The Trips I Kept Putting Off… and Why I’m Not Anymore
There are a handful of trips I’ve been talking about for years.
Not casually.
The kind where I’ve looked up flights more than once. Saved hotels. Even imagined exactly what I’d pack.
And yet… they never made it onto the calendar.
Not because I didn’t want to go. But because Dan wasn’t really interested.
Glamping in Glacier National Park.
A few slow days in Banff.
A hike and spa weekend in Sedona.
Acadia in the Fall with my lobster rolls.
Even a long weekend in the Exumas at Staniel Cay.
All trips I wanted. None of them trips we were both excited about.
So I did what most of us do. I waited.
I told myself we’d get to it eventually. That maybe next year would be the right time. That it would be more fun if we both wanted it. And for a long time, that felt reasonable.
Until it didn’t.
Because here’s what I started to notice… The list wasn’t getting shorter. It was getting longer. And the version of my life where I actually did those things kept getting pushed further out.
Not dramatically. Just quietly.
Year after year.
The Shift
As I was sharing with a girlfriend about all the places on my list, she made the simplest comment.
“But why aren’t you grabbing your girlfriends and creating those memories with them?”
And it stopped me for a second. Because I didn’t really have a good answer.
And I suddenly realized something simple.
Not every trip needs to be a shared interest. Some trips are meant for different people.
Dan and I actually love traveling together, and we have plenty of trips that feel like a perfect fit for both of us. But we also have different ideas of what a “dream trip” looks like sometimes.
And instead of trying to make every experience fit both of us, I’ve started asking a different question:
Who would love this as much as I would?
That question changes everything.
The New List
Now when I think about those same trips, they feel different.
🏔️ Glacier becomes a glamping weekend with girlfriends under the stars.
☕️ Banff becomes long walks, coffee with a view, and no one rushing to the next thing.
🥾 Sedona becomes hiking in the morning and the spa in the afternoon.
🦞 Acadia becomes crisp air, Fall colors, and layers and laughter and lots of lobster rolls.
🏖️ Staniel Cay becomes barefoot mornings and boat days with women who appreciate it just as much.
Same places.
Different energy.
Why This Matters in Midlife
In this stage of life, time feels different.
Not scarce.
But more intentional.
We are more aware of what we actually want. And more honest about what we don’t.
Waiting for the “perfect alignment” where everyone wants the same thing at the same time can quietly turn into never going at all. And that’s the part I’m no longer willing to accept.
If This Sounds Familiar
If you have your own list of “someday” trips sitting in your head…
This might be your sign to look at them differently.
Not as something to wait on. But as something to reimagine.
Who would say yes immediately?
Who would appreciate it the way you do?
Start there.
Because sometimes the trip isn’t the problem. It’s who you’re waiting for.
