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You are here: Home / Lifestyle / The Winning Family: Walking Your Kids Through Life’s Disappointments

The Winning Family: Walking Your Kids Through Life’s Disappointments

April 9, 2026 by Rodney Gage Leave a Comment

One of the hardest parts of parenting is realizing that no matter how much you love your child, you cannot protect them from every heartbreak.

When they are little, you can often soothe their pain with a hug, a few comforting words or just simply being near. But as they grow older, the disappointments grow deeper. Dreams fall apart. Life changes suddenly. Tragedy comes without warning. And as a parent, you realize that even when your children are adults, you never stop loving them, guiding them or helping them carry what feels too heavy to bear.

Recently, our family walked through one of those heartbreaking moments. Our daughter, Ashlyn, who is 28 years old and seven months pregnant, was rushed into the emergency room and had to undergo an emergency C-section. Tragically, our little granddaughter, Elizabeth Barbara Segur, did not survive. The doctors spent 17 minutes doing CPR and doing everything possible to resuscitate her, but she was stillborn.

Michelle and I are deeply grateful we were able to hold our granddaughter in our arms and take in all of her beautiful, perfect features. She weighed 2 pounds, 3 ounces, and she had blonde hair just like her momma. Those moments are treasures we will carry in our hearts forever. And while our grief is deep, we also hold on to the hope of heaven and the comfort of knowing we will see her again.

As I have walked with our daughter through this painful season, I have been reminded just how important a few simple parenting principles really are. These principles matter when your children are young, but they also matter when your grown son or daughter is facing disappointment, heartache or unexpected loss.

1. Validate Their Feelings Before You Try to Guide Them.

Acknowledgment builds trust. When someone you love is hurting, it is natural to want to fix it, explain it or make it better. But most of the time, what they need first is not advice. They need empathy and compassion. They need space to grieve, to ask questions, to sit in the sadness without feeling like they have to rush past it.

That is true whether your child is 8, 18 or 28.

One of the greatest gifts we can give our kids is our presence. Listening without interrupting. Sitting with them without needing to solve everything. Letting tears be tears. Letting grief be grief. Sometimes, the most healing words a parent can say are simply, “I’m so sorry. I’m here. You don’t have to carry this alone.”

2. Look for the Growth Hidden in the Setback.

Perspective shapes resilience. That does not mean minimizing pain or pretending every loss has an easy explanation. Some disappointments are truly devastating. But over time, parents can help their children see that pain does not have to be pointless.

Setbacks can deepen compassion. Hardship can build strength. Loss can remind us what matters most. I have been reminded in this season that resilience is not pretending to be strong. It is learning how to keep going without losing your tenderness, your hope or your capacity to love.

As parents, we help our children when we gently remind them that while they may not have chosen this pain, they can still choose how they walk through it. In time, disappointment can become more than a wound. It can become a teacher.

3. Remind Them That Hope Is Still Possible, Even in the Darkest Seasons.

Hope strengthens the heart. Disappointment has a way of making the future feel uncertain. Heartbreak can make life feel smaller, darker and heavier. That is why hope matters so much. Hope does not erase grief, but it helps us endure it.

As parents, one of the most important things we can do is remind our children that this painful chapter is not the whole story. There is still healing ahead. There is still meaning ahead. There is still life to be lived, even after loss.

Disappointment is part of life, but it does not have to define a life. When we help our children process pain with honesty, compassion, perspective and hope, we strengthen the kind of resilience that will carry them through future storms.

Because, in the end, one of the greatest callings of a parent is not to keep our children from every heartbreak but to help them walk through heartbreak without losing heart.

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About Rodney Gage

Rodney Gage is a family mentor, author, speaker and the founding pastor of ReThink Life Church meeting at Lake Nona High School. His passion is to help families win at home and in life. To learn more, check out thewinningfamily.com and rethinklife.com.

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