Grief during The Holiday's
- Sydney Osterloh

- Dec 21, 2025
- 6 min read
Grief doesn’t take a break during the holidays. In this post, I share how loss has shaped my heart, how remembering can bring both comfort and pain, and how I’m learning to carry grief with grace while choosing to show up fully for the ones I love.
This post took me a while to figure out how to start. Grief isn’t something you can easily put into words — especially when it’s been sitting heavy on your heart for years. But the whole reason I want to share my experiences with those I love is to offer understanding and reassurance: you are not alone, and we can face hard things together.
There was a time in my life when I felt incredibly lucky, almost like "protected" from death. As I’ve shared before, I grew up with a unique family dynamic. I was surrounded by people who some might consider “distant” relatives, but to me, they were immediate family. Because of that closeness, I spent most of my childhood feeling grateful that loss hadn’t touched us deeply.
In 2009, when I was 11 years old, my great-grandpa passed away. Considering the legacy he and my grandma built, it felt almost unbelievable that our family hadn’t faced more serious health issues or loss before then. Even in that moment, grief felt distant, something that was still devastating, but not overwhelming.
Fast forward to my twenties, and it felt like death suddenly found its way into every corner of my life. Within seven months, I lost three pivotal people — three people who should still be here, watching my babies grow.
And that’s when grief stopped being something I observed…
and became something I carried.
Grief, for me, shows up in ways I’m never really expecting or ready for. It happens in a passing thought, a familiar song, or standing in the shower. Often it sneaks into simple conversations that have nothing to do with the person — yet somehow remind me of the ones I’m missing.
Lately, as time has passed, I’ve noticed myself forcing the tears back when grief hits. Almost as if enough time has gone by that I should be “past it” by now. Like maybe crying means I’m not healing the right way, or that I should be stronger than I feel in that moment.
But grief doesn’t work on a timeline. It doesn’t wait for permission. And it doesn’t disappear just because life keeps moving forward.
For some, remembering brings comfort. For others, it brings pain. And both are okay. Grief is not a one-size-fits-all experience, yet in some way, at some point, it touches us all.
I don’t know about you, but for me, the holidays have always had a way of magnifying what I feel. Some years, the joy feels brighter than ever. Other years, I am holding onto personal conflicts, work stress, or an emotional weight that feels heavier this time of year.
And when grief is part of your story, the holidays tend to magnify that too. The empty space feels louder. The memories feel closer. What’s missing becomes harder to ignore when everything around you is telling you this should be the happiest time of the year.
Songs sound different. Traditions feel tender. Even joyful moments can carry a quiet ache of a reminder of who should be here, or how things used to be. And that doesn’t mean you’re ungrateful or stuck in the past. It simply means love doesn’t disappear when someone is gone.
Grief during the holidays isn’t about losing joy — it’s about learning how to hold joy and sorrow at the same time. And for many of us, that balance is one of the hardest things we’ll ever learn to carry.
Honestly, there is no “right way” to grieve — especially during the holidays.
So I want you to know this: you are allowed to
• step away when it feels like too much
• say no to gatherings without explanation
• hold onto traditions — or let them go
• speak their name
• cry when you need to
• smile when you can
Grief doesn’t mean you aren’t grateful.
It doesn’t mean you’re stuck.
It doesn’t mean you’re doing the holidays wrong.
It simply means you loved — deeply.
Growing up, Christmas was magical for me. My Grandpa Carl loved Christmas. One of my favorite holiday memories with him is going shopping together — usually to a dollar store — where he would have me pick out a Christmas gift for every single person in our family. And when I say family, I mean 30+ gifts.
He never questioned my choices.
Never rushed me.
Never asked why I felt so strongly about picking something specific for each person.
Looking back, those moments shaped who I am. Even if he didn’t realize it at the time, he taught me to lead with love, to think about others before myself, and to wear my heart on my sleeve. Gift-giving became my love language — (so Austin, you can now officially blame Grandpa Carl for the hundreds of packages that show up at our house every holiday season.)
Not that long ago, Austin and I were talking about the loved ones we’ve lost, and he said something that stuck with me:
“It doesn’t make me sad to talk about them anymore.”
And it’s not because we don’t miss the ones we’ve lost.
It’s because, alongside the sadness, we’re able to see all the gifts they gave us — the lessons, the love, the pieces of them that live on in us.
That is the true magic.
I think oftentimes we measure success in life by the degrees we’ve earned, the money in our bank accounts, or the Christmases and gifts we’re able to give our loved ones. But losing the people I have loved most has reshaped how I see success entirely.
I've learned, true success, lives in the way we treat others.
In how we show up for people — selflessly, without expecting anything in return.
In being someone others can trust.
In being the person who shows up when it matters most.
In the love we give on days when it’s hard to even love ourselves.
If we can help just one person feel seen, supported, or less alone — that is the true meaning of success.
As the holidays approach, I’m trying to hold a space for all of it — the joy, the memories, the gratitude, and the grief that still finds its way in. I’m learning that it’s okay to feel both at once, and that neither cancels the other out.
Grief doesn’t fade just because time passes. It softens when love continues. It shifts when we choose to carry forward the goodness, the lessons, and the kindness our loved ones poured into us.
More than anything, grief has reminded me how important it is to be present with the ones who are still here. To enjoy the laughter, the chaos, the ordinary moments we so often rush through. To lean on one another, to love deeply, and to keep showing up — especially for Hughes and Graham.
I think about the people we’ve lost — my Aunt Rylee, Grandpa Carl, and Austin’s dad, Dave — and I know with my whole heart that this is exactly what they would want for us. They would want us to push through the hard days, to cling to one another, and to savor the time we’ve been given together. To live fully, love generously, and keep their legacy alive through how we treat the people around us.
If this season feels heavy for you, I hope you know this:
you don’t have to have it all figured out.
you don’t have to be cheerful every day.
you don’t have to explain your heart to anyone.
Just keep loving in the ways you can.
Keep showing up where it matters.
Keep choosing grace — for yourself and for others.
That kind of love — the kind that endures, even in grief — is a love that truly lasts.
And to me, that is the greatest success of all.
If you’re carrying grief this season, I see you.
You are not alone. 🤍



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