Books About Taking Risks

The Best Taking Risks Books for Kids

By the Bookroo Editors

Looking for excellent children's books about taking risks? This collection brings together Bookroo's highest-rated and most useful picks in one place.

Start with our editorial favorites, then browse recommendations organized by reading stage to find the right book for your reader.

The Gutsy Girl
Anne Dares (Graphic Novel)
Series
Graphic Nov.
Don't Look Now Book Four
#4 in Series
I Am Jack Skellington
The Shortlist

Our 7 Favorite Books About Taking Risks

Change of a Dress
Sale price
$574
Chapter Book · Ages 8–12 · 2010

Change of a Dress

By Maya Gold · Book #1 in the Cinderella Cleaners series

A teenage girl working at her family's dry-cleaning shop discovers a pair of Broadway tickets that set her on an unexpected journey of self-discovery and daring choices.

209 pages· 39,160 words· Est. 5.5 hour read
4.0/5 Goodreads · 2,334 ratings
$5.99Save 4%
Paperback
Summary: Thirteen-year-old Diana's mundane life at her family's dry cleaners takes a thrilling turn when she discovers a gala invitation in a coat pocket. With the owner away, Diana seizes the chance to step into a world of glamour and intrigue. Armed with a borrowed dress and her friends' help, she navigates the dazzling event, risking exposure and dreaming of a fairy-tale ending. Will her daring escapade lead to discovery or a magical night to remember?
The Gutsy Girl
Sale price
$1710
Chapter Book · Ages 7–12 · 2016

The Gutsy Girl

By Caroline Paul, Wendy MacNaughton (Illustrator)

Overcome fear and embrace adventure with thrilling stories and activities.

160 pages· 25,420 words· Est. 3.5 hour read
3.9/5 Goodreads · 1,086 ratings
$18.00Save 5%
Hardcover
Summary: Caroline Paul, once a fearful girl, now a daring adventurer, invites young girls to conquer fear and embrace excitement. Through her own thrilling tales and those of other brave women, she offers activities to build confidence and self-reliance. From flying planes to fighting fires, Caroline's journey inspires girls to journal their adventures and develop a zest for challenges. Discover the joy of risk-taking and the power of self-discovery in 'The Gutsy Girl,' a guide to living boldly and fearlessly.
Anne Dares (Graphic Novel)
Graphic Nov.
Sale price
$1248
Chapter Book · Ages 7–10 · 2023

Anne Dares (Graphic Novel)

By Kallie George, Abigail Halpin (Illustrator) · Anne Chapter Book series

A daring challenge leads to a lesson in courage and a mysterious secret at a Christmas concert.

65 pages
4.4/5 Goodreads · 225 ratings
$12.99Save 4%
Hardcover
Summary: Anne Shirley faces a daring challenge at a party, leading to an unexpected injury and a lesson in bravery. As she prepares to recite at a Christmas concert, Anne must overcome her fears. Meanwhile, a secretive Matthew Cuthbert adds to the intrigue. Can Anne find the courage to perform and uncover what Matthew is hiding? Join Anne on this heartwarming journey of friendship, courage, and discovery.
Don't Be Afraid to Drop
Sale price
$958
Picture Book · Ages 5–10 · 2021

Don't Be Afraid to Drop

By Julia Cook, Anna Laura Sullivan;Anna Laura Sullivan (Illustrator)

A raindrop musters courage to leave its cloud and embrace change.

32 pages
4.3/5 Goodreads · 78 ratings
$9.95Save 4%
Paperback
Summary: Hopp, a timid raindrop, loves his predictable life on a cloud. But when he realizes staying put limits his potential, he faces a choice: cling to comfort or leap into the unknown. As Hopp contemplates the drop, he discovers the power of taking risks and the joy of sharing his gifts with the world. Will he find the courage to let go and make a difference? This tale inspires readers of all ages to embrace change and explore new possibilities beyond their comfort zones.
Don't Look Now Book Four
Sale price
$958
Chapter Book · Ages 7–11 · 2013

Don't Look Now Book Four

By Paul Jennigns, Andrew Weldon (Illustrator) · Book #4 in the Don't Look Now series

Can Ricky achieve fame without revealing his secret ability to fly?

264 pages
3.9/5 Goodreads · 50 ratings
$9.99Save 4%
Paperback
Summary: Ricky finally befriends Samantha, but his dream of fame remains elusive. With a secret ability to fly, he faces the ultimate challenge: achieving stardom without anyone discovering his hidden talent. As Ricky navigates the complexities of friendship and ambition, will he soar to new heights or crash under the weight of his secret? Dive into two thrilling tales, 'Hobby Farm' and 'Seeing Read,' where laughter and adventure await. Can Ricky balance his dreams with the need for secrecy, or will his desire for fame lead to unexpected consequences?
Pippa
Sale price
$2495
Picture Book · Ages 3–5 · 2019

Pippa

By Dimity Powell, Andrew Plant

A young pigeon defies her parents to explore the world alone. Will she find her way back home?

32 pages· 366 words· Est. 3 min read-aloud
3.8/5 Goodreads · 18 ratings
Hardcover
Summary: Pippa, a daring young pigeon, dreams of soaring beyond her nest despite her parents' protective warnings. Ignoring their fears, she embarks on a solo adventure into the vast unknown. As she navigates treacherous skies and unfamiliar lands, Pippa must rely on her wits to survive and discover if her heart will guide her back home. Will her journey fulfill her dreams or lead her astray? Join Pippa as she learns that sometimes, taking risks is the only way to truly find oneself.
I Am Jack Skellington
Sale price
$574
Board Book · Ages 2–5 · 2024

I Am Jack Skellington

By Jeannette Arroyo (Illustrator)

Discover what makes Jack Skellington the Pumpkin King in a tale of self-discovery and confidence.

24 pages· 541 words· Est. 5 min read-aloud
4.4/5 Goodreads · 91 ratings
$5.99Save 4%
Hardcover
Summary: Join Jack Skellington, the Pumpkin King of Halloween Town, on a journey of self-discovery and confidence. In this enchanting tale, Jack learns what truly makes him unique and embraces his role with newfound assurance. With whimsical text and captivating illustrations, this story invites readers to explore the magic of being true to oneself. Will Jack find the courage to be himself and inspire others in Halloween Town? Dive into this delightful adventure and uncover the secrets of the Pumpkin King's heart.
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