Trying New Things: Helping Preschoolers Build Confidence, Curiosity, and Courage
One of the greatest gifts we can give young children is the confidence to try something new. Whether it’s tasting unfamiliar food, meeting new friends, learning to ride a bike, or starting kindergarten, every new experience helps children build resilience and independence.
Picture books provide a safe way to explore these feelings before children experience them in real life. As you read together, pause to ask questions like, “Have you ever felt like that?” or “What new thing would you like to try?” These conversations help children recognize that feeling nervous is normal—and that bravery often begins with simply taking the first step.
Picture Books for Preschoolers
The Thing Lou Couldn’t Do
By Ashley Spires – https://amzn.to/4wsLlA0
Lou loves adventures with her friends—until they suggest climbing a tree. Rather than admit she’s afraid, Lou invents excuses. Eventually, she discovers that trying, even if she isn’t successful right away, is what matters most.
Why it’s great: Encourages perseverance and shows that everyone learns at their own pace.
The Magical Yet
By Angela DiTerlizzi – https://amzn.to/4yhVf9A
This uplifting story introduces the idea of “yet.” You may not be able to do something today, but with practice, you can learn.
Why it’s great: Builds a growth mindset in preschoolers that they can understand.
Jabari Jumps
By Gaia Cornwall – https://amzn.to/4h3dzNa
Jabari is excited to jump off the diving board—until it’s finally his turn. With encouragement from his father, he learns that courage doesn’t mean you’re never afraid.
Why it’s great: Perfect for discussing bravery and overcoming fears.
Rosie Revere, Engineer
By Andrea Beaty – https://amzn.to/4vp5HJn
Rosie dreams of becoming an engineer but worries about making mistakes. A special family member helps her realize that every failure teaches something valuable.
Why it’s great: Shows children that mistakes are part of learning.
Whistle for Willie
By Ezra Jack Keats – https://amzn.to/3RmqkIm
Peter desperately wants to whistle for his dog, Willie. Practice and patience eventually pay off.
Why it’s great: Demonstrates that mastering new skills takes time.
The Most Magnificent Thing
By Ashley Spires – https://amzn.to/4aKn686
A determined little girl sets out to build something amazing. It doesn’t work the first—or second—time, but she learns to keep trying.
Why it’s great: Excellent for teaching persistence and problem-solving.
After the Fall
By Dan Santat – https://amzn.to/4h3dMzW
A creative retelling of what happened after Humpty Dumpty fell. He must face his fears in order to move forward.
Why it’s great: A wonderful conversation starter about overcoming setbacks.
Giraffes Can’t Dance
By Giles Andreae – https://amzn.to/4ygMnkw
Gerald the giraffe believes he can’t dance until he discovers everyone has their own unique way of doing things.
Why it’s great: Encourages children to try new activities without comparing themselves to others.
Beautiful Oops!
By Barney Saltzberg – https://amzn.to/4eSkwPZ
This interactive book turns mistakes into creative opportunities.
Why it’s great: Helps children see that accidents can become something wonderful.
What Do You Do With an Idea?
By Kobi Yamada – https://amzn.to/4eWzSkY
A child learns to believe in an unusual idea despite uncertainty and self-doubt.
Why it’s great: Encourages creativity, confidence, and trying something different.
Pete the Cat: Rocking in My School Shoes
By Eric Litwin – https://amzn.to/4gtVVSI
Pete explores his new school with confidence and curiosity.
Why it’s great: A fun choice for children preparing for kindergarten or preschool.
First Day Jitters
By Julie Danneberg – https://amzn.to/4vkX42M
Everyone assumes Sarah is nervous about starting school as a student—but the ending provides a delightful surprise.
Why it’s great: Reassures children that everyone feels nervous about new beginnings.
Parent Books
The Whole-Brain Child
**By Daniel J. Siegel and Tina Payne Bryson – https://amzn.to/4aHnuUO
Offers practical strategies for helping children manage big emotions, including the worries that often come with trying something new.
Helpful for: Parents who want to build emotional resilience and confidence.
How to Talk So Little Kids Will Listen
**By Joanna Faber and Julie King – https://amzn.to/3SQcFtA
Filled with real-life examples for helping young children cooperate, solve problems, and navigate unfamiliar situations.
Helpful for: Everyday conversations when children are hesitant or anxious.
The Gift of Failure
**By Jessica Lahey – https://amzn.to/4pfcLaf
Explains why allowing children to struggle appropriately helps them become more confident, capable, and independent learners.
Helpful for: Parents learning when to encourage and when to step back.
Raising Mentally Strong Kids
**By Daniel G. Amen and Charles Fay – https://amzn.to/4vOWBH3
Provides practical ideas for helping children develop resilience, responsibility, and confidence through everyday experiences.
Helpful for: Families wanting to raise children who embrace challenges rather than avoid them.
Trying something new can feel exciting one day and overwhelming the next—and that’s perfectly normal. The goal isn’t to raise children who are never afraid. It’s to raise children who learn that being brave often means taking one small step even when they feel uncertain.
These books remind children that everyone starts as a beginner, mistakes are part of learning, and confidence grows each time they say, “I’ll give it a try.” Whether your child is preparing for kindergarten, learning a new skill, or simply facing an unfamiliar situation, reading together can help make those first steps feel a little less scary and a lot more exciting.
I have not read all of these books. Inclusion in this post is not necessarily an endorsement of the book, although they are all ones I’d consider purchasing.
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