Typing the Itinerary

Picture This: It is 1986. I am fifteen years old, sitting in a small cubby near my mother’s corner office at 475 Park Avenue South in New York City. My mother founded Valerie Wilson Travel, and this is my first of many summers working for her.

I have a desk of my own, a manual typewriter in front of me, and a fourteen-day itinerary to Europe that I am typing for the first time. Every morning I ride the train into Manhattan with my mother. The desk is only mine for a few weeks each summer, but it feels like the most grown-up thing I have ever done.

The Wider Lens

There is no spell check that summer. No autocorrect. We cannot even reach for the old bottle of white-out, because our itineraries are printed on our signature peach paper, and a single mistake means starting the page over.

Eventually, the typewriter becomes a Brother word processor. The word processor becomes a laptop. The laptop becomes software, and the software becomes an app that produces a finished itinerary in seconds. Each upgrade removes a little more of what the last one required me to know.

I did not notice the trade I was making until decades later, when I sat down with my own child, Ash, to type an itinerary for my mother on a laptop, in Microsoft Word. My mother still prefers her format over the travel app itinerary. She wants her itinerary the way she designed it, and that means someone has to build it by hand, in a document, line by line, until every confirmation number lines up exactly right.

The tools got smarter. The architecture underneath them did not. That is the same gap I see inside organizations everywhere. Leadership tools, technology, and systems keep advancing, while the operating system many businesses run on stays exactly the way it was inherited.

Three Things I Learned

Slow forces you to see the details. Getting every confirmation number, every date, every line of spacing to align is tedious. It is also the only way to notice something is wrong before a client does.

Speed can outpace understanding. An app now builds an itinerary instantly for both advisor and client. It also means neither one has to hold the details in their head the way I once did.

Precision is still teaching, if you let it. Ash and I complained the entire time we worked to match my mother’s exact format in Word. By the end, we knew every detail of that trip, cold.

The Wondering

What did your business used to teach people simply by making them do it the slow way? AI and the apps built on top of it are a real advancement. Truth, I would not trade my hours back. But I am wondering what they quietly cost us in return.

Give It Five Minutes

Take five minutes today. Pick one task in your work that used to take real time and now happens in seconds. Ask yourself honestly: what did the slow version force someone to learn, notice, or understand, that the fast version quietly skips?

My Intention

I am still typing itineraries, in one form or another. Not because I do not trust the app or the AI behind it, but because I do not want to lose the habit of knowing something all the way through. My intention this month is to notice where in my own business I have let speed replace understanding, and to slow back down, on purpose, in at least one place.

With Curiosity,