I first set foot in the Philippines when I was 18 years old, stationed there with the Air Force. By 19, I was rappelling down a mountainside in Baguio, helmet strapped on, my name written across the tape in marker — young, focused, not thinking for a second about how long it would be before I came back to actually see this country rather than just serve in it.

I spent four years in that assignment.

I didn't go back to actually experience the place — not serve there, not pass through on orders, but really see it — until I was 49.

Thirty-one years.

At 18, I didn't have the time or the resources to explore much beyond what duty allowed. There was always another assignment, another responsibility, another reason "someday" made more sense than "now." I'm guessing a lot of you reading this know exactly what that feels like, whether you wore a uniform or not.

Then retirement happened. And with it came something I hadn't had in three decades: the time, and the means, to finally go back and see it properly.

What I found surprised me in more ways than one.

I stood at Camp O'Donnell, in front of a wall of names and a blunt, unforgettable title — Battling Bastards of Bataan — and understood, for the first time, the true weight of the ground I'd been stationed near for four years without ever fully grasping what it held.

I dove in Boracay, nearly talking myself out of it twice, and ended up with a dinner and a handful of new friendships I never would have had if I'd played it safe.

I spent an afternoon at a children's home, arm-wrestling a boy who beat me fair and square, and came away thinking more about what I could give than what I could see.

I hiked to the crater lake at Mt. Pinatubo, rode more tricycles and jeepneys than I can count, and rafted under a waterfall with people I love, holding up a sign that said exactly what I felt: you should be here.

None of that happened because I had unlimited time or money. It happened because I finally stopped waiting for the "right" moment and just went.

Over the next few weeks, I'll be sharing each of these stories individually — what I saw, what I learned, and what I wish I'd known at 18 that I only figured out at 49. Consider this the starting point.

Because here's the thing I keep coming back to: you don't have to wait 31 years like I did. Whatever place has been on your list — the one you've been meaning to get back to, or finally see for the first time — the best time to go is usually just... now.

Why not now? 

I'll be posting each new story here on the blog and sharing more in my VIP Vacations newsletter — travel stories, destination ideas, and lessons learned the hard way. If you want to follow along, I'd love to have you.