Cubans are a proud people - feisty and industrious. They stood up to their overwhelmingly more powerful neighbour and achieved higher literacy, life expectancy and better healthcare in comparison to their Caribbean neighbours.
But their overconfidence is a blessing and a curse. It brings to mind the joke told about certain Middle Easterners: If you buy a Cuban for what he's worth and sell him for what he thinks he's worth, you'll become a multi-millionaire.
Like their esteemed leader of five decades, Fidel Castro, Cubans are in denial about the gravity of past failures, before and during the revolution, and the enormity of future challenges, with or without the Castros.
And they're also terribly polarised between two mind-sets: Those who relish standing up to the US along the lines of "David and Goliath", and those who seek to ride the dragon instead of fighting it; those, who cherish the good old days of resisting the empire, and those who recall the glorious days of an enthralling empire; those who boast of exporting doctors, and those who toast the American dream.
Communism is passe
After 20 years of difficult transitions following the collapse of its closest ally and patron, the Soviet Union, the Cuban regime is trying hard to maintain its dignity and pride while at the same time attempting some real and painful changes that could go beyond communism, to introduce a new form of state-based/sponsored capitalism.
To that end, Cuban President Raul Castro has relied on the church and the military.
On the church front, the first step is to gain Western support and neutralise the sceptics especially in Washington and Miami. Havana has used the visit of Pope John Paul II in 1998, and Benedict XVI in 2012, to underline openness and religious freedoms. The former Cuban Cardinal was also instrumental in rallying Washington to give Raul a chance to change.
On the second front, depending on the military for the management of privatisation and foreign investments has added a new level of ambiguity to an already tightly guarded process. Clearly, discipline, loyalty and kinship are key; not free competitive entrepreneurship.
It's not yet clear as to where all of this leads, but the end result is unlikely to be communism or liberal capitalism. What is clear is that the regime in Havana hasn't come around to fully trusting its people's best instincts or free will.
The Cuban leaders prefer the example of Vietnam than Ecuador, or China to Brazil. They reckon tightly managed economic liberalisation a la Vietnam, ie, without much of a political openness, is the best and most secure way forward.
They're avoiding the "mistakes" of their former patrons by not carrying out political and economic liberalisation simultaneously (Glasnost and Perestroika), that led to the removal of the Soviet Communist party from power and eventually the collapse of the Soviet Union.
Some of the Cubans I've spoken to warn of unrealistic expectations and potential chaos. They are convinced that an evolutionary not revolutionary change is safer and more secure.
Others seek shock treatment leading to a clean break with the past. They consider all of Raul's changes to be no more than cosmetic attempts to beautify an ugly reality.
For now, it's the regime that's dictating the pace and breadth of reform, albeit under popular pressure to produce better results.
In the absence of organised political opposition on the island, expect slow and incremental approaches to persist.
Which brings me to another joke: Why is there no Cuban Olympic swimming team? Well, it's because all those who can swim are already in Miami.
Oh, no wait, that's not the one!
The joke is on you
American political comedian, Stephen Colbert, jeered in his usual sarcasm after Fidel Castro stepped down: "Way to go America! Our plan to slowly deteriorate his health over the course of 50 years is working."
For five long decades Washington has tried relentlessly to unseat Castro and change the Cuban regime, to no avail. But trying again and again and again and expecting a different result, isn't funny. It's foolish.
President Barack Obama vowed to extend a hand if the likes of Cuba unclench their fists. And he did take a number of measures to relax relations and allow for greater contact between Cuba and Cuban Americans as I mentioned in my last piece on US Cuban relations.
He even shook Raul's hand in South Africa a few months ago at the funeral of Nelson Mandela.
The handshake could've paved the way to the mutual unclenching of fists: A courtesy that would lead to diplomacy, shaking the tired old way of doing politics.
But it seems neither side is ready for the next big step.
Obama is drained by Republicans, who vehemently oppose his domestic and foreign policies and by an uncompromising Cuban American lobby that insists on regime change in Havana.
And Castro is preoccupied with the economic and political overhaul of Cuba's antiquated and dysfunctional system.
And yet, some small and tangible steps are possible considering that a majority of Americans and Cubans want a new opening and bilateral normalisation. Whether it's a "civilised relations" as Raul calls it, or one based on mutual interest and mutual respect, as Obama likes to phrase it.
This could start with Obama taking Cuba off the list of countries supporting terrorism. After all, Cuba has become an exporter of doctors and medical workers, not mercenaries: some 50,000 of them.
Such a step doesn't require Congressional approval. And it could lead to the release of US government "contractor" Alan Grossman from prison and perhaps other political prisoners.
Imperialism is passe… in Latin America?
US-Latin American relations have been changing rapidly over the last couple of decades.
Washington has seen its credibility and leverage shrink as democratically elected leftist and nationalist leaders, emboldened by the rise of Brazil, take the continent's affairs into their own hands.
US Secretary of State John Kerry has admitted in a recent Americas summit that the "Monroe Doctrine", which underlined US hegemony two centuries ago, no longer exists - an important declaration that went largely and bizarrely unreported according to Latin American expert, Philip Brenner.
Indeed, the days of the "Banana Republics" are over. US attempts at interfering in their local affairs is terribly unwelcome and will be confronted head on by the Latin American nations.
Washington is already isolated in the Americas on the questions of Cuba and Venezuela. And it could be even more isolated as the countdown to the next Americas summit begins.
The Community of Latin American and Caribbean States (CELAC), which was established as a rival to the US-dominated Organization of American States (OAS) and the Summit of the Americas, has just concluded a successful summit in Havana this winter.
The days when the US Latin America summit convened without Cuba are over. At the last Summit of the Americas, in Colombia in 2012, leaders criticised Obama for the US economic embargo of Cuba and made one thing clear: There is no point in holding another such summit without Cuba.
Marwan Bishara is the senior political analyst at Al Jazeera.
The views expressed in this article are the author's own and do not necessarily reflect Al Jazeera's editorial policy.