(Photo by Kevin Mathewson, Kenosha County Eye)
KENOSHA, Wis. — Nearly twenty years ago, Jo Wynn found herself standing outside a Walgreens downtown with a backpack, her toy Maltese Isaiah tucked inside, and nowhere to go. The pair had been homeless for three days, turned away from every shelter that didn’t allow pets. Wynn remembers looking up at the cold night sky and saying, “After all I’ve done for people, this is what I get?” That heartbreaking moment became the spark for something extraordinary — the beginning of Walkin’ In My Shoes, a grassroots effort that would change thousands of lives across Kenosha County.
Wynn, a Chicago native, had come to Kenosha hoping for a fresh start after losing her mother and battling depression. A friend had offered her a place to stay, but because of her small dog’s separation anxiety, she couldn’t leave him behind. Her refusal to give up Isaiah — her best friend and only companion at the time — cost her a roof over her head. “He was my baby,” Wynn said. “He helped me through depression. I wasn’t going to part with him.”
(Photo by Kevin Mathewson, Kenosha County Eye)
What followed was a string of closed doors and bureaucratic dead ends. Wynn found herself sleeping outside, calling agencies that handed her lists of numbers with no real help behind them. Finally, with the help of then-Congressman Paul Ryan’s office, she was able to get her Social Security disability benefits released. A local couple agreed to rent her a house on Sheridan Road if she could vouch for her well-behaved dog. She did — and that home became the first headquarters for Walkin’ In My Shoes.
“I sat at my kitchen table and created what I didn’t see for people,” Wynn recalled. “That’s how it started.”
A Mission Born From Experience
Founded in 2005, Walkin’ In My Shoes, Inc. is a 501(c)(3) nonprofit that provides direct aid and support to Kenosha residents facing homelessness, poverty, and crisis. Wynn’s goal wasn’t just to hand out help — it was to empower people to rebuild their lives. “Not everybody’s looking for a handout,” she said. “They’re looking for a hand of direction.”
Her early work began with what she called the Survival Backpack Program, handing out backpacks filled with food, toiletries, and resource guides to people living on the street. Those first months of outreach revealed three major unmet needs: overcrowded shelters, lack of housing assistance, and lack of awareness about prevention and rehabilitation services.
Nearly two decades later, Wynn’s all-volunteer organization now runs multiple programs that reach hundreds of people every month.
Programs That Restore Dignity and Hope
Among its many services, Walkin’ In My Shoes operates:
- Ida’s House Youth Program, named after a young mother Wynn once took in. It helps teens and young adults aging out of foster care — or abandoned after adoption — find housing, education, and job opportunities. Wynn has personally helped place students at UW–Parkside, UW–Milwaukee, and Carthage College, ensuring they have a pathway to independence rather than homelessness.
- In the Hands of Hope, an aftercare outreach initiative that works with the Kenosha County Detention Center. For nine years, Wynn has volunteered inside the jail to help inmates who were homeless before incarceration find housing, employment, and food assistance upon release. “I’ve seen the reduction in recidivism because of that,” she said.
- The Bunker Coffee House for Vets, opened in 2022 at 2211 50th Street, offers a “safe space” for veterans, active-duty personnel, and their families to relax, share meals, and access computers for VA benefits and job applications. On the fourth Saturday of each month, Kids Day at The Bunker welcomes children of veterans and surviving spouses for crafts, games, and a warm lunch.
- Steppin’ Up Grandparents Program, which provides school supplies and uniforms to grandparents raising grandchildren.
- Helping Hands, a donor-driven effort to give grocery gift cards to veterans and their families, allowing them to choose their own food rather than rely on food boxes.
- Healthy Livin’ Preventive Outreach, which promotes nutrition and wellness education to encourage healthy lifestyles.
2211 50th St Kenosha
(Photo by Kevin Mathewson, Kenosha County Eye)
Each of these initiatives, Wynn said, was inspired by a real person she met on the streets. “Every program I’ve ever created came from someone’s story,” she said. “We see a need, and we fill it.”
One Woman’s Faith and Ten Thousand Success Stories
Wynn estimates she’s helped more than 10,000 people through her programs. “Everyone I’ve helped, none of them have ever relied on government assistance,” she said proudly. “We’re the least funded organization doing this kind of work, and to me that’s heartbreaking. We’re not trying to keep people in poverty. We’re trying to lift them out.”
Her approach blends compassion with accountability. “If a man don’t work, he don’t eat,” Wynn said with a laugh, quoting Scripture. “We give people a Big Mama push. You can’t just stay stuck. You have to participate in your own outcome.”
That philosophy has won her the trust of both community leaders and the people she serves. Local officials often refer veterans, families, and youth to Walkin’ In My Shoes for emergency help. Wynn even serves as power of attorney for one veteran, personally writing his rent check every month to ensure he stays housed.
“I’m not trying to be a social worker,” she said. “I’m just trying to be what I needed when I was out there.”
Faith, Resilience, and Community Support
Wynn’s impact hasn’t gone unnoticed. Walkin’ In My Shoes has earned Platinum Transparency status from GuideStar, the highest level of nonprofit accountability. But even with that recognition, the organization struggles financially. All of its programs are volunteer-run, and Wynn herself draws no salary.
She credits her faith and a tight-knit network of volunteers — many of them veterans — for keeping the doors open. “We don’t have paid staff, just people with a heart to serve,” she said. “And we serve everyone with dignity, whether they’re a veteran, a single mother, or a teen who’s been thrown away.”
The Bunker Coffee House is now the heart of her outreach. Inside, veterans sign the “Wall of Honor” with their name and rank. Each Thursday, the place fills with laughter, conversation, and gratitude — a testament to Wynn’s belief that healing begins with belonging. “They’re not forgotten,” she said, pointing to the message painted on the wall behind the coffee counter. “That’s what this place is all about.”
How to Help
As the holiday giving season approaches, Walkin’ In My Shoes is seeking donations to continue its vital work. Monetary contributions, new clothing, toiletries, nonperishable food, and grocery or restaurant gift cards are all welcome. The organization also needs volunteers to help serve meals, sort donations, and assist veterans and youth with applications for housing and benefits.
Donations can be made online at www.walkininmyshoes.org or dropped off at 2211 50th Street, Kenosha, WI 53140.
“Every dollar stays right here in Kenosha,” Wynn said. “You don’t have to look far to make a difference. Sometimes, it’s just about walking in someone else’s shoes.”
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3 Responses
What a great story! I would absolutely love to meet this woman!
Thank you for highlighting this particular organization. Jo Wynn has been such an amazing advocate for homeless veterans and kids who have aged out of the foster care system. She is making a difference one individual at a time.
Jo Wynn deserves Kenosha’s person of the year recognition!!!