This post contains a sponsored inclusion of Penguin Random House but all of the opinions within are those of The Everymom editorial board.
"The unfortunate fact of being the oldest child is that your parents are experiencing everything for the first time alongside you. I think about this constantly as I parent my firstborn, standing in front of uncharted territory time and time again. These moments started out simpler, like both of us learning how to navigate breastfeeding, taking those wobbly first steps, or figuring out how to communicate with each other. Each of these milestones, while tricky at the time, felt like they had a clear set of instructions—a “how-to” guide if you will, that I could reference or call upon from friends and family.
But now that my son is 4, those milestones have become less about physical development and more about emotional growth. And if I’m being honest, the instructions feel a little bit harder to come by. It’s no longer just about teaching him how to walk or talk, but also about guiding him through things like making his first friends, managing big feelings, and experiencing the inevitable ups and downs we all know in life. And one of the biggest hurdles we’ve faced recently? Teaching him how to deal with failure—his first real moments of falling short and feeling defeated. Whether it’s at school, within friendships, or in extracurriculars, these moments are starting to become more prevalent, and that has definitely made me a bit anxious at times.
Each lesson feels more complex than the last—and I can’t help but feel like this one, teaching him how to cope with failure, might be one of the most important ones yet. Failure is tricky, even for us as adults, and it’s been a challenge to figure out how to talk about it in a way that makes sense to a preschooler. But over time, I’ve learned a few things that have helped—and I’m sharing them in hopes they’ll work for your family, too.
Read stories about learning from failure
We all know that stories are powerful tools for teaching, whether it’s through sharing our own or through educational books. When it comes to books, however, there’s something magical about how a story can take a complicated or difficult concept and break it down in a way that’s not only understandable but also relatable—especially for little kids. I’ve always turned to books when I need help explaining tricky topics to my son, and failure is no exception. I’ve found that when a story puts failure into context, it makes it less scary and helps my son see it as just another part of life.
One of our favorite books for this is Fail-a-bration, which is all about celebrating the lessons that failure teaches us, and it’s perfect for showing kids that mistakes aren’t the end—they’re a beginning. The characters in Fail-a-bration experience setbacks both big and small, but instead of being discouraged, they learn to embrace the opportunity to try again. It’s a fun, positive approach to something that can feel super overwhelming for kids. My son connects with it because it shows him that even when things don’t go perfectly, it doesn’t mean he’s done—it just means he’s learned something new.
Reading stories like this together is a huge help in opening up personal conversations between us, too. After reading, we’ll end up talking about times he’s felt frustrated or upset when something didn’t go as planned, and it’s a great way to reinforce the idea that it’s OK to not always succeed right away. Books help him connect the dots between his own experiences and the characters’ stories, which makes it easier for him to understand that failure is a natural part of trying new things. It’s made failure feel a little less scary—and for a 4-year-old, that’s a big win.
Brad Montague and Kristi Montague
You are cordially invited to a giant fail-a-bration party. Bring with you the cake that came out lopsided, the spelling test mistakes, or the plant that died. Be sure to put on a party hat and join the fun as we let the fail fires light the way to success.
Read more from Brad Montague and Kristi Montague
Brad Montague
This is the story of a circle. When we’re first born, our circle is very small, but as we grow and build relationships, our circle keeps getting bigger and bigger to include family, friends, neighbors, community, and beyond. This picture book adaptation is the perfect way to start a conversation about how to expand our worlds with kindness and inclusivity—even if it seems scary or uncomfortable.
Brad Montague
Every day, special figment agent Sparky delivers all the mail the FBI receives to the proper department, like the Office of the Unexplainable or the Department of Dreams. It’s a big job, but Sparky keeps everything running smoothly… until disaster strikes when the Cave of Untold Stories overflows and threatens to topple the whole bureau. It turns out too many people have been holding in their big ideas, and now Sparky must recruit more agents to share their dreams, songs, and stories with the world.
Reframe winning (and losing, too)
For my kid, literally everything is a competition. Whether it’s putting on clothes the fastest or eating the quickest, his constant desire to win is pretty intense. Being 20 months older than his sister often makes him the default winner in any race they create, and I can see how much pride he takes in always being “first.” As an only child who only had one step-sibling during my teen years, this kind of sibling rivalry and competition wasn’t something I dealt with growing up. Watching him constantly push to win is definitely new territory for me to navigate as a parent.
But, one thing we’ve been focusing on is reframing the idea of winning and losing. We try to celebrate the losses just as much as the wins, reminding him that a loss isn’t something bad—it’s just a new opportunity to improve or learn something different. “Now you have a chance to try again next time,” we’ll say. This shift has helped ease some of his frustration when things don’t go his way. It’s teaching him that self-worth isn’t tied to always being the winner—it’s about how you respond when things don’t go as planned, and that’s a lesson I’m still learning myself.
“We try to celebrate the losses just as much as the wins, reminding him that a loss isn’t something bad—it’s just a new opportunity to improve or learn something different.“
Fail by example as parents
Any time my son tries something new and doesn’t succeed right away, his frustration is immediate—and honestly, I can relate to that. I know how hard it can be when you want so badly to succeed but fall short, and I want to help him see that not getting things right on the first try is totally normal. That’s why we’ve started ‘failing by example.’ My husband, who regularly plays softball and runs 5Ks, uses his games and races as opportunities to show our son that it’s OK to come in second or third—or even last. After a race or game he loses, he talks with our son about how he handled the challenge, how it felt to not win, and what he learned from the experience.
This has been such an impactful way for my son to see that even grown-ups don’t get it right every time, even someone he looks up to, like dad. It’s become a powerful lesson for him to understand that failure isn’t something to avoid, but something to learn from and grow through. Plus, it gives us moments to bond over something other than winning or competing. We celebrate the effort and talk about the challenges, and it shows him that what truly matters is not the result, but how you move forward afterward. Little by little, he’s starting to understand that failure is just part of learning, and that’s a lesson I think we all can benefit from.
ABOUT THE AUTHOR
Steph Alleva Cornell, Branded Content Editor
Since becoming a young mama in 2020, Steph has found joy in creating beautiful yet relatable content surrounding the raw realities of motherhood. She believes showcasing both the wonders and struggles of being a parent helps other mothers understand that they are not alone in their journey.
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This post contains a sponsored inclusion of Penguin Random House but all of the opinions within are those of The Everymom editorial board.