I love Christmas, I really do. I love that all the stores are closed and there isn’t anywhere to go. I love that the phone probably won’t ring. In the unlikely event the doorbell chimes, it will be a crafty friend with cookies or other homemade goodies.

I understand the deep significance of the holiday for those who celebrate it and mean no disrespect. As a Jew, Christmas for me means a nice day off and sometimes Chinese food and a movie. We never celebrated Christmas when I was a child and I have never hung an ornament. I  think the lights are pretty but I would probably be one of those people that left them up all year round out of sheer laziness.

There’s a book I’ve had my eye on at Powell’s: Rambam’s Ladder, A Meditation on Generosity and Why it is Necessary to Give, by Julie Salamon. A few months into this adventure, I still have a lot to learn about generosity and giving. I forgot that I would not be the only person happy to get out of the house today. The streets downtown were teeming, and people had that wistful post-holiday daze about them.

As I approached Powell’s, I saw a young woman crouched over on the traffic island across the street. I couldn’t really make it out, but it looked like she had some paper or a drawing pad on her lap. People were streaming by in all directions. No one looked at her and she didn’t look up. I decided to try my luck at finding a parking place and then see if she was still there.

A spot opened up halfway down the block, which was amazing. After I parked I went back to the corner. There she was, still hunkered down practically into a ball. People and cars passed without seeming to notice her. I stood watching and it seemed to take forever for the light to change.

She’s the dark bundle at the bottom left

When I finally got across the street, I went over and tried to peek over her shoulder to see what was on the yellow paper in her lap. I was hoping to see an artist’s rendition of the surrounding landscape. Instead, I caught a glimpse of a few words. My heart sank.

“Hey, how ya doing?” I asked. “Oh, I’m okay,” she said cheerlessly. “What’s the matter?” I asked her. “Oh, I’m just trying to make this sign with this dumb pen.” She straightened up just enough for me to see what was in her lap: a sign with block letters that said “Lost My Job. Couldn’t Pay Rent.” She held the ballpoint pen out and said she was trying to fill in the outline of the letters to make it more visible. “It’s taking forever with this.”

It was cold outside and starting to drizzle. The young woman looked 17, maybe 18. I asked her what was going on and she told me that she had lost her job as a house cleaner and had split up with her boyfriend. She couldn’t afford the rent for their small apartment on her own and got kicked out. She told me that the women’s shelters were only for pregnant women or domestic violence victims, and she had nowhere to go. I was somewhat surprised to hear myself say, “How about you let me get you something hot to drink?” There was a pause and then she said, “Okay. If you want to. Actually, I don’t want to give up this spot. I just got here and someone else will take this spot if I leave. A lot of people walk by here.”

“C’mon,” I urged. “Let’s go inside for a bit. Maybe we can get you a better pen in the bookstore.” It really wasn’t hard to convince her. She got up and we crossed the street together. It crossed my mind that I hoped she wasn’t always so trusting. The bookstore was absolutely packed, a madhouse. On our way to the café we passed one of the information desks and I saw a Sharpie sitting on the counter. “Do you sell pens like this here?” I asked. No, they didn’t, but the employee offered to let us use it while we were in the store. “Just make sure you bring it back.”

I asked her name; it was Lauren. When we got to the café I told her to pick out whatever she wanted to eat. They were out of sandwiches but there were pastries in the case, and bagels. “Maybe I’ll get a scone. What do you think looks good?” she asked me. She settled on a lemon scone and hot chocolate. I sent her to find a seat while I waited in the long line to pay.

I wasn’t sure I would even be able to find her again. It was crowded and I had barely seen her face. But there she was: a small woman sitting by the window, hunched over her paper. I asked for extra whipped cream on her hot chocolate and I got one without. She was saving the seat next to me with her bag. As she moved it to make room she said, “I had a real nice backpack but I gave it to my friend. He really needed it.”

We sat together and her story came rolling out as she worked on her sign. She was 21 and had been doing okay until her hours got cut back at work. Her mother lives nearby, in Beaverton, but recently remarried “someone weird”. She’s not welcome in their home and doesn’t even know their address. Her Dad lives in San Francisco. She was hoping to get the money together to take the bus to California; in addition to her Dad she has other family and friends there. “At least I’d have some options.”

She was wearing a lightweight black coat over a blue sweatshirt, the dirty cuffs sticking out and partially covering over her hands. I tried not to stare, noticing dirty nails and chipped dark blue nail polish. She was intent on her task. “If I say ‘Looking for a room’ do you think they’ll know what that means? It’s a lot easier than writing ‘Looking for a place to stay’. I said I thought that sounded fine, flashing back to sitting with my kids while they did their homework.

There were two women sitting next to me, a stack of GRE study manuals on the counter in front of them. Their lighthearted banter stood in heartbreaking contrast to Lauren’s grim narrative. “25 Math Concepts You Absolutely Must Know. Okay, check this out. The area of a triangle, the volume of a cylinder. ‘The complete arc of a circle is 360º.’ Hey, I knew that one!”

The women were laughing about how much smarter they used to be when they were in high school. Lauren was telling me that her new stepfather didn’t want to see her for at least two years, and then only if she was in school or steadily employed. “It’s not like I want to throw my life away.” She continued slowly filling in the letters on the sign. I asked her what she did yesterday, on Christmas. “Nothing. I really didn’t do anything,” she said sadly.

I finished my hot chocolate and watched through the window as people passed by. If they had glanced our way, they might have seen a gray-haired lady holding an empty cup, and a young woman bent purposefully over a piece of paper.

I decided it was time to go and told Lauren I was going to take off. I had a C-note folded up in my pocket and I held it out to her. “I hope this helps out a little. Take care of yourself.” “Oh, thank you! Are you sure?” she asked. “Yeah,” I said. “Look at it.” She opened the bill and let out a gasp. “Are you sure?” she asked again. For the first time, she looked at me full on, relief flooding her features. Her eyes sparkled with intelligence and a flash of optimism. I saw how pretty she was behind the piercings, dirty hair and guardedness.

“I think I’m just going to go right to the bus station and see if I have enough for a ticket to San Francisco. I could be there tomorrow!” She reached out and pulled me into a hug, saying “No one has ever helped me out like this before.”  I told her she was smart and beautiful and I just knew things would work out for her.

On the way out, I passed by the employee who had lent us the pen. “She’ll bring it back soon,” I promised. He shrugged. “We’ll see.” “I’m sure she will,” I insisted. Now I think maybe she held onto it as a reminder of the strange and wonderful thing that happened today. I kind of hope she did.

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Every day of October I will give $100 to someone I encounter during the course of my routine. I got the idea after receiving a check as beneficiary of my mother’s retirement fund. A number of people have asked me to explain more why I am doing this and, particularly, how it honors my mother.

My mother, Gina, died in May at age 89. She was born in Berlin to a wealthy Jewish couple who spoke French at home and travelled extensively. As a teenager in the late 1930’s her parents sent her to supposed safety in England, where she moved in with a family of strangers. She spent the war years in London as an enemy alien and joined the British Army’s search and rescue efforts. Because of her small size and athleticism she was teamed with a dog and sent into the rubble of bombed out buildings to locate survivors. Through a series of miracles (the details of which I could never extract from her), my mother was reunited with her parents in New York City in the 1940’s. Although her education was interrupted and she never finished high school, Gina perfected her English by reading Dickens, eventually spoke without a trace of a foreign accent, and became a nationally recognized expert on the education of gifted children.

Despite my mom’s privileged background, years of displacement and trauma resulted in a scarcity mentality that permeated our family’s emotional life and left me with scars of my own. My father was successful in the Ginsberg family gas station business and, later, as a Legal Aid attorney. That didn’t keep my mother from scrimping and saving with single-minded fervor, budgeting a single dollar for meat to feed our family of four, then holding back half of the meal as “leftovers” for the next day. Until I was old enough to recognize my mother’s shortcomings along with the trappings of middle class suburban life, I thought we were dirt poor.

My father had a heart attack and died suddenly when I was 17, a few months before I was to start my freshman year at Barnard College. Believing financial ruin was just around the corner, my mother told me I was on my own; without my dad’s income there was no money to pay for my education. A serious rupture in our relationship developed when she refused to provide information to the financial aid office, jeopardizing my ability to start school. With the help of the college I became emancipated, took out loans and started classes through a work-study program.

My mother remarried, developed a successful career and lived very comfortably. Yet, she remained convinced until she died that her future held peril and financial uncertainty. As for me – practicing many of the frugal habits she taught me, I worked hard and eventually paid off all my student loans. Some sore spots persisted in our relationship although we spoke almost every day and, finally, found genuine sweetness with each other.

I have to admit that my mother would think this a silly exercise, at best. I tried countless times to convince her that she could afford to be generous with herself, her grandchildren and in support of causes she cared about. But she was always puzzled by the notion of giving money away, and would certainly never have handed cash to a stranger. From her perspective, she had earned everything she had and there was no need to share.

So, why am I giving away a month of hundreds? In part, I want to prove to myself that I can do something a little crazy and unexpected and that life will go on (and – possibly – even improve). I want to be more conscious of the people around me and to challenge my notions of worthy-ness. I believe I honor my mother in striving to be my best self.  And I hope to honor and preserve the person she might have become (had history been more kind) by performing random acts of generosity and sweetness in her name.

Can $100 change a life? For the recipient? The giver?  That is some of what I am setting out to discover. Every day for the month of October, I’m going to give $100 to a stranger I encounter during the course of my routine.

I was recently pleasantly surprised to find that my mother had named me the beneficiary of a small retirement fund. More than usual, I’ve been thinking about money and the role it plays in my life. Although she was raised in an upper class German home, as a Holocaust survivor my mother lived forever with a deeply held conviction that life was defined by scarcity and want. She taught me to be frugal, and modest in my material desires.

I consider myself a generous person and make it a priority to give to causes I care about. Yet I always have questions: how much of an impact does my giving make? Won’t the need always be overwhelming? Should I spread out my gifts, or give more to fewer groups? Should I give anonymously?  Or only to strangers? I worry one day that I am not giving enough away, and the next that I might not have enough for myself and my family.

This project is about making a difference, starting with 31 people, and about exploring my money and giving issues. It is a way to honor my mother’s gift to me as well as the lessons I learned from her. I hope to spark some discussion and maybe even some generosity. Every day I’ll tell the story of the day’s $100 giveaway.

Starting now, I welcome your thoughts and comments.