I've come to believe that the individual designers of many of the vestigial quirks of modern life never really had to come to terms with their creations.

For example, whoever designed the hospital gown clearly never had to shuffle down a fluorescent hallway holding a paper-thin flap of fabric closed over their bare backside while heavily medicated. Someone, somewhere, sat at a drafting table, sketching a garment with the structural integrity of a wet napkin and fabric ties placed entirely out of human reach, calling it a triumph of medical apparel.

They’re everywhere you look. Open floor plans were almost certainly designed by executives with personal offices. Public restroom hand dryers — the ones that roar like a jet engine and perform like a polite suggestion — must have been approved by a committee that presumably had somewhere else to dry their hands. The snooze button on your alarm gives you nine minutes because an engineer in the 1950s was working around mechanical gear constraints, and nobody has revisited the decision since — so every morning, millions of people begin their day inside a choice made seventy years ago by a man who was thinking about cogs.

Every one of these made perfect sense on a whiteboard.

We've all heard some version of the advice that's supposed to prevent this kind of disconnect. Walk a mile in someone else's shoes. Stay close to those who are affected by the decisions you make. Remember the little guy. It’s good counsel, and it's old counsel, and when you say it, nearly everybody nods the way you nod at a flight attendant explaining the seatbelt — yes, yes, I understand, I've heard this.

But I wonder why it became wisdom in the first place. What is actually gained by crossing to the other side of the counter, beyond a vague, congratulatory sense of having been considerate? If the answer is just "it's nice to think about other people," it belongs on a refrigerator magnet, not in the treasury of durable human insight.

The answer, I think, is that the practice teaches you something you cannot learn any other way. And the something it teaches you is not primarily about them. It's about you.

Brian Chesky learned this around 2010. The hard way, naturally.

It's now a favorite parable in business circles. Chesky was running Airbnb from a position of comfortable authority. The company was growing. The dashboards were green. The pitch decks were gorgeous, which is always a reassuring sign that someone is paying close attention to something that doesn't matter.

Then he moved out of his apartment and started living in Airbnb listings, booked the way a normal person books — scrolling through photos of ambiguous vintage, reading descriptions where "cozy" means small, "rustic" means old, and "conveniently located" means the host is being creative with the word convenient. He found lockbox codes that didn't work at midnight in neighborhoods where you really wanted the lockbox code to work at midnight. He found listing photos where wide-angle lenses made broom closets look like ballrooms. He found the specific, low-grade dread of standing on an unfamiliar sidewalk with a suitcase, trying to determine whether the building in front of him was his accommodation for the night or just a structure having an exceptionally rough decade.

None of this showed up in the data. The dashboards were clean. The experience was a fork, a rubber band, and a takeout menu from a restaurant that appeared to have closed during a previous administration.

Chesky rebuilt the product — redesigned check-in, overhauled photo standards, restructured reviews — and he did it fast, because urgency looks different when you've personally stood on the sidewalk with the suitcase. The business press covered this as a stroke of startup genius, and he's still celebrated for the move.

Because what Chesky actually found on those sidewalks wasn't a punch list of software bugs. He discovered the distance between his intentions and their results. He had intended a seamless, delightful experience. What he had produced, in many cases, was a fork and a rubber band. That gap had been there for years, completely invisible from his desk. The only thing that changed was that he finally walked to where he could see it.

We applaud executives who do this, maybe because our whole culture rewards the act of building while offering little incentive for the act of inhabiting what you've created. We are trained from early on to design, execute, optimize, and move on. Self-awareness has always been undervalued because it produces nothing visible.

But every single one of us is a junior architect of someone else's daily experience. Not the whole building — just a room or two. The way you greet your spouse when you come through the door is an architecture someone lives inside. The way you listen — or half-listen, from the other room — when your child tells you something boring with the breathless intensity of a war correspondent is a structure they stand inside every day. From the design side, your side, it all feels perfectly reasonable. You know how tired you are. You know what you meant by that comment.

But people don't live in your intentions. They live in your output.

A man once asked his wife, after fifteen years of marriage, what it was actually like when he came home from work. He expected something affirming, with the simple-mindedness displayed by every husband on earth. What she said was: "It's like a weather system entering the house. We all read your face to figure out what kind of evening it's going to be." He's a decent man. A good father. He had simply never walked around to the other side of his own front door. His dropped keys, his heavy sigh, his monosyllabic answers to simple questions — from his side, a harmless need for ten minutes of quiet. From theirs, atmospheric conditions to be read, interpreted, and carefully managed. The version of himself he met on the other side wasn't a monster. It was something more unsettling: a missed opportunity. A room that could have been warm, and was instead just functional.

That gap — not dramatic, not cruel, just quietly flat — is where much of life's lost warmth accumulates. Not in the obvious failures but in the thousand small architectures we build every day that work fine from our side and land as something a little more lifeless on the other.

People avoid crossing over not because they're lazy but because they sense, correctly, that what they find might unsettle the version of themselves they prefer. The parent discovers her structure felt stiff rather than safe. The manager discovers his clarity landed as cold. The friend discovers his decisiveness felt domineering rather than generous. Moral exposure doesn't just audit your routines. It audits you.

C.S. Lewis once warned about people he called "Men Without Chests" — people whose intellect and appetites were fully developed but whose emotional core, the capacity to feel appropriately in response to reality, had been left to wither. He was writing about moral relativism, but I’m going to borrow the visual. Because that capacity doesn't grow behind a desk or a dashboard. It grows through exposure, through direct contact with the actual texture of experience. You cannot learn to feel correctly about something you have made but stubbornly refused to inhabit.

The goal, then, is something more precise than "be empathetic." Empathy is a fine word that's been sanded smooth by overuse — it asks you to imagine how you'd feel in someone else's position, but you are not them, and your imagination is biased in your own favor.

The task is smaller and harder than that. You are the architect of a small room that someone else has to walk through every day — at your office, in your home, across your friendships. The most useful, most humbling, most quietly courageous thing you can do is step out of the drafting room long enough to ask the one question that almost everyone spends their entire life avoiding:

What is it like to be on the other side of this, and of me?

John

The Mayfly Letter has no algorithms, no investors—just my wife and me folding newspapers at a kitchen table.

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John Conrad