Our Old Dad

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...

  Fear is the guardrail (and I finally named it) I was listening to the Self-Directed podcast (October episode with Tim Eaton), and the conversation kept orbiting fear — not in a dramatic way, more like an ambient force that sits in the room any time you talk about stepping off the standard school path. Today it landed for me because I finally pinned down what the fear actually is: It’s not “I don’t love my kids.” It’s not “I’m trying to neglect their future.” It’s not even “I don’t have a plan.” It’s the system-whisper: What if you ruin them? What if they fall behind? What if they become helpless? What if you take a risk and you can’t undo it? And then two questions cut right through all of that. 1) If I love my kids unconditionally and actually do the work… what’s the worst that can happen that’s within my control? Obviously, horrible things exist in the world. That’s not what I mean. I mean: if the baseline is unconditional love, attention, stability, and purpose —...

 Most people use AI like a search engine with a personality. Type a question. Get an answer. Forget it. Repeat. That’s fine for trivia and small tasks. It’s terrible for changing your life . If you have a big goal—retire early, switch careers, build a business, slow travel, write a book, whatever—you don’t just have one problem. You have 12 different kinds of problems spread across money, work, health, logistics, psychology, family, and more. What I’ve been building (and what you can steal) is a way to turn AI into a structured support system for that kind of goal: You pick a big, long-term outcome. You break it into the domains that actually decide whether it happens . You make one AI “Project” per domain , each with clear instructions. Later, you match each Project with a Custom GPT (or Claude persona, etc.) that thinks in the right way for that domain. My own example goal is slow travel with my two youngest kids , but this structure works for: Changing ...