My friend Joni was very definite: “You have to meet Barbara Fein!" I was telling her about how maybe, eventually, some day if we had the money, we wanted to buy an apartment. Listening to Joni is usually a good idea.

So we met Barbara Fein. She introduced us to the bizarreness of real estate in New York City. She also shattered our stereotypes of the sleazy real estate sharpster, turning out to be funny and warm, always turning up in crazy hats or blue nail polish or both, and cheerfully getting on the phone at midnight to complete the paperwork for yet another doomed offer. She popped out of cabs to see apartments with us in Brooklyn, Harlem, the East Side, West Side…and did a pretty good job of pretending to treat us as rational human beings when we kept finding fault with everything. The true test of her wonderfulness was when, after all her hard work, we bought an apartment through another agent, and she was a great sport about it.

You’ve probably figured out, if you regularly read my column, that I’m fascinated by the journeys women take…how did we get to where we are?

Fein is 53, the same age as me. How did she go from being a small fashion-obsessed Brooklyn girl to brokering multimillion-dollar real estate deals in one of the world’s hottest markets?

She and her brother grew up in Brooklyn. Fein went to a public school and dreamt of being a fashion designer. Her parents were both artists with their own businesses. Her mother had an offbeat fashion accessories business called Chatch-ka-lah Enterprises. She died 10 years ago, and Fein now shares her house with hundreds of sculptures.

Her neighbour, a fashion designer, talked her out of a career in fashion, and into going to Boston University (BU). Fein decided she wanted to pursue journalism, but wound up transfixed by the machines in the computer centre. “I took a course called Rhetoric, and the professor made us do all our homework in the computer centre." She got interested in computer science and decided that it was a field wide open to women. After graduation, she went on to BU’s School of Management, where she concentrated on management information systems. She programmed an airline reservation system: “To this day, I can’t believe I did that!"

Back in New York, she started a 20-year software-related career. She programmed a profitability tracking system for JP Morgan Investment Management Inc. She was a software vendor. She started a helpline for clients. And all the while, she collected plenty of business and negotiating skills.

After falling in love and marrying a colleague, she moved to New Jersey. “I hated it. I felt like I had somebody else’s skin on. I lost myself." It lasted five years.

Back in Manhattan, she bought a flat through a realtor friend. That’s how she caught the real estate bug.

Eight years later, she is an agent for Douglas Elliman Real Estate, but an independent contractor. She loves working for herself. “No boss! It’s a 24x7 job, but if you don’t have anything going on, you can take off." As a native New Yorker, she knows the city well.

The Real Deal, a real estate newsletter, reported that in 2013 there were about 27,000 licensed real estate brokers and salespeople in Manhattan alone. That’s quite a crowd, and in several years of hunting for a home, my family has met far too many of them: The Vanisher, who opened a door mid-conversation with us and disappeared into thin air, never to be seen again; Mr Personality, who never got off his cellphone to answer any questions and insisted on walking at full speed miles ahead of my mother, who couldn’t keep up; Mr Offended, who went purple because when we didn’t like a place, we followed Lady Macbeth’s advice, and stood not upon the order of our going but went at once. Why waste time? And there was miracle worker James Keenan, who found us our dream apartment and still comes over for cake. Real estate in the US can never be as demented as it is in Mumbai, but it’s still pretty crazy.

“I understood the dynamics of the market," Fein explained. She finds her job fascinating. It has an impact on people’s lives. “I’m good with process, navigating the process, negotiating…This business is much more psychological than anything.

“There was no emotion in software. With real estate, you’re right in the middle of people’s lives. You have to help them make decisions."

It’s so true. People are odd and so are our priorities. The wallpaper in the kitchen might be the deciding factor, or the laundry room, or the smell in the hallway. And of course, anything to do with home and family is always fraught.

“Everyone thinks their apartment is the Taj Mahal," according to Fein. “And anytime anything goes wrong, they blame the broker."

Sometimes she has to clean up people’s messes. Sometimes she is surprised, despite all her careful planning: “One time I walked into a $6.5 million ( 44.2 crore) apartment with a client and the owner was in the bed naked."

I asked Fein, who clearly enjoys her job, her vision for the future. Like so many others, she’s starting to circle back to her childhood dream.

“The creative part of me would like to do fashion. I’m always trying to find a comfortable shoe for a businesswoman," she said. She took a shoe design class in Cleveland, and designed a “fabulous" pair of shoes, which someone then manufactured for her. These shoes are made for walkin’, like the boots in the old song. They are fake snakeskin and have a blue heel. She gets noticed when she wears them on the street.

Or maybe it’s the blue nail polish.

Sohaila Abdulali is a New York-based writer. She writes a fortnightly column on women in the 21st century.

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