Some stories find us when we need them most. Wendy Strauss’s began with a slip of paper discovered in her late mother’s tidy little office. It was a simple note titled “Mom’s Christmas Stocking,” asking her children to keep filling a stocking for Mom by giving it to a woman who needed “a shot of love.” That tender request became a calling. What started as one timid lunch-hour drop-off blossomed into an annual community tradition that now fills hundreds of beautifully curated stockings for women in shelters, prisons, and recovery programs across New York City, each one a love letter, a reminder that someone sees you and you matter.
As we enter the Christmas season, Wendy’s story reminds us what the holiday is truly about….it’s not the gifts we buy, but the love we give. It’s about connection, kindness, and finding ways to bring light to those who need it most. Through Mom’s Christmas Stocking, Wendy has turned her grief into grace, transforming loss into a legacy of giving. Her journey captures the real spirit of Christmas: that joy multiplies when we share it. If you’ve ever wondered whether one small act can change a life…..or if you’ve needed a nudge to turn love into action, then Wendy’s story will fill your heart and remind you that the greatest gift we can give is love itself.
Here are a few highlights from our conversation:
Charity Matters: Tell us a little about what Mom’s Christmas Stocking does?
Wendy Strauss: Each holiday season we fill hundreds of Christmas stockings and donate them to a group that distributes them around the five boroughs of Manhattan. Women, often in prisons, rehabs, or shelters receive these beautifully filled stockings to get a “shot of love” and a little holiday joy, women who might not otherwise receive that.
Charity Matters: What experiences did you have as a child that helped shape your giving?
Wendy Strauss: I was the last of five, so I grew up almost like an only child. My mom had me later in life, and I tagged along as she did a lot of spiritual seeking….yoga and meditation before they were popular. She surrounded herself with younger people, almost mentoring these hippie-type kids who were chanting and meditating. That openness to people who weren’t “the norm” formed my childhood. We were vegetarians when it wasn’t really a thing. She was my role model…open, curious, ahead of the curve. It wasn’t about “giving back” yet; it was about discovery, but that spirit of openness and love was the seed.
Charity Matters: What was the moment you knew you needed to act and start Mom’s Christmas Stocking?
Wendy Strauss: In 2007 my mom passed away unexpectedly in March. We already had a trip planned for June to see family. We stayed in her house, she’d fixed it up for us and it felt like she was welcoming us even though she wasn’t there. One morning I wandered into her very tidy little office. She was a wonderful writer—so many articles, Historical Society work, family tree research. I picked up a random file folder and a slip of paper fell to the floor. It was titled “Mom’s Christmas Stocking.” It said:
“Every Christmas you have always filled a stocking for Mom. I want you to continue to do so. Choose the very things I would love and those you love to give to me. Find someone to give this filled stocking to a woman in prison or in a drug rehab or a homeless center. This is the most precious gift I could receive or that you could give, sharing the love we know with someone who really needs a shot of love. And in this way, I will continue to share your Christmases and continue to be a part of my wonderful family.”
I made copies for my siblings. That Christmas I took it very seriously. I filled one stocking, Googled where to bring it, and found Women In Need. On my lunch hour I brought it over, explained why, tucked in a copy of Mom’s note, and they said they’d find someone to give it to. I went back to work and felt so good the rest of the day. At my evening workout my friends said, “Something’s up,” so I told them and they said, “Next year we’ll all fill stockings.” The following year we did eight. Then 75. It just grew. People wanted to donate more and know how it worked, and eventually I looked up how to become a nonprofit and did the paperwork myself.
Charity Matters: What are your biggest challenges?
Wendy Strauss: Starting anything is hard, and once I became a nonprofit the pandemic hit. I got my determination letter in 2020 and then everything closed. I was filling stockings by myself….Amazon donations came, but no gatherings. Funding is always a challenge. Spreading the word is a challenge. Space is a challenge. We host an annual stocking-stuffing event at the gym where it all began, Grassroots Fitness Project, and that’s a gift, but organizing, storing, keeping things moving when you’re doing it primarily alone is a lot. I’m good at admin, but the bigger we get, the more time those pieces take.
Charity Matters: What fuels you to keep doing this work?
Wendy Strauss: Loss has been part of my story….after my mom passed, we lost my dad; my husband passed in 2014; my brother shortly after. Everyone we encounter has something going on. I know what makes me feel better. A dear friend, who had gone through something horrific, came to one of our events and said, “Wendy, giving is healing.” That became my motto. It is so healing. Yes, the recipients get something, but we get so much in return.
Charity Matters: When do you know you have made a difference?
Wendy Strauss: The feedback is beautiful…..families who look forward to the event every year, friends who never miss. People who moved away now run their own stocking-stuffing gatherings; Massachusetts, Virginia, Maryland, Colorado, and now North Carolina. Local New York businesses and schools do their own events and ship stockings to me. That impact and seeing the seeds become their own gardens is how I know.
Charity Matters: Tell us what success you have had and what your impact has been?
Wendy Strauss: I try to prioritize quality over quantity. I get pushed on numbers….“How many this year?” The need is so great that providers want to honor as many moms as possible. I do my best. But success, to me, is the community that’s grown around this. The families who plan their December around coming, the kids who love it, the businesses and schools who join in, the chapters springing up in new places. In one or two hours at our New York event we’ll fill 400 stockings and it goes so quickly because so many people show up. The impact is the joy and connection we create, the “shot of love” that keeps rippling.
Charity Matters: If you could dream any dream for your organization, what would that be?
Wendy Strauss: A solid team. A couple of “sugar donors,” I always joke. More space. My vision is a year-round space where the stocking operation is always set up and groups could come in any time to fill stockings, from small gatherings to big parties. People could take them to distribute wherever they’re needed. I love working with other organizations and donating to them when I can, collecting items so I’m ready when someone calls and says, “I need size 9 sneakers.” I like to manifest, so I’m putting this out there.
I’m also learning to ask for help. I’m a do-it-yourselfer, but when I finally asked a friend to help, she said, “I’m so happy you did. I love doing this for you.” I’d love a teenage intern to help with social media. A countdown to the event or the season and those little things make a big difference.
Charity Matters: What life lessons have you learned from this experience?
Wendy Strauss: Discernment. Everybody has a story and we don’t know it at first glance. Being kind to the worker on the street, saying good morning—those small things matter. They also help me; they soften my shell. People say New Yorkers are tough, but kindness makes the shell flexible. I’ve also learned boundaries—soft ones and hard ones—to help me grow in my life and in the nonprofit. We can only give when our cup is full. The need is always greater than we can meet, so boundaries keep us going.
I’ve planted a lot of seeds. My mom was a wonderful gardener; I’m not, at least not with plants—this is how I garden. I’ve seen growth, and it’s meaningful for so many people that they want to help. That’s beautiful. And I’ve learned that we don’t need that much to be grateful. I’m grateful for the tiniest things now.
Charity Matters: How has this journey changed you?
Wendy Strauss: I’m not the same person I was in 2007…..I hope not. I want to keep growing. I take care of a lot, but I can do it. With focus, there’s more we can do than we expect and while staying within boundaries. My compassion has grown. I’m an empath, and landing in New York City amplified that, but compassion is universal. Once you open up to other people’s stories and to hearing them and serving them, your understanding deepens. That makes you want to keep helping. It gives you gratitude, and gratitude gives you joy.
Charity Matters: Any closing thoughts….
Wendy Strauss: Giving is healing. That’s the heart of this. My mom’s note was her way of comforting us and staying part of our Christmases. Every stocking is a love letter and something a mom would have loved, passed on to a woman who needs that “shot of love.” It began with one stocking, one note, one person. Now it’s families, schools, businesses, and chapters across the country. I’m grateful for every helper who shows up, every year-round donation, every kind word. Christmas should be all year and it can be, if we keep sharing love.
CHARITY MATTERS.
To Support Mom’s Christmas Stocking visit: momschristmasstocking.com
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