I went to Cuba to witness the end of Fidel Castro’s regime 60 years after the revolution. What I discovered was a new social revolution. Behind a façade of old-style Latin machismo, many young women in Cuba are more feminista than many American women are.

Anouska, one of the rare successful state employees I met, is 34 and has it all worked out. She got rid of the baby daddy early on and is raising a super-bright 10-year-old son, Danny, who has four American names, which he recited in perfect English: “Dennis William Danny Brooks.”

Danny’s mother spells out the reason for her fearless independence: “The Cuban women don’t need men anymore. And some of the men are changing. They can’t be machista anymore.”

Imagine our surprise when our first excursion in Havana was to a magnificent colonial building managed by the Catholic Church, whose male seminarians had recently been relocated to the outskirts of the city. Just as in the U.S., the millennial youth of Cuba have little use for religion. So the church offers a program in the new religion of Cuban millennials: technology.

The building has now been turned into a cultural center offering cheap programs in basic coding, Web-site design, and advice on how to initiate private businesses that are today allowed by the Socialist government. The guide tells us proudly, “We have 161 different enterprises created from our program. The majority of men coming here want to become businessmen. They make small businesses. They are just starting.”­­­­­­

“The Cuban women don’t
need men anymore.”

I try a question in Spanish: “You always speak of businessmen. Are there also businesswomen trained here?” The guide looks chagrined. “Yes, the largest number of graduates are female.” I follow up with “How many projects have been launched by women?”

“The majority of them. Women want to be managers of their businesses.”

It was as if the Old Guard–speak was so ingrained that a guide could not even bring herself to acknowledge the new reality in Cuba. According to one study, seventy percent of “professionals”—lawyers, doctors, pharmacists, engineers, teachers—are women in Cuba. And, as we quickly learned, the women of post-Fidel Cuba are changing so fast that many are fearless about stretching their boundaries until the state catches on and says no.

The church ladies have chosen four star student graduates to “pitch” our group. The first was a tall, handsome Afro-Cuban dude who had inherited one of the fabulous artifacts of the 1950s—an American car—and was making a business of showing up at popular tourist events and luring people to be escorted around in his fabulous pink Cadillac.

I noticed three young women sitting to one side literally jumping out of their chairs and waving at the authorities, anxious to do their pitches. In fact, on questioning, I learned that the vast majority of the entrepreneurial students at this cheap project are young women. Suddenly, Camilla Alonzo Guttierez jumps up. She is wearing ripped jeans, a tongue ring, and tattoos on her arms and legs, and has a cell phone jammed into her hip pocket. Camilla gives the most passionate exhibition of her great love: her tattoo studio.

A tattoo studio is not one of the not one of the 178 categories offered in the Lineamentos—new occupations announced by Raúl Castro in 2010, when, for the first time since the revolution, Cubans were allowed to be self-employed. So, Camilla’s business isn’t strictly legal. Camilla claims it is skin art, therefore protected as an artistic business.

Many are fearless about stretching their boundaries until the state catches on and says no.

I was ready to sign up for a tattoo that day. But Camilla is not a tattoo artist. She is the manager. She has hired two tattoo artists. Many of the women graduates aim to rise to managerial positions. Camilla’s fabulous pitch is followed by a young woman with a big idea: tourists could rent her van to navigate the island, seeing what might otherwise be forbidden.

There’s only one hitch in all of this galvanized mercantilism among young women: once they finish their month-long course, they run into another wall. It’s difficult and expensive to promote and sell their wares outside of Cuba or over the Internet. Fortunately, Cubans are experts at reading between the lines to find where they can wiggle.

The Explosion of Private Business

Raúl Castro only began to move decisively out from under his venerated brother’s shadow in 2011, when Fidel was ailing. Suddenly, 178 occupations could be private.

Cubans were permitted to rent rooms as a bed and breakfast and to run small cafés in their homes—a 1990s government reform reinstated by Raúl. From a few tables, these sometimes mushroomed into restaurants occupying one or two floors of a family’s home, with maybe another floor built on to rent as a casa particular. The first recent president without “Castro” in his name, Miguel Díaz-Canel is strongly committed to expanding the private sector. His government’s premise is that Cuba’s social and economic leveling protects them from the U.S. exploiting emerging class differences.

Tattoo studios are not included in the new guidelines. Older Cubans view this generational craze as disrespectful, even deforming. But today, many young women are prepared to overlook former restrictions. That’s what makes Camilla’s story fascinating. To get around the U.S. embargo, she has developed a supply chain of paints and needles coming from Mexico and Panama to build her underground business. She and her girlfriend helped organize last year’s L.G.B.T.Q. march, in revolt over cancellation by the state of a planned gay-pride event.

The Mother-Son Business Model

One night, we were taken to a café, where a five-piece Afro-Cuban band was playing “Bésame Mucho.” A teenage boy appeared with a very young woman who opened the boy’s violin case and handed his violin to him like a jewel. She hopped up on a barstool and fanned herself nervously as she watched him perform, backed by five yellow-toothed musicians.

Maria, the mother of this 17-year-old prodigy, is the devoted manager of her talented young son with his orange brick-topped ’fro and sweet sounds. She is introducing him to bands; he plays two or three nights a week, even while in school.

Her boyfriend, Yanis, dreams of someday starting his own private business as a guide, but for the time being he works as a customer-service agent at a state store. Maria is supporting him. It is clear which male she is counting on as her future provider.

Later, I run into Maria in the state department store, which sells kitchen goods, soaps, perfumes, and men’s shaving lotion at unattainable prices. I suddenly feel a tug on my T-shirt. “I’m the mother of the violinist,” she reminds me.

She is with Yanis, who is 34, two years her junior. In English, he tells me they met 10 years earlier, when they worked at the same state business. She dismissed him as a romantic partner. For how long? Five years! He told her, “I am a patient man.”

But Yanis is cheerful today because for the first time in their 10-year friendship Maria has agreed to join him on the grocery run. They will grill a big fat American chicken. One baby step closer to a live-in non-marriage.

Yanis also tells me, “I want to be able to make my own enterprise as a guide for tourists.” He does guiding on the side but receives no salary for it. “Maybe when I’m 40 or 41 I can have my own business as a tour guide.”

They have been a couple for the last five years. “But still,” Yanis laments, “we live in separate houses. I am her boyfriend. But her son is her husband.”

Gail Sheehy is a journalist, lecturer, and the author of 17 books, including Daring: My Passages—A Memoir