Pick an activity slightly outside your child's comfort zone but still achievable—maybe learning a new skill, trying a presentation, or talking to someone new. The key is stretching without overwhelming. For younger kids (5-7), this might be introducing themselves to a new neighbor. For tweens (8-10), perhaps performing a poem in front of family. For teens, maybe leading a group project or trying a sport they've avoided. The challenge should feel a little scary but doable.

Take the big challenge and chunk it into manageable pieces. If the goal is performing a song, steps might be: 1) Choose the song, 2) Practice alone, 3) Sing for one parent, 4) Perform for the family. Breaking it down makes the challenge feel less daunting and creates natural progress markers. Write down the steps together so your child can see the path forward.

Start working through the steps together. For the first few attempts, stay close by—offering encouragement, modeling if needed, and helping troubleshoot. Gradually reduce your involvement as your child gains competence. Practice in a safe, judgment-free space where mistakes are okay. Focus on effort and improvement, not perfection. Build repetition so new skills become familiar.

When your child feels reasonably ready (they'll never feel 100% ready—that's normal), it's time to actually do the challenge. Whether that's performing for an audience, striking up that conversation, or trying that new sport, this is the moment to put practice into action. Remind them they've prepared, you believe in them, and that trying is what counts—not perfect execution.

After the challenge, take time to celebrate the effort and reflect on the experience. What felt hard? What surprised them? Do they feel differently about themselves now? Help them see that confidence grows each time they push their boundaries, even in small ways. Talk about what they learned and how they might apply this bravery to future challenges.