Wrong Seat Moments

I rushed to board my LATAM Airlines flight departing from Arturo Merino Benítez International Airport in Santiago de Chile.

Well, it was really more of a brisk walk…

And I don’t believe much in rushing anymore but let’s save that for another day.

I had completely lost track of time in the lounge and it wasn’t because I drifted into some kind of productive flow state either…

It was because I was choking on the worst double espresso imaginable. The taste was bad enough to force my entire body into convulsions. Dramatic but whatever.

Imagine drinking a putrid combination of rusted water and industrial acid prepared by someone with a lackluster attitude towards life?

Usually I don’t go to lounges anymore… (and the coffee was a stark reminder of that).

They’ve become like high-school cafeterias with forever shrinking selections of bad processed food, undrinkable coffee, disgruntled staff, cheap wine, and are packed to the brim with people hauling around large carry-on bags (they seem to let anyone in).

It’s more pleasant to hang around the terminal, people watch and walk for the sake of walk to get one’s steps up as a way to offset the bodily damage from long-haul flying.

(In defense of LATAM Airways, their lounge in Santiago is one of the best in South America and quite cosy overall).

I arrived at the gate with just two minutes to spare.

I’d booked this trip just three days earlier out of pure curiosity.

On paper, this was a city that made no sense for me…

In fact, the country is so random, I doubt many could even locate it on a map.

These “off-the-beaten-path” type places in my experience deliver some of the most rawly authentic experiences (think Tbilisi, Georgia or Sofia, Bulgaria).

One thing that became immediately obvious on this half-full flight was the warm and friendly atmosphere inside the cabin.

The energy was high.

People were alive.

Many were smiling, laughing, and even making out (I counted three different couples), and engaging in long conversations.

Quite the contrast to flying within Europe where people are often stone-faced and desperately avoiding making eye contact at any cost.

We blasted off and my eyes were glued to the immaculate views outside what felt like an ancient Airbus A320.

Santiago is possibly one of the most stunning airports in the world to fly in and out of because of its proximity to the Andes. They stretch over 7,000 km along South America’s western edge through seven countries.

Think vivid long orange and purple sunsets that stretch on as far as the eye can see with the snow-capped Andes perched ominously in the background.

The flight whizzed by in a blur and we started our approach.

I was taken back by how there was nothing anywhere close to the city except a majestic forest that stretched into infinity around a winding river.

We landed smoothly and I felt an immense energy of anticipation wash over me as I peered out the window.

Multiple flags were flying strong over the somewhat dilapidated airport.

I walked off the plane into the tiny airport. There were just two passport control booths. The officer asked me a couple of questions, and aggressively stamped my passport in a mad hurry.

In the world of AI, Palantir and facial recognition, passport stamps are refreshingly analogue. They possess a nostalgic charm of an old world quickly melting away and I savored every moment of the experience.

I grabbed my bags, threw them through the scanner, manned by a customs agent madly chatting to his colleague, and stepped out into the arrivals area.

It was rather empty aside from one guy who stood out right away.

He looked like a mob boss from Naples, Italy.

He was standing on his own in a slightly menacing posture dressed in a jet-black suit, a white shirt and slightly oversized black tinted aviator sunglasses.

He was holding a handwritten sign made from ruled notepaper with ‘Mr Raymond’ scribbled on it. As it turned out, he was my driver. Yay.

He begrudgingly grabbed my suitcase and muttered a few words in Español.

Or was it Guaraní…?

I wasn’t sure…

I shrugged my shoulders and eagerly followed him outside to what appeared to be a rented black Toyota van. Kidnap vibes I thought to myself.

We were instantly hit by the humidity that hung in the air like a thick mist. It was even more intense than South East Asia.

We hopped in the black van, cranked the air conditioning to full blast and drove out of the airport located about thirty minutes from the city centre.

I was immediately struck by a sense of unconstrained freedom.

Like a different way of living with frontier style energy.

It was like being back in another time.

Maybe the 1960s or the 1970s…

Not that I would know of course…

Yet it felt like I’d teleported to a time before society somewhat lost itself (or maybe we’re recalibrating?) in a sea of smart phones, social media, AI and idiocracies.

We became simultaneously more connected and disconnected all at once.

I looked around and saw people just hanging out shooting the breeze.

Interactions between people were more pure.

People weren’t glued to their phones 24/7.

Instead they remained fully immersed in the present moment.

There wasn’t a frenetic anxiety energy running through people either.

They remained muy tranquilo.

At least this was my first impression but would it hold true?

I glanced at my phone (ironic?) and saw a message from a friend in Buenos Aires. I told him I was doing a three day trip and he was convinced I must meet two of his colleagues based in the city.

The car frantically jerked from side to side as we navigated the cobble-stoned roads.

Just a few minutes later, we swerved to avoid a massive pothole that was so deep it might just lead to China. Weirdly, in the backdrop, there was a shiny shopping mall called Shopping Del Sol.

I looked around and the mall was surrounded by a staggering amount of new apartment construction sites.

Yet the roads in the area remained in dire condition.

Days later I’d come to realize that the majority of the roads in the city seem stuck in this condition. A few people revealed that locals in wealthier areas prefer the roads to remain this way because it’s more difficult for criminals to rob the houses.

I found this quite bizarre, especially when it seemed quite safe overall.

You can’t argue that it’s probably effective though. The side roads are paved with sharp pointy rocks. You can’t drive faster than 10-20 kilometers per hour on such surfaces. Good luck trying to walk without rolling an ankle too.

My mind drifted back to my friend’s messages…

He’s an entertaining guy, successful across many businesses and real estate developments, which meant his colleagues were likely solid people to meet.

On the other hand, my mind recoiled.

There was an intense inner resistance.

I had arrived in Asunción, Paraguay right in the middle of my own messy transition.

And I wasn’t excited about having to explain it to other people.

I hadn’t even made sense of it yet myself.

In the years prior, I’d had this feeling, call it an intuition or whatever, that I wanted a change. And I was currently watching a slow-motion collapse of my past self that was starting to make way for something new.

From the outside it appeared I had everything figured out.

I operated a large successful business for close to ten years.

Yet over the past few years, I wasn’t able to shake this underlying feeling that it was no longer the right path for me.

I’ve come to define these as Wrong Seat moments.

From the outside it looked like success.

People were impressed and it checked all the boxes.

Yet at a point that is difficult to pinpoint, it began feeling like I was performing.

It was also becoming alarmingly obvious to me that this performance was now costing a tremendous amount of energy in more ways than one.

I kept going because the inherent sunk cost bias was too big.

The biggest question I couldn’t get out of my mind was who I’d be on the other side…

The car swerved again to avoid another giant road crater.

Screw it I thought… I decided to take the chance.

I grabbed my phone and hurriedly sent a WhatsApp message to my friend’s contact.

Later that evening while wolfing down a giant Ojo de Bife, three of the tastiest empanadas I ever had and an odd custard dessert that translated into English as “mother’s milk,” I received a reply telling me to meet tomorrow at 12pm for lunch.

The message was in Spanish and I became nervous that he didn’t speak any English. I can read and understand Spanish to a decent level but speaking it over an hour-long lunch was another matter.

It was 11:58am the following day. I arrived at a restaurant in the Shopping Mariscal mall. The morning had been unusually productive and I was floating on a creative high from hours of writing.

There was a man hunched over his phone in a pink polo t-shirt wearing gold spectacles sat by the window. That must be him I thought as I walked over with a smile and shook his hand.

And as it turns out, I was right…

He didn’t speak much English at all.

I awkwardly sat down and nervously smiled, simultaneously whipping out Google Translator to save the day. You’d be surprised at the lively conversations you can have with people that don’t speak the same language. All it takes is some patience, perseverance and a flurry of carefully constructed hand gestures.

We spoke for half an hour and I began to grow frustrated.

We were laughing a lot, even when we didn’t speak the same language. I wanted to know this guy at a deeper level because he seemed awesome. Luckily, his business partner was arriving soon who allegedly spoke English.

A half hour later, a serious looking guy in a black suit walked into the restaurant.

He had an introspective way about him and a confident presence to boot. His expression remained neutral as he pulled up a seat while looking at me.

I continued babbling away in Spanglish to his business partner and felt the black-suited man staring at me from the left side.

The pink polo man smiled across the table to his business partner. He was obviously relieved that someone arrived to save the day as a translator.

I was awash with a strange feeling. I turned my head and just stared back at the black-suited man. At the time I didn’t know what that feeling was. It wasn’t something I felt often when meeting a new person.

I’d later come to understand it as a deep sense of knowing.

It was as if I’d known this man for years.

Decades even.

I was overwhelmed with a sense of relief as he started speaking in perfect English. Yet, I was now feeling bad for his business partner who was now kind of left out of the conversation. He went back to his phone and chimed in from time to time.

I started pitching him on turning Paraguay into a connector hub, a Singapore or Dubai of South America. It’s a strange thing to say to someone you’ve just met, but it’s something I’m genuinely obsessed with, and Paraguay is uniquely positioned for it.

He listened deeply, told me he had some errands to run and asked if I was doing anything. Before I could think, I just said “I’ll come with.”

We left the restaurant and jumped into a new beige SUV.

As we drove I felt comfortable talking to this guy. I started volunteering more to him as we drove towards the Paraguay National Library. A lot more than I usually would with someone I just met. He was able to listen deeply without any judgement or jumping to fast conclusions.

A rare trait in this world.

We stopped off at the library. I met a cheerful and somewhat withered older man who was the record keeper. He offered to give me a tour of the archives. There was a musky smell that permeated through the entire room because of the decaying old documents. We walked through archives lined with dense shelves of newspapers and chronicles from centuries ago.

He pulled out a pristinely preserved newspaper from 1967 and I keenly started reading it while muttering “claro” on repeat, which means I see / of course in Español, to appease the old man.

The tour came to an abrupt end as I exclaimed “muchas gracias, adios amigo” to the old archive man. We jumped back in the car and continued our wide-ranging conversation as we hit bumper-to-bumper traffic.

We pulled up at his office. It was a lovely dark orange-bricked house that contrasted superbly against the vivid rain-soaked grass and old trees in the front garden.

As our conversations became increasingly layered, I appreciated how he was able to listen. He offered a few wise words of advice before dropping me back at my hotel.

This black-suited man had unknowingly helped reaffirm I was on the right path…

Despite how hazy everything appeared right now.

We bid farewell and vowed to see each other again.

I popped up to my room in a state of deep reflection. I glanced at my phone and saw a message from another contact I’d been speaking to in Asunción.

I smiled and put my phone back on the table.

“You’re overthinking again…” ran through my mind in flashback to an earlier conversation with the black-suited man.

With that in mind, I messaged back “let’s meet Thursday at 8pm.”

It was Thursday evening and I was sitting on a ledge outside Shopping Mariscal trying to act like nothing mattered. The truth was that I was nervous.

You just never know what to expect when meeting a person for the first time…

I surveyed the yellow taxis pulling up to the curb across the road with a dimly lit tree-lined park in the background. Two drivers were high-fiving one another.

Another was drinking Tereré, a national beverage of Paraguay that consists of Yerba Mate leaves in cold water. “He won’t be sleeping tonight,” I thought to myself…

Then, there was a taxi parked further away than the others… The driver looked somewhat shady and his taxi looked like one of those kidnapping-style ones from the movie Man on Fire.

I kept looking around and checked my phone… It was 8:31pm. Somewhat agitated, I distracted myself by looking at the street food cart perched on the nearby curb.

It was a hive of activity with people coming and going. A dim blue light from the cart cascaded across the rain-soaked street creating an almost Mad Max vibe.

I looked at my phone again and it was getting close to 8:45pm. If this was in Northern Europe, I would have left already but since it was Latin America, I was used to people being late and honestly, I shouldn't have arrived right on time either.

“Stop thinking so much and just feel” drifted slowly through my mind yet again. I relaxed my body and simply enjoyed the smell of the balmy evening air.

I suddenly heard a voice and turned my head to the right.

There was a man standing close to me in a tropical print shirt and a pair of three-quarter denim shorts. His hair was dark brown with a messy middle part. His eyes a haunting brown color with a certain softness about them. The kind of eyes that were warm but were able to see right through you.

“Matt?”

“Yes” I replied with a beaming smile.

We both awkwardly babbled away for what seemed like a few minutes.

The initial awkwardness washed away as we walked to a nearby supermarket to get a bottle of wine.

The conversation began flowing effortlessly and I was relieved that he happened to have a sharp sense of humor.

We selected a bottle of red wine from Chile and headed to the cash register.

I joked that the friendly woman serving us was hitting on him. He laughed back and replied “I don’t think so Matt jajajajajaja…”

“Don’t be so sure” I quipped back with a grin.

The night slowly drifted on all at once like most nights in Latin America do.

Before I knew it, it was 2pm the following day and I was finishing up a marathon Zoom call. It was one of those calls where your cursor hovers around the big red LEAVE button for the last thirty minutes because the other person refused to know when to stop talking.

My eyes darted to a nearby window wishing I was outside instead of being stuck in Zoom hell. It was a balmy 34 degrees celsius outside and the afternoon sun shone gently through the slightly open window.

The restaurants across the road were slowly filling up with people clocking off work early. A gentle hum carried through the open window into my cramped hotel room.

I slumped onto the armchair right next to the open window in exhaustion once the call ended. I felt mentally hollow.

Yet I also couldn’t help feeling noticeably lighter. Like I was floating.

The feeling of lightness was accompanied by a felt sense of reconnection.

It was the kind of feeling where you’re both deeply connected to the essence of who you are and to your immediate surroundings.

Come to think of it, I felt more like myself than I had in years.

I sat back into the comfy dark red armchair and closed my eyes.

The chair was so soft that it absorbed my entire body like a cocoon.

An intense warm sensation came up through my stomach.

I sat there simply feeling it.

A tear wept from my right eye.

Three days in Asunción slowly melted away into three weeks.

Those weeks were packed with many dinners, deep conversations, emotional ups and downs, a priest dowsing gym equipment in holy water, rawly engaging daily interactions, roads that transformed into river beds and two near car crashes…

It started to feel like I was no longer just someone passing through the city.

Instead it felt like I was someone who was arriving.

My alarm went off.

All I wanted to do was stay in bed.

I walked outside with my suitcase that I packed the night before.

The light from the early morning soft pink sun cast itself against the newly constructed glass skyscrapers.

I let out a deep sigh and jumped in a black van.

We hurried off to the airport navigating the chaotic roads.

Five minutes into the trip, I double checked my flight.

The flight was delayed four entire hours, a usual occurrence for Aerolíneas Argentinas.

I let out a sigh of irritation because I specifically woke up early for this flight.

I was struck by the feeling that maybe it wasn’t time to leave the city just yet.

A feeling that was seemingly running on repeat for the last three weeks.

Was it time to extend my stay again?

I thought about it for a moment and this time, it felt wrong.

Staying longer would have been a wrong seat moment.

The inherent sunk cost bias came up again.

The city had already given me so much.

I knew it was time.

The journey had come to its completion point and it was time to move on.

Which raises the question…

What in your own life feels like it’s come to its completion point?

And what’s keeping you in that wrong seat?