Our Old Dad

I think about regrets a lot. Not in some grand reckoning kind of way. More in the ordinary way a person does when he gets old enough to see how small decisions turn into bigger ones, and bigger ones slowly become a life. I can look back on almost every stretch of my life and see where I should have been steadier, braver, less foolish. And if I’m honest, it doesn’t take many changed decisions to start changing everything. Even a few would have thrown the trajectory off. A different job taken. A different relationship held onto or let go of. A different move made earlier or later. A few degrees one way or the other, and maybe I do not end up here at all. But I would not trade here away. Because here means Raven and Xander. Not just children in the abstract, but these children. I was old enough by then to know that the best things don’t always show up when you expect them, or looking the way you expected. They were not part of some clean master plan. They were ...

Post 4 in the Slow Travel series · Constraint #1: Weather In Post 2 I introduced the constraint system — 11 filters that decide where we go. Weather is the first one, because it's the most ruthless. A place can be cheap, safe, beautiful, and full of opportunities. If the weather makes daily life miserable for six weeks, none of that matters. This isn't about chasing perfect beach days. It's about sleep, routines, and whether the kids can play outside on a normal Tuesday. These filters reflect our family as it is now. They'll shift as we do — that's why the system is built to be tuned, not carved in stone. People hear "weather constraints" and think high-maintenance. It's the opposite. The planet has hundreds of places with great weather in any given month. We're not limiting our options by being specific — we're choosing from an enormous list of places that actually fit, instead of landing somewhere and gutting it out. Exacting stand...

Post 3 · The Family Meet the Family (And Why We're Doing This) Before we go deeper into constraints and systems, you should probably know who "we" are. That photo is from the Philippines about 17 years ago — where this whole story really starts. The Short Version I'm Will. I'm 60. I'm a public school teacher in Colorado, a domain investor, and a dad of four. My oldest — Christopher (18) and Alexa (17) — are nearly grown and doing their thing. I'm proud of both of them. And then came the surprises. Raven (4) and Alexander (2) were not part of any plan. They turned out to be the best part of my 60 years. They're the ones who'll be slow traveling the world with me when I retire in about seven years. They're triple citizens: the United States, Ireland, and the Philippines. That matters — those passports open doors and simplify some visa decisions. Their mom is a US and Filipino citizen. She hasn't decided yet whether she...

Post 2 · The System The Constraint System That Will Pick Our Next Places In Post 1 I laid out the mission: slow travel the world with my two youngest kids when I retire in about seven years. This post is how we'll decide where we go next—without turning travel into a constant argument, a constant scramble, or a constant money leak. We're building a constraint system. Not an itinerary. A filter. So when we ask: "Give us 20 places that fit our family from May 1 to August 1." …we don't get fantasy answers. We get places that actually work. How It's Structured Each constraint category is its own short document. That keeps everything modular and adjustable. Every constraint has: — Dealbreakers (hard filters that remove a place entirely) — Preferences (what we'd like, if we can get it) — Modes when needed (overseas base vs. North America camping/road) — Overrides for special trips or once-in-a-lifetime opportunities The constra...

Post 1 · The Mission Slow Travel: Our Plan to See the World (Without Rushing Through It) I'm an old dad. I'll be retiring in about seven years. When that happens, I'm doing something that sounds ambitious but is really just stubborn planning: slow traveling the world with my two youngest kids. Right now they're 2 and 4. When we leave, they'll be roughly 9 and 11—old enough to remember it, old enough to participate, and old enough for a life that isn't built around one zip code. This post is the why and the what. The next one is the how. The Goal See the world. But not the way most people mean it. Not a frantic checklist of landmarks. Not bouncing every few days, living out of suitcases, trying to cram a country into a week. The goal is to live inside places long enough to understand them—and to do it in a way that works for kids and works for me. That's what slow travel means. What That Actually Looks Like Slow travel is a st...

  Talking It Into Existence I used to dream out loud constantly. Walk around Chicago, see something I wanted, and just announce it to whoever was listening. "I'm getting a Harley." That's what I did one night in Lakeview—Scott Kell and some girls, Harley's rumbling past, me declaring I'd own one. Kell called bullshit immediately. Said I was full of it. And he was right to call it. At that moment, it was just talk. But something about saying it out loud—especially to someone who'd hold me accountable—made it stick. Once it was out there, my brain wouldn't let it go. The idea kept pulling my attention back. The hows and whys started working themselves out without me forcing them. Eventually I owned not one but two Harleys. This wasn't a one-time thing. I've done it over and over. The pattern's always the same: announce the thing, lock myself in publicly, remove the wiggle room, then watch my brain figure out how to make it real. The tri...

  I’ve started deleting things from my life—not dramatically, just ruthlessly. If it doesn’t serve the plan—retire and slow travel with my kids—it doesn’t get time. That shift has been weirdly exhilarating. And it comes with a hard truth: we’ve got about six years. That’s not “someday.” That’s now. If this is real, I need all six years to build the logistics and the learning system that can survive life on the road. The new focus and realness of it all has made me start second-guessing myself and letting fear creep into the planning.  “Fear is a planning input, not a stop sign” I keep noticing how much of parenting—and especially education decisions—is governed by fear. Not the healthy kind of fear that keeps you from doing something stupid. The institutional kind. The kind that whispers: “If you step off the approved path, you can ruin your kids.” School systems (and the culture around them) lean on that fear. It’s subtle, but it’s everywhere: the idea that professionals m...