Published: November 2012
Cuba’s New Now
After half a century under Fidel, Cubans feel a wary sense of possibility. But this time, don’t expect a revolution.
By Cynthia Gorney

“I want to show you where we’re hiding it,” Eduardo said.

Bad idea, I said. Someone will notice the foreigner and wreck the plan.

“No, I figured it out,” Eduardo said. “You won’t get out of the car. I’ll drive by, slowly, not so slow that we attract attention. I’ll tell you when to look. Be discreet.”

He had borrowed a friend’s máquina, which means “machine” but is also what Cubans call the old American cars that are ubiquitous in the Havana souvenir postcards. This one was a 1956 Plymouth of a lurid color that I teased him about, but I pulled the passenger door shut gently, the way Cubans always remind you to, out of respect for their máquinas’ advanced age. Now we were driving along the coast, some distance from Havana, into the coastal town where Eduardo and nine other men had paid a guy, in secret, to build a boat sturdy enough to motor them all out of Cuba at once.

“There,” Eduardo said, and slowed the Plymouth. Between two peeling-paint buildings, on the inland side of the street, a narrow alley ended in a windowless structure the size of a one-car garage. “We’ll have to carry it out and wheel it up the alley,” he said. “Then it’s a whole block along this main street, toward that gravel that leads into the water. We’ll wait until after midnight. But navy helicopters patrol offshore.”

He peered into his rearview mirror at the empty street behind him, concentrating, so I shut up. Eduardo is 35, a light-skinned Cuban with short brown hair and a wrestler’s build, and in the months since we first met last winter—he’s a former construction worker but that day was driving a borrowed Korean sedan and trying to earn money as an off-the-books cabdriver—we had taken to yelling good-naturedly and interrupting each other as we drove around La Habana Province, arguing about the New Changing Cuba. He said there was no such thing. I said people insisted there was. I invoked the many reports I was reading, with names like “Change in Post-Fidel Cuba” and “Cuba’s New Resolve.” Eduardo would gaze heavenward in exasperation. I invoked the much vaunted new rules opening up the controlled economy of socialist Cuba—the laws allowing people to buy and sell houses and cars openly, obtain bank loans, and work legally for themselves in a variety of small businesses rather than being obliged to work for the state.

But no. More eye rolling. “All that is for the benefit of these guys,” Eduardo said to me once, and tapped his own shoulder, the discreet Cuban signal for a person with military hardware and inner-circle political pull.

What about Fidel Castro having permanently left the presidency four years ago, formally yielding the office of commander in chief to his more flexible and pragmatic younger brother, Raúl?

“Viva Cuba Libre,” Eduardo muttered, mimicking a revolutionary exhortation we’d seen emblazoned high on an outdoor wall. Long live free Cuba. “Free from both of them,” he said. “That’s when there might be real change.”

If there is in fact a Cuba under serious transformation—and you can find Cubans all over the country engaging now in their own versions of this same debate—Eduardo is a crucial component of it, although not for the reasons you might think. “Dissident” is the right label for a subset of politically vocal Cubans, notably the bloggers whose critical online missives have gained big followings outside the country, but Eduardo is no sort of dissident. He’s not fleeing persecution by the state. He’s just young, energetic, and frustrated, a description that applies to a great many of his countrymen. Ever since he was a teenager in high school, Eduardo told me, it had been evident to him that adulthood in revolutionary Cuba offered exactly nothing by way of personal advancement and material comfort to anybody except the peces gordos. The big fish. (Well, literally translated, the fat fish—the tap-on-the-shoulder parties.) Nothing works here, Eduardo would cry, pounding the steering wheel of whatever car he’d hustled on loan for the day: The economic model is broken, state employees survive on their tiny salaries only by stealing from the jobsite, the national news outlets are an embarrassment of self-censored boosterism, the government makes people crazy by circulating two national currencies at once.

“I love my country,” Eduardo kept saying. “But there is no future for me here.”

Over nine weeks of traveling around Cuba this year and last, I heard this particular sequence of complaints so often, and from so many different kinds of people, that it began to form a kind of collective national lamentation: I love my country and it doesn’t work. There were loyal optimists among the complainers, to be sure, and after a while, whenever I encountered one, I found myself marshaling ammunition to bring Eduardo. I wanted to hear how he’d respond, but when I was being honest with myself, I realized that I also wanted to talk him out of the boat. (Sharks swim in those Cuba-to-Florida waters. The currents are dangerous. There are drownings, people never heard from again.)

Optimist: Roberto Pérez, a shaggy-haired environmental biologist, filled with enthusiasm about the progress of Cuba’s extensive urban agriculture and organic farming projects. Pérez is six years older than Eduardo. Eighty percent of his own high school graduating class, Pérez told me, has left the country. “But things are changing,” he said. “Very fast. And there are so many good things here that people take for granted, because they were born with them. You tell me another place where a kid can grow up so safe, get his vaccinations, get his education, not be involved in gangs or drugs. I can see people crossing the river north from Mexico, to get away from that. But from here? To face the Florida strait? I fail to see it.”

Still no? OK. Optimist: Josué López, exactly Eduardo’s age, just immigrated back to Cuba after six years in Florida and a growing disenchantment with the values of some of his hyper-acquisitive Cuban émigré neighbors in Miami. López and his wife are going into business for themselves, taking advantage of the new self-employment laws and new flexibility in agricultural land use, and developing a bed-and-breakfast resort on a few acres they’ve acquired outside Havana. “I’m telling my friends who went to the States,” López told me, in his practiced slangy English, “Dude! If you want to start something, the place to be is Cuba.”

Eduardo would listen, interested, his face sober. He would shake his head. We were arguing in a café one morning, a rooftop spot in the historic part of Havana, and Eduardo grabbed a glass saltshaker from the table. “My whole life, the government has been telling us, Look! I’m giving you this nice full saltshaker!” he said. “But it’s never full.”

This one wasn’t either. A half inch of salt, maybe. Eduardo put the shaker down and told me he had gotten hold of some oars. The men would have to row for a while, before they could risk motor noise that might alert authorities; the departure itself would violate Cuban law, since none of them had a tarjeta blanca, a white card, the government permission required of all citizens before they may leave the country, even temporarily. Cubans hate the tarjeta blanca, and the government subsequently hinted at doing away with it entirely—but on this early spring morning Eduardo hadn’t even applied for one, since he assumed the tarjeta would be denied, as they sometimes are, with no explanation beyond the bland, omnipresent No está autorizado—It is not authorized. Besides, a Cuban applying for a tarjeta blanca is supposed to have a visa from the destination country. Just to secure a spot on the consideration list for a U.S. visa, a Cuban must pay $160 and produce a written invitation from some actual person living in the United States.

Eduardo had neither. I had expected him to solicit help from me, the money or the invite, but he never did; he just blurted out the boat plan one day in the middle of a long, talky car ride, as though he’d been desperate for a non-Cuban confessor, and now here we were staring at a saltshaker and brooding about Eduardo’s son, who was nine and didn’t know his father was going.

“I don’t know if it will be better to tell him or worse,” he said.

At least the money he’d send home would buy his son new shoes, Eduardo said. “Everything has a risk in life,” he said. “I’m not worried. Use my real name. I’ve told you this before. Use it! I’m not afraid of anybody!” He spread his arms wide, trying to look unworried, and repeated his name the Latin American way: first name, paternal surname, maternal surname. I told him to quit being foolish, that he still lived in a one-party state in which people get roughed up or arrested or excoriated as mercenaries for criticizing their leaders too vigorously, and that we were talking about this in public only because the café waiter was a friend of his and nobody else was nearby. So forget it, I said. Sorry. No real name. We were quiet. Beneath us spread the most famous district in Cuba, the streets the tourists want to see first. There were shining 19th-century tile work, the filigreed top of a Corinthian column, a glimpse of the turquoise sea.

The whole city seemed to be shining, that morning with Eduardo, even though there’d been a derrumbe in the neighborhood where I was staying. That’s a building collapse, a thing that occurs with some regularity, especially in Havana. Buildings that were once beautiful and grand are rotting now in the tropical air, and the country has no money to repair them, so they cave in, partially or all at once, a giant rumbling roar followed by rubble and grief. This derrumbe killed four people, three of them teenage girls; the building had been designated unsafe, but Cubans are inventive about their living space in Havana, where parts of the city are so crowded that multiple families and generations wedge into residences that in more decadent eras served as single-family homes. Eduardo had the idea that the number of deaths in my neighborhood derrumbe was 21—he had heard this via radio bemba, the radio of lips, which is what Cubans call the word on the street, the only censor-free method for the dissemination of discouraging domestic news. But I had been reading Granma, the national Communist Party daily, which to the surprise of many people had actually run articles about this derrumbe rather than pretending it had never occurred and was steadfast about the death toll of four. Anyway, the city looked shiny. The tourists were charging all over by the busload, maps in hand, and from what I could see they appeared to be having a great time, sipping their rum-and-mint mojitos, following their multilingual Cuban guides, and applauding the happy cacophony of rumba and son that spilled out into the plazas from restaurants and street corners and bars.

Unmistakably, and provocatively, unusual things were transpiring in the streets. In some neighborhoods half the buildings’ doorways seemed to have been taken over by new self-employed vendors, the men and women sitting hopefully alongside makeshift displays of hair accessories or homemade pastries or DVDs of movies and television shows. “For Sale” signs, prohibited during the decades when it was legal to exchange residences but not to sell them, now appeared in house windows. In a few weeks Pope Benedict XVI was due to arrive, the first papal visit to Cuba in 14 years. Along the route the papal cortege would follow, state workers were cleaning and painting house facades so assiduously that I heard people joke that they wished the Holy Father would show up more often, just for the urban cleanup.

Hefty half-built structures stuck out here and there—the anti-derrumbes, as I came to think of them, into which the country’s sparse investment resources were being directed. High cranes and scaffolding delineated the rehabilitation of historic buildings, the gussying up of tourist destinations, the construction of new port facilities. From certain spots along the shoreline, you could make out the shape of the huge deepwater rig exploring the Cuban seabed, believed to contain billions of barrels’ worth of oil. If large-scale oil production is merited, the possibilities for the country’s economic future are profound.

Most of the Cubans I talked to seemed consumed, in fact, by this whole idea of possibility. Not permanent transformation, most would say, not yet; the Cuban government has a history of switching signals on its citizens, encouraging private enterprise and then pronouncing it counterrevolutionary and shutting it down again. But Raúl Castro is not his brother, and there’s a particularly Cuban combination of excitement, wariness, calculation, black humor, and anxiety that accompanies even the possibility of real change—the suggestion that after a half century under Fidel, something big may truly be happening to the way Cubans live day to day. “The rebuilding of the house of Cuba,” an ecclesiastical lawyer and editor named Roberto Veiga said gravely, pronouncing the Spanish words with the elegance of a pastor at the pulpit: La reconstrucción de la casa Cuba.

Careful, though: The rebuilding metaphor implies a blueprint. Those outside Cuba who imagine that this blueprint is agreed to by some clear Cuban consensus are deluding themselves. The unconstrained individualism of the United States, where neither health care nor a college education are free? The showy wealth and environmental havoc of modern China? The economic woes and internal tensions of Europe? The narco wars of Mexico? “This is our great challenge,” Veiga told me. He helps run a publication of the Archdiocese of Havana, Espacio Laical (literally, Secular Space), which, like the Cuban Roman Catholic Church itself, has become one of the few venues in which semicritical debate about the country’s future is aired in public. “What will it be like, this house of Cuba?” Veiga asked. “These are changes that should have begun two decades ago. But they didn’t. And now we are a nation trying to define itself.”

Eleven million people live in Cuba, less than the population of central Tokyo. It’s the biggest island in the Caribbean, and famously only 90 miles from United States territory, but Cuba still grips the international imagination mostly because the dueling narratives of its history are so exaggerated by myth. Either a ruthless revolutionary took power in 1959, seized American corporate property, forced out his country’s own professional classes, and silenced all opposition by creating a totalitarian police state (that’s the version audible to this day on Miami’s Radio Mambí, the broadcast voice of Florida’s most vehement anti-Castro community); or a brilliant revolutionary led the overthrow of a corrupt dictatorship, shook off the colonialism of foreign companies and the Mafia, brought literacy and health care and egalitarian values to a mobilized people, and created a university-educated bastion of socialism in spite of a half century of U.S. efforts to destroy it by prohibiting Americans from doing business with or spending tourist money in Cuba.

Both narratives contain substantial truth, both at the same time. This is why Cuba fascinates and makes people’s heads hurt. The placebis exhausting in its complexity and paradoxes—Cubans are the first to tell you that—and the questions modern Cuba sets off in a visitor are big, serious, unwieldy. What is the definition of freedom? What do human beings need? What do they owe to each other? What do they want, beyond what they need? “We’ve all been the subjects of an experiment,” a 58-year-old university-educated woman who works in the arts told me thoughtfully one evening, chopping sweet peppers in her kitchen for supper. She lives in an airy place, with a fenced front lawn and a backyard patio, in a leafy part of Havana; the home has belonged to her family since before the Triunfo, the Triumph of the Revolution, as Cubans generally refer to the events of 1959. Her lightbulbs are compact fluorescents, the woman pointed out—one legacy of an ambitious national project a few years back, directing all Cubans to switch to lower watt fixtures in the interests of energy independence and the environment.

“They’d come to check,” she said. “They would break your old bulbs, in front of you, to make sure you didn’t sneak any back into your lamps.” She smiled and looked over her glasses at me to make sure I was listening closely enough. She has one child, a son a decade younger than Eduardo—gone now, having bailed out on Cuba and obtained a therapy credential in Spain. “The idea was marvelous, to change all the lightbulbs,” she said. “The problem is how they did it.”

In its headline version, the rebuilding of the house of Cuba looks like this: Capitalism intrudes, around the edges, small bits at a time. Since 2010 more than 150,000 Cuban workers have left or been laid off from their state jobs, a concept previously unimaginable in a system that was supposed to provide all the work and all the social benefits. President Castro himself has said that the state apparatus is bloated and too conducive to dependence and corruption, and that the state must trim a half million workers. State agricultural land is now being leased in pieces to private farmers and cooperatives, and other kinds of legal self-employment are being gingerly promoted as well. Over the past two years the government has authorized 181 job-specific categories of cuentapropismo, as it’s called—the keeping of one’s own account.

Even the ration book—the libreta issued to all Cuban households, with its check-off columns for the state-subsidized basic foods every citizen is supposed to get each month—may be an artifact near the end of its time, Raúl Castro has said. The libreta! This is big. Nothing is more evocative of the bewildering Cuban economy, and Cubans’ complicated reaction to it, than the baseball card-size libreta, each one stapled together from thin cardboard and white paper and listing the items the holder may buy at artificially low prices: rice, sugar, and milk, if the family includes children under eight. There are squares to be checked off by hand. The pages look like the accounting ledgers of Dickensian clerks.

Here are things I have watched Cubans do with the libreta:

Reinforce its fraying cover carefully with decorative paper and tape.

Hold it in one hand, a plastic shopping bag in the other, while sweating in the moist heat, gossiping with neighbors, waiting for subsidized bread.

Whip it from their purses or off kitchen shelves, shoving the opened pages at me, exclaiming simultaneously that it demonstrates Cubans’ care for each other and that the allotments have been so cut back the government might as well be trying to starve them all.

Once I was in the home of a priest of Santería, the Afro-Cuban religious practice that is the faith even of many professed Cuban Catholics. I was still trying to compose myself because the priest had just completed an initiation ceremony that included slitting the necks of pigeons and chickens and bleeding their corpses into sacred dishes and praying in Yoruba. But what the priest really wanted to talk about was his libreta. “Look at this!” he cried. “Eight ounces of oil, per person, for a month! Ten ounces of beans! One package of pasta maybe every three months!”

There’s a term Cuban housewives use as they make their rounds in search of the day’s family food: pollo por pescado. It means “chicken for fish”: You have promised fish for dinner, but in the stores there is no fish, so you get a little chicken and pretend it’s your fish. Cuba is surrounded by seawater, of course. Where is all the fish? Ah, any Cuban will tell you, leaning in close, a merry gleam in his eye: glad you asked, mi amor. The fish is in the restaurants. The fish is in the hotel buffets, a popular amenity for tourists, where long counters are piled high with varieties and quantities of food no ordinary Cuban ever sees. The fish is being sold out of private homes, if you know which doorbell to ring.

In many of these locales the fish—like nearly every desirable product in Cuba, from nightclub admission to hair dye and plasma TVs and acid-washed blue jeans—is being sold in CUCs.

Now we come to that aspect of present-day Cuba that causes the yuma (that’s the grammatically adaptable slang for “American,” “foreigner,” and also “the general outside world to the north and east”) to reach for a calculator and some aspirin and a crash course in recent Cuban history. The CUC, which is shorthand for Cuban convertible peso, is one of the two official currencies of Cuba. Like the libreta, the double-currency system is in theory destined for extinction; things are so fluid in Cuba that by the time you read this, it’s conceivable the government will have begun ending it. But to appreciate fully the elaborate survival negotiations that have dominated so many Cubans’ daily lives in recent years, you have to come to grips with the essential weirdness of the CUC.

It’s a recently invented currency, introduced a decade ago as a replacement for the dollars and other foreign money that began flooding and disrupting the country after the Soviet Union collapsed in 1991, thus ending the big-socialists-to-little-socialists financial support that had been holding up the Cuban economy. The multiyear Cuban depression that followed the Soviet breakup was catastrophic (fuel shortages, 14-hour blackouts, widespread hunger), and the government set out to counter it by throwing the island open to international tourism. This was all done rather fiercely, with a flurry of beach hotel building that continues to this day—current plans include multiple golf courses and jet-capacity airports—while anticapitalist admonishments still declaim from highway billboards and urban walls:

SOCIALISM OR DEATH!
THE CHANGES MEAN MORE SOCIALISM!

In its purest concept the CUC is used for goods and services somehow connected to foreignness: hotel bills, international transactions, Fidel T-shirts in the souvenir shops, and so on. One CUC is worth about one U.S. dollar, and it’s simple to obtain them; whether you’re a yuma or a Cuban, state employees at exchange centers will take whatever currency you hand them and count out your reciprocal CUCs, wishing you a pleasant day when they’re done.

These employees, like the rest of the Cubans who work for the state—currently about 80 percent of the country’s labor force—are not paid in CUCs. They’re paid in the other currency, the Cuban national peso. One national peso is worth 1/24 of a CUC, or just over four cents, and in socialist Cuba state salaries are fixed; the range as of mid-2012 was between about 250 and 900 pesos a month. Some workers now receive a CUC stimulus to augment their peso wages, and recent changes are lifting top-end salary limits and linking pay more to productivity than to preset increments. But it was Cubans who taught me the national comic line about public workplace philosophy: “They pretend to pay us, while we pretend to work.”

In the city of Santa Clara, where the principal attraction is a massive monument to revolutionary martyr Ernesto “Che” Guevara (fought with Fidel, died trying to foment insurrection in Bolivia), I spent an afternoon with a visiting emergency physician whose medical salary was fixed at 785.35 national pesos per month. That works out to CUC$32.72. Like so much about Cuba, this isn’t straightforward; Dr. M owes nothing for his professional education and his own family’s medical care. His son’s lifetime schooling is free. Produce and certain other basic foods not on the family libreta can be purchased in pesos, as can Cuban books, baseball game tickets, fares on the crowded public buses, and admission to museums and movie theaters and the ballet. The currency in which he is paid as a doctor will buy Dr. M the very kind of 1960s ascetic nationalism Che Guevara liked to espouse—in other words, as long as Señora M uses only the poor-quality peso soap, the M family brews only the peso coffee that comes with fillers ground in, and nobody ever buys deodorant.

“The toy truck I wanted for my son, with the little motor and remote control?” Dr. M said, as we stood side by side beneath the gigantic monument pedestal, craning our necks up at Che. “Forty CUCs.”

Forty CUCs in a state store, that is. Cubans maintain a robust black market—por la izquierda, they call it, “over to the left”—in which anything can be obtained. But the most surrealistic aspect of life in Cuba 2012 is the vigor with which the government, the same entity paying Cubans in pesos, sells goods to Cubans in CUCs. Retail stores, like pharmaceutical factories and nickel mines, are national enterprises, run by the state. Clerks often don’t bother specifying “CUC” on the pricing of merchandise either; if a thing whirs or glitters or comes in good packaging, Cubans know the currency in which it is being sold, and regardless of whatever the ghost of Che may be whispering in their ear, they want it.

By the time I met Dr. M, I had done so much confounded window-shopping that there were numbers all over my notebooks: Pepsodent toothpaste, CUC$1.50 per tube. Electric blender, CUC$113.60. Upholstered loveseat-and-armchair living room set, CUC$597.35. Multistory malls, with cafés and video game halls and clothing stores, all functioning exclusively in CUCs.

The cell phones Cubans depend upon—pre-Raúl they were prohibited; now they’re everywhere—are sold, both the device and the per-minute fees, in CUCs. Even a Bucanero Fuerte, one of the good Cuban beers, is likely to be sold in CUCs. The Bucanero price of one CUC, not an unreasonable sum in many countries for a bottle of beer, constitutes a full day’s medical pay for Dr. M. You see the problem with the toy truck. This is why for four days a week, when he’s supposed to be recuperating from his 24-hour emergency shifts, Dr. M drives a cab.

Technically, he drives his own car, the aged Russian beater he inherited from his father. But he picks up tourists in it, because tourists pay in CUCs. Over one high-season month Dr. M’s cabbie days earn him the CUC equivalent of 15 times his salary as a physician. In Cuba there’s nothing remarkable about this. The taxi fleet, like the rest of the tourist industry, is replete with splendidly educated Cubans no longer practicing their professions because their years of study to be of service to the nation—in engineering, medicine, psychology—produced salaries in “the money that’s worthless,” as a kindly Cuban bank teller once remarked to me. The phenomenon is referred to as the “inverted pyramid.” Every Cuban who repeated that term to me did so in a tone of despair, as in: This, you see, is why the ambitious young keep leaving.

Dr. M and I studied the object Che was holding in his giant fist above us, determined that it was a hand grenade, and went into the museum. Che Guevara was an Argentine medical school graduate when he met Fidel Castro, and as we walked past the glass-encased displays of the Che medical journals and the Che lab coat, I glanced over at Dr. M. In the 15 years since Che’s ashes were delivered to Santa Clara, Dr. M told me, this was the first time he had visited the museum. But he was silent and impassive, and when we came out, all he said was, “I don’t get this about us now—how a taxi driver can make so much more than a doctor.” The expression on his face made it clear that Che Guevara was not a topic he wished to continue exploring. “I don’t get it,” he said.

Eduardo told me the boat’s departure date was set, depending on what the men could learn about tide and weather predictions, for the days just after the pope’s visit ended. When I was away from Havana, in the island’s interior, text messages from his number showed up every so often on my temporary Cuban phone: “hi my friend am going soon on vacation.”

I was doing a lot of walking, or strapping on flimsy passenger helmets and climbing (imprudently) onto the backs of unlicensed motorcycle taxis. To my outsider’s eye, the New Changing Cuba looked both real and raggedy, as though an enormous flea market had been busted up and scattered the length of the country. Young men sat in stairwells, offering to repair cell phones or refill cigarette lighters. Families lined their front porches with display tables of used kitchen merchandise or thermoses of coffee and chipped plates of wrapped ham-and-cheese sandwiches.

Here were small corner businesses that used to be run by the state but now, experimentally, were not: barbershops and snack bars, for example, in which management was being transferred to the employees. Here was a former high school math teacher, a soft-spoken 42-year-old who had learned to speak Russian fluently back in the comfortable days of life support from the U.S.S.R. Now he was selling baby clothes for CUCs from one corner of a rented street-front foyer in the central city of Camagüey. “My wife does the sewing,” the former math teacher said. “She used to be a teacher too.”

And here, in the middle of one residential block back in Havana, was a chic new restaurant called Le Chansonnier. No signage marked the entrance; Le Chansonnier is a paladar, a privately run restaurant inside a home, and people with money—correction, people with CUCs—know where it is. Paladares have been legal for years in Cuba but used to be strictly contained, under the pretense that they were all tiny family operations siphoning no business from state restaurants. Since 2011, though, they’ve been allowed to expand and hire staff, and like the guest rooms Cubans may rent to foreigners inside their own homes and apartments, some of the popular paladares have basically turned into busy CUC cash registers for their owners. “I always dreamed of having my own business,” the co-owner, a 39-year-old named Héctor Higuera Martínez, told me the afternoon I stopped by. “I used to think I’d be an engineer. But I saw that there was a living in working with tourists.”

Higuera waved a hand at somebody and in short order produced an amazing salad for me, with beautiful butter lettuce, shaved chicken, and a dusting of chocolate. He was trying to figure out how to manage the evening’s multiple parties of ten; dinner at Le Chansonnier, which draws foreigners and Cubans alike, runs about 40 CUCs per person. His business partner, Laura Fernández Córdoba, who’s run the restaurant with him since they opened in fall 2011 with the help of French investors, was approving a tableware purchase in the next room. It was easy to envision money flying in and out of the building, in a New Changing Cuba sort of way, and part of what had been flummoxing me during my early weeks in Cuba was starting to come clear. Not every Cuban drives a taxi or tends bar for tourist tips, right? So how on Earth, I had wondered every time I examined all the nonpeso merchandise being hawked at Cubans from every direction, were they accumulating these CUCs?

Part of the answer is remittances, the dollars and euros sent from relatives abroad. The amount of money sent to Cuba annually is hard to track, but some economists estimate the number may surpass $2 billion this year. That means the modern Cuban state is being nourished partly by people who’ve left it. And because both the U.S. and Cuban governments have eased restrictions on émigrés returning to visit family, the Cuban Americans who arrive to weepy reunion embraces at the Havana airport are usually carrying both money and goods: televisions, appliances, duffel bags full of clothing, and anything else their relatives can resell por la izquierda for CUCs.

There’s stealing too, which during the post-Soviet-collapse depression years emerged as a nationwide mechanism for family survival. The verb luchar, which means “fight,” also translates loosely in Cuba to “transfer workplace items into one’s personal possession, which the system impels us to do because our salaries won’t cover a lousy Bucanero.” The standard lucha involves eating, drinking, using, bartering, or selling the items in question. Reform campaigns pushed by Raúl Castro have produced scores of high-level corruption arrests, but one defining quality of any attractive workplace, still, is the nature of the lucha. (“If you can’t look around and find things you can take home or resell,” a woman in her 40s from a working-class neighborhood outside Havana told me firmly, “then it’s not a good job.”)

Nothing about this combination, remittances plus pilfering, is unusual in a small tropical country without abundant raw material for export. Neither is the third important way CUCs arrive in Cubans’ pockets: legal commerce, of any sort, that directly or indirectly procures foreigners’ money. But the government of the Cuban proyecto socialista, or socialist project—in official dispatches that remains the preferred term—has tried for a half century to wall off much of the country from the very buy-sell system that generated that money in the first place. Watching Cubans grapple, as they consider just how many of those walls ought now to be dismantled, is a sobering experience. Take Higuera and Fernández: Their private, for-profit business and their ten employees are legal under the new self-employment laws, as long as they pay their taxes.

But business taxes, in themselves a relatively new concept in Cuba, increase sharply as employers hire more people. The system is weighted against much private expansion while Cubans experiment with new tax and regulation policies, and this question of limits—of just how successful individual entrepreneurs should aspire to become—is a matter of great philosophical and political contention in the New Changing Cuba. Last year, after months of discussions around the country, a remarkable official document called “Guidelines for the Economic and Social Policy of the Party and the Revolution” was published—313 guidelines, to be exact, each one addressing a specific subject, like land use or the civic importance of sports. Guideline number three declares that the “concentration of property” by individuals, as opposed to the state, “will not be permitted.”

What does that mean, exactly? The guidelines don’t say. The cynical will tell you it means the government shall countenance no threat, no real business competition, to the bureaucracies and personal fiefdoms of government companies. The less cynical will tell you that it means Cuba must manage this move toward privatization carefully, while trying to protect the services Cubans have come to expect—that there remains some genuine national conviction in Cuba, no matter how exhausted the SOCIALISM OR DEATH! slogans may now appear to the young, that it’s deeply wrong for certain citizens of a nation to make themselves thousands of times wealthier than others.

“We just don’t know yet,” a veteran University of Havana economist named Juan Triana Cordoví told me, when I asked about guideline number three. “You can do this big bang style, as Russia did, but I don’t think that worked very well. Or you can do it step-by-step, watching what will happen. I am one of the ones who prefer step-by-step. I think of it as testing the stones of the river, one foot at a time, to see if each stone will hold.”

I could see how the guidelines, which were released to great fanfare, might look from a certain perspective like one more saltshaker only a quarter full. This is why so many young people spend a lot of time talking to their peers about their futures in Cuba, about whether to stay or go. There are multiple routes away now, most much safer than little boats pushed out to sea in the dark. Family members wait out the long delays for visas to join relatives abroad. Professionals overseas on Cuban service missions, like the thousands of medical professionals and sports trainers now working in Venezuela, sometimes decline to return home. “You’re always trying to convince people not to leave,” Higuera said. “Always. I have a friend in Madrid now. He got there just in time for the crash.”

What might he and Fernández say, I wondered, if they could talk directly to a Cuban I knew, halfway between their two ages, buying canned tuna this very week for an illegal departure into the Straits of Florida?

Higuera sighed. “I’d say to him, If you’re going to do this thing, do it,” he said.

I had heard this before, after asking other Cubans the same question, and it still surprised me a little; I expected to hear the word gusano, worm, which in an earlier era was the famous public castigation for anybody who abandoned the revolution. But I never did. People would nod and say they understood. Or they’d point to a framed picture—on a wall, hanging from a rearview mirror—of a relative who’d already done the same thing. “But I’d tell him to make sure he’s doing it for himself, not somebody else’s expectation of him,” Higuera said. “And I’d ask him to look hard at what he sees in other places. I really do have hope that things are improving here.”

A week later I went home, and I waited for Eduardo to call me collect, as we’d both arranged, from somewhere in South Florida. Two weeks passed without a call. Then another week, and then another. I tried the Havana cell phone Eduardo had been using, but there was no answer, and finally I called his brother, who immigrated to Mexico a few years ago to marry a Mexican woman he had met in Cuba.

The phone connection was bad, and I wasn’t sure how much was safe to say. I was an American who had befriended Eduardo in Havana, I said, and I just wondered—how he was, that was all. I said he had spoken of an impending vacation. His brother became very excited. “He didn’t make it,” he said in Spanish. He was shouting into the phone. “There was a problem with the boat. El timón. They didn’t make it.”

I didn’t have my dictionary in reach, and I didn’t know what a timón was, and all I could think was that it was like tiburón, which means shark. “Tell me what that means,” I said urgently, and Eduardo’s brother said he didn’t know how to describe it exactly but that it was a boat part, a thing that had failed before they were too far out, and it was all right, they had used the oars, they were back in Cuba. No one was arrested. He was going to wait a while, Eduardo’s brother said, and stay in their mother’s apartment with his wife while he saved some more money.

After we hung up I got the dictionary. A timón is a rudder. I had a picture in my mind now, what had happened to Eduardo: Floating in the sea, the rudder broken, he and his companions had surely discussed it for a time, what would happen if they tried to motor on, toward a landfall they couldn’t see, with nothing beneath them to keep the direction true. Then they turned the boat around, back into the piece of the ocean they already knew, and rowed home.

Cynthia Gorney is a contributing writer for the magazine who frequently reports from Latin America. Paolo Pellegrin is a Magnum photographer who lives in Rome and New York City.