Our Old Dad

  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 —...