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KIND LEADER ESSAY CONTEST
At Riley’s Way, we know Kind Leadership is leading with empathy, purpose, and community at the heart of everything you do. Kindness is a strength—it shows up through compassion, respect, and truly listening to others.
Kind leaders stand out by being authentic, celebrating different perspectives, and creating change through collaboration. This approach builds stronger teams, sparks innovation, and shapes spaces where everyone feels valued, included, and supported.
Now it’s your turn: tell us about the kind leaders who inspire you—because kind leaders are the future. They’re the ones guiding us toward a world that’s better and kinder for all of us.
Contest Details
Deadline: World Kindness Day – November 13, 2025, at 11:59pm ET
Essay Question: Who is a kind leader in your community (it could even be you!) and how do they inspire you to lead with kindness?
CLICK HERE TO SUBMIT
Riley’s Way “Kind Leader” Essay Contest
Here’s what you need to know before you enter:
Prizes & Recognition
– Up to 5 winners will each receive a $500 Kind Leader Award 🎉
– Up to 20 runner-ups will have their stories featured by Riley’s Way on our website and social media to inspire others to lead with kindness.
Who Can Enter
– Open to anyone between the ages of 14 to 23 living in the U.S.
– If you’re under 18, you’ll need a parent/guardian’s permission if you win.
– If you have an Instagram account, you must be following @rileyswayfoundation.
How to Enter
– Choose one format:
📝 Written essay: 250 words or less
🎥 Video essay: 1 minute or less
– Answer the question: “Who is a kind leader in your community (it could even be you!) and how do they inspire you to lead with kindness?”
– Submit through our online portal by World Kindness Day, November 13, 2025 at 11:59pm ET.
– One entry per person. Entries must be in English.
How to submit
Upload your essay through our online portal (LINK) by November 13, 2025, at 11:59pm ET.
Before You Hit Submit Check:
✔️ You’re between 14–23 years old and live in the U.S.
✔️ You’re following @rileyswayfoundation on Instagram (if you have an account).
✔️ Your essay or video answers the question clearly and is your original work.
✔️ You’ve reviewed the Terms & Conditions.
How Winners Are Chosen
Entries will be reviewed by a panel of Riley’s Way staff and community judges using the following criteria:
– Inspiration & Impact: Does it move or inspire others?
– Authenticity & Voice: Is it genuine and personal?
– Connection to Riley’s Way Values: Does it reflect kindness, empathy, and inclusion?
– Clarity & Expression: Is it clear, engaging, and within the word/time limit?
Important Notes
– By entering, you agree that Riley’s Way can share your essay or video publicly (website, socials, events).
– Be original. Submissions must be your own voice.
Need Help? Questions? Email us at info@rileysandler.org
🌟Tips for a great video🌟
1. Plan your story. Think about a leader who inspires you and embodies Riley’s Way’s definition of kind leadership as shared above. This can be a teacher, friend, family member, coach, community member, or even yourself.
2. Start strong. Open with a sentence that grabs attention, why this person matters, or how they’ve shown kindness as leadership.
3. Be authentic. Speak naturally, like you’re telling a story to a friend. You don’t need fancy editing or equipment; your phone is perfect.
4. Show your personality. Let your enthusiasm, gratitude, and creativity shine through.
5. Keep it clean and clear. Make sure we can see and hear you clearly. Avoid copyrighted music, logos, or images. Only use royalty-free or original music if you include sound.
6. Review before uploading. Double-check your video is under 1 minute, appropriate, and follows Riley’s Way values (kindness, empathy, inclusion, & collaboration).
🌟Tips for a great essay🌟
1. Tell a story. Describe how this person leads with kindness. What makes them stand out? How do they make others feel included or valued?
2. Be specific. Use examples — how do they show empathy, respect, or compassion in action?
3. Use your own voice. Write how you speak — it should sound like you.
4. Reflect on impact. Explain how this person’s example has shaped your own ideas of leadership or inspired you to act.
5. Keep it positive and clear. Proofread your work, stay within 250 words, and make sure your essay reflects Riley’s Way values.
FAQS
Program Overview
What is the Riley’s Way “Kind Leader” Essay Contest?
A contest that invites young people to share stories of kind leadership in their communities through a short written or video essay.
Does it cost money to apply?
No. Entry is completely free.
How do I apply?
Follow Riley’s Way on Instagram (if you have an account), then submit your essay (written or video) here by the deadline.
Do you accept mail-in submissions?
No. All entries must be submitted through the online portal.
Can I submit with a friend?
No. Entries must be individual.
I missed the deadline; can I still apply?
No. Late submissions will not be accepted.
Who is judging the contest?
Entries will be reviewed by a panel of Riley’s Way staff and community judges including members of our Youth Advisory Board.
Eligibility
I’m already in college. Am I still eligible?
Yes. Individuals between the ages of 14 and 23 years old at the time of submission are eligible to apply.
Is this contest just for Riley’s Way program participants?
No. It is open to all eligible applicants nationwide.
Submission Guidelines
What types of files can I submit?
Written submissions must be 250 words or less. Videos must be 1 minute or less and in a standard format (MP4 or MOV).
Can I change my submission after sending it?
No. Once submitted, entries are final.
Can I include other people’s images in my video?
Yes, but you must have their permission. Only one person will be awarded the prize.
Can I use music in my video?
Only royalty-free or original music may be used.
Prizes & Use of Funds
What can the $500 prize be used for?
Prizes are intended to support education, leadership, self-care, or community projects; however, winners may choose how to allocate the funds.
Is the prize taxable?
All federal, state, and local taxes associated with the receipt of a prize are the sole responsibility of the winner. Riley’s Way does not provide tax advice—winners should consult their own tax advisor.
For Minors & High School Students
I’m under 18. Can I still apply?
Yes, but you must have parent/guardian permission if you win.
What happens if I win and I’m still in high school?
You’ll still receive the award. Riley’s Way recommends using funds for your future education or leadership journey.
For additional eligibility or contest questions, email info@rileysandler.org