Start a $20 Kindness Challenge
A note from Kristina Ulmer, founder of the $20 Kindness Challenge:
In 2018, I started the $20 Kindness Challenge as a way to honor my late sister and teach my ninth-grade students about empathy. What began as a simple classroom project became one of the most meaningful experiences I’ve had as a teacher. I watched students slow down, notice others, problem-solve, collaborate, and care in ways no traditional assignment could capture—and I never imagined how quickly it would grow beyond my classroom.
As other teachers began asking how they could bring the challenge to their students, I created this space to share what I’ve learned: what has worked, what hasn’t, and what I recommend after years of doing the challenge with my own students.
The resources here are meant to support and inspire, not prescribe. Every teacher, group of students, and school community is different, so these are suggestions based on my own experience rather than requirements.
At its heart, the $20 Kindness Challenge empowers students to use a small amount of money to carry out an intentional act of kindness. But it has never really been about the money. It’s about helping students notice the needs of others, make thoughtful choices, take action, and reflect on their impact—often through the simplest acts.
While the concept is simple, thoughtful planning and clear expectations can make the experience more meaningful and manageable. The guidelines that follow reflect the lessons and best practices I’ve learned along the way.Thank you for considering bringing the $20 Kindness Challenge to your students. I hope it becomes as meaningful for them as it has been for mine.
1. Get to Know the Basics
Before You Begin
What is the $20 Kindness Challenge?
The $20 Kindness Challenge is simple: each student receives $20 and is challenged to use it to carry out an intentional act of kindness.
Unlike traditional random acts of kindness challenges, students aren’t given a list of acts to complete. Instead, the $20 gives them both an opportunity and a constraint: enough to make real choices, but limited enough that they must think creatively and intentionally about how to use it. Students identify a person, group, or need they care about, then plan, budget, problem-solve, and turn their idea into action. They can work independently or combine their money with classmates for a larger impact.
The goal isn’t simply to spend or donate $20. It’s for students to take an active role in kindness and discover that making a meaningful difference doesn’t require a lot of money or a grand gesture. Afterward, students document and reflect on what they did, why they chose it, and the impact their actions had on themselves and others.
The $20 provides the challenge. The students decide what to do with it. And when many small acts of kindness are added together, they can make a much bigger difference.
2. Establish a Clear Timeline
Students need structure and accountability.
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Set a firm window for completion. For my high school students, a four-week timeline has always worked well. You may decide to provide less time. However, I would not give more than one month. You will most likely have students who ask for an extension. I always allow this (teenagers have busy lives), but one or two students with extensions is more manageable than the whole group turning in their documentation late. You may also have students who run out of time and do not complete their act of kindness (This happens at least once a semester for me). There are two options I offer to these students: donate the money to a charity of their choice (however, in this instance, I still require the student to submit a reflection) or return the $20 and you can save it for the next group of students or donate it to charity.
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Avoid times during the school year when there is a lot going on in the students’ lives. For example, I’ve noticed if I offer the kindness challenge too late in the school year, my 12th graders feel too overwhelmed with the end of their school career to participate. However, while December can often feel busy for us adults with many of us preparing for and celebrating holidays, my high school students seem to have an easier time coming up with acts of kindness during this time of the year because there are a lot of organizations asking for help. This may not be the case, however, for younger students who will require more adult help.
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Share all deadlines in writing and revisit them regularly
3. Obtain Guardian & Student Permission
Because students are receiving money and may need support from home, parent/guardian permission is essential.
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Send home a permission form explaining:
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the purpose of the challenge
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how the money will be used
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that students may need adult assistance
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how documentation will be handled
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if and how students’ acts of kindness will be shared (school district social media, etc.)
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that students must complete their act of kindness in a safe and responsible manner and may require adult guidance and supervision
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Require a signed permission slip from both the students and guardians before distributing funds.
You may find an example of this permission form here.
4. Provide a Central Place for Documentation
Students must have a consistent, organized place to submit their documentation.
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Create a shared Google Drive or OneDrive folder and provide students with the link to upload their photos, videos, and/or thank you letters.
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Have students rename their files as their names. Trust me. This will help you sort them later (I have my students rename their files LastName1, LastName2, Lastname3, etc.).
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Remind students that documentation is required. I require students, at bare minimum, to submit a video reflection because I compile those into a larger video to share with our students, school district, and donors. All of this documentation gets submitted to a OneDrive folder I link in Canvas. However, you may choose to showcase the acts of kindness another way (An email, a newsletter, a district social media post, etc.). However, I highly recommend that students take photos and/or videos of their acts of kindness. In the beginning, I only required students to submit a video reflection, but I realized the donors and the community love seeing students doing the act of kindness, so I very quickly began requesting they submit at least photo documentation as well.
5. Set Clear Expectations for Documentation & Privacy
This is critical and should be explicitly taught.
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Students should document their act of kindness, but:
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Do not include anyone who has not given permission. If they do include someone without being given permission, you should block out their face before sharing the photo publicly.
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Do not take photos or videos that could embarrass, exploit, or expose someone in need.
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Example to avoid: photo of a homeless person receiving a blanket.
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Documentation can include:
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photos of purchased items
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photos or videos of students doing the act of kindness (Examples: Making meals for a shelter, baking cookies for the police, buying treats and toys for an animal shelter, etc.)
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drawings or written descriptions (for younger students)
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You should decide what documentation you’d like your students to submit. However, be specific and provide examples of what they should submit and where, how, and when they should submit this documentation.
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Emphasize that the goal is impact and reflection, not social media attention.
6. Allow (and Encourage) Group Projects
Especially for older students, collaboration increases engagement.
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Students may work individually or in groups.
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Older students often prefer to pool their money to create a larger impact.
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Require groups to:
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list all members
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clearly explain how funds were combined
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share responsibility for documentation and reflection
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7. Guide Students Toward Ideas (Without Limiting Them)
Some students will feel overwhelmed by open-ended choice.
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Provide a list of possible ideas for students (Check out our ideas list).
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Emphasize that:
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ideas can be simple
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kindness does not need to be flashy
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thoughtful planning matters more than scale
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choose ideas that do not put themselves or others at risk; if they are unsure whether an idea is safe or appropriate, they should ask a trusted adult before moving forward
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Encourage students to choose something that feels meaningful to them.
Note about donations to charities: While financially supporting charities is valuable and important, this project is intentionally designed to focus on active acts of kindness. While I have made exceptions for students who have a personal connection to a certain charity, the goal is for students to engage directly in kind acts and/or helping others so they can experience the planning, effort, and personal impact that comes from taking action. Hands-on acts of kindness help students build empathy, problem-solving skills, and a deeper understanding of how their choices affect others.
8. Prepare to Support Students
Students often need guidance beyond the classroom.
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Be ready to help students:
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refine ideas
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adjust budgets
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think through logistics
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problem-solve challenges
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Remind students that it’s okay to ask for help from family, teachers, or community members as long as the kindness remains student-led.
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Younger students will require more guidance and adult assistance.
9. Use a Tracking System
To keep the project organized and accountable, create a checklist for yourself.
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Your checklist should include:
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students’ names
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confirmation that the student received the $20 (I require a student signature on my checklist)
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checkboxes for required submissions, such as:
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Photo/Video evidence submitted
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Reflection completed
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Thank-you letter submitted
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This protects both teachers and students and simplifies tracking.
10. Close the Loop
The reflection and gratitude pieces matter.
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Build in time for:
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student sharing (optional and respectful)
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reflection on the impact
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writing thank-you letters to sponsors
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This reinforces accountability, gratitude, and the purpose behind the challenge.
Final Thoughts
The $20 Kindness Challenge works best when expectations are clear, privacy is respected, and students are trusted to lead with empathy.
When structured well, this project becomes a powerful lesson in compassion, empathy, and civic engagement — one students will remember long after the money is spent.
Thank you for helping me expand this project to other schools. I am so excited for your students to experience how deliberate and thoughtful acts of kindness positively impact themselves and society. Please contact us with any questions.