The Gift of Disappointment: Building Resilience in Our Children During the Holidays and Beyond

The holidays are when our children have a lot of asks and high expectations for receiving what they want. For little kids, it's the list for Santa or for Hanukkah gelt. As they grow and the magic fades, those asks transfer onto us parents. The challenge? It's easier to let Santa disappoint than to do it ourselves.

Some requests fall within budget, some don't. We pick and choose what we can afford, trying to balance delight, expectations, financial reality, and disappointment. No parent wants their child disappointed over the holidays. We'd rather save disappointment for literally any other day.

But what if learning to navigate disappointment, especially during the emotional intensity of the holidays, is one of the most valuable skills we can help our children develop?

When the Ask Is Coming Home

For parents of kids in treatment, the ask can be tougher: coming home for Christmas, Hanukkah, or winter break. It seems so reasonable, yet, unfortunately, it could trigger regression, conflict, even harm if the child isn't ready. Even if financially possible, the emotional cost could set back all the progress your child has made.

In every therapeutic program we work with, there's serious family work happening. Parents are learning how to better parent their tough-to-parent child. These kids have worn us down over the years, sulking when Santa didn't deliver, throwing tantrums when the eighth night of Hanukkah disappointed, becoming sullen when we couldn't fulfill unreasonable asks.

These patterns took years to develop. The child continues to manifest unhealthy behaviors when disappointed. The parent avoiding the "no" because it triggers the conflict they're too exhausted to navigate. Whether your child is in treatment or thriving at home, the task is the same: learning to tolerate disappointment, sit with uncomfortable feelings, understand that not getting what we want isn't a catastrophe, but rather a normal and expected part of life.

Learning to Sit in the Maybe

Part of good parenting is learning how to manage disappointment, yours and your child's, It's okay to say "maybe." It's okay for your child to sit in the maybe, especially for our ADHD kids chasing dopamine hits and immediate gratification. Sitting in uncertainty teaches lessons that last a lifetime.

When we rush to relieve our children's discomfort, we rob them of building distress tolerance. They don't learn that uncomfortable feelings pass, that they can move past not getting what they want. As a parent, you can hold the discomfort with your child, stay present and manage your anxiety when they are upset. By doing this, you convey that you believe that your child is strong enough to learn how to tolerate not getting what they want.

Why This Matters

The Stanford marshmallow experiments are worth understanding. In the late 1960s, researchers gave young children a simple choice: eat one marshmallow now, or wait 15 minutes and get two marshmallows. Some kids ate it immediately. Others tried creative strategies to wait, covering their eyes, singing songs, anything to distract themselves. About a third successfully waited for the second marshmallow.

The fascinating part of this experiment came years later. Researchers followed up with these same children as they grew into adolescents and adults. The kids who had waited for their marshmallow tended to have better academic performance, healthier stress management, and better overall life outcomes.[1]

The good news is that this ability can be taught. When children practice tolerating the discomfort of waiting, they're building neural pathways responsible for executive function and emotional regulation.[2]

Every time you say "maybe" instead of "yes," every time you help your child sit with uncertainty, you're helping them build a stronger brain.

Operate from Values, Not Guilt

Start by getting clear on your values. What do you want your children to remember about holidays? Operating from values rather than guilt makes decisions clearer.

Have honest conversations before the holidays about expectations and limitations. Use it as an opportunity to teach about finances and budgets, about wants and needs. As adults, we don’t always get what we want, and we certainly can’t afford all that we want, and that’s ok. These are lessons to learn early. Sit with your child's feelings without fixing them. "I know you're really disappointed. That makes sense. This isn't what you hoped for." Full stop, no explanation.

For families with children in treatment, talk with the treatment team early. Trust the professionals who see your child daily. They understand readiness in ways loving parents, desperate for normalcy, might not assess objectively. Your child being in treatment during holidays isn't failure, it's investment in their future.

Swap a Gift for a Shared Experience

This holiday season, make different choices. Make this a family discussion and decision. Choose one experience over one material gift. Feeding the homeless or food impoverished folks. Visting elderly relatives in assisted living. Attending to the needs of a neighbor who is sick or elderly.

Practice saying "maybe" and sitting in it. Get curious about your own discomfort with your child's disappointment. What about their not getting everything they wish for feels wrong to you?

Redefine what is meaningful to you this season. The holiday isn't everyone getting everything they want with no disappointment. It's people feeling connected, feelings honored even when requests aren't granted, love present in the midst of hard things.

This is a Gift of a Lifetime

Years from now, your children won't remember exactly what gifts they received. They'll remember how they felt, whether they felt safe enough to be disappointed..

More importantly, they'll carry the skills you helped them build: tolerating discomfort, delaying gratification, navigating disappointment without falling apart.

This holiday season, give your children less stuff and more presence. Fewer things and more experiences. Less rescue and more support in building skills to handle disappointment.

That's the gift that truly lasts.

If you're navigating these questions with a struggling child, whether in treatment or at home, reach out to your treatment team, a parent coach, or contact us at Crossbridge Consulting. We're here to support you in making hard choices that serve your child's long-term wellbeing.

References:

[1] Mischel, W., Shoda, Y., & Rodriguez, M. L. (1989). Delay of gratification in children. Science, 244(4907), 933-938.

[2] Casey, B. J., et al. (2011). Behavioral and neural correlates of delay of gratification 40 years later. Proceedings of the National Academy of Sciences, 108(36), 14998-15003.