THE BLOG
08/12/2015 04:22 pm ET Updated Aug 12, 2016

The Last Mile to Havana

Distance -- and its absence -- has always been a chief protagonist in the U.S.-Cuba relationship. Historically, we see its mark in everything from a handful of brief, but eventful U.S. occupations, to economic and cultural ties that have existed over time, and the hemorrhaging emigration of the last 56 years. To this day, several thousand Cubans annually attempt to flee to Miami in makeshift rafts, hoping that the borders and obstacles separating the two countries can be shortened by willpower alone. At times, our worlds have been disarmingly far; at others, tantalizingly close.

Even for Americans who do not understand or care about what until recently had been the prolonged, immovable state of our affairs with yet-another-tropical-paradise-gone-awry, the 90 nautical miles that separate our two countries have become a well-known trivia fact. And yet for Cubans both in exile and on the island, that same distance is tainted by an acute pain -- of separation, struggle, loss, inequity, insult, theft -- that has spanned generations. Those wounds have remained open, perhaps becoming duller with time and habit, but never disappearing, rather morphing into new versions of the same, ever-present ghosts.

Given the discussions over recent months, the ongoing normalization of U.S.-Cuba relations, and the many important questions ahead, the topic of proximity has once again been placed on the table for our degustation.

As most things in the real-life Macondo that is Cuba, the beginning of this shift in December 2014 was mired with contradictions and absurdities - traded spies and prisoner releases, covert meetings with papal involvement, ongoing acts of artistic and political repression in Havana, grandstanding of the old political guard on both sides. But as embassies reopen and legislative actions continue to chip away at the U.S. embargo, this rapprochement has become no less complex, but increasingly more concrete.

Travel restrictions have lifted, ferry, cruise, and flight services to Havana have been renewed for the first time in decades, U.S. credit cards may be accepted on the island sooner than expected, and diverse private sector institutions -- Airbnb, Netflix, technology powerhouses, banking institutions, agricultural interests, telecommunications giants, et al. -- have already sauntered across the Florida Straits to explore. Cuba is starting to feel like a neighbor, for many of us in a strange, complicated, but déjà vu kind of way.

Ultimately, the shortest distance between two points is a straight line, and this resembles the beginning of an exercise in basic geometry.

Cautious optimism

Just about the only thing we know with certainty is that the road ahead is knee-deep in unknowns.

What lies ahead could be a dramatic disaster with all the trappings of a Euripedean tragedy or a slow, devastating disappointment. Cuba could become a kleptocracy, a plutocracy. The country could follow all too closely the model of China over Vietnam, granting no increased political freedoms even as the economic vestiges gives way. Dissident and opposition movements on the island could themselves remain disorganized and fragmented, never forming a coherent political alternative to incumbent power. The infrastructure necessary to create a viable economy -- banking, wholesale markets, interaction with International Financial Institutions (IFIs), et al. -- could either never materialize, or come in fractured, ineffective and corrupt pieces. The Cuban government could continue its political censorship and detentions, conceding little to the State Department's human rights agenda.

However, in equal measure, this moment also represents the opportunity for average Cubans to be included in a global discourse from which they have been entirely sidelined, and to have their hunger for information, technology and growth answered with increased flexibility and connectivity. This could be the opportunity to double down on the ingenuity and optimism of average citizens to create a more inclusive and innovative economic model. This could be the time to support, engage and help locals define the kind of society they want because for the first time in decades, there are increasing pathways for interaction.

In a sense, this is the moment to test what levers and incentives adequately chip away at Cuba's system and its lack of opportunities and civil liberties in exchange for the desired fruit of participating in a regional economy the country is desperate to enter. Moving forward, we must be careful not to give in to willful blindness -- a state in which we ignore threats and contradictions so as to feel better about a situation -- but rather speak clearly about the motivations, shortcomings and tradeoffs on the table. That said, the perils are many and the concerns are legitimate, but in the words of Nelson Mandela, "May your choices reflect your hopes, not your fears."

Eyes on Cuba

"The last mile" is an industry term used to denote the final leg of a communications, shipping or logistics network, the part that physically reaches the front door of an intended recipient. It is the most expensive and labor-intensive part of these complex systems. It is where bottlenecks occur, where implementation can be extremely challenging, where some are left behind and most mistakes are made. In this context, we shouldn't look at U.S. actions, but rather at "the last mile" in Cuba as the true test of recent and future changes. How will Cubans be impacted, not just foreign companies or the government? Will ordinary citizens have access to economic opportunity? Will this engender civil freedoms and protect their rights?

Technology will be an important barometer, as will entrepreneurship. Cuba remains the least connected country in the hemisphere, with Freedom House estimating that approximately five percent of the population has regular access to the Internet and less than 20 percent own cell phones. Granted, Cubans have found clever and at times incredible ways of circumventing obstacles - monopoly, cost, censorship, restrictions -- to gain access to information, connect to each other, and engage with the outside world through technology. But, when and how the government begins to change its stance toward access will be a landmark of real vs. feigned forward movement. Earlier this summer, 35 public Wi-Fi areas opened across Cuba, for example, but Google's repeated offer to radically improve the country's communications infrastructure remains unanswered. Ultimately, Cuban citizens are clamoring for technology and connectivity and the question remains: what will it take for accessible and uncensored Internet in Cuba?

Entrepreneurship will be an equally important needle to watch. As limited private enterprise became permitted in recent years, Cubans have jumped at the opportunity to launch small businesses. In response to the most immediate market forces, the first waves of entrepreneurship have mostly been focused on tourism services and the food industry, but now there is increased movement toward providing more complex professional services. Companies in Europe and even Miami have started to outsource to Havana, with work ranging from graphic design and software development to robotics and pharmaceutical research.

Notably, the small business sector in Cuba is almost entirely financed by remittances, donations, small loans, or informal equity arrangements from relatives or friends abroad, given that the country lacks almost all of the necessary infrastructure to create and sustain a true entrepreneurial ecosystem. Whether these characteristics -- including small business loans, banking and financing regulations, a legal framework to support and protect investments, et al. -- are enacted and upheld is perhaps one of the most acute temperature readings of what change could mean.

Ultimately, Cuba is not a Communist theme park, but a nation in crisis. The next steps will be complicated and the destination is not guaranteed. But for the first time in decades, families around breakfast tables in Havana are cautiously entertaining a different conversation. They ask questions -- somewhat rhetorically -- about the possibility of accessing the Internet at home, incorporating their small business, exporting the goods they make, or what American tourism will bring. They don't have the answers, but the questions themselves have changed and in a matter of months, their family and their country don't feel as circumscribed. And suddenly, the distance between us is shortened once again.