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In My Checked Bags, Not Baggage Era: What I packed, what I left behind, and where I’m heading.
The Flights Are Calling… And I’m This Close to Answering
Every time I get an email from Going telling me about some ridiculous flight deal—$600 roundtrip to Thailand, $400 to Italy, $200 to Aruba—it takes everything in me not to drop everything, pack a bag, and go.
Because, honestly? What’s stopping me?
I have no kids, no PTA meetings, no standing Sunday brunch with the in-laws, no real reason not to just buy the ticket.
Except for one: the fear of not knowing what comes next.
The Art of Romanticizing Travel (And Yet, Never Going)
The funny thing is, I constantly romanticize travel. If a movie involves exploring ancient ruins, uncovering long-lost secrets, or setting off on a grand adventure, I’m already invested.
The Mummy is my holy grail of travel movies—the desert landscapes, the adventure, the sense of mystery, the pure chaos of it all. And don’t even get me started on The Tudors. People back then were just out here crossing entire countries for love, power, or because they got bored—and I can’t even book a flight when it’s on sale.
Under the Tuscan Sun? Please—if I had the money, I’d be buying a crumbling Italian villa right now.
And yet, despite this lifelong obsession with going, I stay.
The Internal Tug-of-War: Book It or Close the Tab?
Every time I get an email about a too-good-to-be-true flight deal, I open it, stare at the destination, and feel that familiar tug in my chest.
You could be on that plane. You could be drinking fresh mango juice in Zanzibar, eating street food in Bangkok, feeling like you just stepped into your own adventure movie.
For a few minutes, I let myself believe that I might actually book it. I click through, check the dates, imagine the possibilities.
But then I close the tab.
I tell myself I need to be responsible. I should have a plan. I should wait until it makes sense. But deep down, I know I’m just afraid. Not of the travel itself, but of what comes next.
What happens after I go? What happens when I have to come back and figure out my next move? What if I get out there and feel lost, not just physically, but emotionally?
And at the same time, I wonder—what if I stay here and regret never going?
The Fear of Leaving vs. The Fear of Never Leaving
Because the fear of leaving is real, but so is the fear of never leaving at all.
Sometimes I think about how easy it would be to just go. Nothing is tying me down except my own hesitation. No one would have to be consulted. No permission needed. I could literally pack a bag, book the ticket, and disappear for a while.
So why don’t I?
Maybe it’s because I’ve spent so long convincing myself that there’s one right way to do things. That I should have a perfect plan, a detailed itinerary, a clear sense of what comes next.
But the reality is, most people who take the leap don’t have everything figured out. They just go.
What If I Just… Went?
And maybe that’s what I need to do, too.
Maybe I need to stop waiting for the perfect time. Maybe I need to trust that whatever comes next, I’ll figure it out when I get there. Maybe I need to finally answer the call that’s been ringing in my inbox for years.
Because at this point, I know one thing for sure—if I don’t go now, I’ll keep waiting forever.
And I refuse to let my life be a series of almosts.
Have You Ever Felt This Way?
So tell me—have you ever almost booked a flight and stopped yourself? Or did you go for it?
Drop a comment and let me know. Maybe your story will give me the final push I need.