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The Best Picture Books about Following Your Dreams

The Best Picture Books about Following Your Dreams

If you’ve read even a handful of articles on Dad Suggests, you’ve probably learned by now that I’m passionate about imagination, creativity, the wonder of childhood, and being yourself. And I’m relatively grumpy about the state of education and the priorities that society tends to pass on to kids, whether it’s intentional or not.

Discover our favorite picture books about following your dreams. Help your kids pursue their true passions and chase their dreams. Teach them to keep that curiosity and childlike wonder alive, even in the face of societal pressure.#picturebooks #kid…

As a society, we generally tell kids all the time to “follow your dreams”, but very seldomly do we actually mean it. On the contrary, we tend to actually bombard kids with very clear messages about what success looks like, and what they should actually aspire to do and be when they grow up - typically something that pays well and is generally revered.

School itself is of course the biggest culprit here, and nothing makes me grumpier than how much importance schools place on sports and test scores, and how little importance schools place on the arts. And, believe me, kids are getting the message loud and clear. I was just having the conversation recently that students have most certainly noticed that, in many schools, every single extra-curricular activity except for football has been cancelled during the coronavirus pandemic.

I have to admit, I wasn’t exactly sure how to title this picture book list at first. I’ve already written an article about picture books that teach you to be yourself, but this is something different entirely. While all of these books most certainly encourage you to be yourself, they also fit a much more narrow theme as well. They all celebrate wonderful passions that could lead to viable career choices, and generally dismiss the voices of society that might stand in the way.

These books let it be known that happiness can be found by pursuing your passions and your dreams. You can do anything you want when you grow up. Society doesn’t get to decide that for us. After all, when the robots take over all of our jobs, the only things humans will be useful for is using our creativity and creating art. So we might as well start now!

Disclosure: Some of the links in this post are affiliate links. Affiliate links will lead you to view the items’ listings on Amazon.com or other affiliate partners.


This is Ruby

Written by Sara O’Leary and Illustrated by Alea Marley

I love This is Ruby just as much as I love its predecessor This is Sadie, but the reason this sequel makes a good fit on this list is that it tends to focus on how Ruby’s interests might end up turning into future jobs. What makes me love both of these books so much is that O’Leary puts such a strong emphasis on imagination and creativity and childlike wonder - and those are exactly the very things I want to help cultivate.

Ruby is kind and thoughtful, and she has a lot of interests too, which is great. I can’t help but think of the all-too-common push to specialize in something too soon in life. Too often it’s a sad attempt by parents to craft a virtuoso or a professional athlete - instead of giving kids time to discover their own passions. Of course I’m diverging far from the contents of this book, because there are certainly no negative thoughts to be found here. Just a beautiful celebration of the excitement life has to offer and the limitless possibilities kids have in front of them.


Gustavo the Shy Ghost

Written and Illustrated by Flavia Z. Drago

This book is truly amazing, but the inclusion of Gustavo the Shy Ghost on this list might surprise you, because it doesn’t seem to come with an obvious message about following your dreams. But, on the contrary, there’s one moment in this book that makes Gustavo the absolute perfect role model when it comes to doing what makes you happy.

Gustavo has trouble making friends, and he desperately wants to overcome his shyness and put himself out there to meet others. But, more than anything else in the world, he loves to play the violin.

And there’s a spectacular moment in this book - where there’s a little confusion about an invitation to his concert and it seems that nobody is coming. Gustavo is completely alone, but he plays his violin just for himself, and it’s a magical scene. Not only is this a fantastic work of art, but it’s a great example of pursuing your dreams and doing what makes you happy. Do it for yourself.


Oliver Button is a Sissy

Written and Illustrated by Tomie dePaolo

More so than any other book on this list, Oliver Button is a Sissy tackles the difficulty of pursuing your dreams in the face of societal norms. Oliver likes to walk in the woods, play jump rope, read books, draw pictures, dress in costumes, and dance. He didn’t like sports like the other boys, and because of this, the other kids in school call him a sissy.

And it gets especially bad when he starts taking tap class and the other boys see his tap shoes. This book reminds me an awful lot of the magnificent movie Billy Elliot, especially because Oliver sadly has to even win over his own father. But stories like this are incredibly, powerfully important. If you want to dance then dance. And shame on old societal norms for standing in the way, even to this day.


All the Ways to Be Smart

Written by Davina Bell and Illustrated by Allison Colpoys

I talk about this book just about every chance I get, and for good reason. it comes packed with a powerful message about how we all have many different talents and interests - and scoring high on school tests is not the only talent that matters. Art matters, dance matters, kindness matters, curiosity matters, imagination matters - and if you’re looking for the one picture book that drives home that concept better than any other, this is it.

If you want to teach your kids or your students that they can chase their dreams and be who they want to be when they grow up, they need to read this book. The message in this book is what will start them down that path. It’s beautiful and sweet and brilliant, and it’s a true champion for celebrating who you are. It’s sadly all-too-easy to fall into a pit of despair in school these days, because of the ridiculous focus on test scores, and kids desperately need a reminder about the various paths to true happiness out there.

You can read more about All the Ways to Be Smart in our featured article.


Pokko and the Drum

Written and Illustrated by Matthew Forsythe

If you haven’t read Pokko and the Drum yet - what are you waiting for?! Matthew Forsythe blessed us all with this delightful and whimsical book that’s just perfect in every way. One of our favorite picture books ever crafted without a doubt. And it also just so happens to fit this theme of following your dreams quite well.

Pokko loves to play her drum. Her parents think it may have been a mistake to get her that drum, because of the constant noise, so they recommend that perhaps she play it outside. Before she knows it, she has an entire band following behind her as she marches along playing. And it doesn’t take long before she impresses her parents with her talent.

It’s a quick synopsis to explain, and obviously it fits in well with this theme, but it’s impossible to convey how special this book truly is. It’s in the art and the whimsy, it’s in the wit and the dry humor, and it’s in the very eyes of the characters. The joy is simply never ending.

You can read more about Pokko and the Drum in our featured article.


Picture Books for Following Your Dreams - Khalida and the Most Beautiful Song.jpg

Khalida and the Most Beautiful Song

Written and Illustrated by Amanda Moeckel

Khalida and the Most Beautiful Song is the epitome of this picture book list, and it was the very first book that came to mind when I wanted to put it together. In fact, this picture book means so much to me, I was trying to craft a list around it somehow. To me this story about a girl who has a song stuck in her head and just wants to find time to play the piano is the absolute perfect metaphor for how we sadly stifle kids and their imagination and creativity.

Khalida continuously has trouble finding a moment to just sit down at the piano and get this beautiful song out of her head. It’s a wonderful concept, and it makes me just want to scream “let this girl play the piano!”. The most powerful moment for me is when she’s rushed along to her next class in school when she wants to sneak into the piano room. I love that scene because it reminds me of what I wish school could be, built around the interests of the children.

But, most importantly, the moment when she finally gets her song out is perfection. People stop and listen, blown away by its beauty. It’s clear this is what Khalida loves and what she’s meant to do. And we all need to do our part to help our kids discover what they love, and help them to express themselves and get it out of themselves at all costs.

You can read more about Khalida and the Most Beautiful Song in our featured article.


Can you think of any other books that celebrate chasing your dreams and pursuing your passions? Have you read any of these great books before? Let us know in the comments!

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