He Thought He’d Be Your Rabbi. Now, He’ll Get You a Mortgage.

So he thought he might be a camp director or a rabbi at a Hillel, a Jewish organization on college campuses. But as much as he loved text study and translation, he eventually figured out that his outspoken nature and skills were not a perfect match for the rabbinate. Classmates found internships and jobs that suited them, and he wasn’t always getting the offers that he believed he was qualified for. “I didn’t understand that,” he said. “It didn’t feel right.”

Over a lunch of falafel and shwarma-spiced fries, Mr. Frankel, 44, eventually allowed that he had a few rough edges back then that he had done his best to smooth out in the years since.

Still, he left rabbinical school with something greater than a career: a spouse. He followed his wife, Erin, a cantor, to Evanston, Ill., where they bought a townhouse (fully attached) and he began selling real estate.

Or trying to, at least. It’s not exactly easy to show up in a new place, where you know no one, and be a rookie in a business built on relationships.

“It’s one of the things you do when you’re naïve and oblivious,” he said. “The model was, make phone calls once a month, and ask everybody if they know somebody. It wasn’t a terribly popular thing, but I didn’t know anyone, so I didn’t have that many calls to make.”

He officiated at a few marriages on the side, and some of the betrothed bought homes through him. His first commission came nine months after he arrived in the Midwest, and it took him four years to match his wife’s earnings.

The couple had two daughters, now 9 and 10, and moved to Phoenix in 2009 (detached house, rental). Mr. Frankel had turned to commercial real estate, in search of a more family-friendly schedule. That turned out to be an ill-timed move, given the state of property markets at the time.

The family then moved to the Boston area (another rental), where Mr. Frankel ran a Jewish nonprofit but ultimately…

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