Dear Readers: I am continuing my journey of giving away 100 $100 bills to strangers in 2011 and have moved my blog to a new website. Please come visit, and re-subscribe to continue receiving notification of new posts. Thank you, Jill

Cheryl's Hundred

The other day, a mere couple of blocks from home in my affluent neighborhood, I was shocked to see two people curled up in a doorway. So covered in blankets and rags, they almost escaped my notice. Every week there are new people trolling the streets, their shopping carts piled high with recyclables. What kind of country are we becoming, really?

I have moments of cynicism when I wonder how much good any one of us can do, when it feels like the world is broken beyond repair. What will it take to make our world better? What is required of us as human beings? How do we rise to the challenge, day after day after day?

I struggle with my own brokenness as well. Miserliness was etched into my DNA long before I had anything to say about it. It’s not a fatal mutation; I see that now. And it needn’t keep me from living a full and generous life, although that will always be hard work.

I have found a way to make a difference. For me. For now. Every time I surprise a stranger with a gift, I look them in the eye and promise wordlessly to shoulder a tiny fraction of their burden. Whatever they’ll give me for $100. Sometimes I get more than I paid for, which I normally would consider a real bargain.

In 2011, I’ll be giving away 100 C-notes.

The actual corner

I’m definitely smiling more at strangers since the month started. Something about giving away money puts me in a really good mood. This morning I was about to get off the bus when a man in a wheelchair got my attention. “Ma’am?”, he said from behind me. I turned around. “I just want to say that you have a beautiful smile.” “Thank you”, I said. “You have a pretty nice smile yourself” (which was true, despite a few missing teeth). “I always like to point it out when I see a beautiful smile”, he continued. “It’s one thing I can do to make the world a better place, and we all have to do our part”. Wow! I thought.

If I’d been quicker on the draw I would have loved to give that guy $100 but we pulled up in front of my office building and I got off. Also, I was planning to make today my random giveaway day, it being October 11th and all.

I was downtown near Pioneer Courthouse Square during the lunch hour. The farmer’s market was going on and there seemed to be a lot of tourists about. People were lined up at the food carts as well as just lounging about, almost as if it were still summer. I took care of an errand and then decided to get serious about giving away $100. I was headed to a corner on the south end of the square where there was a good amount of foot traffic. On the way I passed panhandlers and people slumped in doorways, as well as a woman with a suitcase who was arguing with a couple of cops outside Peet’s Coffee.

I had decided to give the money to the 11th person who walked by, so when I got to the corner I stood there expectantly. People were rushing by from all directions and it was hard to get an accurate count. OK, I told myself. The 11th person to walk by headed east. And they have to pass right in front of me.

Suddenly it was as if the lunch break was over, because the foot traffic almost completely stopped. I stood there for a long time and missed my train back to work. I finally got up to number 7 but it was taking forever. People kept veering off at the last minute and walking behind me. Number 9 eventually passed and I could see two fairly nondescript guys headed my way. They weren’t together but were walking at a similar pace.

The suspense was killing me to see which one would walk past me first, blowing his chance at $100. Finally Mr. Number 11 walked by and I took a step toward him. “Excuse me”, I said. “Can I talk with you for a minute?” The man froze for a split second and then started walking faster. “No!”, he shouted over his shoulder.

I thought about running up to the guy and telling him I had been about to give him $100, but I thought better of it. He seemed to be having kind of a bad day as it was. So I had to start counting all over again and the traffic was still light. Two young women and a small boy of three or four walked by in the other direction. The women were both smoking and the kid was walking between them, talking and gesturing excitedly. “He’s Laserman! When he takes off his glasses, lasers shoot out of his eyeballs!” He acted this out convincingly.

A few more people walked by. A man with a cat on his shoulder crossed the street and passed behind me. Then I saw the two women and little kid headed back in my direction. It looked like one of them was going to be Number 11. The first woman and the boy walked by, cigarette smoke wafting behind them. As the other woman passed in front of me, I stopped her. “Excuse me, can I talk to you for a minute?” The next train was coming, and I knew I didn’t have much time. “OK”, she said. “Until the train comes, anyway.” I told her a quick version of what I was doing and that I had been waiting for the eleventh person to pass. “It’s me?”, she asked with a smile. I gave her the $100 and asked her if she knew what she was going to do with it. “I’m going to spend it on that little guy right there!” The three of them got on the train and I could see her talking and smiling.

Choosing randomly was interesting and a surprising amount of work. I get a lot of satisfaction out of making my selections based on some combination of intuition, observation and imagination. I probably never would have picked that woman otherwise, and I like how it worked out today.

I briefly considered giving $10 each to ten people today, in honor of 10.10.10, but decided to stick to my plan. So far, no one has balked at the $100 bill. I’ll need to replenish my supply this week.

The President’s Day sales inspired me to consider a major purchase – a couple of new pillows – and I decided to make a trip to the nearby mall this afternoon. I drove right by Goodwill on the way, and there was a parking place out front. I was feeling lucky, so I pulled up and headed in. I have found some really nice things at Goodwill, although it’s hit and miss.

October makes for kind of a weird scene in there, with all the second-hand costumes and decorations. There were well-dressed college types shopping for Halloween, as well as the regulars picking through the sweaters and work clothes. I’m not really a regular but I know my way around the place and within a few minutes I had found a few nice blazers to try on.

The dressing room doors each have a punch-code combination and you have to wait for one of the staff to come and open it unless someone inside holds the door for you on their way out. I was standing and waiting alongside a rather rough-looking middle-aged woman and a young boy of six or seven. The dressing rooms are adjacent to a bunch of the Halloween stuff, so he was looking through that and kept asking the woman to buy things for him. She said she would buy him one of those orange plastic pumpkins that you can take trick-or-treating. He found something else he wanted and the woman said, “Let’s just pick one thing a day instead of a whole bunch of things.”  The boy kept up a polite chatter, pointing out things he liked. The woman, clearly impatient, said, “Don’t ask for anything else here. I’m just getting you that pumpkin. I don’t know what you are going to ask for at the next store.” “I know it’s something you don’t want me to have”, said the boy. “And how do you know that?” “Because I already ask-ed you for it and you said no”. “Then why are you asking me for it again?” The boy was holding the plastic pumpkin and looking around. “Because maybe you will say yes a different time.”

It seemed like an innocent enough conversation but there was an ominous undertone that put me on edge. I felt sorry for this boy. I imagined that he was regularly subjected to the tyranny of the woman’s impatience and borderline hostility. Someone came out of the dressing room and held the door open for the woman. “You go ahead,” she said to me. “I’m waiting for my daughter.” Trying my stuff on just took a few minutes and I came back out just as the daughter came out of the next room. She was the right age to be the boy’s mother, but I wasn’t expecting the multi-color dreadlocks and facial piercings. The door slammed shut behind her. “Why’d you close the door?”, accused her mother. “Now we have to get someone to open it again.” She sent the boy crawling under the door to open it from the inside.

I was standing in the checkout line when the young woman with the dreadlocks came up behind me with her selections. I had been hoping she was shopping for Halloween costumes but she had a long sweater-dress folded over her arm, and a pair of shoes in her hand. “I like your boots”, she said shyly to the cashier. Her mother took the little boy outside to wait in the car.

I felt pulled to help this young woman and her boy, although there was something distasteful about the family dynamic. I finished paying and stepped outside, where I saw the boy and his grandmother heading to their car. I was still thinking about what to do when the young woman came hurrying out of the store and swept right by me, eyes downcast.

I let her go. I felt kind of crummy about it, but told myself the older woman would probably have gotten her hands on the money somehow. Or she would have punished the daughter for having it. Weird to just get a feeling like that.

Once at the mall, I knew exactly what I wanted to do. First, I picked out my pillows (buy 1, get 1 free). Then I went up to the food court. I saw a small man in a uniform sweeping the floor. He was at least 60 and was wearing a cap that said “Mexico”. I said hello and he stopped, standing up straight and looking me in the eye.  “Alberto”, he said, smiling and revealing a broken front tooth. We talked for quite a while and then I told him, in my rusty Spanish, about my project. I gave him the $100 bill and he tucked it in his pocket. “Muchas gracias!” He said he worked very hard but was always coming up short and having to borrow money from his brother. He was grateful but didn’t seem particularly surprised. Maybe where Alberto comes from the idea of a gringa handing out $100 bills is not that strange.

If you look right at the center of the photo, you can see him in the background.

Alberto, in the background

The Grant HS Generals

It was a pretty dreary day here in Portland, with lots of drizzle. Bank robbery, teen suicides and gang violence dominate the news.

As I came out of our neighborhood grocery store this evening, a handsome young African American man in a football jersey from our local high school quietly asked for my attention. He was selling a discount coupon book and he showed me the book and all the local businesses where you could use it. “Jiffy Lube is a really popular one. You get $10 off.”

I gave the kid what in retrospect seems like a real grilling, and he indulged me politely.  What were they going to do with the money? He said they give it to their coach. Why do they give it to the coach? Well, the coach knows what the team needs and makes sure they get stuff. What kind of stuff? Well, like every two years they get new jerseys. And every Friday they have a team meal. The school doesn’t pay for any of that so they have to raise the money. What kind of food do they eat at the meal? Spaghetti. And healthy stuff. Fruit and carrots and stuff.

He said his name was Cleon and he’s a senior. He’s going to college next year but hasn’t yet decided where. Maybe North Carolina, or University of Oregon. He’s had scholarship offers at smaller schools and he’s keeping his options open. He was bright-eyed, serious and wearing just a hint of cologne.

I told Cleon I wasn’t going to buy a coupon book but that I wanted to give him something, just for him. “It’s not for your coach, it’s for you and you can do whatever you want with it.” I handed him the $100 bill and he stared at it. “Oh! Thank you, Ma’am!” He slipped it in the pocket of his shorts. “Thank you! That’s very generous of you, ma’am! Thank you very much! Thank you!”

I told him I could tell that he was going places and wished him the best of luck. “Oh, I will, ma’am! Thank you, ma’am!” I couldn’t resist pointing out: “Good things happen all the time, you know.” “Yeah”, he said. “This just made me think of that.”

Not the actual bus

Some might be surprised to learn that I am a real cheapskate. Like, one of the worst. I don’t totally blame myself and I make a big effort to abandon my contemptible habits. That’s part of what this month of $100 giveaways is about for me.

As I was growing up, my mother took her role as the family economist very seriously in a world she perceived to be full of people trying to take advantage by charging too much. Anything not store brand, on sale, day old or sold in a discount store was automatically “extravagant”, too expensive and off limits.

I didn’t know it then, but our family’s financial situation did not actually warrant this perspective. My father was a professional with a steady job and we lived in a nice home in the suburbs. And now, as a physician, there is no rational reason for me to be the cheapskate that I am. I guess that is the nature of being a cheapskate. I have noticed that most people have an easier time parting with their money than I do, even when they have less of it. While I consider myself basically frugal (and I think I do have a few sound ideas about money), the reflexive and relentless pursuit of a bargain comes from some deeply scarred place in my soul where times are truly tough.

All this to explain why I usually park 10 blocks from my office, where there are no parking meters, rather than pay $5 for parking. Paying for something that you can get for free is downright stupid and basically inexcusable where I come from.

As I was leaving the office today I realized I had time to do a quick errand downtown and revisit my random giveaway plan from yesterday. Starting my trek back to the car, I saw the bus approaching and decided to jump on for the short ride. (I have a discounted transit pass available through my employer – I would never pay $2.00 to ride 10 blocks). There were a whole bunch of people at the stop. I was lost in my own little world and didn’t take in much, except for one very cute little boy of about two standing with his hands on his hips as his dad struggled to collapse his stroller.

The bus pulled up, the door opened and everyone just stood there, which seemed really strange. Okay, maybe they were waiting for a different bus or just a bunch of losers. After a split second I marched through the crowd and started up the steps. The driver immediately put his hand out as if stopping traffic and shouted, “Hold on!” Bomb scare? What? Then I noticed a tiny woman in a wheelchair on the sidewalk and realized that everyone else had been patiently waiting for the ramp to come down so she could board first. DUH. What an idiot!

I made damn sure I was the very last person to get on and squeezed into a slot up front since I was only going a few stops. The bus was packed and the driver kept imploring everyone to “move back, please step back, move on back. Please move back.” It took forever and I could see his patience draining away. When we finally got moving I told him I hadn’t been paying attention and felt like a fool for not noticing the woman in the chair. “Oh, don’t worry about it!”, he soothed. “It’s the end of the day. For some.”

Riders kept signaling for a stop and then changing their mind. One guy started to get off, then decided to get back on and could no longer find a place to stand. We swept right by the the next stop, and the people waiting were gesturing with disbelief and frustration. I was pressed up against the back of the driver’s seat and kept catching his eye in the rear view mirror. He was keeping his cool, but clearly exasperated. “Maybe this day should be over for me!” he said, with a pained chuckle. He said his shift had just started. I imagined this kind, young handsome guy getting home late at night to his family, his kids asleep as he goes to give them a kiss.  It really bothered me that his day was off to such a rough start.

As the bus pulled up to the next stop, I reached into my pocket for the $100 bill. I folded it up real small. I sidled up to the driver and slipped it into his hand, saying “I hope you have a good day after all”. He exhaled with a grunt and I could feel a question rising up behind me as I skipped down the steps and out onto the sidewalk.

Day 7. In giving away $100 each day this month I am stumbling upon some amazing people and some fascinating stories. I’ve been thinking today about one of my original objectives for this project, which is to pry out and examine some of my assumptions about need, worthiness and generosity. The questions have been rolling through my head.  Am I following my heart or trying to sniff out a good story? If I stay focused on the stories, will I still be able to keep my eye on myself? What would it feel like to close my observing eye? How does it feel to keep it open?

Instead of relying on my instincts to pick the recipient for today’s giveaway I decided to shake it up a little. I had a plan; an errand was taking me to a part of town I don’t know too well. My plan was to stand on a well-traveled street corner and stop the 10th person who walked by. Seemed pretty foolproof.

First I had to stop at Free Geek to drop off two old printers and a defunct iMac. I was pleased with myself. as this has only been on my to-do list for a couple of years. Free Geek takes donations of old equipment and refurbishes it, teaching people how to build computers in the process. They also have a program where you can volunteer there to “earn” a computer. It’s very cool.

I pulled up and went inside to get a cart. The woman in charge introduced me to Patricia, one of the volunteers, and asked her to give me a hand. We went outside and unloaded the trunk as she told me a little of her story. She had gotten a laptop from Free Geek not too long ago and it recently was stolen from her apartment. Today was only her second day volunteering. She said she told her son that she was going to learn how to build her own computer and he said, “Don’t get electrocuted, Mom!” She thought that was pretty funny and told me that of course he was joking. “He has a very dry wit like that.”

She kept talking and I could feel my brilliant plan slipping away. Patricia’s husband is a disabled veteran and they get by on Social Security. “We know how much we have, and that’s what we spend. There’s some banks that could stand to learn that!” She encouraged me to come back sometime to take a tour of the building and learn more about Free Geek’s work. “I love it here!”, she said.

I thanked Patricia, put the cart away and made a small donation at the front desk. Then I went back and asked to talk with her for another minute. She was clearly puzzled but followed me and invited me to sit down on one of the chairs stacked up outside. She listened intently as I told her about honoring my mom with this project. Even after I said that I wanted to pass a gift along to her she asked a lot more questions and showed no curiosity about what the gift might be. When I put the bill in her hand she said, “Are you serious? Wow.”

Patricia asked my mom’s name and said she was an artist and would make a collage in Gina’s memory. She told me a little about her own mom, whose name was Anita Idaho and died when Patricia was 30. “I’m 68; four years older than she was when she died.” She told me more about her three kids and her husband of 41 years, who supports her with “unconditional love”. They hope to get a place with 5 acres someday so she can build big iron sculptures. She said I could take her picture and put it on the blog. I showed her the photo and she laughed. “That looks just like me!”

As we were getting ready to say goodbye, she looked me in the eye and said, “Thank you. I’m gonna put this aside and think about what I want to do with it.” She smiled, shaking her head. “You just never know what’s going to happen in this world.”

I was doctoring out in Gresham today, as I am most Wednesday mornings. I finished up late and it was almost 2:00 by the time I got back to Portland. I was famished and all I could think about was getting something to eat. I parked and walked over to the Burgerville just down the block from the office. As I was getting ready to pay, the cashier said, “That’ll be $5.29… Unless you want the senior discount.” Heck, yeah, I want it!! Turns out, at our local burger chain here in Oregon you can get a 10% senior discount starting at age 50! I had no idea. I was so tickled with saving 52¢ that I almost forgot I had $100 to give away.

I was heading back to the office with my sandwich when I saw two youngish white guys on the corner standing chest to chest and yelling at each other. One of them had apparently bumped into the other guy by accident. They looked so utterly ridiculous that, at first, I thought they were fooling around. Chins raised and lips curled, they were up on their toes and inching ever closer with their puffed-out chests. I saw a small group of people from work that I recognized. They had been taking a cigarette break across the street and now were watching the scene unfold.

Suddenly a mildly scruffy-looking middle-aged African American man walked up to the two guys and wedged himself between them. We all watched, mesmerized. Somehow he pushed them apart, holding each one at arm’s length. “Hey!” he said, “Look up there!” He pointed to the blue sky. “It’s a beautiful day! It’s much too nice to be fighting! You guys need to just walk away.”

Amazingly, they did. One of the two guys was still muttering and cursing but the tension was gone and they took off in opposite directions. The scruffy guy came across the street to where the small group was standing, and I got there about that same time. “Dang”, said one of my co-workers. “I was hoping to see a fight!” “Oh, no”, said the peacemaker. “You don’t want that! You carry that negativity around with you all day! Why would you want to ruin a beautiful day like this?”

I really liked this guy and watched as he talked with her for a few minutes. When he started to walk away, I stepped up next to him and matched his stride. After we were out of earshot of the others I thanked him for stepping in and sparing all of us an uglier scene. He shrugged. “We shouldn’t fight, that’s all. No need to be fighting. We just need to get along or move on”.

I introduced myself and he said his name was Tony. Then I told him about honoring my mom and that I had something I wanted to give him. He laughed. “Ha! Is it a piece of advice?” “No, here.” I put the bill in his hand. “What?! Seriously? No! You can’t give me this! I won’t take it, even if I do kinda need it.” I told him he could do whatever he wanted with it and he admitted that he really did need about $50.

Tony was a real talker, and kept up a pretty steady flow about his family and his life philosophy. We realized we were the same age and he told me about his two sisters and his fiancee, all of whom had died within a single year. Every so often he would interrupt himself and burst out with something like, “No! Why are you doing this?! Your mama wouldn’t want you just giving money away!” and “I thought you were gonna ask me out! I was trying to think what I was gonna say!”. Then he said, “This is the best thing that ever happened to me!  In my life! No strings attached! Just giving away money!”

I loved that guy. He was brave and gentle and radiated intelligence and earnestness. I really hope he keeps the money for himself, but I have the feeling he’s going to share.

When you’re looking for the right person to give $100 to, things look different – and everything is more memorable. I could hardly concentrate in exercise class this morning because I was so distracted by the ankles of the woman in front of me, each of which was tattooed with a very large skull and crossbones.

I saw a man rush into the open bay of an auto body shop with a large bouquet of flowers. That was interesting. Lots of little kids doing weird kid things like riding their tiny bicycles around in circles on the sidewalk. I came up behind a woman limping painfully along on bad knees. She was talking on her cellphone and I heard her say, “I don’t have much but I like to help out when I can.”

My eyes were scanning as I was on my way to the library. A woman and pre-teenish boy came out the library door and turned the corner. The boy was carrying a large bag full of books, swinging it in a mildly aggressive way. He had a hard look in his eyes, like maybe he was having a bad day. Like maybe he wanted to stop at McDonald’s and his mom said no, it’s almost dinner time. I hoped it wasn’t worse than that. The woman seemed just a little too old, but I figured she must be his mother. Suddenly I really wanted the boy to see something nice happen to her. I followed them down the street and caught up with them at their minivan.

“Excuse me!”, I started off.  The boy got into the van and closed the door. His mom turned to me with a questioning look and I launched into my little spiel, warning her what I was going to say might sound a little strange. I told her what I was doing and why. “Yes”, she said. “That does sound odd.” When I handed her the bill she protested: “Oh, no! You can’t give me that!” She tried to push the bill back into my hand and I stopped her. “It’s a gift. You can do whatever you want with it.” She looked puzzled for just a split second, then she got it. “Oh! I’ll pass it on! We’re fine. We don’t need it. But I’ll pass it on to someone who does.” Then she said, “Your mother must be proud of you. Thank you”, and she gave me a big hug.

I saw the boy watching us with practiced nonchalance from the front seat of the van. As the woman climbed in I turned and went on my way.

Day 4 of 31 October days. October, my Month of Hundreds.

I spent almost the whole day in either a building or my car, and I was starting to wonder how I was going to pull off my $100 give. This afternoon I drove down Stark Street into Gresham. That is one sad trek past pawn shops, trailer parks, boarded up motels, strip malls, strip joints and used car lots. There were people about, but I didn’t want to just whip over to the curb, screech to a halt and jump out with the dough. I was looking to make a connection.

I really didn’t need to go into Grocery Outlet but, when I got back to Portland, I drove right by it and found myself pulling around into the parking lot. It’s kind of a fascinating place, with a noteworthy mix of brand name products and oddball knockoffs. I wandered around for a while, looking at all the stuff on the shelves. I watched two cute Spanish-speaking kids with their parents, who were cheerfully making a selection from the ground meat area.

Then I saw a tall, lean, young man with a ponytail puff of curly hair. He was headed away from me down the aisle and I slipped into the next aisle thinking I might bump into him. I saw him turn the corner and head in my direction. The carefree yet earnest way he carried himself reminded me a little of my older son, Aaron. He was clearly stocking up on some necessities, and I watched him put a bunch of cans from a low shelf into his cart.

I waited until no one else was nearby and then walked over to him. I said hello and he gave me a broad smile. He kept smiling as I launched into my pitch: “This might sound a little strange…”. “OK”, he said, “I’m prepared.” “Are you sure?”, I asked. “I think so!”, he said, the faintest shadow of concern flickering across his face. I told him what I was doing and handed him the $100 bill.

“Wow!”, he said. “This is so weird. I mean, this is amazing! I can’t believe this! Wow!” He told me he had just moved into a new place, was looking for a job and was really short on cash. He said he felt like he had just entered a parallel universe. Then he stuck his hand out and said, “Hi. My name is Colin.” He wanted to know more about me and what I was doing and said I could take his picture and put it on the blog. I showed him the picture and we both laughed at the “FRESH MEAT” sign in the background. He asked if he could give me a hug. Then he said, “I wish you much good fortune and blessings”. That was very sweet and kind of funny, because it was just what I was hoping for for him.

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