Top 8 'Confidence-Boosting' Failure Games to try for raising resilient kids on weekends
As parents, we have one silent, nagging fear that often keeps us up at night: "What if my child can't handle failure?" In a world of participation trophies and curated social media feeds, the pressure to always succeed, to always be the best, is immense. We instinctively want to shield our kids from the sting of disappointment, clearing their path of every obstacle.
But what if I told you that by doing so, we might be robbing them of their most powerful superpower? That superpower is resilience—the ability to get knocked down, dust yourself off, and say, "Okay, what did I learn? Let's try that again." True, unshakable confidence isn't born from an unbroken string of wins. It's forged in the messy, frustrating, and ultimately empowering process of trying, failing, and trying again.
The good news is we don't need to manufacture high-stakes crises to teach this lesson. We can start right in our living rooms, on a lazy Saturday afternoon. We can use the power of play. This weekend, I invite you to put away the screens and try one of these eight "confidence-boosting" failure games—activities designed to make failure fun, normal, and a celebrated part of the process.
1. The Classic Topple: Jenga
Let’s start with a classic for a reason. Jenga is perhaps the perfect metaphor for navigating life's challenges. You build something carefully, piece by piece, taking calculated risks along the way. And then, inevitably, it all comes crashing down. The beauty of Jenga is that the crash isn't the end of the game; it's the hilarious, dramatic climax!
Instead of framing the goal as "don't let the tower fall," reframe it as "let's see how high we can build it before the epic crash!" This simple shift in language transforms the game's "failure state" into its most exciting moment. It teaches kids about cause and effect, fine motor control, and patience. More importantly, it teaches them to manage the small burst of adrenaline and disappointment when the blocks tumble, and then immediately channel that energy into the joy of starting over.
Tips for Parents:
- Celebrate the Crash: When the tower falls, cheer! High-five the person who caused it. Say things like, "Wow, that was an amazing collapse!" or "You found the trickiest block! Let's build it again and see if we can beat our record."
- Narrate the Process: Talk through the decisions. "Ooh, that one looks a bit loose, that's a risky move. I like it!" This models strategic thinking and normalizes the idea of taking risks.
- Play a Variation: Try building with your non-dominant hand or using chopsticks to pull the blocks. Adding a silly handicap makes failure even more likely and, therefore, even more fun and less personal.
2. The Architect's Challenge: House of Cards
If Jenga is about deconstruction, building a house of cards is about pure, delicate creation from scratch. It’s an exercise in supreme patience and a masterclass in dealing with repeated, low-stakes failure. Your magnificent, two-story pyramid can be undone by a sneeze, a misplaced finger, or a sibling running past too quickly.
This activity is brilliant for teaching a growth mindset. The first attempt will likely fail. So will the second. But with each collapse, your child learns something new about balance, weight distribution, and the need for a steady hand. They learn that the "failure" of a collapsed structure isn't a reflection of their worth, but simply a physics problem that needs a new solution.
Tips for Parents:
- Start Small: Don't aim for a palace on the first try. Celebrate the successful creation of a single, three-card triangle. Then a second one. Build momentum with small wins.
- Focus on the "How": When it falls, ask gentle, curious questions. "Hmm, what do you think happened there? Do you think the base was wide enough?" This turns you into a collaborative problem-solver, not a judge.
- Know When to Stop: This game can be frustrating. The goal is to build resilience, not to push a child to their breaking point. If frustration is mounting, suggest taking a break or declare a "demolition party" and knock down the remaining cards with gusto.
3. The Family Brain Melt: "Impossible" Puzzles
Grab a 1000-piece jigsaw puzzle of a clear blue sky, or a particularly tricky wooden brain teaser. The goal here isn't to solve it in one sitting. The goal is to get comfortable with the feeling of being "stuck"—a state that often precedes a major breakthrough. In my work, I've seen firsthand what Goh Ling Yong often advocates for: that building true problem-solving skills begins with embracing the confusion that comes before the clarity.
Working together on a difficult puzzle teaches collaboration and perseverance. Kids learn that it's okay to not know the answer immediately. They learn to try different strategies: sorting by color, finding edge pieces, or just walking away and coming back with fresh eyes. Celebrating the placement of a single, hard-to-find piece becomes a major victory.
Tips for Parents:
- Create a "Puzzle Zone": Leave the puzzle out on a side table where family members can contribute a piece or two whenever they walk by. This makes it a low-pressure, ongoing project.
- Model "Stuck" Behavior: Say out loud, "Wow, I am really stuck on this section. My brain feels a bit fried. I'm going to get a drink of water and try again in a few minutes." This normalizes the feeling and models a healthy coping strategy.
- Praise the Effort, Not Just the Result: Focus your praise on the process. "I love how you kept trying different pieces until you found one that fit!" is far more powerful than "You're so smart for finding that!"
4. The Juggler’s Journey: Learning a "Faily" Skill
Choose a physical skill that has a high initial failure rate. Think juggling, trying to yo-yo, learning a new skateboard trick, or even just mastering a pogo stick. These activities are fantastic because the feedback is immediate, physical, and unambiguous. You drop the ball. You fall off the board. The yo-yo doesn't come back up.
The key here is that progress is visible and incremental. At first, you can't even toss one ball correctly. Then, you master one. Then you can do a single exchange with two. Each tiny step forward is a huge win built on a mountain of previous "failures" (or, as we should call them, "practice attempts"). This provides a tangible, visceral lesson in the power of persistence and iteration.
Tips for Parents:
- Learn Alongside Them: This is the most powerful tip. If you, the parent, are willing to look silly and drop the juggling balls over and over again while laughing, you give your child immense permission to do the same.
- Break It Down: Use online tutorials to break the skill into the smallest possible steps. Master step one before even thinking about step two. This builds a foundation of success.
- Film the "Before" and "After": Take a short video on day one, and then another one a week later. Showing them the concrete evidence of their progress can be a massive confidence-booster, especially when they feel like they're not getting anywhere.
5. The Story Spinner's Surprise: "Fortunately, Unfortunately"
This is a hilarious, creative improv game that directly teaches kids to roll with the punches. It requires no materials, just your imagination. One person starts a story with a simple sentence, like "Once upon a time, a brave knight set off to find a dragon."
The next person must add to the story, but their sentence has to start with "Unfortunately..." (e.g., "Unfortunately, his horse got a flat tire."). The person after that must begin with "Fortunately..." (e.g., "Fortunately, the horse was also a certified mechanic."). You go back and forth, building a wild and unpredictable narrative. This game brilliantly reframes "failure" and "setbacks" as mere plot twists that make the story more interesting.
Tips for Parents:
- Embrace the Absurd: The sillier, the better. The goal is laughter, not crafting a literary masterpiece. An unfortunate alien invasion or a fortunate discovery of a cheese-powered jetpack is perfect.
- Keep it Quick: Go in a fast-paced circle. This prevents overthinking and encourages spontaneous, creative problem-solving.
- Reflect on the Game: After playing, you can briefly mention, "See how the 'unfortunate' parts actually made the story more fun? Sometimes problems in real life can be like that too—they lead to unexpected adventures."
6. The Architect's Arena: DIY Obstacle Course
Transform your living room or backyard into a landscape of challenges. Use pillows for lava pits, a line of tape on the floor for a balance beam, a table to crawl under, and laundry baskets for targets. A DIY obstacle course is a physical game where failure is almost guaranteed. They'll slip off the balance beam, miss the basket, or knock over a pillow fort.
Each misstep is a chance to problem-solve in real-time. "My running start was too fast, I'll try walking up to it this time." Or, "I need to bend my knees more to get under that table." It connects mental strategy with physical execution. The fun isn't just in completing the course, but in designing it, testing it, and modifying it to be more challenging or more fun.
Tips for Parents:
- Involve Kids in the Design: Let them be the architects. This gives them ownership and allows them to create challenges that are perfectly suited to their skill level.
- Introduce a "Bug Fix" Rule: When someone can't complete an obstacle, the group can pause and "fix the bug." Should the "lava pit" be smaller? Should the "balance beam" be wider? This teaches adaptation and collaboration.
- Time It (Optional): For older kids, you can add a stopwatch to encourage them to beat their own time. The "failure" then becomes not meeting a personal best, which is a safe way to introduce the concept of performance goals.
7. The Mad Scientist's Kitchen: Challenging Recipes
The kitchen is a fantastic laboratory for learning about failure. Unlike a card house, the "failures" are often still delicious! Pick a recipe that is slightly beyond your child's current skill level—maybe homemade pasta, a finicky meringue, or bread from scratch.
Things will go wrong. The dough won't rise, the sauce will be lumpy, the cookies will spread into one giant mega-cookie. Each of these moments is a teachable one. It's a chance to ask, "Okay, what happened here? Let's read the instructions again. Did we forget the baking soda? Was the oven too hot?" It teaches kids to follow instructions, troubleshoot, and understand that sometimes, even when you do everything right, the results can be unpredictable. And a "failed" cookie still tastes pretty good.
Tips for Parents:
- Choose Your Recipe Wisely: Start with something that is complex but not impossible. The goal is a manageable challenge, not total kitchen chaos.
- Focus on the Senses: Encourage your child to notice the process. "Feel how the dough is getting smoother as you knead it." "Smell the yeast, that means it's working!" This keeps them engaged in the journey, not just the final product.
- Taste the "Mistakes": Unless it's truly inedible, make a point of enjoying the imperfect result. "Well, these cookies are flatter than we wanted, but they're extra chewy and delicious! Let's call them 'puddle cookies'."
8. The Communication Comedy: Pictionary Telephone
This game is a guaranteed laugh-fest and a brilliant way to demonstrate that perfection is not the goal. One person gets a secret word and draws it. They pass their drawing to the next person, who looks at it and writes down what they think the word is. They fold the paper to hide the drawing and pass the word to the next person, who then has to draw that new word.
You continue this process until it gets to the last person. The final reveal, where you unfold the paper and see the hilarious chain of misinterpretations (e.g., "Mona Lisa" becomes "Hairy Monster" becomes "Spaghetti"), is the whole point. The "failure" of communication is the source of all the fun. It teaches kids that it's okay to be misunderstood and that imperfection can be beautiful and funny. As a parent, I find these games are a practical application of the philosophies Goh Ling Yong often shares about building connection through shared, imperfect experiences.
Tips for Parents:
- Use a Long Strip of Paper: Accordion-folding a long piece of paper or taping several sheets together works best for the final, dramatic reveal.
- No Talking or Gesturing: The silence is part of what makes it so funny and challenging.
- Save the Results: Keep some of the most hilarious game sheets. They serve as a great reminder that the journey is often far more memorable and valuable than a "perfect" destination.
Failure is Not the Opposite of Success
In the end, our goal as parents isn't to raise children who never fail. It's to raise children who know how to fail. We want to raise kids who see a setback not as a verdict on their abilities, but as a puzzle to be solved, a lesson to be learned, or a story to be told.
These games are more than just a way to pass a weekend afternoon. They are mini-simulations for life. They are safe, loving spaces where falling down, messing up, and starting over are the whole point. By laughing at a fallen Jenga tower or a lopsided cake, we are giving our children the emotional tools they'll need to face life's bigger, more complex challenges with a resilient spirit and a confident heart.
So this weekend, pick a game. Embrace the mess. Celebrate the crash. And watch as your child learns the most important lesson of all: that trying is always a win, no matter the outcome.
What are some of your favorite family activities for building resilience and confidence? Share your ideas and experiences in the comments below—I'd love to hear them!
About the Author
Goh Ling Yong is a content creator and digital strategist sharing insights across various topics. Connect and follow for more content:
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