Our Old Dad

Be like Mr. Walker and expect nothing for it. 04/13/2026 Hey, Dudes! Years ago, I moved back down to Boulder from Nederland. I was still working full time at IBM and also doing work for a friend who owned a computer hardware wholesaler in Boston. Things were going pretty well for me then, if you take my disastrous love life out of the equation. Looking back, I can see that the restlessness that brought me down from the mountains was about to disrupt everything completely. But I did not see that then. I just knew it was time. Or maybe more accurately, I just knew I was being directed. I rented a nice house in North Boulder, catty-corner from the open space that led to the North Boulder Rec Center. It was my first time living in that part of town, and I liked it. Next door lived a man named Mr. Walker. His family had owned the Walker Ranch that was later donated to the Boulder County open space program. He was close to ninety years old. ...

  Raven recently started taking photos to preserve memories and exercise her artistic abilities. This is one of her first staged shots that didn't involve photographing her little brother in uncomfortable poses.  That is Stuffy's cheese and cracker on the ledge. Raven muttered something about dreams being out of reach for most of us, but wouldn't elaborate too much. Here's to a long, creative career for Raven!

I'm on a train somewhere in Europe. Not actually—I'm in a pickup truck in Aurora, Colorado, sixty years old, half thinking about grading something I don't care about. But in my head I'm on a train, and there's a woman across the aisle, and we're about to have the conversation that changes everything. Inside the fantasy, age drops out. I'm just the guy across from her. And then I remember I'm in a truck and nobody's across from me. When I was eight or nine, my parents sent us to stay with relatives we barely knew. My dad's uncle Bob and his wife Earline, out in Normal, Illinois—flat, farm country, nothing to do. Cover story: go see how they live. I think my parents needed us gone for a night. We never asked why. Earline's mother lived with them. Ninety-something—slouched in a chair in the corner of a room that smelled like dust and menthol, a few stages short of puddling. We walked in. Introductions. You remember Grandma —whatever ...

  The Why Statement: What LifeEducation Is Actually For I've been building something called LifeEducation for a while now. I've written about pieces of it here — the slow-travel plans, the worldschooling idea, the general philosophy. But the project has gone from "a dad thinking out loud" to something with real structure behind it. The short version: LifeEducation is a lightweight operating system for raising capable, self-directed humans. It's built around one question — what should an 18-year-old actually be able to do? — and it works regardless of whether the kids are in school, homeschooling, or some mix of both. The project has three layers: The Why defines the thesis — what this is for and what we're optimizing for. The Floor is the contract — the non-negotiable minimum a young adult should be able to do by 18. The Domains are the broader map — ten areas of human competence that keep the full picture in view without pretending everything ...

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...

I dream out loud constantly. See something I want and just announce it to whoever's listening. Not because I think saying it makes it real. Because once I've said it, I'm stuck with it. That's what happened one night in the Lakeview neighborhood of Chicago, 1989 — Scott Kell and some girls, Harleys rumbling past, me announcing I'd own one. Kell didn't even pause. Just looked at me sideways with that flat Kell face and said I was full of shit. No malice. Just total disbelief that I was standing on a sidewalk on Belmont making promises to strangers about a motorcycle I couldn't afford. He was right to call it. At that moment, it was just talk. But that was the point. Now Kell had heard it. Now the girls had heard it. Even a couple of random people walking down the street heard it. Now backing off meant admitting I was exactly as full of shit as he said. So my brain went to work. Not because I willed it. Because I'd backed myself into a corner and the...

  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 ...