Whether it’s diving off the high board, drawing a first dot, or facing a fear of failure, these stories celebrate kids who are willing to take chances and explore the unknown. Each book on this list highlights the value of courage, creativity, and persistence in a way that feels relatable and inspiring for young readers. Perfect for children who are learning that growth often begins with trying something new—even if it feels a little scary at first.
1. Jabari Jumps by Gaia Cornwall
Jabari has finished his swimming lessons and is ready for the high dive… or so he thinks. He watches other kids leap off the diving board with ease, but when it’s his turn, his confidence starts to wobble. With gentle encouragement from his father, Jabari takes a deep breath and finds the courage to jump. The story combines soft, expressive illustrations with an honest portrayal of fear and determination, making it perfect for kids facing new challenges.
2. Flight School by Lita Judge
A little penguin has the soul of an eagle and dreams of flying. Even though he is not built to soar through the sky, he signs up for flight school with high hopes. His determination, creativity, and the help of some kind friends lead to a heartwarming solution. With humor and charm, this book encourages readers to pursue their dreams, even when the odds seem against them.
3. What If… by Samantha Berger
A poetic tribute to resilience and imagination. The narrator explores all the ways she would express herself if one form of creativity was taken away—from drawing and painting to sculpting and storytelling. With vibrant illustrations and lyrical language, this book reminds readers that the creative spirit cannot be silenced. It encourages kids to adapt and persevere, even when faced with limitations or unexpected changes.
4. Trying by Kobi Yamada
A powerful story about failing, learning, and trying again. The boy in the story wants to create beautiful sculptures like the artist he admires, but his early efforts fall short. The artist gently explains that mastery comes from persistence and mistakes are part of the journey. This book’s timeless message and stunning pencil-and-ink illustrations make it a great conversation starter about courage, effort, and emotional resilience.
5. Giraffe Problems by Jory John
This funny tale of a giraffe who feels self-conscious about his neck turns into a story about self-acceptance and helping others, even if it means stepping out of your comfort zone. Edward the giraffe compares himself to other animals and feels awkward—until he meets Cyrus, a turtle with a completely different perspective. The humor and bold illustrations keep kids laughing while offering a subtle lesson about perspective, empathy, and confidence in trying something new.
6. Mae Among the Stars by Roda Ahmed
Based on the life of astronaut Mae Jemison, this inspiring book tells the story of a young girl who dreams of going to space. When she shares her dream at school, others—including her teacher—try to redirect her to something more “realistic.” But with the support of her parents and her own determination, Mae holds on to her dream. This story encourages kids to believe in themselves and reminds them that aiming high, even when others doubt you, is an act of courage.
7. The Thing Lou Couldn’t Do by Ashley Spires
Lou is brave, adventurous, and always ready to take on a challenge—until her friends suggest climbing a tree. Suddenly, she hesitates and comes up with every excuse to avoid trying. The story gently explores what it feels like to encounter a fear and not be ready just yet. With humor, empathy, and expressive illustrations, this book shows that trying new things can take time and that it’s okay to take that time at your own pace.
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