when you feel like you’re disappointing your teen: the weight and the lesson

Parenting teens comes with a unique and sometimes heartbreaking challenge: the realization that, at times, you will disappoint them. It’s inevitable. Whether it’s walking out of a store with your daughter disappointed because you decided not to buy her an uber-expensive prom dress, or telling your son that even though he doesn’t want to work his current summer job anymore, he needs to stick with it until he finds a new one, there will be moments when your teen looks at you with frustration, sadness, or even anger. And that feeling—the one that sits heavy in your chest, the one that makes you second-guess yourself—is the weight of disappointment. It’s inevitable. Whether it’s saying no to a party, or to buying their 20th Chipotle bowl this month, or refusing to buy them that trendy new thing that “everyone else has,” there will be moments when your teen looks at you with frustration, sadness, or even anger. And that feeling—the one that sits heavy in your chest, the one that makes you second-guess yourself—is the weight of disappointment.

But here’s the truth: we are no longer the fixers of their world but the guides through it. And sometimes, guiding them means letting them experience discomfort, frustration, or even sadness.

The Weight of Disappointing Them

It’s hard to see your child suffer, even in small ways. When they’re younger, we can often step in and make things better—a hug, a distraction, or a simple “yes” can turn tears into smiles. But as they grow, our role shifts. If we continue to fix every problem for them, we deny them the opportunity to learn resilience and problem-solving. Instead, we must step back and allow them to navigate challenges, even when it’s hard to watch.

Sitting with the weight of their disappointment can feel unbearable at times. You may wonder if you’re being too harsh, if you should give in, if they’ll resent you for your choices. But standing firm in your values and decisions—even when it hurts—is a powerful act of love.

The Lesson in Their Disappointment

Life is full of disappointments. If our teens never experience it in a safe space—within the security of our family—they won’t know how to handle it when life inevitably doesn’t go their way. Allowing them to sit with their feelings of frustration and sadness teaches them resilience, patience, and problem-solving.

If we rush in to fix every difficult moment, we rob them of the chance to grow. We unintentionally send the message that discomfort should always be avoided, that someone will always come to rescue them. But true growth happens in the struggle. Learning to process disappointment now will help them navigate bigger challenges later—heartbreaks, job rejections, failed dreams—without falling apart.

The Best Thing You Can Do

Instead of fixing, try this:

  • Acknowledge their feelings. 

  • Stay present, but don’t rush to make it better. 

  • Help them process, not escape. 

  • Reassure them of your love.

It’s okay if they’re suffering sometimes. It’s okay if they’re upset with you. And it’s okay if you feel the weight of it. Because in the end, the lessons they learn from disappointment will be far more valuable than a momentary sense of happiness.

So, when that heavy feeling creeps in—when you start questioning if you’re doing the right thing—remember this: Your job isn’t to make your teen’s life easy. It’s to prepare them for a life that won’t always be. And sometimes, the best way to love them is to let them sit with the disappointment, knowing they have a parent who loves them enough to let them grow.

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the art of allowing: letting teens take the wheel (literally and figuratively)