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A Stirling example

The only time I get up early these days is for flights; we have a knack for booking 7:00 AM departures, which means in order for us to get to the airport "on time" - or by my calculations, roughly six hours before boarding - we usually need to leave our house around 2:00 AM.

This morning is no different, except instead of getting on a plane, we'll be getting on a hot air balloon to float over the city of San Miguel de Allende, the most recent in a long line of Mexican towns that has charmed us during our travels.

We arrived here expecting to be turned off by the hordes of wealthy expats and professional Instagrammers we heard spend most of their time posing in front of the brightly colored colonial façades and various flower-covered doorways. And while we saw plenty of both this past week, we also found a city with a deep history and rich tradition of foreigners giving back to the community; there are over 100 active nonprofits here, which can all be traced back in one way or another to a gangly (and balding) foreigner from Chicago who stepped off a train in 1937 to a very different - but I imagine no less charming - San Miguel de Allende.

Stirling Dickinson thought he came here to write a book for a couple of months, but ended up staying for the the rest of his life; co-founding an arts school, building a house and laying the foundation for foreigners who would come after him to do more than snap pictures and bark gracias at locals, choosing instead to participate in the community he was welcomed into.


It's 6:00 AM when the driver comes to pick us up in a white van with a cartoon drawing of a hot air balloon on the side. As we climb in, it starts to dawn on me that we're about to get into a very real ballon with very hot air that will somehow take us up and over the countryside in a wicker basket.

This is fine, I think to myself as we pull away, what's the worst that can happen?

My mind returns to Stirling to avoid thinking about the worst that could happen, which is clearly plunging back to Earth in a container meant for decorative flowers and not six to eight fully-grown adults and their iPhones.


What I know about Stirling so far are the quick-hit biography bullet points; birth, school, accomplishments, death.

Born in Chicago, he went to Princeton and later the Art Institute of Chicago before traveling through Mexico with a college buddy in an old Ford. They wrote a book about their travels that sold well, and then wrote a follow-up on their subsequent adventures through South America. Along the way they met a famous actor and singer from Mexico who mentioned he was headed to San Miguel de Allende, a town neither of them had heard of.

The pair eventually decided they wanted to write a novel and came here aiming to work remotely, years before those two words went together.

They arrived at the empty train station early in the morning and were met by a cart pulled by a pair of donkeys which took them up the hill and deposited them in the main square. When he first saw the ornate tips of the town's now famous Parraquoia stretching through the morning fog, Stirling said he somehow knew he wouldn't be leaving any time soon.

Ten days later he bought a parcel of land on the grounds of an old tannery and began building his home.


As our van rumbles through the cobblestone streets, I wonder about the parts of Stirling's story I haven't yet explored. His friend eventually married and left San Miguel while Stirling stayed, living out his life tending to his community and impressive orchid collection alone.

One article I read mentioned how Stirling's work to make sure the art school he co-founded was accredited in the US meant he was able to recruit veterans who could spend their GI Bill tuition here, a boon both to the school and local economy. This new wave of Americans who came to study included many gay soldiers who didn't see a place for themselves in the States but discovered they could have a more open life as a foreigner in Mexico.

Almost a century later, we're still here.


Our van stops in front of a large field where two balloons lay half-deflated next to their accompanying baskets; the whole scene looks like someone forgot to clean up after a giant's birthday party. The driver points to the far balloon, whose colored cloth is starting to take shape thanks to the angry eruptions of what can only be described as a flame thrower at its base. By the time we walk over, the balloon is fully upright and the pilot motions for us to climb in.

There is no door on the basket, no boarding ramp, no ticketing agent. There is only a small cutout on the side of the basket and I watch as the Mexican couple we'll be traveling with use this as a foothold while hoisting themselves up and into the wicker container. David and I follow suit and without any announcement from the pilot or explanation of emergency exits, the flame thrower roars to life and we start slowly drifting upwards.

Floating in a ballon is not the same as flying in a plane; there is no propulsion, no forward motion, no inflatable devices under the seats - mostly because there are no seats. As we stand inside the basket and watch the ground move slowly away, I am keenly aware our fate seems to rest less on the skill of the pilot who orchestrates staccato bursts from the fire tank and more on the weather; strikingly similar to life, only I can't figure out if in this metaphor I am the pilot, the balloon or the basket.


As if starting an internationally renowned art school wasn’t enough, Stirling also found time to foster an organization to help bring shoes, books and healthcare to children in the surrounding countryside. Every year he would drive to the hundreds of schools they served, and because the roads he navigated to get there weren’t always roads yet, he ended up needing to replace his car roughly every other year. The organization still exists today, connecting thousands of kids and families to life-changing resources and is only one of the reasons there’s a bust of Stirling sitting in town.

An avid baseball fan, he also formed, played in and then eventually coached numerous teams, winning regional championships and helping to build baseball fields around the city.

Oh, and in his spare time he saved some orchid species from going extinct, propagating them in his growing collection and sending seedlings up to an organization in Indiana.

Maybe I should start getting up earlier.


We drift up and over the countryside as the sun begins to rise behind the mountains. The warm light hits the tip of the Parroquia's steepled towers first before spilling onto the rooftops and cobblestone streets stretching in every direction. We pass vineyards and horses, look down over new gated developments being built and spot an ornate campground where workers are busy combing a manmade beach next to a sign with the word GLAMPING in a font big enough to be visible from a hot air balloon.

As I watch the fog lift on the now sizable city, I wonder what Stirling would think about the region's growth since his death in 1998. Could he have possibly envisioned this when he decided to stay all those years ago?

And while I'm sure it would surprise him to hear David and I are here trying to make a living mostly appearing on people's phones, I'm certain he would understand why a gangly guy from Chicago wants to travel and write stories.

My only hope is - like him - I can leave behind far more than I take with me.


This essay appeared on my Substack - subscribe to read more!


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