When David and I first traveled together, we put the car in long-term parking and took a shuttle to the airport. Not long after that, when Emily entered our lives, we allowed ourselves the indulgence of parking at the terminal. Then, with Ali’s birth, more accustomed to our resources and willing to use them, we began hiring a town car and a driver named Boris. Although he didn’t wear white gloves or a black cap like the chauffeurs in old movies, Boris preferred to be seen and not heard. Picking us up at our house and dropping us at the curb outside check-in, he maintained a relationship with me that was nothing like the one I shared with Noreen, our housekeeper, or with May, our nanny—and it was surprisingly nice to simply be served. But was being driven by Boris a problem for the girls? They hadn’t experienced anything else.
One afternoon, when we were on our way to the airport, Boris driving, David in the front, and me between Emily and Ali in the back, Emily asked if we were late.
“We could have left a little earlier,” I said. “But we’re fine.”
“Will the plane wait for us?”
My eyes dropped to the pink princess backpack on her lap. Emily was not an inexperienced traveler. She knew how planes and flights worked.
“What do you mean?” I said, staring at the back of Boris’ head.
“You know,” she said. “Will it be one of those small planes just for our family?”
“No,” I said. “This one won’t wait.”
“Is it a lie-down plane?” Ali asked. “Will the seats turn into beds?”
My head swiveled around to look at our younger daughter, snuggled into the plush leather of the town car as we glided down the highway toward the airport for our flight to Hawaii. She looked innocent enough. But imagining her with a pink feather boa, whipping out her wand, turning princes into frogs and squash into flying saucers, I was concerned. Both girls had traveled more often and in more luxury than most people did in a lifetime. With our six-year-old wondering if we were taking a private jet and our four-year-old questioning whether we were flying international first class, I believed something had to change.
“What have we done?” I muttered to David as we helped Boris unload the trunk. “And what are we going to do?”
“I’m not sure,” he admitted.
It was fun to drive up to the plane and see a good-looking man in a uniform at the top of the stairs, but the excess and indulgence of flying private made me worry about the girls. What attitude would they adopt? How would they view their future and the world around them? Emily and Ali were already living in a small corner of the world. It didn’t seem wise to push their experience even further away from what most people knew. We could tell them flying alone was rare and special, that not many people could even consider such a thing. But if we continued to fly alone as a family, would they truly understand? Private jets would seem like just another normal part of their lives. So, while David’s fascination with planes had him chartering another jet for a weekend with friends, I put private jet travel into the same category as a high-fashion wardrobe. I didn’t want either in our life.
The irony of giving up private jets to keep Emily and Ali grounded in the wider, wilder world was not completely lost on me. Private jets simply seemed like an obvious and relatively easy place to draw a line. For their sanity and awareness of normal life, I wanted Emily and Ali to experience getting to the airport on time, going through security, and waiting in line with everyone else. I wanted the same for myself. Or at least, I wanted a sense of understanding and connection that came from being with other people. It felt important to be in touch with the experiences most people knew. But as I shunned private jets, declaring them overly indulgent and excessive, I fully intended to continue flying first-class—and the hypocrisy was not completely lost on me either. Neither was the fact that we were highly advantaged to be flying in the first place.
A decade later, when Emily and Ali were away at college, my relationship with private jets would change yet again. Flying private still felt excessive, but with David and me alone in our nest, no watchful eyes upon us, I enjoyed the ease and efficiency. We hired a plane to get from San Francisco to New Jersey for David’s twenty-fifth college reunion. Later the same year, I flew eight friends from Napa to Tucson for a girls’ tennis weekend. And when a friend asked me to join her and a group of women for a hiking trip in Patagonia, one of them flew the six of us from Oakland to El Calafate on her company’s corporate jet. But as David signed up for NetJets, I was still glad we had stopped flying private when our daughters were younger.
When talking about wealth, some people I interviewed mentioned private planes quietly under their breath as though testing my reaction before sharing their experiences.
“My husband loves his toys,” Betsy finally said. “He owns a quarter of a plane.”
“Do friends know?” I asked.
“No!” she said, her eyes growing large. “No one has any idea. I want to be sensitive to other people and not make it a big deal.”
Betsy then told me about taking a couple of family members on the plane from San Francisco to Washington, D.C. in January 2017 for the Women’s March.
“I told them it was a once-in-a-lifetime thing,” she said.
Julie, who spent years trying to hide her wealth, found it easiest and most comfortable to think about money as a way to buy time. When her oldest was starting high school, her family began flying private, and she justified the decision as a time-saving move.
“At first, the kids were amazed. They thought it was so cool,” Julie said. “Now the older ones tell me they’re worried about our youngest. They say he doesn’t know any different and needs to fly coach.”
Laurie laughed as she imagined the rude awaking her children would have when they were out of the house and living on their own.
“I never flew first class, not until I was in my thirties and had saved enough miles to upgrade,” she said. “But our kids have only flown first or private. When they’re in their thirties, they’re going to take a huge step backward.”
Back when I was rejecting private planes, when Emily was six and Ali four, Kim, a friend and fellow UCDS parent, asked if I wanted to carpool. At first, I said, “No.” It was easier to let May, our nanny, do the driving. But then, hoping to be more connected with other mothers, and more involved in the school community, I gave carpooling a try—and as soon as I became Emily’s chauffeur, I realized just how much I’d been missing. Picking up Emily and her friend and taking them to ballet class, I got to listen to the two of them chattering and giggling in the back. They had so much to say. Once they started laughing, neither could stop, which made me laugh too.
After a few weeks of taking my turn driving, in addition to enjoying the conversations, I felt a growing closeness to Kim. When I dropped off her daughter, the two of us spent time talking in the driveway, discussing a problem we had with another parent at school or telling one another about a recipe we liked. We started depending on one another in other ways too. When I was running late and needed someone to pick up Ali and Emily, instead of immediately calling May, I turned to Kim. It made me happy to have her request my help too, asking me to let a repairman into her house when she couldn’t get home in time. What’s more, as our lives intertwined, Emily got to know and trust another mother, giving me the sense of being part of a village. So, when another mother from UCDS suggested a swap, asking if Ali could spend Tuesday afternoons at her house and her daughter could spend Thursday afternoons at ours, I jumped at the opportunity.
“It’s isolating to hire help,” I said to a friend whose husband worked at Microsoft. “Relying on our nanny, I was missing out on what so many mothers share.”
“Maybe,” she said. “But it’s easier to just pay someone.”
It was easy. May was a huge support. So was Noreen. Boris too. A lot of independence was gained from hiring help. It was a luxury to have other people do everyday tasks I didn’t want to do myself. But there was a downside. Paying someone else to do what other mothers did for each other kept me on the outside, disconnected. I missed out on the community and closeness that developed when neighbors and fellow parents shared chores, complaints, and advice, in touch and in tune with one another’s lives.
“She has a pool inside her house,” Emily said one afternoon when I picked her up from a playdate.
“Sounds nice,” I said, looking at my daughter in the rearview mirror.
“She has an elevator inside her house too,” Emily said. “It’s glass. I wish we had an elevator.”
“We don’t need an elevator.”
“They have a trampoline room,” Emily said.
When my mother had picked me up from an overnight decades earlier, she’d been uncomfortable with the wealth of my friend’s family and hadn’t liked hearing me talk about their fancy living room and private club. With Emily excited about elevators and indoor pools, I too was uncomfortable. But I wasn’t envious or worried about keeping up. I wasn’t concerned about Emily being too interested in money either. Not only had I joined the socioeconomic class my mother never much liked, I’d vaulted into a strangely disconnected, unfairly advantaged stratosphere, living in territory I hadn’t known existed. I could join the after-school shuffle and wrangle kids into our car, doing my best to be connected and involved, but I wasn’t grounded in the reality most people knew. How would Emily and Ali be down-to-earth? Driving carpool and avoiding private jets didn’t seem like enough.
With money an off-limits subject, not something other parents discussed, David and I turned to Charles, our financial advisor, looking to him as confidant and friend. He knew our financial situation, and with him, money was an acceptable conversation topic.
“We’re concerned about Emily and Ali,” I told him. “They’re living in such a bubble.”
Charles reassured us Emily and Ali were fine.
“You won’t have the same issues as some of my other newly wealthy clients,” he said. “One guy has built a huge wine cellar and is collecting expensive bottles of wine. He’s teaching his kids to spend and won’t have anything left to give them. He’s on a trajectory to go broke in five years.”
As Charles told us that creating a trust fund for each of our daughters was an obvious and necessary building block for a solid estate plan, I thought he was missing the point. Trust fund kids had been on the periphery of my life during college and seemed strange and unknowable. I wanted the girls to be aware of their advantages, respectful of others, and in touch with the world around them.
“It’s a good idea to give them some money when they are relatively young, like twenty-five,” Charles told us. “That way, they can blow it all and get another chance five years later.”
I looked at David as Charles continued.
“From my experience, even if money has been part of their lives all along, kids don’t know how to handle large sums.”
“I guess it will depend on who they grow up to be,” I said. “They’re two different people. What ends up being right for one might not be right for the other.”
“Statistically, it’s your kids’ kids who will have the problems,” Charles said.
After growing up middle-class, working part-time jobs, and making financial trade-offs, David and I were still somewhat connected to normal life. Our understanding of reality was a benefit to Emily and Ali. When that same connection to regular life was a generation removed, children often failed to have the same values and work ethic that built the wealth in the first place. The third generation was notorious for losing everything. In fact, the phenomenon was described in proverbs such as, “Shirtsleeves to shirtsleeves in three generations.” In Lancaster, England, where workmen wore heavy-soled shoes people said, “Clogs to clogs in three generations.” In Japan, the saying was, “Rice paddies to rice paddies in three generations.” And the Scottish proverb was, “The father buys, the son builds, the grandchild sells, and his son begs.”
Once, in a writing group, when a British woman asked if we were raising our daughters to work, I didn’t understand her question. How could you raise kids not to work? But she’d never been expected to get a job. Instead, she’d been taught to value education, artistic pursuits, and philanthropy. While I realized there were many kinds of valid, happy lives, there was still no question in my mind that Emily and Ali needed to get jobs. David felt the same. Work was central to the way people lived. Not only did a job provide financial, psychological, and emotional independence, a job offered a sense of purpose, structure, and a way to connect and contribute to society. As Joseph Conrad suggested, work could help the girls know themselves better too—and was still something I missed. But how would they be motivated and driven if there was no financial reason for them to earn a paycheck? Would wealth dampen their sense of ambition? Would it hurt their sense of satisfaction and fulfillment? What about their ability to connect with friends?
Thankfully, in addition to talking to Charles, I could talk to Donna and Lynn. After being co-workers at Microsoft, we’d seen one another through courtship, marriage, and the birth of our first and second children. We were also classmates in the school of new wealth and shared an understanding, our mutual good fortune part of our bond, giving me a sense of community, especially when it wasn’t possible to talk with other people. No one wanted to hear about issues they wished they had, or about problems that sounded inconsequential. Donna and Lynn understood and shared my concerns, and I was grateful the three of us had gone through so much together.
Later, Julie would tell me how thankful she was to have experienced new wealth with a group of other women.
“There were several of us all going through the same thing together,” she said. “It was so nice not to be alone.”
Over time, even though she didn’t handle her money the same way her friends handled theirs, she continued to be thankful for their presence in her life.
“Most of them think I’m crazy,” she said. “They’re into jewelry and handbags and wonder why I’m not more decked out. But those women mean a lot to me. We’ve gone through something significant together, which has made us quite close.”
My experience with Donna and Lynn was similar. When it came to money and our children, I was happy we could share ideas.
“Are you worried about how money is affecting your kids?” I asked them.
“Not really,” Donna said. “But everyone else seems to. My sister is always asking why we don’t buy our kids more stuff and friends want to know what we’re doing to keep them from being spoiled.”
“People are hoping to see a train wreck,” Lynn said. “They’re imagining themselves in the same position, wondering what they’d do, probably thinking they’d handle things better.”
“Will you give money to your kids?” I asked Lynn.
“No way. They need to work,” she said.
“Aren’t you worried they’ll be resentful?” I asked.
“It’s our money, not theirs,” Donna said.
“Your financial situation could be a real benefit to them,” I said. “Why not let them follow their dreams?”
“What will motivate them to get started?” Lynn asked. “How will they start dreaming in the first place?”
“There are plenty of motivators. Maybe they’ll feel a call to create or help others. Or they’ll want to work in an animal shelter,” I said.
“You’re too idealistic,” Lynn said with a snort. “Money is the best way to motivate people. It’s the way society works. We need to eat. We need shelter. Then we want some jewelry.”
“But money isn’t the only motivator,” Donna said. “People work for many reasons.” Turning to me, she said, “Lynn knows fear is very motivating.”
The three of us laughed. Lynn had no obvious reason for concern, but she’d long been worried about ending up shoeless on the street, which was one of the reasons she was continuing to work, keeping her skills up to date, and ensuring she would always be employable.
“I want our kids to see me getting up every day and going to the office,” Lynn said. “My dad worked three jobs when I was growing up.”
“Kids learn from what’s going on around them,” Donna said.
Donna then told us that her children had recently drawn a picture for Matt to hang in his office.
“They made me a picture too,” she said. “I was supposed to ‘take it with me to the stores.’ Can you believe it? Do my children think all I do is shop? That’s not the behavior I want to be modeling.”
I laughed. But I wouldn’t be laughing as loudly a couple of years later when Ali wrote a Mother’s Day poem about a mother who spent too much time at her computer and not enough time with her daughter.
When friends told me, “Your daughters are so nice,” or “Your kids are so grounded,” I heard these comments as code for surprise that rich kids could be pleasant, not obnoxious. Given the expectations and preconceptions around wealth, it seemed Emily and Ali would need to work extra hard and be extra nice to prove themselves likable and competent. People would likely link their achievements and failures to money too—for good reason. Wealth gave our daughters many advantages. They were set up to succeed. Growing up in a stable home, they were already well ahead of kids whose basic needs were not being met. And with access to education, healthcare, and social connections, they were way more privileged than most. But wealth could cause problems too, distorting their view of the world and paralyzing them with too much freedom and too many choices.
When Ali was in third grade and the two of us were walking home from school together, she told me that kindergarteners looked small.
“When I was in kindergarten,” she said. “I thought I was bigger than that.”
“Now that you’re in third grade, you are bigger,” I said.
“When I’m in fifth grade, like Emily, will third graders look small?”
“Probably.”
“When I’m in middle school, the kids in elementary school will look small. When I’m in high school, the middle school kids will look small. Then I’ll go to college. Then I’ll go to work. Then I’ll stop working.”
“Most people don’t stop working,” I said. “Most people work until they are Grandma’s and Grandpa’s age.”
Thinking about Ali’s view of the future, hoping to teach her the value of money, David and I started giving the girls an allowance, doling out a weekly dollar fifty to Emily and a dollar to Ali. We assembled cardboard piggybanks from Charles, our financial advisor, encouraging them to put their money aside for saving, spending, and giving.
At first, allowance was a hit and we felt successful. But after several months, once the novelty had worn off, we forgot to give the girls their money. Since Emily and Ali forgot about allowance too, weeks passed without any cash exchanging hands. Then, when we were out and Emily or Ali asked for some candy and we told them to use their allowance, they said we owed them, asked to borrow, and it was clear no lessons were being taught or learned. Even when we tried a monthly schedule, telling Emily and Ali they needed to ask for their allowance at the beginning of each month, we didn’t have success. But I wasn’t worried.
Allowance didn’t seem as critical as making sure our daughters felt loved. I also wanted them to be integral, contributing members of our family, which meant having dinner together. Not only were meals a good time to connect and share stories from the day, everyone could participate. I cooked, while Emily and Ali set the table. Then, after eating, the girls cleared the table, and David did the dishes. The girls had other responsibilities too, like making their beds and keeping their room tidy. But it could be difficult to enforce the rules. One afternoon, when Ali called out, asking if Noreen was coming tomorrow, I found her sitting on the floor of her bedroom in a sea of tiny white papers. It was tempting to let Noreen make the mess disappear the next day, but I told Ali she needed to clean up when she was done.
It seemed important that the girls take responsibility for their messes and for us to eat together every night but I believed the best way to ensure Emily and Ali were grounded was to exhibit the behavior and attitude I wanted to see from them. They knew that we viewed affluence as a tool and a benefit, not something to flaunt or a source of pride. They witnessed us making tradeoffs, compromises, and not buying whatever we wanted. We enjoyed meals at nice restaurants and traveled abroad, but we saved dinner leftovers for lunch the next day and were appreciative of our ability to travel as a family. They also observed David working nonstop and saw my involvement at their school.
By the time Emily and Ali were in high school, they were both working hard and succeeding academically. Emily had dedicated herself to a sport she loved for a decade. Ali had a job in a clothing store where she worked after school and on weekends throughout her junior and senior years of high school. But I continued to worry, unsure how our wealth was affecting their lives—and my concern was shared.
“When I was in high school, I felt the pressure of necessity,” Sue told me. “I needed to get a job and knew I’d have to work for a living. That knowledge and need shaped who I am. Our boys don’t feel that same pressure. It’s hard to know who they’ll become without that same need to work.”
“We’re not planning to give the kids any money,” Nicole said. “They’ll get money when we die, but not before. They need to work.”
When Nicole’s oldest went to college and she told him how much she was giving him as an allowance, he complained, saying he was accustomed to a certain lifestyle and needed more.
“I told him he’d have to work if he wanted the same lifestyle,” Nicole said. “If he needed money, he’d have to make it himself . . . and he got a job as a deejay.”
Betsy, who described herself as the “family CFO,” made a point to teach her three children how to manage their money. Early on, she helped them set up checking accounts, gave them a monthly allowance, and taught them the importance of living within a budget. But with one of her children in the workforce, another in college, and the youngest at boarding school, she was concerned.
“We’ve been giving the two at school quarterly allowances,” she said. “But they keep running out of money. We’re paying room and board, but they’re constantly having food delivered, going out to eat, and using up their allowance.”
Over spring break, when her college-aged son went on a trip with a friend, and called her from the road, asking for money, Betsy wanted to tell him he needed to figure things out. But her husband, who had grown up never having enough, didn’t want his son to go without, especially when he didn’t have to.
“It’s a problem. I’m not sure what to do,” she said. “My husband and I try to set limits, but the limits are artificial—and our kids know it.”
Her oldest wanted to live off campus for his final year of college, so Betsy told him he first had to successfully live on campus without overspending.
“An off-campus apartment has become my carrot,” she said.
Meanwhile, her twenty-three-year-old son had a job but wasn’t making enough to cover the cost of rent and had asked to move back home “for a month,” which turned into two, then three, then longer. Neither Betsy nor her son was happy with the arrangement.
“I’ve begun charging him rent but it’s backfiring,” she said. “He owes me money. But he knows the situation is contrived. What am I going to do? Kick him out?”
Loren, who had grown up in poverty, was frustrated by her boyfriend’s older children, who seemed ungrateful for their advantages.
“After growing up with nothing and seeing all they have, it’s hard not to feel resentful, even jealous,” she said. “They can be so rude and careless. When I cook for them, I have to make them thank me.”
Julie’s oldest son was about to start college.
“I’m not sure what to give him for an allowance,” she said. “He wants us to ‘throw him to the wolves’ so he can learn to fend for himself.”
Julie and her husband were considering giving him a large lump sum, encouraging him to invest, and telling him he had to live on the money for the next four years.
“The experience of managing money on his own would be good for him,” Julie said. “He needs to understand how finances work before he turns twenty-five and gets a lot more.”
Laurie, who had three children in middle school, wasn’t particularly concerned about them being spoiled. She attributed their good attitude and awareness to the closeness of their family and to each of her children having jobs. Her oldest worked at the business her husband started, her daughter babysat, and all three did chores around the house.
“But I’m always questioning our decisions,” she said. “For example, I wasn’t sure what to do when the kids outgrew their bikes. My husband wanted to just buy three new ones, but it seemed like we should wait until Christmas or a birthday. Finally, I accepted that we didn’t need to make it a special purchase. We just got the bikes so we could ride together as a family. But I’m concerned we’re setting them up for a shock in the future.”
Janet, an heiress, did her best to keep her money a secret when she was in college and in her early twenties.
“I flew under the radar a lot,” she said. “When I first started working for our family foundation, I learned to say I worked for ‘a’ family foundation. I wanted to be transparent but didn’t want to open that whole side of myself up when meeting someone for the first time. It made dating hard.”
After spending a lot of time in Guatemala, where she’d started a nonprofit, Janet found it difficult to transition to and from Manhattan.
“When I’m working with indigenous people, I can become numb to the poverty. A child begging starts to seem normal—and that bothers me,” she said. “It bothers me how quickly I become numb to wealth too. Back in New York, living in a multimillion-dollar apartment, surrounded by people who fly in jets, I hear myself saying, ‘I’m not that rich.’ But compared to who? It’s hard to feel grounded, to remember this is not how most people live. I try to focus on the good we are trying to do with philanthropy. I try to spend a lot of time in Guatemala too.”
Karen’s ex-husband lavished their two children with expensive gifts and money.
“When they were younger, the kids wanted to vacation with their father, not me,” Karen said. “I liked going on more educational trips, and he’d fly around in a private jet and take them to extravagant resorts.”
When their daughter needed a car and Karen was thinking about getting her a Chevy, her ex-husband bought her a Range Rover.
“She didn’t want it,” Karen said. “But he told her she didn’t have a right to an opinion if he was paying.”
Soon afterward, Karen’s daughter decided not to take any more money from her father. She sold the Range Rover and sent him the cash.
“When she was no longer dependent on him, she accidentally used one of his old credit cards for a medical appointment,” Karen said. “He called her immediately, saying he noticed she was taking his money.”
Meanwhile, Karen’s son was thrilled when he could drive his father’s Tesla.
“He drove up wearing sunglasses, moccasins, and driving gloves,” Karen said, looking skyward. “He’s now about to start a job in finance, just like his dad. He’s going to be making a lot of money. I’m a bit worried about him. I’m worried about my daughter too. Given her interests, she won’t ever make much.”
Experts recommend talking to children about money when they are young, but just as David and I weren’t good with allowance, we never felt the timing was right. Conversations about money hadn’t been part of our own childhoods and it was difficult to know how to bring up the subject. We had no idea what to say or how Emily and Ali would react. There were so many potential pitfalls. What’s more, with them in school, going to class, involved in sports and activities, and spending time with friends, the details of our financial situation didn’t seem relevant to their lives. They were just kids. They were lucky money wasn’t a worry or something they needed to think about. So, although we did our best to make sure Emily and Ali knew they were lucky, we fell back on what we’d learned growing up and allowed the specifics of our finances to disappear.
A 2017 New York Times article titled, “How the Wealthy Talk to Their Children” confirmed that wealth was difficult to discuss, even within families. According to the article, “Two-thirds of the [fifty-seven] people polled by Wilmington Trust . . . said they were, ‘apprehensive about sharing inheritance details.’” Only one in ten had fully disclosed amounts to their children. Wealth advisors acknowledged that families who’d lived with wealth over generations had an advantage over people like David and me, who had no system in place to serve as a guide—all of which was a relief to hear. Many other parents felt the way we did.
When the girls were twenty and eighteen, Emily a junior in college and Ali about to start her freshman year, we agreed it was time to talk to them about money. But we still didn’t know how to broach the subject or how much to divulge. Even good news could be difficult to digest. Emily and Ali were doing well, happily hiking along, aiming for the summit, facing setbacks, making progress, and sharing their joys and fears with their friends. Telling them about the money they had would be like giving them a pair of magic shoes. Those shoes could get them to the top of the mountain in half the time and with less effort, but would they feel overwhelmed, their goals called into question, their future uncertain? Would they want to keep those shoes a secret, pleased about the security, but wary of being singled out, their friends looking at them differently? We believed Emily and Ali needed to know about their wealth and wanted them to see it as a benefit. But money represented obligation and responsibility. The doubts and dilemmas were real too.
Before talking to our daughters, curious what other parents in our situation were doing and had done, we decided to ask—and there was clearly a lot of pent-up energy around the topic of children and wealth. As soon as David sent an email to a couple of friends, suggesting we get together for dinner to discuss giving money to our children, the responses were immediate. And when we met, conversation was animated. None of us had ever discussed wealth in such detail with other people.
Our first dinner was with John and Claire, an Amazon executive and his wife. John had grown up middle-class and had been extremely successful at Amazon. Early on, he and his wife had set up college plans and trusts for their two children. Then, when each of their children turned seventeen, John and Clair had them meet with their financial advisor.
“We wanted our kids to understand how their college education was being paid for,” John explained. “It was a good way for the kids to get to know our family advisor.”
Later, John and Claire told their children about their trusts.
“The money is theirs,” John said. “They have complete freedom to use it any way they want. We wrote them each a formal letter explaining that the money had been invested to provide for their health, maintenance, education, and support.”
Without divulging the total amount, the letter also explained that their children could expect to receive a lump sum every year with larger sums at age twenty-three and twenty-five, half of the remaining value of the trust at thirty, and the balance at forty.
“We had each of them meet with our financial advisor alone, so they could ask questions without trying to please us or meet our expectations,” John said. “We want them to see this as a gift that helps them feel secure and gives them choices.”
We next spoke with our good friends, Donna and Matt who had set up trusts for each of their three children, the oldest of whom was a junior in college.
“We’re not sure what to tell our kids,” Matt admitted.
Donna was concerned about the decisions their children might make and didn’t think any of them were ready to get a large sum of money.
“It’s more our money than theirs,” she said. “I want to guide them as they make choices.”
The four of us agreed that information about money needed to be doled out slowly. Too much too soon seemed problematic.
“I think they’ll need prenuptial agreements,” Donna said.
“I completely agree,” I said.
If things went wrong, at a time of emotional turmoil, I wanted our daughters to be protected from financial loss. More than that, it was important that Emily and Ali discussed money with their partners and had ongoing conversations about finances. Having a shared understanding about money was not only critical to any union, talking created trust and built intimacy. There was nothing romantic about taking out the garbage or doing the dishes, but just as couples needed to negotiate those tasks, conversations and agreements about how money was spent, saved, and divided were essential too.
After talking with Matt and Donna, we enjoyed dinner with Joe and Ann. Joe, an ex-Microsoft manager had grown up lower middle-class, became an engineer, joined Microsoft, and had done extremely well. His wife, Ann, hadn’t worked in years, and their three adult children were all in the workforce, two with families of their own. Joe and Ann hadn’t set up trusts but had always supported their children financially.
“For a long time, Ann and I talked about tailoring gifts to each of the kids,” Joe said. “But in the end, it didn’t make sense.”
When their oldest was about to buy a house, they gave all three children the same large amount, explaining that the money was intended for housing. One of their children ended up buying a big home, another purchased a smaller place and put money in the bank, and the third hadn’t yet settled down.
“They know we’re here for them, but they don’t expect us to give them money,” Joe said. “They don’t need it either.”
After hearing directly from other couples, talking to the girls about their trusts didn’t feel as overwhelming, and our next dinner conversation was with Emily and Ali during a family vacation. We let them know ahead of time that we wanted to talk about finances, and after being shown into a recommended restaurant, down a narrow staircase to a small room surrounded floor-to-ceiling with bottles of red wine, we ordered drinks, bruschetta, artichokes, and burrata, and Emily asked what exactly we wanted to discuss.
To begin, we reiterated that we were fortunate to be on vacation, together as a family. We talked about being lucky, about the choices we’d made, and the benefits of education. David then explained how we were paying for college.
“When you were little, we set up funds specifically for education,” he said. “The money we invested will cover the cost of college and probably graduate school too, if you want to go.”
“What if we don’t want to go to graduate school?” Ali asked.
“You don’t have to go,” I said.
“What happens to the money if we don’t?” Emily asked.
“I’m not sure,” I said. “But it’s there if you need it.”
“It needs to be used for education,” David said. “If you don’t use it, we could probably give it to one of your cousins.”
We then explained that we’d invested additional money in trusts for each of them, that the investments were doing well, and that they would get large sums of money in the not-so-distant future. Then, hoping to help them get more accustomed to handling cash, we told them we were going to give allowance another try.
“We’ll have money deposited into your accounts every month,” David said. “It’s to buy things for yourself, to take your friends out. It’s to spend, not save.”
Starting in middle school, influenced by her two best friends—and by us—Ali had become very careful with her spending. Even after working for two years in high school to earn money of her own, she didn’t spend much.
“I know it can be hard to spend money on things when your friends can’t,” I said. “You don’t want to make people uncomfortable. But I bet your friends would appreciate you taking them out to lunch.”
“It’s too awkward,” Ali said. “I don’t want to show off. It would be embarrassing.”
“It’s lucky I have Hannah as a friend,” Emily said, referring to a college buddy who was from a wealthy family. “She has no issue with being rich. She spends a lot of money and she’s super generous with everyone. It makes it easier for me to spend and be generous too.”
“Sometimes, when a bunch of us get coffee, one of my friends says she can’t join us, that she doesn’t want to spend the money,” Ali said. “But she clearly has enough. I don’t want to be like that, using money as an excuse or pretending not to have it when I do.”
“You can’t hide what you have or cover up how much our family has because you’re embarrassed or want people to like you,” Emily said. “It’s annoying. People know and it’s irritating when people pretend.”
“Yeah, I know,” Ali said.
“Some of my friends can’t afford to go out,” Emily continued. “They’re so appreciative when I buy drinks or pay for dinner. It feels good. I’ve never had a bad experience. I’d rather be overly generous than not go out because a friend can’t afford to.”
It was a relief to hear Emily and Ali talk. They had each other. They seemed to have a relatively grounded view of money too. If anything, I wished they would spend more freely. It was hard to know how wealth would influence their choices and decisions in the future, but in the present, they seemed to be enjoying the advantage of not having to think much about finances at all.
Contemplation & Conversation
•Do you give your children an allowance? What have they learned from having their own money?
•What do you think motivates people? What can lead to apathy? Does motivation come from nature or nurture? What role does money play in motivation?
•What is your biggest concern about money and your children? What attitudes and actions do you hope they adopt?
•What are your thoughts about prenuptial agreements? Would you want your children to have a prenuptial agreement or would it upset you if they did?