The $20 Kindness Challenge: How One Teacher is Creating a Legacy of Giving

Every year, teacher Kristina Ulmer hands her students a crisp $20 bill and gives them a simple but powerful assignment: Use this money to do something kind for someone else.

There are no strict rules, no limitations—just an open-ended opportunity to make the world a little brighter.

For seven years, Ulmer’s $20 Kindness Challenge has sparked a wave of thoughtful, creative, and deeply meaningful acts of kindness. Some students buy groceries for struggling families. Others bake cookies for first responders. Some choose to donate to charities, while others use their talents to create something special—like crocheted hats for premature babies or handmade pillowcases for children in hospitals.

What started as a classroom project has grown into something much bigger. And it all began with a story of love and loss.

A Sister’s Legacy of Giving

The idea for the challenge traces back to 2014, when Ulmer’s sister, Katie, tragically passed away in a car accident at the age of 29.

At the time, Katie had just completed her training to become an emergency medical technician (EMT). She had big dreams of helping others, but sadly, she never got the chance—she passed away before she could start her new career.

When police recovered her belongings from the crash, they found her purse containing about $100 in tips from her morning waitress shift. That small pile of loose bills was all the money she left behind.

Ulmer (R) with her late sister Katie (L)

“I knew it had to do something worthwhile with it,” Ulmer said.

For years, she searched for the right way to honor Katie’s memory. Then, one day, while discussing Fahrenheit 451 with her students, she had an idea. The dystopian novel describes a world where people are glued to their screens, disconnected, and lacking empathy. It struck a chord with Ulmer, who wanted to remind her students of that kindness matters, connection matters, and small actions can make a difference.

So she converted her sister’s tip money into $20 bills, added some of her own, and launched the $20 Kindness Challenge.

A Small Bill, A Big Impact

Each year, Ulmer’s students find new and inspiring ways to use their $20 to help others. One student crocheted tiny hats for premature babies in the NICU. Another sewed bright, cheerful pillowcases for hospitalized children. Some wrote heartfelt holiday cards for veterans, ensuring they felt remembered. Others used their money to buy warm meals, groceries, or supplies for people in need.

One student, Sydney Cassel, was so moved by the experience that she continued the challenge even after leaving Ulmer’s class.

“The first time I participated in the challenge, I didn’t think it would be possible to make a difference with $20, but I learned that’s really not true,” Sydney said. “You don’t have to have millions—anyone can make a difference.”

The Power of Paying It Forward

What started as a deeply personal project has grown into an annual tradition of kindness. Thanks to donations from the community, Ulmer continues to fund the challenge year after year, proving that small acts of generosity can inspire something much greater.

At its heart, the $20 Kindness Challenge isn’t just about giving money—it’s about teaching compassion, awareness, and the power of human connection. And it’s a reminder to us all: Kindness doesn’t have to be big. It just has to be shared.

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