This case study is an offbeat ethnographic investigation told via the lens of street art. Though deep immersion into this magical island, the modern realities of socialist revolution reveal a paradox. Cuba is a portal into the future, but you can only see by stepping into the past.



The genesis of this case initially started as an idea for a documentary film that I planned on making with a friend of mine.

  • The point of travel wasn’t for leisure or hedonism, but to understand what life was really like living in a communist country.

Image of three resonant waves.
'Be realistic, ask for the impossible’. Survival is the way of life, so you have to find a way to make the impossible a reality. This means you basically have to make magic happen otherwise you don’t survive.
  • You can’t understand how to begin implementing solutions to real problems, until you really understand the context, culture, and value system surrounding said place/problem.

  • The main premise of the exploration was framed around a simple question. Who is more free - those with tech and cash or those who have not been corrupted by it?

Digital Ethnography

Learning new percussion techniques with street musicians in Havana.

An ethnography is just a fancy way of saying your intention is to understand a culture by immersing yourself through direct participation.

  • Ethnography explores ‘in the field’ to create a detailed first hand account of the current circumstances surrounding a group or community.

  • Coming from a decade of UX consulting, this was actually a natural extension of my interest and skill set (qualitative experience design).

  • The aim is to gain a deep understanding of the customs, behaviors, and beliefs of people and their culture.

The Writing is on The Wall

Keith shooting street art in New York City on New Years Eve 2009. Was Fidel Castro Dead or Alive? (Photo credit: Rob Moon).

For as long as I can remember, I have been studying street art wherever I went.

  • There are hidden messages displayed that can’t always be voiced out in the open.

  • Street art is secret messages hiding in plain sight.

  • Sometimes, you even catch street artists having conversations with one another based on where they ‘tag’ or curate their work relative to other artists' work.

[R]EVOLUTION stencil Buenos Aires, 2010.

In 2010, I lived in Argentina for five weeks with a friend of mine.

  • He worked remotely while I went to Spanish school in the morning and hung out with musicians and shot street art in the afternoon.

  • I got sick and missed a class, and the kindness of my teacher offered a makeup date for me.

  • I told her that I wanted to walk the street together and have her translate the cultural context of what I was seeing.

Image of sketchbook and patches.
We Are Here to Take Care. FFAA is the Armed Forces of the Argentine Republic. Buenos Aires, 2010.
Image of sketchbook and patches.
Capitalism. Buenos Aires, 2010.
  • Argentina experienced a brutal economic collapse post 2008, and the street showed it.

  • While I was in Buenos Aires, Néstor Kirchner (think Argentina’s version of the Kennedy dynasty) suddenly passed away from a heart attack.

  • The subsequent street art exploded all over the banks downtown.

  • Cubans aren’t allowed to speak freely, so the street art was going to serve as their voice.

Te Estoy Mirando

The title of this case: ‘Te Estoy Mirando’ translates to ‘I’m Watching You’.

  • There is an old joke in Cuba - the locals say Cuba is so safe because half the country is police.

  • The joke being that everyone works for the government, and if you're not careful one of your neighbors will rat you out.

Image of sketchbook and patches.
Wall full of graffiti and street art in Havana Cuba. Yesterday they sent me to shit... and it’s incredible the amount of known people that met me there.
  • The idea came from street art that I saw all colorfully drawn on a wall.

  • The translations said ‘here there is no fear’ and ‘yesterday they sent me to shit, and it’s incredible the amount of known people known people that I met there.

Image of sketchbook and patches.
The same wall 24 hours later, literally white washed to erase the truth - except for the all seeing eye above the door keeping watch. Perhaps with neighborhood watch below.
  • The next day, the whole wall was literally whitewashed, obfuscating the unspoken truth that everyone knew but dared not speak publicly about.

The all seeing eye above the door and inspiration for this ethnography. Te estoy mirando translates to I’m watching you.
Homeless man who never talked, drawing under the doorway of an abandoned building.

One day when I was walking up a random street in Habana Vieja (old Havana), I came across a homeless man who was drawing and speaking what sounded like gibberish.

  • He didn’t make eye contact but definitely knew I was there. As I gave the nod and walked away, he blurted out ‘but I never talked!’

  • It’s difficult to truly understand what the consequences of speaking the truth really are - the moment you say or do anything against the state, you’re disappeared.

  • There is no real rule of law or presumption of innocence until proven guilty like we have in the United States.

The Happy Zombie is seen throughout Havana. Cubans aren’t allowed to voice any dissent or speak negatively against the government. Everyone must reflect and honor the singular prescribed narrative.
  • The net effect is that Cubans become like the happy zombie.

  • Their exteriors reflect their indomitable spirit, finding happiness under difficult conditions.

Someone or something is always watching no matter where you are.
  • No matter where you go or what you do, the street is full of extra eyes and ears - watching and listening.

There were lots of converted carts where people would sell vegetables or random trinkets they collected or modified from the street. In this case, a man is selling onions.
  • Case in point, as I became transfixed on the man, the cart, and his wares - I failed to notice that I was being cased out by two women in the background.

Two women waiting to entice customers for their restaurant.
  • I spoke to them for about fifteen minutes until they realized that I wasn’t going to eat at their restaurant. They were very nice and curious about why I was solo in Cuba.

CDR logo spray painted on a wall.

The CDR: Committees for the Defense of the Revolution are “the eyes and ears of the revolution.’

  • Their goal is to ‘promote social welfare and report on counter-revolutionary activity.’

  • As of 2018, 8.4 million Cubans out of 11.2 million were registered as CDR members.

CDR member home with Che Guevara stencil and a nice vehicle.
  • Some homes with CDR logos looked like nice places relative to the rest of Havana.

CDR member home that looked more typical with what you would find in Havana.
  • Others looked like they fit right into normal life.


Time Warp

The spirit or vibe of Havana feels like a modern-day  post apocalyptic Pirates of the Caribbean.

Cuban parking garage complete with classic cars, push carts, and pedal bike carts. The revolutionary hand rising from the grave (left) and reminder of revolution above.
  • It was as if Las Vegas had been teleported into an island, and injected with a sultry shot of quixotic debauchery added for good measure.

  • The constant haze of classic son music and cheap liquor obfuscated the realities of a poor country.

  • Cuba wasn’t just 3rd world, it was trapped in time.

Map of the Bermuda Triangle. (Source: AP).
  • Cuba’s magic may be accounted for by the fact that  the island runs along the southern axis of the Bermuda Triangle.

Crumbling building in Havana.
  • Dilapidated buildings crumbling onto the street are common.

Road construction as people pass by.
  • But the bones of colonial Spanish beauty still exist.

The Specter of Revolution

The canon would go off to symbolize when the gates to the city would be closed. Supposedly this has gone on for hundreds of years. Today it serves as a reminder to authentic Cuban traditions - and probably tourism.

Cuba has a long history of occupation and revolution dating back to Columbus in the 1400’s.

  • The Spanish, Russians, French, English, and Americans all had a hand in shaping Cuba's unique history.

The Wall Lives Forever.

It’s unclear if ‘The Wall Lives Forever’ is a reference to the embargo when Castro sent people ‘to the wall’ for execution.

  • Or if this is a reference to the symbolic closing of the gates closing every night at 9PM.

  • Either way, the message is clear about the feeling of containment from the outside and the unspoken fear and knowing of consequences if you speak the truth.

Che Guevara propaganda poster: ‘The strength of your gaze guides us. Firm in principles.’
  • The iconic headshot of Che Guevara is typically the first thing that comes to mind when you ask people about Cuba.

Che Guevara on the $3 peso bill, not in use any more.
  • Che’s face on the $3 bill is ironic, as it symbolizes something fake.

  • When you buy used bills at the souvenir market, the $3 bill is more expensive than the $100 bills.

Propaganda wall in downtown Havana. With the Cuban Communist Party (PCC), Fidel and Raoul (Castro) forever. The revolution is the people. July 26th, heroism and rebellion.
  • The ghost of revolution past still lives on as a faint din of propaganda painted on walls and billboards throughout the country.

Vox chronicles the story about how CIA spy plane photography revealed Soviet SS-4 medium-range ballistic missiles on Cuba. John F. Kennedy unveiled the photos to the surprise of the world at the UN and barely averted WWIII. (Source Vox via Youtube).

The most prominent event in everyone’s mind however, is likely the Cuban Missile Crisis.

  • The Cuban missile crisis was prevented by a more high tech ‘eye in the sky’ - the U2 spy plane.

  • President John F. Kennedy had secret imagery from a U2 spy plane presented to the UN in a surprise reveal, and arguably stopped the world from entering WW3.

Wing from Rudolf Anderson’s U2 plane, shot down by Cuban Military during the Bay Of Pigs.
  • One U2 was even shot down and ended up being the only casualty of the Cuban Missile Crisis.

Monolith Media

The Voice of Cuban Heritage - Radio Havana.

There is no freedom of speech or freedom of the press in Cuba, only a single source of truth provided by the government.

A limited collection of ‘the history’ of Cuba. Most books project the glorious revolution of Che and Fidel. There are also books about the mafia's brief stint in Havana.
  • Typical bookstand you find throughout Havana keeping the narrative of the glorious revolution alive.

1960’s propaganda posters glorifying the revolution. ‘Country or Death. Death to the invader.’

Warped Reality

2+2 = 5 is a theme from George Orwell’s 1984. It was in reference to whatever the party believes is true, regardless  if it is true or logical or not.

Cubans don’t have the right to speak out against their government or protest.

  • If anyone does speak out, they’re quickly and ruthlessly disappeared.

  • 2+2 = 5 is a theme from George Orwell’s 1984, where the only truth is what the party declared as truth - no matter how absurd.

2+2 = 5 on a garage wall in Havana.
Definition of 2+2 = 5 from Urban Dictionary. There is only one monolithic version of the truth.
2+2 = 5 motif. Do you juggle this questionable truth, or do you take a bullet?
Education has produced a vast population able to read but unable to distinguish what is worth reading - G.M. Trevelyan.
  • Everyone mentioned free education and free healthcare with a sense of national pride, but then immediately talked about their plan to leave the island.

Dreams of Freedom


Cubans are subject to strict visa requirements in order to leave the island.

  • The clothes they wear and phones they use are typically gifted from family traveling back and forth from the United States.

  • 2+2 = 5 is a theme from George Orwell’s 1984, where the only truth is what the party declared as truth - no matter how absurd.

1 UP in video games is an extra life. The Cuban dream to leave the island and gain an extra life was prevalent.
  • Everyone I spoke to dreamed of an extra life, a life that was equal and just.

The scales of justice.
Turbo Flight.
  • If they could just get off the island, their life would be turbo charged and their dreams would take off.

Image of sketchbook and patches.
Image of sketchbook and patches.
Running to stand in place is a euphemism for having to work as hard as possible, only to survive. This is daily life in Cuba.
  • Dreams and imagination are what keep people alive in Cuba.

Art studio with the all watching eye.
  • But don’t tell anyone, because you know who is watching.

  • Cubans can’t speak the truth or publicly acknowledge the ‘true’ reality, therefore their imagination is the only weapon to survive.


Socialist Power Dynamics

5 CuC = $5 USD, or around 100 Cuban pesos. 1 CuC would equal $1 USD.
5 Cuban pesos = $0.25, or about 1/5 of a CuC.

Until recently, Cuba operated on a dual currency system - one for tourists and the government (the CuC), and one for everyone else (Cuban peso).

  • The typical Cuban salary for everyone is around $35 USD per month.

  • Over the last few years, Cubans were allowed to file for a license to drive cabs and open small shops.

The resulting dynamic is that normal Cubans have more money, but less power.

  • However, if you’re a government paid Cuban, you have more power and can ruin a person's life by turning them into the government.

Image of sketchbook and patches.
Our cab driver was escorted away from the vehicle to have a talk with a Cuban police officer.
  • One of our cab drivers was pulled over and told to get out of the car.

  • After 25 minutes, when he came back in the car he said thank god you guys are Americans, meaning if it were anyone else - his license would have been revoked.

  • He was stopped for nothing - existing basically.

Storm off the coast of The Malecon made extra large waves one night.

Like everything in life, there is always a spectrum that powers exist on.

  • One night there was a storm offshore and I went to the Malecon (a boardwalk on the ocean) to go film with my GoPro.

  • The waves were crashing up to 30 feet in the air, and the freshly installed LED lighting on the highway lit up the chaos perfectly.

Helping push a police car after the carburetor flooded. The car finally kicked over, but this felt like pushing a bus. Check off supporting the Cuba people on my visa!

I noticed a police car pass by with the lights on, then turn around and stopped.

  • I realized that the car stalled out because one of the officers got out to push the car.

  • I ran down and helped him push the car, and we eventually got the beast to kick over.

  • There is no AAA in Cuba, so both the police officers were super happy that I was there to help, but puzzled that some random gringo was out filming the ocean breaking over the Malecon.

Cruise Supply & Demand Dynamics

Norwegian Sun cruise ship parked at the port in Havana.

When a cruise ship was at the port, you lost negotiation leverage because there was so much fresh money roaming around Havana.

People trying to bring you into their restaurant. The more people they brought in, the more they received from restaurants.
  • However, when the ship left, all of a sudden you could negotiate a better rate for cabs and reservations.

Black Market

Image of sketchbook and patches.
Small suitcase filled with hardware that you can’t easily get in Cuba: blue painters tape, light switches, light fixtures, coffee, and granola bars.

The black market in Cuba is not centered around drugs or people; but car parts, clothing, and construction materials - all smuggled in via 50lb suitcases.

  • There is no Home Depot or modern hardware stores, so items like concrete, light switches, electrical tape, and light bulbs are a precious commodity.

  • Castro banned the import of foreign cars and car parts in 1959, so items like brake pads and shock absorbers are also a precious contraband.

Building renovations require lots of cement.
  • We spoke to one person who helps renovate buildings in Cuba, and he said that he got arrested and detained one night because he had a few bags of concrete in the trunk of his car.

  • When he was released, the concrete magically disappeared.

A typical bodega (corner store) in Havana. Items are expensive and in limited supply.

Bodegas or corner stores are usually expensive and sparsely stocked with item that most Cubans can’t afford.

Cuban taken to an American grocery can hardly believe his eyes with how much food there is. (Source: Youtube).
  • When a Cuban was taken to a typical American grocery store, he could hardly believe how much abundance was available.

Imagination is Key

Resources are so scarce in Cuba, that you have to use your imagination in order to survive.

In times of crisis, only imagination is more important than knowledge. Albert Einstein.
Cars in Cuba might look exotic, but they’re really a Frankenstein of random car parts that don’t match.
  • Car parts are hard to come by in Cuba and typically don’t match with the proper make and model.

  • Therefore most repairs are hacks or random modifications made to fit with whatever is available.

Cab to the city broke down on the Malecon.
  • Everything breaks in Cuba, so you have to learn how to adapt and fix it.

Help. Stencil parody of the power fist, but with tools to fix your problems.
One guy begs for money, another walks by with a modified bumper that looks heavily MacGyvered.
MacGyver muffler close up.
  • Cubans work hard not just to survive, but because they desire to have a better and more free quality of life.

Image of sketchbook and patches.
A giant plastic tank to collect rainwater.  Clean water is a scarce commodity in Cuba.

Water is another scarce resource. Cubans save money to buy tanks to put on their roofs to collect rainwater.

The Heart of Cuba is The People

This is the heart of the island.

The heart of Cuba is without a doubt its people.

Pirate guy selling pictures in downtown Havana.
Love is greater than money.
  • When you have no money, love and relationships become the main currency.

Focused good luck, strength, balance, love. Cyclone love, go traveling now - yes, ha yes, love achievement.
With the lack of resources in Cuba, the street art isn’t always as colorful or extravagant as what you might see in NYC. However, the messages go straight to your heart.
Two workers walking down the street, one drinking a beer.
Three men watching the neighborhood and exchanging gossip.
For such a lack of resources, Cubans are some of the best dressed in the world.
Father watching the little ones play.


Garden Level Bodegas

Typical garden level apartment in Havana.

One of the perks of having a ground level apartment is that you can have your own bodega (because there are no zoning laws) and sell small items to tourists.

Artist with garden level bodega.
Closeup shows the artist selling water and cigars.
  • People will sell cigarettes, beer, water, and cigars right outside their house to make some extra money.

Ad Hoc Speakeasy

Image of sketchbook and patches.
Image of sketchbook and patches.
Small letter pressed invitations get handed out in person to come to the Conga Room, an Ad Hoc speakeasy.

Since the internet is limited, analog invitations are printed out and handed out in person - inviting people to come to a homemade speakeasy.

Stickers advertise the Conga Room on the back of Cuban pedal bikes.
  • There is even analog advertising that is instantly recognizable by tourists.

Cuban Apple Store

Image of sketchbook and patches.
Image of sketchbook and patches.
Cuban Apple Store (local phone repair shop). Cubans loved American brands. You saw apple stickers everywhere because they associated Apple with ‘high tech.’

Cubans love American brands, especially Apple products, because they represent hi-tech and future innovation.

Image of sketchbook and patches.
Cuban Apple Store advertising.

Tourism Entrepreneurs

Some entrepreneurs make money by inviting people to come eat at the restaurant they work for.

  • There is even analog advertising that is instantly recognizable by tourists.

Image of sketchbook and patches.
Image of sketchbook and patches.
Text messages with my new Cuban friend.
  • I got to see my new friend’s home and left him with a 2TB hard drive and emergency contraception as a small token of appreciation.

Cuban Internet

3G advertisement.

It’s hard to understand how much we take fast phones and fast internet for granted.

  • Cuba is just beginning to roll out 3G speed cellular service.

Scratch off cards for internet and cellular access.

In order to use a cell phone and internet, you have to buy scratch tickets with codes on them to get access.

  • Sometimes the scratch tickets didn’t scratch off properly, and you couldn’t end up reading the number.

  • Remember, Cubans were on a fixed state salary - so if they bought airtime that didn't scratch off properly, they were out of luck.

The Pineapple is greater than spray paint. A wifi pineapple is a hacking tool for security professionals.
  • Interestingly, there was street art about a wifi pineapple - a wifi hacking tool for security professionals.

Mini documentary about El Paquete Semanal  - the weekly package. (Source: Youtube).

The real Cuban internet is known as El Paquete Semanal - a weekly thumb drive you can buy with new music, video, and books.

  • Thumb drives get copied and passed around. It’s a truly decentralized system.

Whatever It Takes

Man collecting used water bottles to recycle for extra change.

Everyone else has to do whatever it takes to survive. Some collect spare water bottles, and other have to beg for milk and grocery money for their kids.

Women asking for spare money to feed her children.
Every little bit goes a long way in Cuba.
For Diana of Osmany, it is only necessary to distinguish what is temporary from what is definitive.


Currency Devaluation

Cuban ATM machines, barely in use.

There were previously two currencies in Cuba, but in December 2020 - the Cuban government suspended the dual currency system and took a devaluation of 1 $USD = 24 CUP.

Imports from January 2019 to March 2020 fell from $700 million to 315 million, cutting more than half Cuba’s imports. (Source IMF Direction of Trade statistics via Columbia Law School).
  • The embargo combined with the pandemic has cut the government’s biggest revenue stream (tourism) by half.

  • The net effect was massive inflation in the Cuban economy with no fresh capital entering the system.

  • On their last straw, the Cuban people did what they never did before - protest the government for freedom and outside support.

Breaking With Tradition

Victor painted inside Morro Castle in Havana.

With revolutionary fervor in their blood, the Cuban took to the streets in Havana to call for a better way of life.

Video of an unprecedented Cubam protest in Havana. (Source: Youtube).
Cuban influencer Marissa Daniela explaining the Cuban protest. (Source: Youtube).
  • This was highly unprecedented because public assembly and voicing your opinion against the government is illegal in Cuba.

Nationwide Spread

Map of the spread of Cuban protests throughout the entire country. (Source: AFP).

Armed with new higher quality phones, Cubans recorded and broadcast the protest live on the internet even with slower speeds.

  • The protests quickly spread like wildfire across the country.

Tweet from Antonio Garcia Martinez explaining how fast the protest spread.
  • Antonio Garcia Martinez (born to Cuban refugees) and author of Chaos Monkeys explained the situation best.

The Government Responds

Internet access chart by Netblocks, demonstrating how many sites were blocked from the government when the protests flared up.

The government quickly cut internet access, thus making it hard to get the truth out.

There are only a few undersea cables running connecting Cuba to the outside world. (Source: Submarine Cable Map).
  • There are only a few undersea internet connections that connect Cuba to the outside world.

Disappearing The Dissidents

Video of a protester disappearing at night, never to be seen again. When people get arrested there is no trial by jury of your peers. Whatever happens to you in prison is usually akin to brutal nightmares.

Protestors were quickly rounded up at night, but this time people recorded and  broadcast the video live.

  • Something that never happened before in Cuba.

ANTIFA graffiti in downtown Havana.
  • Antifa uses black bloc tactics, where people dress up in black (making it difficult to identify individuals) and usually engage in violent and destructive activity.

Video of black dressed Cuban soldiers loading into trucks to quell protests.
Street art of a mother protecting her children by covering their mouth, as to not speak the truth.

Rage Against The Monolith

The iconic face of Che Guevara is losing its meaning with the younger generation.
  • Che is more of a hologram today. An illusion representing something from the distant past that current generations have no recollection over.

  • The revolution has shifted to ‘us’ versus ‘them’, i.e. the people vs the government.

The hand of the revolution reaching for freedom.
  • The ghost of revolution past is rising from the grave, except it’s a new generation with a different vision and value system.

Father driving his kids to school on a bike.
  • The ghost of revolution past is rising from the grave, except it’s a new generation with a different vision and value system.

Young kid giving everyone ‘the freedom bird’.
  • The younger generation has no fear and nothing to lose.

  • For they are wild and free in their hearts.

Click your heels three times and say, there's no place like home.
2+2=5 variation. Fingers Crossed - good luck and hoping for a good outcome. Eyes closed as if the character knows they’re about to go through pain.
  • Fingers crossed that their dreams of freedom may come true.