Hey Reader,
In the fall of 2018 I was grinding.
I'd been working weekends for a few years straight. I had PTO that wasn't going to roll over. I was single, no obligations pulling me anywhere, and I hadn't done anything for myself in longer than I could remember.
So I did something that was, by my standards at the time, completely impulsive.
I booked a solo trip to Greece.
Nine days in Santorini, Athens, and Mykonos. Right after Thanksgiving, in the off season, and completely alone with no one to navigate it with me.
And almost immediately after booking it, the second guessing started.
What if I get there and feel completely out of place? What if I spend all this money and it's not worth it? Is this really the right time for this?
I almost convinced myself out of it before I even packed a bag.
But somewhere in the back of my head a quieter thought kept surfacing.
If not now, when?
That question is the one most people never actually sit with.
Because here's what I've learned after years of traveling across the world and talking to people who want to travel more:
The reason most people don't book the trip isn't money. It's not that they're too busy. It's not that the timing is wrong. Those are the reasons they tell themselves.
The real one is that they're waiting for permission, for life to feel settled enough to justify it.
And that version never comes.
There is always something. A work project ramping up. A bill that feels too big right now. A season of life that feels too uncertain. A voice in the back of your head that says wait until things calm down or I'll do it when I'm in a better place or maybe next year.
That voice sounds responsible. It sounds like good judgment.
But most of the time it's just fear with a reasonable excuse attached to it.
It never feels like quite the right time. So you wait. And while you're waiting, life keeps adding new reasons to keep waiting.
I landed in Santorini not knowing what to expect.
But within hours, standing in front of my first winery, following an itinerary I'd built myself and talking to locals about what was actually worth seeing, those fears were already gone.
I did a catamaran cruise. I hiked the caldera. I found a rooftop bar in Athens and watched the Parthenon light up at night. I wandered around a mostly closed Mykonos and stumbled into a nightclub because a local pointed me in the right direction.
None of it happened because the timing was perfect.
It happened because I stopped waiting for it to be.
On the flight home I remember feeling something I hadn't felt in a long time.
Proud. Genuinely proud of myself.
And already thinking about planning the next one.
That solo trip was eight years ago. It changed everything about how I travel.
🧭Travel Tip of the Week: Stop waiting for the right time to book
The right time is a moving target. Here's how to stop chasing it:
1. Separate the real obstacles from the imagined ones
Ask yourself honestly: is there actually something preventing this trip or are you just uncomfortable with the uncertainty of committing? Most of the time the obstacle is the second thing dressed up as the first.
2. Book something small to break the inertia
You don't have to commit to two weeks in Europe. Book a long weekend somewhere you've been curious about. The act of booking something real shifts your identity from someone who wants to travel to someone who does it.
3. Give yourself a deadline
Open-ended intentions stay intentions. Pick a travel window, even a rough one, and work backwards from it. "I want to take a trip in October" is a plan. "I want to travel more this year" is a wish.
🛫 Coming up on the Next Flight Path
The travel rewards most people don't know they already have access to.
Here’s to smarter, easier travel.
Until next time,
Joe
Follow the journey → @heavilyinkedpassport
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