How we actually travel

Why I Drove My Son 2.5 Hours to San Juan Instead of the Airport Down the Road

On Friday, my 15-year-old flew to California. I bought the ticket on Thursday.

If you have teenagers, you already know that a same-day-minus-one plane ticket is priced somewhere between "car payment" and "small kidney." Tom knew it too. He had actually saved up over $600 of his own money to buy himself a one-way ticket to California on what I can only describe as a whim, because he is 15 and the future is a rumor. I want to be clear that I admire this. The kid can figure things out. If he applied that level of resourcefulness to, say, answering a text from his mother before the third attempt, he would be unstoppable.

Tom, 15, at the kitchen counter with a plate of mac and cheese, giving a deadpan look
The resourcefulness in question, pictured here conserving energy.

The trip was in question until the last minute because it was conditional on his grades, and his grades were, let us say, a work in progress. He then pulled off a small academic miracle in roughly 48 hours, which tells you everything about what he is capable of when properly motivated by a plane ticket. Fine. He earned it.

What he was not going to do was overpay for it. Not on my watch.

So here is the part that looks insane from the outside. Instead of driving to the airport down the road, I drove Tom two and a half hours to San Juan. Past the closer airport. Past a perfectly good runway. All the way across the island, the day before the flight.

I did not do this because I enjoy driving in Puerto Rico traffic with a teenager and his one bag. I did it because Tom had points. American Airlines points, specifically, and the award seat that made this trip affordable routed out of San Juan, not the airport nearby. The drive was the price of the ticket. The actual ticket was close to free.

Where a 15-year-old gets airline points

Here is the boring secret. Tom did not earn those points last month. He earned them starting before he could read.

I have three kids. I started banking frequent flyer miles for my oldest when he was about five, and for my youngest, I started the day he was born. Every flight this family has taken, every one, went onto the kids' own frequent flyer accounts, in their own names. They do not manage this. I manage it for them. They just show up at the airport and occasionally lose a passport.

Jillian and Tom standing in a towering bamboo forest in Japan
Japan, a few years back. This trip is a big part of why a teenager could suddenly afford California.

A big chunk of Tom's balance came from one flight in particular: a long-haul from Tokyo to Boston. Long-haul international flights dump a satisfying pile of miles into an account, and because that flight was credited to Tom's number and not mine, it sat there quietly compounding into the future version of a $600 problem, solved.

That is the whole trick. There is no trick.

How to actually do this (start today, no wealth required)

If you fly with your kids even occasionally, you are currently leaving miles on the table. Here is the entire method.

Sign each kid up for the airline's loyalty program. Yes, babies can have a frequent flyer number. Yes, it is free. Do it for every airline you fly with any regularity, not just your favorite one.

Put their number on every booking. When you book the family's flights, enter each kid's own frequent flyer number for their own seat. The miles for that seat go to them, not to you. This is the step everyone skips, and it is the step that matters.

Let it compound. A single kid ticket does not feel like much. Neither does one long-haul. But you are not playing this year, you are playing the next decade. A number entered when a child is five is a bank of miles when that child is fifteen and suddenly needs to be in California.

Consolidate and shift as you go. I move points around to maximize them, between the kids' individual accounts, across airlines, and through credit card points that can transfer to airline programs. You do not need to be an expert to start. You need to open the accounts and enter the numbers. The optimizing can come later, once you have something to optimize.

The point

We are not a rich family. We are a family that opened some free accounts a long time ago and then remembered to type a number into a box. That is not mindset. That is not manifesting. It is clerical work you do when your kid is a toddler so that your kid at fifteen can go to California without you refinancing anything.

Jillian in a Last Life Ever cap taking a selfie with her two sons on a street in Budapest
Budapest, same crew. Every one of these flights went on their numbers, not mine.

The drive to San Juan was the visible, slightly ridiculous part. The invisible part was ten years of entering a number. That is how this family actually travels, and there is nothing stopping yours from starting the same boring, powerful habit this afternoon.

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