A Holiday Season, Reimagined… When Life Rewrites the Plans

Learning to meet the season where it is, when life rewrites the holiday plans

Ahhh ‘tis the season. Equal parts magic, pressure, and plans you were supposed to already have figured out. You’re supposed to know where you’ll be, who you’ll be with, and what the traditions look like. And usually, that works, until one year it doesn’t. Not because anything went wrong necessarily, but because life did its thing.

This article exists for that year.

For a long time, I cared a lot about what other people thought of me. What they assumed. What story they were telling themselves based on a small snapshot of my life. I know I am not alone in that. We spend so much time worrying about how things look that we forget how they feel.

And the holidays have a way of amplifying that noise.

This year, I am spending the holidays alone. Not in a cinematic, main character way. Just realistically, that’s how the timing landed. And with that came feelings. All of them, because the holidays are emotional multitaskers. They manage to be exciting and heavy at the exact same time. They sit right at the end of a year and the beginning of another, which means your brain can’t help itself. You’re replaying the last twelve months like a nostalgic montage in your head. The good moments. The weird ones. The ones that still sting a little. All of it, playing softly in the background.

There’s a strange privilege in having the space to sit with those memories alone. Of course, sometimes you want your people there. Someone to laugh about it with, to say “remember when,” to fill in the parts you forgot. And sometimes, they’re just not there. Not because anything is wrong, but because life is happening for everyone at once, just in different directions.

Being alone during the holidays doesn’t mean you’re disconnected. It often just means your season is unfolding differently.

What I had to unlearn was the idea that being alone meant I was being judged. That people were imagining a story about me I couldn’t control. The truth is, we can’t read other people’s minds. They will have their thoughts and assumptions regardless. Letting that weight follow you into moments of quiet only steals the joy you are still allowed to have.

So I stopped letting it matter.

I carried on with my life. I did things that made me happy, unapologetically, even if they looked a little cheesy from the outside. Especially because they did.

Because when we were kids, the holidays were pure spectacle. Eyes wide. Brain fully offline. The air felt electric. You ran around the Christmas tree like it was a racetrack. You shook every present to feel what it could be. You left a note for Santa, cookies on the table, carrots for the reindeer, because obviously they needed a snack too. Snow meant snowball fights, not slush in your boots. The music, the lights, the energy, it all felt huge and important. 

Somewhere along the way, we traded that wonder for logistics.

Now the holidays are schedules, travel days, budgets, and quiet mental math. Who can make it, who can’t, how long you can stay, how much you can spend. It’s not worse, it’s just different. And sometimes, that difference feels heavy.

This year, being alone forced me to notice that shift rather than distracting myself from it. And once I noticed it, I made a decision. If the season was going to feel different, I would meet it where it was, instead of wishing it into something else.

And that is where travel, even in small ways, comes in.

You don’t need a big faraway trip to experience a place differently. Sometimes it’s about moving through your own city with curiosity. Becoming a tourist in your routine. Letting yourself explore without needing a reason or a plus one.

So I did the holiday things. All of them. 

I wandered through the Christmas Market. I stepped into a wildly over-the-top Christmas pop-up cocktail bar because it screamed jolly vibes. I watched the Nutcracker simply because it felt like December. I laced up skates and circled the rink, horribly but happily. I leaned fully into holiday movie marathons to amplify the spirit, like Harry Potter, The Holiday, Elf, with twinkle lights on, snacks nearby, and no guilt. 

None of it was about filling time. It was about choosing to experience the season as it was, not as I thought it should be.

But sometimes, a change of scenery helps too.

Not everyone can disappear on a two-week holiday in December, and you don’t have to. Even a small getaway can shift your perspective. A short train ride. A nearby town or city. Somewhere close enough to feel easy, but different enough to pull you out of autopilot.

For me, living on the East Coast, that meant options. New York City is close. Familiar. Simple to get to. The kind of place you can visit for a few days without turning it into a production. But during the holidays, it becomes something else entirely. Louder. Brighter. Full of movement and momentum. A city that doesn’t ask why you’re alone, because everyone is too busy living alongside you.

If you’re alone this time of year, this is your reminder. Don’t shame yourself for it. Don’t shrink your joy because someone else might misunderstand it. Treat yourself. Bask in all of it, the sad, the happy, the quiet, the sparkle. Another year has passed, and this one just looks a little different.

That pull, the need for perspective without pressure, led me somewhere familiar, yet transformed by the season. If you’re going to be alone during the holidays, even unexpectedly, you could do it somewhere that meets you where you are. Somewhere that fills the quiet without demanding anything in return.

So I took myself to New York City…