The highly educated taxi driver
Education is free in Cuba, and standards are incredibly high. It’s common to meet people with Masters degrees or even PhDs, but research jobs are hard to come by and are poorly paid. If you have access to a car or a rental property you can make many more times the state salary by ferrying tourists around or renting them your spare room. Highly qualified taxi drivers are one of the most famous Cuban tropes, as it’s one of the best-paid professions on the island.
Decades of living under embargo means that everyday items can be very hard to find. In turn, this has made Cubans incredibly good at finding inventive solutions to common problems, creating an island of fixers. Whether you want tickets to the ballet in Havana or a restaurant recommendation, bartenders are great people to ask.
The street hustler
Anyone working in the tourist economy in Cuba has access to far greater wealth than those who work for the state. This means that the incentive to get involved is incredibly high, even for those who can’t get a job in formal roles in a hotels or with a tour company. As a result, hustlers known as jineteros are a reliable fixture in tourist hotspots. They’ll take you to restaurants, bars, or hotels in return for a commission from the owner of the establishment, the cost of which will likely be added on to your bill.
The Cuban–American entrepreneur
Cuban emigration to the United States has been a constant theme since before the revolution, but recent economic reforms have enticed some Cuban–Americans to make the return journey. They might not be coming back to live on the island permanently, but instead to set up businesses serving the growing tourist industry, while leveraging their old family contacts.
The motherly B&B owner
Staying in Cuban B&Bs, known as casas particulares, is the best way to see the island and get to know the locals. The most important character in the casa is often a matronly woman who does everything she can to look after her guests. Be prepared for unsolicited advice on everything from dating to fashion, as well as helpful tips on what to see in whichever Cuban town you are visiting.
The communist devotee
Cuba remains a communist country, and there are plenty of people who remain convinced that the revolution was the best thing that ever happened. Many Cubans criticize the government for the state of the economy or the one-party system, but there are others who will wax lyrical about the Cuban Communist Party for hours. If your Spanish is up to it, a sit-down chat with one of these committed communists is a real eye-opener.
The internet card salesperson
In Cuba, most people can only get online at one of the limited number of WiFi hotspots, and the cabins where you buy the card that you need to use them are only open at certain times of the day. As a result, enterprising locals (or price-gouging resellers, depending on your point of view) stock up and sell them on at a profit outside of normal trading hours.