Holiday Grief: Why the Most Wonderful Time of the Year Can Feel Bittersweet
The holidays are supposed to be the most wonderful time of the year, right? The decorations, the traditions, the family gatherings, the magic. But what happens when all that holiday cheer comes with a little sadness, too?
In this episode of You Handled That Perfectly®, we're talking about something that doesn't always get enough attention during the holiday season: grief. And not just the grief that comes from losing someone we love, but the quieter, sometimes unexpected grief that comes with growing up, watching our kids get older, changing family dynamics, and realizing that the holidays will never look exactly the same as they once did.
Because here's the thing: you can absolutely love the holidays and still miss the way they used to be. Both things can be true.
Missing the Magic of Our Own Childhood
Remember being a kid during the holidays? The excitement, the anticipation, the absolute magic of it all? There was something so special about waking up on Christmas morning without a care in the world, knowing that somehow everything had magically come together.
Of course, now that we're moms, we know exactly how all that magic happened. Someone was shopping, wrapping, decorating, baking, planning, coordinating schedules, and making sure everyone had the perfect holiday experience. And chances are, we didn't appreciate nearly enough of it at the time.
It's funny how becoming a parent changes your perspective. Suddenly, you're the one responsible for creating those memories, and you realize just how much effort went into the holidays you remember so fondly. There's a whole new appreciation for our parents and everything they did to make those moments special.
But there's also a little grief in realizing that our own childhood holidays are over. We can't go back to those carefree mornings or recreate every tradition exactly as we remember it. And sometimes, the expectations we carry from our childhood can make our adult holidays feel disappointing when reality doesn't quite measure up.
That's why we've become big believers in managing expectations. Not eliminating them entirely, because where's the fun in that? But recognizing that we don't have to recreate every magical moment from our childhood to give our kids a wonderful experience.
Instead of trying to do everything, pick a few traditions that really matter to your family. For us, things like riding the Polar Express and having a family baking day are holiday non-negotiables. They're the things we look forward to every year, and everything else is a bonus.
Because the magic isn't in doing more. It's in enjoying what you're doing.
Grieving the People Who Made the Holidays Special
Of course, one of the hardest parts of the holidays is missing the people who are no longer here to celebrate with us.
For Carly, Christmas Eve was always spent with her Grandma Joe and a huge extended family. It was a tradition filled with familiar faces, laughter, and memories. When her grandmother passed away in 2015, Christmas Eve was never quite the same.
And that's one of the hardest things about grief. Sometimes you're not just missing the person. You're missing the entire experience of being with them. The traditions they created, the way they made you feel, and the version of your life that existed when they were still here.
During our conversation, we shared a sentiment that really stuck with us: sometimes homesickness isn't about missing a place. It's about missing a person.
How true is that?
Sometimes grief shows up in the smallest ways. A holiday recipe that no one makes anymore. A decoration that reminds you of someone. A family gathering that feels different because one person isn't there. Or simply wishing your children could have known the people who meant so much to you.
And grief doesn't necessarily get easier just because more time has passed. It can sneak up on you when you least expect it, even in the middle of a perfectly happy moment.
We think it's important to acknowledge that. You don't have to push those feelings aside just because it's the holiday season. Missing someone is part of loving them, and those memories deserve a place in your celebrations, too.
Watching Our Kids Grow Up (And Wishing Time Would Slow Down)
Okay, moms. This one might hit a little close to home.
There's a particular kind of grief that comes with watching your kids grow up. It's not necessarily sadness about where they are now, because every stage brings something wonderful. It's more about realizing that the stage you just loved is already over.
One day they're toddlers who barely understand Christmas, and the next they're sitting at the top of the stairs waiting for permission to come down and open presents. Before you know it, they're sleeping in on Christmas morning, asking for clothes instead of toys, and deciding they're too old for certain family traditions.
And while we're so proud of them for growing up, we also kind of want to yell, "WAIT! NOT YET!"
Carly recently experienced one of those moments when her daughter announced that she no longer wanted her mom saying goodbye to her at the school gate. It was something they'd done since kindergarten, and suddenly, just like that, the tradition was over.
Was it a completely normal and healthy part of growing up? Absolutely. Did Carly cry about it? Also absolutely.
That's motherhood in a nutshell. We're raising our children to become independent, confident people, but every step toward independence means letting go of a little piece of the childhood we've loved so much.
And the holidays have a way of making those changes feel even bigger.
We find ourselves wondering how many more years we'll have of certain traditions. How many more Christmas mornings will be filled with toys? How much longer will everyone want to pile into the car in their pajamas to ride the Polar Express? When will our kids decide they're too cool for the things we've always done together?
But here's something we reminded ourselves of during this conversation: traditions can evolve, too. Sometimes kids grow out of something for a while, only to come back to it later with a whole new appreciation. The things that embarrass them as teenagers might become their favorite memories as adults.
And in the meantime? Take the videos. Record their little voices. Enjoy the mispronounced words and the excitement over the smallest things. Because someday, those ordinary moments are going to feel pretty extraordinary.
When Family Dynamics Change, So Do the Holidays
Another type of holiday grief that doesn't always get talked about is the sadness that comes with changing family dynamics.
Families are constantly evolving. People move, change jobs, get divorced, remarry, have babies, adopt puppies (sometimes against their better judgment!), and eventually send their kids off to college.
And every one of those changes can affect the way we celebrate.
Sometimes it's something as simple as realizing that your family won't all be together for the entire holiday break anymore. Maybe your oldest child is away at college, or your siblings now have families of their own and need to split their time between multiple celebrations. Maybe the house that was once overflowing with kids and chaos is suddenly a whole lot quieter.
These changes don't have to be bad to feel sad.
We talked about how different family dynamics can be even within the same household. When your oldest child leaves for college, your younger child might still have several years at home. Suddenly, the family routines you've known for years look completely different.
And as moms, we're not just adjusting to those changes ourselves. We're also helping our kids navigate them.
One thing we've learned is that every family has its own version of holiday magic. Carly grew up celebrating Christmas over several days while visiting different sides of her extended family. Now, as a mom, she's made Christmas morning at home a priority for her own kids.
Neither way is right or wrong. They're just different chapters, with different traditions and different memories.
And maybe that's the beauty of it. We get to carry forward the things we loved, let go of the things that no longer work, and create something new for the season of life we're in.
The Pressure to Make Everything Magical
Can we talk about the pressure moms feel during the holidays?
Because somewhere along the way, we became the official magic makers. We're responsible for the gifts, the traditions, the decorations, the holiday outfits, the baking, the family photos, the schedules, and making sure everyone has the BEST. CHRISTMAS. EVER.
No pressure, right?
And the funny thing is, we actually love a lot of it. We love seeing our kids' faces light up. We love creating traditions they'll remember. We love making things special for the people we love.
But there's a difference between creating magic because it brings us joy and feeling like we have to manufacture happiness for everyone around us.
Sometimes the pressure to make everything perfect takes away from the very experience we're trying to create.
That's where a little mindset shift can make a big difference.
We talk about mindset a lot on the podcast, and for good reason. The way we approach a situation can have a huge impact on how we experience it. If we spend the entire holiday season worrying about everything that could go wrong, we're probably going to miss a lot of the things that are going right.
One idea we talked about is the difference between spiraling and snowballing. When we spiral, one negative thought leads to another, and suddenly we're overwhelmed by everything that isn't working. But what if we could do the opposite? What if we let the good things snowball?
Instead of focusing on what didn't happen, what if we noticed what did? Instead of worrying about whether every tradition was perfect, what if we appreciated the moments that made us laugh? Instead of comparing this year's holidays to last year's, what if we allowed this season to be something completely different?
We love the reminder that our thoughts aren't always facts. Just because we think something is going to be disappointing doesn't mean it will be. And just because the holidays look different doesn't mean they can't still be wonderful.
Of course, this doesn't mean forcing yourself to be happy when you're genuinely sad. Grief deserves space, too. But it does mean giving ourselves permission to find joy alongside the sadness.
Because sometimes the most magical moments are the ones we didn't plan at all.
Making Room for Both Joy and Grief
If there's one thing we hope you take away from this conversation, it's that feeling a little sadness during the holidays is completely normal.
You can miss your childhood and love being the mom who creates the magic now. You can grieve someone who isn't at the table and still enjoy the people sitting around it. You can wish your kids would stay little forever while being incredibly proud of the people they're becoming.
You can be grateful for your life exactly as it is and still miss the way things used to be.
The holidays don't have to be perfect to be meaningful. They don't have to look the same every year to be special. And you certainly don't have to carry the responsibility of making everyone happy.
Maybe this year, instead of trying to recreate the magic of the past, we can focus on appreciating the magic that's right in front of us. The messy kitchen after baking cookies. The kids laughing in the backseat. The traditions that have survived every stage of life, and the new ones we're creating along the way.
Because life is constantly changing, and the holidays are no exception. Every season brings something new, something different, and sometimes something we have to let go of.
So if you're heading into this holiday season feeling a little nostalgic, emotional, overwhelmed, or all of the above, you're definitely not alone. We're right there with you.
Give yourself permission to feel all of it. Celebrate what you have, remember what you've lost, and don't put so much pressure on yourself to make every moment magical.
You're showing up. You're doing your best. And that is enough.
Remember: handling it perfectly isn't about being perfect.
Listen to the full episode, "Holiday Grief," on You Handled That Perfectly® with Kelly Avalon + Carly Cruickshank.
And in case no one told you today, you handled that perfectly.