It doesn’t take much to get me antsy. Theoretically, I was attending the American Institute of Architects annual convention last month. In reality, I was mostly idling in Manhattan traffic. Mornings were half spent in taxis between Javits Center and the New School’s Parson’s School of Design. Every trip took forty minutes. Time to bail, I finally told myself one morning, getting out of a cab at the convention center. This town wasn’t meant for automobiles.

I’m never happy riding around mazes like New York, Hong Kong, or Florence. I’d much rather walk these labyrinths. Like a wandering pilgrim in search of Revelation, it’s my zen time to think.

On the edge of I.M. Pei’s convention center are stairs to the High Line. The old rail spur was converted into an elevated park some years ago. You can stroll along the Hudson River for a mile and a half to the new Whitney Museum of American Art. Sketchbook in one hand, camera in the other, I morphed from conventioneer to flâneur and immediately found a surprise—an ocean of glistening rail cars disappearing under a bridge. Spotting a bench in front of Hudson Yards, I sat down and drew. Seconds later, an old radio show came to mind.

SOUND EFX: CHOOGA, CHOOGA, CHOOGA, CHOOGA, CHOOOOOO! (The sound of an approaching locomotive.)

NARRATOR: (In a booming voice) Grand … Central … Station!

SOUND EFX: (The train rumbles ever closer, bell ringing.)

NARRATOR: As a bullet seeks its target, shining rails in every part of our great country are aimed at Grand Central Station, heart of the nation’s greatest city. Drawn by the magnetic force of the fantastic metropolis, day and night, great trains rush toward the Hudson River, sweep down its eastern bank for one hundred and forty miles, flash briefly by the long red row of tenement houses south of 125th street, dive with a roar into the two-and-one-half mile tunnel which burrows beneath the glitter and swank of Park Avenue, and then …

SOUND EFX: SSSSS. (Steam belches as the train rolls to a stop.)

NARRATOR: Grand … Central … Station! Crossroads of a million private lives. Gigantic stage on which are played a thousand dramas daily.

Grand Central Station was a half-hour radio series that beamed across America from 1937 to 1954. Each program was a thirty-minute drama or romantic comedy about a traveler arriving in New York City by train. After passing through Grand Central’s main concourse, the protagonist walked into the “fantastic metropolis” outside, setting the story in motion.

The terminal (technically, Grand Central is not a “station”) has framed countless novels, plays, television shows, movies, and songs, which, for me, begged the question, why? Why have more than forty feature films been shot there? The Avengers (2012), for example, turned Grand Central into a fortress, and Alfred Hitchcock shot a famous North by Northwest (1959) scene with Cary Grant inside a concourse phone booth. The building is a star of prose literature. J.D. Salinger symbolically used Grand Central throughout The Catcher in the Rye as have numerous other novels. The old terminal has appeared in hundreds of tunes. Mary Chapin Carpenter wrote the song Grand Central Station as a tribute to a 9/11 ironworker.

I wondered what about the building’s architecture—its monumental spaces and vaulted corridors, its starry dome and exquisite details, the Oyster Bar and Whispering Gallery—motivated storytellers to pick up a pen. Passing buildings on the High Line, I made a mental note to walk into Mid Town and sketch Grand Central when I left the High Line.

Oh, that’s nice, a beautiful old Cass Gilbert building. I made a quick thumbnail and took a few photos. Isn’t that a Neil Denali? Click. I snapped and sketched James Stewart Polsheck, Zaha Hadid, and Frank Gehry, all the while humming the theme music to that old radio show (Alfred Newman’s Street Scene).

I was thinking.

The radio show had bragged about a “magnetic force” attracting people to New York City, which was undoubtedly typical New Yorker braggadocio. Or was it? Whatever makes Grand Central a narrative engine also makes it the world’s tenth most visited tourist attraction. That’s remarkable given everything there is see and do in New York City. Twenty million annual visitors bask under window light illuminating silhouettes dwarfed by an immense cavern. Folks from Kansas City and Tokyo aren’t there to catch the 12:05 to Poughkeepsie, so what’s motivating them to see Grand Central?

It has to be love, I thought, itself a kind of lodestone. People come to Grand Central because it is a beloved building. As if underscoring the thought, I remember reading about a “kissing room” in the terminal, a designated place “where arriving travelers once embraced their sweethearts.” I scanned buildings along the High Line and wondered if any of them would ever garner such mass adoration in their lives.

I doubted it.

Other possibilities: Maybe Grand Central was a romantic icon of a bygone era. In the 1930s, a $50 one-way ticket ($650 in today’s dollars) would streamline you from Chicago to New York in a Henry Dreyfuss designed Pullman car outfitted with curtains and a bed. You’d board inside the majestic LaSalle Street Station designed by Frost and Granger, find comfortable seats, and dine on good food as you rumbled east. If needed, there were secretarial services, a post office, and barbershop aboard. Sixteen hours later, you’d arrive on Grand Central’s center stage. Maybe it wasn’t the Beaux-Art temple to wanderlust that people loved, merely the building’s atmospherics. Grand Central captures the zeitgeist of another age, the time of great trains, The Twentieth Century Limited running between Chicago and New York, the Flying Scotsman that linked England and Scotland and the Orient Express from Paris to Istanbul. Like an Agatha Christie novel waiting to be read, Grand Central promises to sweep you into an adventure. Was that the building’s attraction?

Nah. Not every symbolic building is treasured, especially when it comes to train stations. Chicago razed that historic LaSalle Street Station in 1981. Washington’s gorgeous Union Station was neglected for years, and McKim, Mead, and White’s majestic 1910 New York Penn Station fell to the wrecking ball in 1963. Somehow, Grand Central survived. How?

Perhaps Grand Central exuded more gravitas than rival Pennsylvania Station could muster. According to The New York Times, the terminal was born a legend when it opened in 1913 (three years after Penn Station): “Without exception, it is not only the greatest station in the United States, but the greatest station of any type in the world.”

As the old-time radio show suggested, passengers and visitors remained enamored with Grand Central throughout the 30s, 40s, and 50s. Interest waned in the 1960s as air travel eclipsed trains and competitive economics caught up. Many great train stations were demolished. Grand Central, too, was slated to come down.

And then Jacqueline Kennedy Onassis took up the building’s cause, and history changed course. Was it civic pride that compelled her to act? Yes, but where was Jackie when the wrecking ball showed up at the equally grand Penn Station?

I thought about that as I reached the end of the Meatpacking District. By then, I had a book of drawings under my arm, but no conclusion. Keep walking, I told myself. You’re not there yet.

Jacqueline Lee Bouvier spent her early years as one of the “millions of daily dramas” playing out on Grand Central’s “gigantic stage.” Her grandfather, James T. Lee, helped build the Manhattan skyline of her youth. A prolific developer, Lee constructed multiple projects around Grand Central. In Jackie’s mind, that old train terminal may have symbolized her family’s stake in the city. The building meant something to her. Grand Central resonated with Jacqueline Kennedy Onassis in ways Penn Station could not.

Eureka, a working hypothesis. Personal meaningfulness was how Grand Station avoided demolition, and public meaningfulness was how the building burst the boundaries of its façade to become lore.

Exiting the High Line, I glanced at Renzo Piano’s new Whitney Museum of American Art and felt nothing. The building left no impression on me, the exact opposite of my initial experience with Marcel Breuer’s Brutalist Whitney Museum on the Upper East Side. I opened my sketchbook and asked myself what the ingredients of architectural meaningfulness were. Awaiting my answer, I drew a blank.

I needed more examples. A comparative analysis of other significant transit centers seemed like a good idea, so I walked for another mile and a half to visit a building in Lower Manhattan, the newly opened World Trade Center Transportation Hub. I also wanted to revisit the landmark TWA Flight Terminal at JFK.

Critics have not been kind to Santiago Calatrava’s massive sculpture, nicknamed the “Oculus.” The New York Times wrote, “For a dozen years, the World Trade Center Transportation Hub was a train wreck…[the] winged dove, beefed up to meet security demands, devolved into a dino carcass.” The Globe and Mail opined, “those ribs themselves felt, to me, unmistakably like the remains of something enormous and dead. We were in the belly of a beast; it’s a remarkably insensitive vocabulary for a place where almost 3,000 people were killed.”

WTC was built with public money, so part of the adverse reaction may be its $2 billion cost overrun. Not all of the barbs, however, can be rationally accounted in dollars. WTC was supposed to symbolize a child’s hands releasing a peace dove. Unfortunately, the image doesn’t read. “I found it … straining for higher meaning,” wrote Christopher Hawthorne in the LA Times. The Guardian compared WTC to branding, saying the building was “a little too similar to Calatrava’s own work: his rail station in Lyon, France (completed in 1994), for instance, as well as the Milwaukee Art Museum (2001), and Agora in Valencia (2009). The avian form might as well be a logo.”

Depending on whom you ask, WTC is a pair of hands, a flappy bird, the beached remains of a giant whale, or a corporate identity mark. Eyeball as metaphor isn’t mentioned, so why WTC is called an “Oculus” baffles me. My takeaway from WTC is this: Confusion reigns when communication gets lost in translation, and derision results when the wrong message is received.

I was ten years old the first time I saw Eero Saarinen’s TWA terminal, but I remember seeing the bird without having the wings pointed out to me. I entered the building from under its beak, which appeared to have just raised its head after sipping from a small fountain. Saarinen’s goal was expressing “the drama and specialness and excitement of travel.” In my mind’s eye, it was message received. Some contemporary critics knocked the design for circumventing the then prevalent form-follows-function dictum. The rest of the professional community admired the building. Architectural Record said, TWA “surely meets any man’s criteria for distinction and drama, for excitement and dynamics.” Architectural Forum called it “an eye-stopping design, appropriate as the symbol of an airline.” TWA “took its place in the vanguard of modern design,” said The New York Times.

The coffee bar and restaurant were designed by Raymond Loewy, adding to the “masterpiece of expressionist architecture.” Progressive Architecture claimed the TWA Flight Center “had the most original interior in decades.”

How to reconcile Grant Central, TWA, and WTC—buildings with similar purposes located in the same city but with significantly different receptions? Each terminal houses a breathtaking space. Each is an architectural and engineering marvel. Yet Grand Central is adored, TWA revered, and WTC panned. You can’t pin Grand Central and TWA’s win on style. TWA is as devoid of classical orders as WTC (even though Robert A.M. Stern called TWA the “Grand Central of the jet age”). When TWA’s landmark designation was upheld in 1994, The Times’ Herbert Muschamp wrote, Saarinen’s “design is as tightly controlled as that of a Beaux-Arts monument,” while also noting TWA was nothing like a classical building.

Grand Central is a Greco-roman temple designed to elicit a response to the existential question: Is life a journey or a destination? The building’s answer is “destination,” and it supports the notion with divine starlight from a cosmic-painted ceiling. The terminal is a Beaux-Arts allegory about arrival, a celebration marking the end of a journey. Its main concourse communicates your entrance into New York City was written in the stars, that New York is a city of grand dreams.

If Grand Central celebrates the end of a journey, the TWA and WTC terminals are about the trip itself. Instead of iconography, they use organic imagery to deliver their message. Whether child fingers or bird wings, biomimicry is a way of using nature as a basis for design. Humans allegedly respond to organic-based environments due to biophilia, the idea that we instinctively care about Nature. The term comes from psychoanalyst Eric Fromm, who called biophilia “the passionate love of life and all that is alive.” Fromm says the phenomenon is a remnant of early humans living outdoors and alongside other lifeforms. Technology eventually pulled us inside, but our predisposition to nature remains.

The opposite reaction, I think walking into the Oculus, is biophobia, an aversion to other life forms (also an evolutionary instinct). TWA’s interior maintains its organic connection to nature; we feel tucked under a wing about to lift off. WTC, on the other hand, brings visitors below ground into a retail center of bleached white ribs. In my eyes, the space biomorphed from fanciful to fearful, and the optic was disconcerting. As I sketched, it seemed to me that H.R. Giger (set designer for the early Alien movies) could have conjured up WTC’s shopping arcade.

In the end, the success or failure of these three buildings rested on the clarity of their message. From a Christoper Alexander perspective, it was about form language. Two of the buildings successfully conveyed their designers’ intent. One didn’t. Grand Central became an edifying edifice about life. TWA invoked the feeling of flight but offered no tutorial on life. Up, up, and away, was as far as it would go.

Leaving the World Trade Center, I considered how meaningfulness makes some buildings cherished and why, without it, architecture is forgotten, or worse. Beloved buildings signal their intent. The effect is as much art as it is psychology. The search for meaning looms large in the human psyche.

There are three Viennese schools of psychotherapy, one based on Sigmund Freud’s “will to pleasure,” the other on Alfred Adler’s “will to power,” and the third on Viktor Frankl’s “will to meaning,” or what he called logotherapy. The first two schools are fascinating, but it’s the last school that the architectural profession should study.

The conventional notion of “boring” connotes something dull or monotonous. We associate the label with “banal” and “apathy.” However, the scientific definition of boring is precise. According to researchers, boredom is “the aversive experience of wanting, but being unable, to engage in satisfying activity.” Scholars describe two models of boredom: trait boredom, a chronic condition based on personality, and state boredom, in-the-moment attention failure linked to environmental conditions.

Trait boredom is beyond the scope of my ability to theorize, but speculating on how architecture can induce state boredom hits home. Scientific studies have measured situational meaningless in the context of environments and associated it with boredom. That’s an architectural design lesson that can’t be ignored.

In my view, architecture loved by generations is the result of satisfying people’s innate search for meaning. Beloved buildings play to our hardwired need to know what things mean. When a structure screams for attention but fails to deliver a message worthy of our attention, or confuses its message, we are disappointed, and then bored.

Good buildings have a point, but the best buildings also make their point. Architecture parlante is a term for buildings that figuratively speak their purpose. The subject is not on the National Architectural Accrediting Board requirements list, but it should be.

Grand Central Terminal’s 1913 opening day brochure described the building as “a poem in stone,”  a prophetic portrayal of the building’s emotional power. I sauntered back to Javits along the High Line and found my bench. Flipping through sketches solidified my position. Relationships and connections emerged while mixing watercolors. As I brushed, a kind of taxonomy bled through the pages.

A revelation if ever I saw one.

After a while, I looked across Hudson Yards and spotted one of the strangest objects I had ever seen—Thomas Heatherwick’s 16-story high public art project called, “Vessel.” I knew exactly how to classify it. “Love be a many-splendored thing,” I penciled in the margins in my sketchbook, “As is architecture.”

All drawings by the author.