Nobody Tells the Story of the Flight That Left on Time
On travel, kids, and productive friction
I am a planner, but not the disaster-prepper kind. I'm the kind who wants to know all the things. Find the café that isn't in any guidebook. Arrive at the airport absurdly early because the buffer feels good. Pack the jacket. My kids actually call me "Jacket Guy," because there is always, always a jacket in my bag, just in case someone's cold. The planning isn't fear. It's wanting the trip to be the best possible version of itself.
So believe me when I tell you: none of it saves you from the dice roll of travel.
My daughter had been to three countries before she turned two. People hear this and ask how??? Like there's a trick. (There is one: lap infants are free. Use it while you can. That's the whole hack.) But the question underneath is usually fear. How did you do it without something going wrong?
The thing is, something always went wrong. And somewhere along the way I stopped treating that as the problem. There's a term educators use for the good kind of difficulty: productive friction — the idea that the struggle isn't a bug in the learning, it is the learning, and that the moment the easy path closes is the moment something actually gets built. Family travel might be productive friction in its purest form. The friction isn't what ruins the trip. The friction is the trip.
She's eight now. Her brother's six. Things still go wrong. Constantly. Here are four of them.
The flight that didn't exist.
We woke up at 3am for a 5:30 out of Boston to Mexico. Pulled our kids out of bed in their PJs, got to the terminal, got to the desk — cancelled. Rebooked for tomorrow. WTF? And then: we went home. Took a nap. Went out for brunch. Spent the day being people in our own city with nowhere to be, and flew out the next morning, and the trip was exactly as good as it would have been minus one day.
The wrong city, on purpose.
Coming home from that same trip, we were supposed to connect through Dallas. Weather. They diverted us to Austin. The crew had timed out, so nobody could tell us when the plane would leave again. My husband had a great idea, we just… left. Got a hotel in Austin. Ate extremely well. Drove the three hours to Dallas the next day and made our flight at 6pm, rested, fed, no inflight meltdown to manage. We didn't get unstuck by planning harder. We got unstuck by deciding Austin was allowed to be the plan.
The morning-after.
My daughter has vestibular processing issues — something with her inner ear and balance. The last few long-haul flights, she throws up the next morning. Not on the plane. The next morning. On cue. For a while this was terrifying in the specific way that unexplained-kid-symptoms are terrifying: is this contagious, is this serious, what is happening. With more research, I found this is related to her vestibular processing. There is such as thing as a vestibular migraine and the experience of the heat and lights in customs after her ear being irritated makes her throw up. With this info, I’m able to find a specialist to prescribe meds (And until the meds kick in: I travel with ziplock bags and a spare change of clothes. Always. This is the one piece of over-preparation that has never once let me down.)
The bag that arrived a bit off schedule.
I was flying to the UK with both kids, by myself, for two weeks, meeting my co-founder, who lives there, with my husband coming a few days behind us. At the airport I'm told the checked bags can't go: something about it being unsafe to have them in the hull, our one big suitcase (two kids! two weeks!) would follow two days later. WTF. So we stood there on the floor and repacked — not two weeks of life, just enough for the next two days, because the suitcase was going to catch up with us. Triage. What do we actually need before Saturday? My daughter was an absolute champ about it. The suitcase showed up right on schedule, delivered to our airbnb in Somerset. We were fine.
Here's what I keep landing on. None of these were preventable by being more prepared, because the dice roll isn't a planning failure, it's just the nature of travel. It always was. Kids didn't introduce the chaos; they just raised the stakes and the price. And not one of these was ever actually dangerous. No one was in peril. Things just required a little more creativity than the plan accounted for.
As someone who builds with AI all day: this is human creativity. The kind a model can't generate for you. No system was going to look at a diverted flight and a timed-out crew and suggest stay in Austin, the food is great, drive to Dallas tomorrow. That's not optimization. That's a person deciding what counts as a good outcome and inventing a path to it out of nothing.
The struggle isn't a bug in the learning, it is the learning. That the moment the easy path closes is the moment something actually gets built. Travel with kids is productive friction in its purest form.
So pack the jacket. Pack the ziplocks. Arrive early. Find the secret café. Do all of it. Just don't believe for a second that any of it is what makes the trip perfect. The friction is the trip.
The smooth parts you'll forget. The meltdowns you'll be retelling for years
