Navigating distant family holidays as parents age

family at Christmas with members on laptop

The holiday season has a way of highlighting how families evolve over time. My parents are aging, and the distance between us feels more significant with each passing year. I'm settled 2,000 kilometers away in another province, while my brother works an offshore rotation—three weeks on the rigs, three weeks off. This Christmas, they'll be spending the holidays alone. Between flight costs for my family and my brother's work schedule, neither of us can make it home.

When I talk to them, they reassure me they're fine, that they've grown accustomed to our absence. But I hear what they don't say. I know it's difficult, especially when they see other family members surrounded by children and grandchildren while their own family connects from a distance.

The guilt weighs heavily on both sides. I struggle to balance creating meaningful holidays for my own family while carrying the knowledge that my parents are alone. Meanwhile, my brother and I are navigating new territory ourselves—this year, for the first time, I suggested we stop exchanging gifts for our kids. They're older now, more independent, and the gift exchange has started to feel like a transaction rather than something meaningful. But without that tradition, how do we show we're thinking of each other during the holidays?

I find myself unsure how to navigate this new phase—with aging parents on one side and grown children on the other.

A memory surfaces: my grandmother at Christmas, watching the door, sighing softly about wishing it would open to reveal my uncle and his family of six who lived far away. Now I realize my parents must feel exactly the same way.

My brother is planning a visit before his next rotation, but it'll be three weeks before Christmas. Close, but not quite the same. Still, you adapt. You find ways forward.

As I watch this unfold, I can't help but think about my own future. One day, my children will have their own lives, their own distances to manage. When that time comes, I'll need strategies for coping with holidays that look nothing like the crowded, noisy gatherings I remember from childhood—tables full of grandparents, aunts, uncles, and cousins, all the beautiful chaos of family together in one place.

---

Here are some practical suggestions for managing these family transitions during the holidays:

Rethink When You Celebrate The calendar date matters less than being together. Consider celebrating Christmas in early January, late November, or whenever schedules align. Creating your own "family Christmas" on a different day can feel just as special and removes the pressure of impossible logistics.

Embrace Technology Meaningfully Schedule video calls during key moments—opening gifts, preparing meals, or just sharing coffee. Some families set up tablets at the dinner table so distant members can "join" the meal. It's not the same as being there, but it creates connection beyond a quick phone call.

Create New Traditions That Span Distance Watch the same movie at the same time while on a call. Send care packages that arrive on Christmas Eve with instructions to open together over video. Start a shared digital photo album where everyone posts holiday moments throughout the season. These rituals acknowledge the distance while building something meaningful across it.

Plan Rotating Gatherings If annual visits aren't feasible, commit to gathering every two or three years. Knowing there's a plan—even if it's far out—gives everyone something to anticipate and makes the in-between years feel less permanent.

Shift Gift-Giving Focus Instead of exchanging gifts between siblings, pool resources for your parents—perhaps funding a house cleaning service, meal delivery, or an experience they'd enjoy. For kids, consider donating to a charity in each other's names or doing a family gift exchange game when you do gather.

Send Presence, Not Just Presents Mail handwritten letters, voice recordings, or photo books that arrive before the holidays. These tangible reminders that someone took time to create something personal can mean more than store-bought gifts.

Check In More Throughout the Year Regular contact during ordinary months can ease holiday guilt. A Tuesday afternoon video call in March might matter more than you think, making the holidays feel less like the only time connection happens.

Accept the Grief Acknowledge that this transition involves loss—loss of traditions, of the family structure you once knew. It's okay to feel sad about what's changing while also embracing what's ahead. Give yourself and your parents permission to miss the old days without guilt.

Create Micro-Moments Even if you can't be there Christmas Day, could you manage a long weekend visit in December? Sometimes a few days together earlier in the season, without the pressure of "the perfect Christmas," can feel more relaxed and meaningful.

Start Conversations Now Talk openly with your parents and siblings about what matters most to everyone. You might discover your parents would prefer a summer visit when the weather's better over a stressful December trip you can barely afford. Their priorities might surprise you.

The hardest part is accepting that family life evolves, and the crowded, chaotic gatherings of your childhood may not be sustainable forever. But that doesn't mean the love diminishes—it just finds new expressions.

Retiring Young While Raising Adults: Our Unconventional Timeline

How We Got Here (a.k.a. The Math We Definitely Didn’t Do)

My husband and I met in our early thirties, when we were both already fully formed adults with careers and opinions. I worked in government, he taught grade school, and neither of us was wandering around “finding ourselves.” We found each other instead, which felt efficient.

We got married when I was in my mid-thirties and instantly became a blended family, welcoming his seven-year-old daughter (will son at that time, but that is a story for another time) into the mix. No pressure—just parenting on hard mode right out of the gate.

We knew we wanted kids together, and since biology does not care about your life plan, we moved quickly. I had my first daughter a year after we married and our second two years later. My husband was in his late thirties and early forties when our kids were born—older than most first-time dads in the delivery room, but not so old that the nurses looked concerned. So… still winning.

What we didn’t really think about back then was the math.
You know. Minor detail.

Starting a family later meant we’d be in our mid-fifties when our youngest graduated high school—almost perfectly lining up with our early retirement dates. At the time, retirement felt like a distant, dreamy finish line. So when we finally crossed it, we thought, We’re ready.
Narrator voice: They were not.

I retired at 55. My husband retired at 58. We are incredibly fortunate—excellent government pensions, solid financial security, the kind of stability people politely envy while asking, “So what are you going to do now?”

What we were actually doing was parenting.

At retirement, we had one child finishing high school, one in her second year of university, and my husband’s daughter from his first marriage navigating her late twenties and early career—also known as the “I’m an adult but still have questions” phase.

Our story doesn’t follow the traditional timeline. But really, whose does? Life rarely cooperates with neat sequences and colour-coded plans.

We’re one of those couples living in the overlap—retired but parenting, financially stable but emotionally confused, technically free but still packing lunches (not really. Lunch money was my new normal). This isn’t advice or a roadmap. It’s just the honest, slightly chaotic experience of navigating a life stage that refuses to stay in its lane. 😌

The Financial Blessing We Don’t Take for Granted (But Yes, We Hear About It)

Yes, we have two public sector pensions. And yes, people love to point that out—usually with a tone that suggests we won the lottery sometime in the late ’90s. “Wow, you’re so lucky!” they say. And sure, we are. No argument there.

But here’s the part that rarely makes it into the conversation: those pensions weren’t free. They didn’t fall from the sky. No pension fairy visited us in the night. We paid for them. For decades. Every. Single. Paycheque. Pension contributions came off the top, meaning our take-home pay was noticeably smaller than many of our private-sector friends who were out there enjoying bigger salaries and nicer lunches.

It was a trade-off. We chose future security over immediate gratification. Very glamorous at the time.

We also did the responsible thing and saved for our kids’ education while we were working. RESPs, ongoing support, part-time jobs—team effort. Nobody was handed a blank cheque, but nobody was abandoned to the student loan abyss either.

This financial setup now allows us to retire early without hyperventilating. We’re not lying awake at night choosing between our retirement and our kids’ education. We can do both. I fully understand how rare and privileged that is.

I also know many women our age are still working not because they’re deeply fulfilled, but because bills are persistent and pensions are mythical creatures. The kind of plans we benefited from are becoming increasingly uncommon, and that’s putting it mildly.

And let’s be clear—this wasn’t all hard work and virtue. Yes, we worked. But we also benefited from good timing, stable public-sector jobs, and plain old luck. I won’t pretend this was some heroic bootstrap story.

Here’s the twist no one talks about: even when the money is sorted, this life stage is still emotionally complicated. Turns out financial security doesn’t automatically come with a manual for letting go, redefining yourself, or figuring out what’s next. Who knew?

Identity Beyond Work and Parenting

For decades, my identity was neatly wrapped up in two very time-consuming roles: my career and motherhood. Between the two, they occupied most of my energy, brain space, and calendar. There wasn’t much room left for existential reflection—and honestly, I didn’t miss it.

Now, with my career officially ended and my children increasingly independent, I’ve had to face a question I’d been far too busy to ask: Who am I when I’m not needed by everyone, all the time?

I’ve always been the person with the schedule. The deadlines. The important meetings. The color-coded calendar. Suddenly, I had wide-open, unstructured time—which sounds dreamy until you actually have it and realize you don’t know what to do with it.

Turns out, I’m not great at “nothing.”

Within four months, I was restless. So naturally, instead of learning to relax, I accepted a six-month contract with a bank. After that, I took on a two-year government management role—because clearly I just needed one more job to really understand retirement.

Now, as this contract comes to an end, I’m finally starting to get it. Retirement isn’t about stopping. It’s about choosing differently. I still feel like I have something valuable to contribute—but the mindset is completely different when work is optional.

Working post-retirement isn’t about climbing ladders or proving anything. It’s about engagement, purpose, and knowing you can walk away if it stops being worth your time. And honestly? That might be the best part of all.

What We’re Learning (So Far)

Retirement is not a moment—it’s a moving target.
We didn’t retire and immediately settle into some serene, well-lit version of life. There was no magical “ahhh” moment. Instead, retirement turned out to be an evolving phase that keeps changing the rules.

What early retirement looks like for us now will be completely different in five years—when all the kids are fully independent. Or at least, theoretically independent. We’re learning to hold our expectations loosely and adjust as this stage unfolds, because rigidity and reality are not friends.

Financial security doesn’t cancel emotional complexity.
Two pensions solved the money part. Bills get paid. We can help our kids. Panic is off the table. Very solid, very grateful.

What it didn’t do was magically provide purpose, identity, or a sense of fulfillment. Apparently, those are still our responsibility. Money bought us options—but choosing how to use those options required a whole different kind of work.

Flexibility beats perfect planning.
We entered retirement imagining complete freedom: spontaneous trips, slow mornings, and doing whatever we felt like that day. Adorable, really.

Instead, I realized fairly quickly that I wasn’t ready to stop working entirely. Within months, I was back—first one contract, then another. My husband, on the other hand, has embraced retirement with an enthusiasm I find both admirable and mildly suspicious.

But here’s what we both gained: flexibility without desperation.

We’re available when our daughters need help with college decisions. When my stepdaughter calls while navigating a major life choice. We can say yes to what matters because our pensions mean we’re not chasing paycheques. Relationships take time, and the security we built gives us the freedom to actually show up—even if my version of retirement looks nothing like the brochure.

There is no “right” timeline.
Our path—late parenthood, early retirement, kids still half-in and half-out—doesn’t follow the traditional sequence. Friends our age have grown children and grandchildren. Some are still climbing career ladders. We’re standing awkwardly in the middle, wondering how we got here.

And honestly? This unconventional timeline is teaching us things we never would have learned if life had gone “according to plan.” Turns out the messy middle has a lot to say—if you’re willing to listen.

Advice We’d Give Our Younger Selves

If I could go back to our thirties, would I do anything differently?
Maybe.
Maybe not.

Would I have children earlier? Possibly. But then they wouldn’t be these children—the ones I can’t imagine life without—so that thought ends pretty quickly.

Would I plan retirement differently? Honestly? I don’t know. We made the best decisions we could with the information we had at the time. And let’s be real—hindsight is a luxury, not a strategy.

What I would tell our younger selves is this:

Save aggressively.
Not in a panic way—but consistently. Boring, responsible saving. The kind that quietly changes your future. Financial security doesn’t solve everything, but it makes almost everything easier.

Take the long view on career planning.
Titles fade. Paycheques fluctuate. But benefits and pensions? Those matter more than anyone tells you when you’re young and invincible. Whether you have a pension plan or you’re self-funding your retirement, future-you will be deeply grateful you paid attention.

Stay physically healthy.
Retirement is far more enjoyable when your body cooperates. Feeling good makes freedom feel like freedom instead of a recovery period.

And finally—stop comparing your timeline to everyone else’s.
There is no single right order for building a life. Some people do everything “on time.” Some do it sideways. Some redo the whole thing. All of it counts.

If there’s one real takeaway, it’s this: you’re doing better than you think. Keep going.

Looking Forward (With Cautious Optimism and a Raised Eyebrow)

In a few years, our youngest will graduate from college, and our oldest will finish her second degree. The house will quiet down. The calendar will open up. Our days will be… well, I honestly don’t know yet. TBD.

When I first left my career at 55, I thought I had retirement figured out. Freedom. Time. Choice. The holy trinity. And for a while, I really did have all three. It was lovely.

Now, as my current contract winds down, I’m facing questions I didn’t expect to still be asking: Do I actually retire—or do I extend the contract? What does retirement even mean when you still want to work? Is there a definition for this, or are we all just making it up?

What I’m slowly learning is this: maybe retirement isn’t about stopping. Maybe it’s about choosing differently. Working when it feels meaningful. Saying no when it doesn’t. Accepting that the next chapter doesn’t have to look like anyone else’s highlight reel.

Right now, I’m still working. The “freedom” I once imagined feels a bit more theoretical than practical. But here’s the key difference—I’m not trapped. I have pensions. I have a safety net. I can walk away whenever I’m ready.

And that knowledge alone changes everything—even if I’m not quite done yet.

Spoiler alert: I extended the contract.

So yes, after all that reflection, questioning, and philosophical pondering about the meaning of retirement… I chose the option that involved another calendar, more meetings, and a continued sense of usefulness. Apparently, I’m not quite ready for full freedom just yet.

But this time it’s different. I’m working because I want to, not because I have to. And that distinction matters more than I ever expected.

Retirement, it turns out, isn’t a finish line. It’s more like a dimmer switch. And mine is still sliding slowly toward “off.” 😌