When I was a kid and stopped to stare at a man playing guitar on the street, mesmerized by his singing and the shiny coins in his guitar case, my parents urged me to keep walking, telling me we didn’t give to beggars.
“That guy probably makes a good living,” my father said to my mother. “I bet he dresses in old clothes to get more.”
During my childhood, my mother and I took bags of clothes to Goodwill, donated canned peaches to food drives, and talked about the importance of helping the needy. But I never saw my parents giving money away. With my father worried about bills and my mother fearful of spending, there never seemed to be anything extra to give. I also got the sense that charity was for chumps, that people asking for money were out to take advantage of people like us who worked hard and paid taxes.
“We’ve been saving, so we have to pay full college tuition,” I heard my father complaining to my mother. “Other people cheat the system. They have nothing in the bank, but have big houses and expensive cars—and get financial aid.”
Just as it took time for my thinking about saving and spending to change, my understanding of giving and charity took time to grow and evolve—longer than I might have expected, and longer than I might have hoped. When I first joined Microsoft, it wasn’t my good salary or stock options that prompted me to give. It was the people around me. Only after witnessing co-workers donating to local causes did I even think to do the same. Then, inspired, I signed up to donate a small percent of my paycheck to United Way and sent a $1,000 check to Planned Parenthood for the good work they were doing.
Similarly, when I first joined the board at Emily’s daycare, giving wasn’t top-of-mind. But during a board meeting, as we grappled with how to increase employee pay, talking about raising tuition, expanding the facility, and cutting back on staff, my heart began to pound. It suddenly dawned on me I could do something to help. As soon as that meeting was over, I drove directly to the bank and withdrew thousands in cash. It was exciting to think of giving gifts to all the caregivers and staff. But uninterested in being seen as somebody rich, I made the donations in secret, sneaking into the daycare at night and putting envelopes with $200 into each of the fifteen mailboxes.
Not long after giving anonymously at the daycare, I met with one of the caregivers for coffee and watched as she put a five-dollar bill into the tip jar.
“That’s nice,” I said.
“What?”
“Giving such a big tip.”
“It’s nothing,” she said. “They work hard.”
“You work hard too. Do you really have an extra five dollars to give away?”
“I don’t like having too much money,” she said. “It makes me uncomfortable. It’s the way I live. When I have money, I spend it. Or I give it away.”
She then shared a story from when she was ten years old and found a wad of bills on the street. She’d taken the money into a nearby store, and when the guy at the counter told her to keep it, she didn’t know what to do.
“It must have been sixty bucks,” she said. “I took it home. But I got rid of it somehow. I don’t feel good when I have too much. I don’t want to be like rich people.”
Breezing past her comment about the rich, drawn to her lack of attachment to money, I felt compelled to be more generous. Soon afterward, hoping to ensure other women benefited from the support and camaraderie I’d experienced in my PEPS group, I gave the largest amount I’d ever given, writing a $5,000 check to the PEPS organization. Then, after years of listening to public radio, David and I gave $10,000 to NPR, proud to be stepping up and giving to an organization that was an important part of our lives. We then attended our first UCDS auction.
Parents, teachers, and staff had dressed for the occasion, many in elegant evening wear and sparkling jewels. The event space was elaborately decorated too. Colorful DNA chains dangled from the ceiling and bent wires and beads were nestled into centerpieces, reminders of the school’s goal to raise funds for a new science lab.
For the first hour, David and I talked with other parents and surveyed the silent auction items. We then sat down at our table with friends and I began searching through the centerpiece for Emily’s artwork.
“I think they’re supposed to be atoms,” someone said. “Is that Emily’s?”
I held up a colorful jumble of beads and peered around the table, silently assessing the other creations, believing Emily’s just might be the best. Our children’s art was meant to tug at our hearts and provoke generosity. There was also competition in the air.
The mesclun salads arrived and the head of school took the microphone at the front of the room, welcoming us to the evening and encouraging us to give. She then asked us to raise our paddles for teacher enrichment and financial aid, and as the auctioneer called for $5,000 gifts, David held our number high.
The salad plates were cleared, the chicken and salmon entrees arrived, and we gossiped about the items to be auctioned off during dessert.
“Did you see what the Boylston family donated?” someone asked. “Time at their Palm Springs home, including flights and a chef for the weekend. I bet their place is beautiful.”
“Yeah, but what’s up with the Williams? It’s not like they couldn’t afford to buy several restaurants. They only gave a dinner for two.”
As the live auction began, I nudged David to raise our paddle for an Indian cooking class and dinner for twelve. He waited a few minutes, then held up our number, pushing the price to $800 and making us the winners. Energized, we bought the use of a new Mini Cooper for a weekend and four backstage passes to the Nutcracker. Then, it was time for the class projects to take the stand.
Works in progress for months, the class projects were the crown jewels of the evening. Every teacher at the school had contributed an idea and every child had participated in the process of creation. There were wood-and-steel sculptures, tables with hand-painted tiles, mobiles of yarn and cloth, all meant to affirm the wonder of our offspring and certify how smart we were to be at the school. David and I had no need for a collection of papier-mâché animal masks displayed on a coat rack, but buying the creation Emily and her classmates had made was a good way to demonstrate our support, give to the science lab, and show how proud we were of our daughter, her teacher, and her classmates.
“We could keep the masks for a couple weeks, then distribute each one to its creator,” I suggested. “Go slowly. Let’s see what other people do.”
As wine flowed and music blared, the auctioneer surfed the crowd, pointing from one table to the next. The price moved upwards $50 at a time until it reached $1,000, then slowly crept to $1,100, at which point, everyone in the room was looking at our table, the auctioneer pointing directly at us.
“Going once. Eleven hundred dollars. Going twice . . . Do I hear eleven hundred and fifty? For the school?”
Suddenly, the crowd’s attention turned. Someone at the back of the room had entered the bidding. Looking around, I saw a man holding a paddle over his head, a determined expression on his face. The woman at his side had her hands over her eyes. Was he trying to prove himself? Was she nervous about spending too much? Was she embarrassed? Had they talked about this beforehand?
No longer interested in Emily’s project, I reached for David’s arm. We didn’t need to prove how much we could give or grab more of the spotlight.
“Let them have it,” I whispered.
I tugged at David’s sleeve attempting to pull our paddle to the table.
“The school will get the money either way. That’s what matters,” I said.
But David kept our paddle high until the price reached $1,300 and we became the owners of sixteen animal masks and a coat rack.
Walking to the car in the dark, I looked down at the pavement.
“That was ugly,” I said.
“Aren’t you glad we got it?” David said. “Emily’s going to be excited.”
“I guess we can point to Emily,” I said. “But what were we trying to prove?”
“We’re going to give each family the mask their child made. Do you know the other couple that was bidding?”
“I’ve seen her at school, but I don’t know her.”
“Well, they’ll end up getting their child’s mask.”
“Yeah. We’re being so generous,” I said. “More like playground bullies.”
A few days later, thinking about the auction, I declared myself both generous and self-centered, proud we did our part, but aware we’d been shamelessly showing off too. Later still, in discovering the auction raised nearly half a million dollars, I wondered if the money was a testament to the generosity of our 300-student elementary school or if, by donating to the school where our children were attending, we were just a bunch of overly privileged families giving to ourselves.
When Ali started preschool and Emily entered first grade, a mother of a boy in Ali’s new class asked to meet with David and me. With more experience, I would know what to expect. At the time, however, I was clueless. After we’d been chatting for a few minutes, this mother looked directly at me and asked us to consider making a $100,000 donation. I was shocked. One hundred thousand dollars was an incredibly large amount of money. I couldn’t believe she was asking for so much.
Over the days that followed, I kept running into this other mom at pick-up and drop-off and found myself hoping to impress her. I wanted to contribute to the school and make a positive difference as a generous community member and likable parent. Again, with more experience, I would know that a donation intended to please or gain status didn’t often bring the desired results. Giving was best done without expectations, especially of being liked. At the time, silently contemplating the gift, I dug deep into my motives and intentions. What was I hoping to achieve? Did I expect something in return? Did we get when we gave? Did altruism exist? Whether a good feeling, a way to avoid guilt, gain peace of mind, or check “good deed” off a list, giving had benefits. Charity could be self-serving.
As I continued to contemplate what I wanted to do and why, I began to worry about not having enough, and wondered how much impact we could make. There were so many wealthy families at UCDS. No matter how much we donated, other parents could give more. Should we give to a school with fewer resources? If we gave the amount requested to UCDS, what would we do the following year? Should we be donating a certain percentage of our yearly income and considering tax breaks? We needed a plan. We needed charitable goals. There was research to be done. I wanted to do giving right.
When David joined the board of the Seattle Girls’ School, a new middle school for girls, my questioning and learning continued. Philanthropy had a language of its own. I hadn’t known “development” meant raising funds, an “endowment” was a large pool of money, “capacity” referred to the depth of a person’s ability to give, and donors needed to be “cultivated.” It was surprising to hear how David’s committee “targeted” potential donors by going through lists of names, commenting on each one, and coming up with a strategy for extracting the largest amount possible when making an “ask.”
“We’re friends with that family,” a committee member might say. “He just had back surgery. We should wait until he’s feeling better to approach them.”
Moving down the list and pointing to another name, someone might suggest requesting a “major gift.”
“They have huge capacity. Their third child just graduated from college. Tuition is no longer an issue. They’re ready to start focusing on philanthropy. Who can reach out to them?”
“They live next door to my brother,” someone might say. “I’ll talk to my sister-in-law and find out what she knows.”
In many ways, fundraising was calculated and businesslike. But it was highly emotional and personal too. After David’s committee identified potential donors, they spent months building connections, holding evening talks about the school’s mission to give underserved girls access to an excellent education, and meeting with people over lunch. They thought about “stewardship” as well, keeping their donors informed and helping them feel good about being involved in something bigger than themselves. After all, an informed, engaged donor was likely to give again.
While I was shocked by UCDS’s ask, the $100,000 requested got me thinking bigger than I’d ever imagined, my idea of what was possible expanding exponentially. Thinking about the need for everyone in our country to have access to a good education, we decided to give UCDS twice as much as we’d ever given and earmark our $20,000 gift for financial aid. Months later, also in support of education, David suggested we make an even larger gift to provide scholarships to two underprivileged girls every year for the lifetime of the Seattle Girls’ School.
“Let’s donate $80,000 to the endowment,” he said.
Twenty thousand dollars already felt like a generous amount. At first, it was hard to imagine letting go of four times as much. But, with my heart ready to give, and my head reminding me of enough, we added $80,000 to the endowment, which left me feeling proud, then humbled. It was gratifying to make a positive difference in other people’s lives.
With increasing exposure to big numbers, larger gifts began to sound normal, and given the abundance in our life, I felt an increasing need and desire to give. Philanthropy became part of our social life too. Friends started to invite us to auctions and luncheons, asking for contributions to causes they cared about, proving peer pressure could be a positive force. In fact, in years to come, Bill and Melinda Gates, along with Warren Buffett, would use peer pressure in creating The Giving Pledge to inspire other billionaires to donate their wealth to charity.
In 2002, David and I put $600,000 into a donor-advised fund. But it soon became clear that letting go of the cash was not the hardest part of philanthropy and far from the most rewarding. Although the money was no longer ours, I had no idea where to direct the funds. I wanted to reach outside our immediate community to support women and children. David wanted to do more to improve education. Neither of us had specific ideas or organizations in mind. Browsing the internet in search of worthy nonprofits was not the answer. There was no way to evaluate an organization based on a website. And without an emotional connection or knowing any of the people involved, I felt little impetus to give. In fact, for years, I was stuck. I felt guilty. I wanted to be doing more but wasn’t sure where to start—and I let my obligations and responsibilities as a mother take precedence.
Years later, when the girls were older and I no longer felt the need for a grand plan or to do giving perfectly, I viewed philanthropy not only as an obligation and responsibility, but as a benefit and a joy. Giving was highly personal, an expression of my values, and a show of what I cared about most. Every gift was a statement about what was important to me. I felt fortunate to be able to donate $5,000, $10,000, and $20,000 to organizations that were doing good work and aligned with my values. When a gift had an impact and people were benefitting, I often gave again. Aware of our net worth and the abundance in my life, I didn’t need to overthink philanthropy. I was doing giving my way. Meanwhile, my peers continued to help me increase my generosity. Many introduced me to organizations I wouldn’t have discovered on my own, and I appreciated requests, often giving simply because I’d been asked. David was an inspiration too.
In 2010, David would cofound a nonprofit called Worldreader, giving people in the developing world access to digital books. He worked on the project full-time for three years without taking a salary, only paying himself once Worldreader began proving successful. Then, in 2015, David and I pledged a million-dollar gift to Worldreader, which was a milestone. Not long afterward, we made a second million-dollar pledge. And with Worldreader clearly helping to create a world where everyone had the books they needed to improve their lives, aware of the abundance in our own lives and hoping to inspire other potential donors to think bigger, we pledged five million dollars.
The people I spoke with about wealth were each at a different stage in their charitable thinking and giving, which meant a gift of $100 was as meaningful and generous to one person as a $100,000 gift was to another.
Loren, whose financial situation had changed dramatically after she met her boyfriend, spoke of how rewarding it was to give money to causes that were important to her.
“I visited an equestrian rescue farm with my mom last summer and ended up donating $250,” she said. “My mom couldn’t believe I could give so much. But it felt great, especially when the guy in charge told me it cost $250 a day to feed all the horses.”
Laurie was worried she wasn’t doing enough.
“We give to a couple places like the children’s school, but I want to start doing more,” she said. “I need to make the time. It’s hard to know where to begin.”
Meanwhile, after learning about charity from her children’s schools, Julie had joined the board of a public school and was helping them raise money.
“The independent school my children attended taught me about philanthropy. I learned about things like capital campaigns,” she said. “Over the years, I’ve made a commitment to myself never to give more in a year to our kids’ schools than I give to the public schools.”
Betsy had long been involved in charity, and when she and her husband wanted to start giving more, they determined how much to give their children, set a certain amount aside that allowed for their lifestyle, then put $30 million into a donor-advised fund with the intention of distributing the money over the coming fifteen years.
“I try to think locally, nationally, and internationally,” Betsy said. “I’m most interested in women and education. I’m on a couple boards and have commitments to them. Over the years, we’ve given to our children’s activities and interests too. Now, we give big to a couple of organizations and give smaller gifts of $5,000 and $10,000 to other places.”
Denise, whose husband had sold his technology company when they were both in their mid-thirties, put $25 million into a family foundation the same year.
“We had so much,” she said. “I needed a way to break the amount down and wanted to give it away myself. Too many foundations end up dispersing money once the founder has passed away. Where’s the passion in other people blindly trying to figure out what I might have wanted or trying to adhere to restrictions once I’m gone? I wanted to make a difference in our community here and now.”
For many years, Donna’s financial advisor had budgeted an amount for her and Matt to give away every year.
“At the time, it was helpful to be told an amount,” Donna said. “Having a set sum to give away got me to make a multi-year million-dollar pledge to women and girls through Women Moving Millions. But I don’t think about charity that way anymore. Now, I get a sense of purpose through volunteering and making things happen in the nonprofit space and don’t think about giving away a set sum.”
Janet, who worked for her family foundation, set a goal for herself to give away ten percent of her salary, donating to organizations where she volunteered and giving smaller amounts to friends who asked for her support when running a marathon or raising money for a cause.
“Since my job is to help people with their philanthropy, it’s important for me to experience what my donors are experiencing and to give away some of the money I’m earning,” she said.
In the future, fundraising as a board member of a nonprofit arts organization, and both watching and helping David raise money for Worldreader, I would see how generous people could be but also how the amount a person gave wasn’t necessarily correlated with their net worth. Most seemed to approach charity based on what they’d known growing up. And since giving was a skill that could be learned and improved, the amounts people gave often increased over time. Most gave locally to organizations run by people they knew or to causes that touched their hearts.
Soon after we put $600,000 into a donor-advised fund, I came face-to-face with a scruffy-looking homeless man holding a bent cardboard sign and reaching his gloved hand toward our car. I stared straight ahead, relieved when the traffic light turned green and I could escape up the street.
“Why was that man standing there?” Emily asked from the back.
I was silent.
“Did he want money? Why didn’t you give him any? Do you have money?” she asked.
“Yes, but I don’t just give money to people on the street,” I said.
“Why not? Is he hungry? Did his sign say he was hungry?”
“There are places he can get food,” I said. “It’s better to give to an organization that can help him. That way, all the dollars are put to good use—for food, a place to sleep, to find a job.”
Halfheartedly congratulating myself on addressing Emily’s questions, I continued toward home in our Volvo sedan, not feeling all that good about myself. That man probably wasn’t going to find a job. Would he have anything to eat tonight? Why didn’t I give him any money? I’d watched someone a couple of cars ahead hand him a few bills but hadn’t considered giving him anything myself. Like the caregiver at Emily’s old daycare who empathized with the baristas, other drivers probably empathized more readily with the hardship he was facing. I’d read that people like me, who didn’t have much direct contact with adversity or need, tended to lack compassion. I didn’t want to be that person, following my own larger philanthropic agenda without opening my heart to those around me.
A few days later, when we were having dinner with Donna and Matt, I told them about the homeless man.
“I’ve never given money to people on the street,” I said. “I was raised to believe it wasn’t good to give to beggars. But that’s not very compassionate. Next time I pass someone, I’m going to give them some money.”
“We should all be more generous,” Donna said. “Why don’t we challenge ourselves? We could give gifts to unsuspecting strangers.”
“Random acts of kindness,” David said.
“What do you mean?” Matt asked. “We can’t just walk up and down the street handing out cash.”
“Let’s each give away a thousand dollars,” Donna said. “One hundred dollars at a time.”
“I want to look another person in the eye and give from my heart,” I said. “But it makes me nervous. Giving money feels so intimate, so vulnerable. Will people be suspicious? What if they refuse to take the money?”
“I don’t think it’ll be an issue. People will be happy,” Donna said. “I’d like a hundred bucks for free.”
A few weeks later, on a cold, drizzling evening, David and I stopped at a Christmas tree lot with Emily and Ali. A grey-haired man wearing a red-and-black flannel shirt and a clear plastic rain poncho, pointed out several trees, fluffing out the branches. We made our selection quickly, and the girls and I returned to the car while the tree guy sawed the end off of our tree and hoisted it onto the roof with David’s help.
“That guy looks cold,” Emily said.
“It’s wet outside,” Ali said.
When David opened the driver’s door and leaned in to get his wallet, the two of us looked at one another and nodded.
A few minutes later, David jumped into the car.
“I did it!”
“What happened?” I asked.
“I paid for the tree then handed the guy a hundred-dollar bill. At first, he just looked at the money. When he understood it was for him, he was so happy. It made his day. Mine too.”
The following week, with a hundred-dollar bill folded in the pocket of my dark purple coat, I walked into the dry cleaners to the sound of the bell and smell of hot wool. After paying and picking up the clothes, hardly noticing the metal hangers digging into my palm and not worrying about the dangers of plastic bags, I focused all my energy on getting the timing right.
“Happy Holidays!” I practically shouted, handing the woman a hundred dollars.
After years of greetings and pleasantries, it was as though the two of us saw each other for the first time. We stared. I smiled. She nodded.
“Thank you very much,” she said.
“You’re welcome,” I said. “Thank you. It’s always a pleasure to come in here.”
Then I scurried out the door.
That evening, when I told David about the experience, his face contorted.
“I gave some money away today too,” he said. “You know the woman at Starbucks?”
“The one who makes perfect latte foam?” I asked. “You gave her a hundred dollars?”
“I did,” he said. “But, well, I went in there, planning to tell her what a great barista she was, but there was a long line. So, I waited around.”
“Did she notice you?”
“I’m sure she did. I was hanging out, looking at espresso machines for quite a long time. Finally, I got a coffee as an excuse to talk to her,” he said. “But it was like a comedy. Just as I got up to the counter, she went over to arrange things on the shelves.”
“What did you do?”
“It was so awkward.”
“Why didn’t you just leave?”
“I should have. But I was determined. I went over and let her know that we thought she was a great barista and handed her a hundred dollars. But she refused to take it.”
“Oh no!”
“Yeah, it was bad,” he said, beginning to laugh. “It got worse. I didn’t give up. I insisted. Finally, she told me to put the money in the tip jar.”
“Did you?”
“Yes . . . and ran out of the store.”
Several weeks later, David had more success. On our way to Napa, we stopped at an In-N-Out Burger. David placed our order while Emily, Ali, and I found a table and arranged napkins, ready for our meal. Suddenly, David was standing by my side, asking for one of our special bills. I handed him a hundred dollars and watched him hurry back to the counter where he stopped in front of a young couple. He said something to the woman then handed her the bill. She covered her mouth and began hopping up and down, while the man pumped David’s hand, a huge smile on his face.
“When I was paying for the food, I needed ten cents,” David told me when he returned to the table. “I was fishing around in my pocket, trying to come up with the change and that guy gave me a dime.”
“And you gave him a hundred dollars?”
“That’s right. Did you see his reaction?”
“He looked ecstatic,” I said. “He looked the way this makes me feel.”
I had no idea what a hundred dollars meant to the couple or what they would do with the money, but I felt connected to them, our lives touching for a warm, happy moment. The element of surprise was joyous too. Whether a dime, a dollar, or a hundred, being charitable was not about amounts or philanthropic strategy but about opening our hearts and doing our personal best to make a positive difference in one another’s lives.
Contemplation & Conversation
•What did you learn about giving during your childhood? Has your attitude toward giving changed? If so, how and why?
•Do you give enough? What does enough mean in this context? Do you think of yourself as generous? Does peer pressure affect your giving?
•What do you gain when you give? What keeps you giving or stops you from giving again?