the time. She died in February of 2008, and I didn’t start liquidating the retirement accounts until after the fall of 2008, which was when the market crashed. So they all were worth a lot less.

Now we live in a house that’s worth $1.6 million, and I would never have owned a house, period, if I hadn’t gotten that money from my mom.

I didn’t actually take the lump sum and pay off law school, because the debt had a low interest rate that was set for 30 years. What we really wanted to do, because we had a baby, was buy a house. Because this was after the mortgage crisis, you had to have 20 percent down to buy a house.

I knew that my mom wanted me to own a house. She was very explicit about that, and we had even talked about her buying a place that we would all live in together before she died, which didn’t happen. So I felt like I had a responsibility to spend the money in a way that she would approve of. So we did that, we bought a house, and I never felt bad about that choice.

The house earned a lot of money. It gained a lot of equity while I lived in it, and then we put it into our current house, which has gained a lot of equity. Now we live in a house that’s worth $1.6 million, and I would never have owned a house, period, if I hadn’t gotten that money from my mom, because we never would have had a lump sum to put down, ever.

I tried to be really, really responsible with the rest of the money. I did dedicate probably about $50,000 or $60,000 of it to my husband as he tried to start a company, even though I knew that it was not going to succeed. It was an internet start-up, and they usually don’t. It was just really important to him, and it was like an investment in our relationship more than anything. It also meant that he was home a lot during that time. My life philosophy is that when I die—if I’ve lived my life right—there won’t be a lot left over. It’s not that I don’t want to leave my kids anything. I intend to help them along the way in whatever way I can while I’m alive, which my mom did also do. But I want to actually use the money we have. You really don’t know how much time you have.

—As told to Andy Wright

THE LAWSUIT WINNER: Haley Houseman

Writer living in Methuen, Massachusetts

AMOUNT: $10,000 HOW: Lawsuit over a childhood bike accident SPENT ON: Pre-college trip to India

I grew up in the suburbs north of Boston, and my parents owned a small law firm. We were comfortable but not particularly well off. My parents bought me a new bike for my tenth birthday in 2000, and a couple months later the bike fell on me. It didn't have a guard on the gears, and it cut open my leg. We were on a family vacation in deeply rural Maine. It was an hour-and-a-half drive to have a clinician—who was not somebody who normally gave stitches—sew up this poor, screaming ten-year-old's leg. I got like 16 stitches. It was very traumatic for everyone involved, and I was really embarrassed about the scar for many years.

It turned out the part that was missing on the bike was, like, a two dollar part. My mom had worked in personal-injury law, and my parents sued the bike company and got me a lump sum of $10,000, which was put in a trust for me until I was 18. I remember them telling me they had gotten the money, and I never questioned it. I moved on with my life.

I turned 18 while I was still in high school. I was applying to colleges, and the school I got into, NYU, was quite expensive. I had a good scholarship, but was also going to have to take out loans. My parents told me, “Listen, you will end up taking loans out against your trust and it will get eaten up by your tuition, so consider using the trust in a way that is meaningful for you before you go to college.”

I had several friends who went on international exchange programs, so I applied for a Rotary International Exchange, which a lot of friends had gone on, and I got picked. I said, I don't really care where you send me, I just want to go. I had never left the country, and I didn't want to go to college yet. It turned out I was going to go to a very small city in northwestern India.

If I had been in Mumbai, that $10,000 would not have gone as far as it did. But because of where I was placed, it not only paid for my expenses—housing, food, and schooling—but covered three separate trips: one around the state of Gujarat, where I lived; one around the state of Rajasthan, and then Punjab; and then another trip that took me from Mumbai, by train, all the way south to Kochi, which is the southernmost tip of India.

I came back from India and did a year and a half of college at NYU and did not like it; the experience was a bit of a culture shock. NYU has a bunch of satellite campuses in different countries. And because of the experience in India, I persuaded my guidance counselor to let me do three consecutive semesters abroad. I went to Ghana for a semester, Argentina for a semester, and the Czech Republic for a semester.

Looking back, I can say I was fearless. I packed a single suitcase at 18, and I just went. I could never do that now, as an adult—almost two years living out of a single suitcase. I have a partner, and a dog, and a job. Also, having the experience of going to India and being independent gave me the confidence to do college in such an unconventional way. And I'm really grateful for that now, because I am a freelance writer and content marketer, so international travel is not really in my budget.

It made me appreciate what a difference money given can make in someone's circumstances. If someone gave me $10,000 right now, that would be great, but it would also be very different than being given $10,000 that early in my life, before I had loans, and before I was working, and before I had commitments. That $10,000 would go to bills now.

—As told to Andy Wright

THE EARLY INVESTOR: Bill Wasik

Deputy editor of the New York Times Magazine in New York City.

AMOUNT: About $100,000 HOW: Investment returns from 1999 to 2000 SPENT ON: Living expenses, peace of mind

When I got out of college in 1996, I didn't know what I wanted to do with my life. I wound up getting a low-level research job at a firm outside of Boston that made investments in start-up tech companies. And one of the perks of the job was that you could make investments in companies the firm was investing in—up to $5,000 per firm, per investment—which was hilarious because I had zero money. Whatever I invested in I had to carve out of whatever it was I was making. So I would siphon off $250 and invest it in this company, or $500 for that company. I was this 21-year-old researcher who was siphoning off rent and beer money to make my own little investments in these companies.

Three years later, I decided I wanted to do something more creative. I had enough money saved to move to New York to do an unpaid internship at a magazine. But then the weirdest thing happened: the year I was doing the unpaid internship happened to be the point at which a bunch of the investments that I had put $200 or $500 in suddenly started to pay off. So for a $300 investment, I would suddenly get $10,000 in stock. There was one time that I made a $500 investment that wound up becoming $50,000 in stock.

I was 25, and I made more money the year I was an unpaid intern than I had been making at the investment firm. The people around me were scrounging and making very little money, and I suddenly had cleared around $100,000 from these investments.

‘I feel like having this money, it was like I was a secret trust-fund kid.’

At the time I came to New York, everybody pretended they had the same amount of money. Even people who you knew or suspected were very wealthy would act like they didn't have wealth, and people who really were living close to the bone would still feel like they wanted to or had to come out and get beers, get a drink, and do things socially to the same extent as everybody else. Because of the money I made, I was able to live in a very expensive city and do the things that people around me were doing, without the feeling of anxiety that so many people had hidden—or didn't hide—about money in an industry where nobody gets paid very well.

I mostly put the money in the bank. I don't know that I would use the word “save” in that it wasn't in a savings account. I probably was able to pay more in rent than I would have otherwise. I did keep my car, which I had needed in Boston but didn't need in New York, and which was totally a luxury. I wasn't really at a point in my life when I was looking to spend money on anything. Because it was about just being there and working, and I was involved in the stand-up comedy world, and I was trying to write. It gave me the freedom to do all of that. I feel like the main thing the money did for me was it freed me from the kind of anxiety that can be so tricky for people at that time of their lives, when they’re trying to be creative.

After I did the unpaid internship, I got a job as an editorial assistant at a magazine. And about a year into that, the other magazine that I had done the internship at said that there was an editor there who was going on maternity leave, and if I was willing to quit my job, I could come and be an editor there. I’d be on the masthead and get to do my own editing, but with no guarantees that when the other editor came back three months later, I would have a full-time job. And I did it. I think I never would have done that if I wasn't sitting on a nice big bank balance. And lo and behold, that did turn into a permanent job. And it put me on a career track working at magazines that I don't think would've happened otherwise.

Americans love to tell themselves lies about class. And of course, wealthy Americans like to tell the biggest lies about class. And I feel like having this money, it was like I was a secret trust-fund kid. I hadn't grown up with that kind of money, but the fact that I got it in this weird and unexpected way wound up giving me insight into the bubble that people who have a lot of available money live in. I'd like to say that it made me realize how soulless it is inside that bubble. But in fact, it's super nice inside that bubble. And I only wish that my own version of the bubble had been bigger, such that I feel like I could still be living inside it. But it doesn't quite feel that way.

—As told to Andy Wright

THE POET/PHILANTHROPIST: Heather McHugh

Poet in Port Angeles, Washington

AMOUNT: $500,000 HOW: Winner of a 2009 MacArthur “Genius” grant SPENT ON: Caregifted, a nonprofit that paid for long-term caregivers to go on vacation

I was teaching at the University of Washington in Seattle when I received the grant. I had the comfort of a secure teaching position. At first, the MacArthur people couldn't get in touch with me. I'm not a person who is disposed to telephones. I kept getting messages that they wanted me to call them, a state of affairs I thought infuriatingly inefficient.

I believe I was pretty petulant when they finally called: I had made an appointment—and walked half a mile to the pay phone at the breakwater on the island in Maine where I live during the summers—to tell them so. Finally, there I was with the damned receiver shoved in my face, the fishing boats coming and going around me. A voice in the phone asked me to sit down.

By my lights, $500,000 is a lot of money for any one person of my constitution to consider all at once—or to administer. As it happened, they distributed it in five separate payments over five years.

I never had children myself. The kid I was closest to had just married and had his first child, who was microcephalic and would probably need lifetime care. I used part of the money to get them the care they needed to find new work nearer his wife’s parents, where they had moved to organize their own local support system. They wouldn't accept much more.

Their experience as parents prompted me to find out more about all caregivers of the severely disabled. Millions of people worldwide, mostly women, do this kind of care with diminished resources, often with no relief. They are generally out of our sight—partly because they are unable to come and go freely, partly because we, in our discomfort with the sight of them, make life less comfortable for them.

It was a jolt of joy to give away that money—the kick of actually materializing a dream for someone who unquestionably needs it

After the few gestures I made to these young parents, and then after taxes (one doesn't immediately consider the falling branches of the revenue agencies in windfall territory), I used the money to found a nonprofit, Caregifted.

The money went to the costs of administering the nonprofit and to travel, food, excursions, etc. on the getaways we did. We did between eight and eleven getaways a year, for five or six years, only for caregivers of the most severely disabled family members, caregivers who had been at that devotion for ten years or more.

We asked what their dream vacations would be if they could choose, given the locations we had lined up (on islands, mostly). Some simply wanted to sleep late. Some wanted a meal out. Some read a book for the first time in years. Some brought a spouse for a much-needed recharge of strained relationships. All wanted to see new territories, visit the ocean, visit gardens, wineries, fishing, markets, tourist excursions.

People who heard about Caregifted often came to us because of my life in the arts—many were artists who had not been able to reflect or catch their breath since giving birth to a child who had to battle severe challenges. All of them recovered some perspective on their own choices, chances, and changes in life. Some person they'd not been in years began to start a conversation with their futures.

It was a jolt of joy to give away that money—the kick of actually materializing a dream for someone who unquestionably needs it. No fancy home or golden furniture or vacation indulgence of your own can ever give you back the gift this gifting does.

—As told to Andy Wright

THE ENTREPRENEURS: Courtney and Tye Caldwell

Cofounders of ShearShare, a mobile platform that connects salon owners with stylists to fill empty chairs by the day in McKinney, Texas

AMOUNT: $1.1 million funding round, which included $100,000 in a Google Demo Day competition HOW: Venture capital funders SPENT ON: Renovations and branding, hiring staff

Courtney: We met in Tye’s salon 20 years ago in Plano, Texas. Tye’s been in beauty and barbering for 25 years, and I work in tech marketing. Together we’ve managed a family-owned business salon out in North Dallas for two decades now.

One day, Tye got a phone call from a stylist who had moved an hour away from Dallas and was concerned about losing her clientele. She said: “Hey guys, I know you’re an award-winning salon, but I’m not looking to do this whole long-term-commitment thing. I just need a space to come every other weekend to do my clients so I don’t lose them.”

I laughed at the idea—this was not done in the industry, popping in and out when you want to—but Tye said: “I’m going to give it a try because that suite is empty right now, so there is no use in me letting it collect dust. I’d rather it collect dollars.”

And so we started working as a concierge service, pretty much. After a few years we finally looked up, because I was traveling over five continents in my corporate job in digital marketing for Oracle, and Tye was finishing up his doctorate degree. And he was like, “Oh, my gosh, this feels like a full-time job, so can you just go find an app that does what we do so the next time somebody calls, we can nudge them in the right direction?” I went online and couldn’t find anything. And that’s when we looked at each other and said, “We have to build it.” ShearShare was born.

Tye: I’m seven of eight kids, so I come from meager beginnings, and one of the things I’ve always believed in is being an entrepreneur and doing things on your own. I grew up in a family of 13 in a three-bedroom, one-bathroom house, so I always learned how to share, or as my mom called it, divide, amongst each other.

Courtney: We began by really bootstrapping ShearShare, not paying ourselves. We lived on rice and beans, and actually went vegan. You can make rice and beans taste really, really good if you add different spices.

Fundraising hasn’t changed much for us personally, but it allows us to think on a higher level versus having to think about what’s happening today. So we’re renovating, going through a brand change, different logos, name, et cetera. Before the capital, we had three to four team members; we now have 11. Hiring the right people really does take off a lot of stress from you.

Tye: Hopefully, one day we can be just like those investors who believed in us, and be investors in our own right.

Courtney: Money is like water to me. I know it’s supposed to come to us when we’re in the flow, and then we’re supposed to use it to give back to make sure that the next generation has it better.

—As told to Haley Cohen Gilliland

THE REALITY SHOW CONTESTANT: Chip McAllister

IT consultant in Laguna Niguel, CA

AMOUNT: $1 million HOW: Winner, with his wife, Kim, of the CBS reality series The Amazing Race in 2004 SPENT ON: Two iPods, a laptop, church tithe

I wish I could say differently, but I had never been one who respected money enough. I’m a man of faith, and I knew not to love money. It was just always easy to make and easy to spend. If you look at my finances, it’s like a heart monitor. Up and down, and up and down, and up and down.

The Amazing Race was, and still is, our favorite show on television. For a while, my wife, Kim, would say: “We should go on the Amazing Race.” I said, “Kim, leave me alone. You can’t do push-ups or climb stuff. I’m 40 pounds overweight and hate to work out.” Then a bunch of other people told us we should go on.

We just did it to get in a positive place. Right before we went on the show in 2004, we started an information-technology consultancy with a business partner. My wife and I, and the partner, starved to death together for 18 months without making any money. Then we got this huge account and our company became a $30 million business. But as soon as we started making money, the business partner kicked us out. He used our company money to pay for high-powered attorneys; we couldn’t afford any attorneys. So Kim and I were in bankruptcy and foreclosure. Losing that business—the loss of money was really bad, but the betrayal by somebody you trusted like family is even worse, you know?

Man, that was the first dang time I ever thought, This must be what it feels like to be rich.

I thought of going on the show as having some long-deserved fun—being with Kim, traveling the world. Because there was not even one iota of me that believed we could win.

At the beginning, we were always right near the bottom. I remember about halfway through the show, the producer, Bertram van Munster, came up and he said, “Chip, Kim, you know, you guys could win this show.” Then we said, “Oh, thank you, Bertram, thank you.” And when he went away we said: “He’s so full of crap … he must want us to run faster or something.”

Then in the last episode, we learned that a crucial flight was delayed, and we were able to book another flight while the other competitors were asleep. Still, we didn’t know we were going to win until our taxi cab pulled up to the finish line. I will never forget that feeling. Just the crying—the convulsive crying.

We had absolutely no plans for the money because we didn’t even think we had a chance to win the damn money. We had no idea.

For almost six months, we knew we had $1 million, and we couldn’t tell anybody because we had to wait for the final show to air to claim it. Eventually, two checks for $500,000 came in our regular mailbox.

To celebrate, I went to CompUSA and got an iPod, which had just come out. I got my son an iPod. Then I thought, “Shoot, man, I just got $1 million, I can get a laptop.” Man, it was the best day.

I went up to the checkout and the kid ran my debit card and said, “Oh, sir, I’m sorry. There are no finances on this.” The checks hadn’t cleared yet. Then the manager poked his head out and said, “Bobby, that’s okay, just let him go through.” Bobby looked puzzled: “But I…” The manager said, “Bobby, just let it go through. I’ll talk to you later.” The manager obviously had seen the show and knew that the money would be good.

Man, that was the first dang time I ever thought, “This must be what it feels like to be rich.”

—As told to Haley Cohen Gilliland

THE BIG BOOK ADVANCE: Lydia Kiesling

Writer, author of the novel The Golden State (2018) in San Francisco

AMOUNT: Low six figures HOW: Sold a book in 2017 SPENT IT ON: Retirement, childcare

It was what Publishers Marketplace would characterize as a “good deal.” It was something like five times as much as I allowed myself to hope that I would get for the book. So it was, to me, a tremendous amount of money.

On paper it seemed like this huge number. But you get it in four chunks over what I think in my case will be three years. I sold my book in 2017, so that year I got the first two chunks, and of that 85 percent appeared in my bank account, because your agency just immediately takes 15 percent. I paid 40 percent of that in estimated quarterly taxes. Then I put about a quarter of what remained into a SEP IRA.

That was the best thing, I’d say, about the money that I got. The fact that I could put something toward a retirement. And if I hadn’t done that, I couldn’t have used the money, because I would’ve just paid it in taxes; that 40 percent that I paid would have been higher.

So for three years I have a salary of some kind. It works out to having a job that pays $15 an hour, which is a minimum-wage job in San Francisco, where I live. For 2018, the year my book came out, it looks like I’ll pay 36 percent in taxes, put a smaller amount into that SEP IRA, and with what’s left, it’ll be like I had a job that pays eight bucks an hour. The X factor is that I have two kids.

I had worked full-time and then took a part-time freelance editing job for a website called The Millions, and I said I would give myself a year to try and finish a draft of this book, and if I hadn’t done something with it at the end of the year, I had to get a full-time job again.

I was able to sell the book, so I was like, “Thank God I did it, I did the thing,” but basically we had been paying for childcare for my daughter in that time, and my Millions thing didn’t even totally cover that. My husband has a full-time job that covered rent and expenses; my freelance income mostly covered the daycare, but we had been kind of operating at a loss.

So part of me is like, Wow, I’m an idiot, I got this money on the book, but I spent it on that. But if I didn’t have childcare, there’s no possibility of writing another book

So let’s say I was surprised on the one hand that it was completely life-changing, because I had kept that Millions job for almost three years. I didn’t have to go and get a full-time job. But I’m now in a position where I either need to sell another book pretty quickly—like in the next three months—or I need to get a job.

So in the one sense, it was amazing. But it’s also really driven home that we, my husband and I, can’t live where we live. He has a good job—he works for the city and has great health care, which is another thing that allowed me to try this career path—but a low income for a family of four in San Francisco is now $117,000 a year. Which is just absolutely absurd. For two kids, we currently pay $3,095 a month in childcare, which is more than our rent, and we just can’t continue to do that.

So part of me is like, “Wow, I’m an idiot, I got this money on the book, but I spent it on that.” But if I didn’t have childcare, there’s no possibility of writing another book. Many choices could be different, and having children was not one of the ones that I would take off the table, so that’s what I mean when I say, “OK, clearly we don’t live in the right place for me to have this particular career.” You can’t count on a set amount of money from books.

My hope is that if I sell another book, I will be spending a lot less on childcare, maybe having fewer days of it, and saving a chunk of money that is an emergency fund, so I don’t feel spent down. If I could sell another book, that would be, I hope, something we could use toward a down payment in an area with a reasonable cost of living.

—As told to Andy Wright