Thomas Motamed, fresh out of law school, found the legal profession too dry.
So at a friend's suggestion, he tried another field he thought might be more interesting: peddling life insurance.
But that got old fast.
"I really didn't like sitting around kitchen tables at night telling people, 'When you die, your spouse is going to be living in a refrigerator box by the railroad tracks if you don't buy insurance,'" Motamed said. "It didn't come out exactly that way, but that was the message."
After a year of selling life insurance, he joined Chubb Corp. — which sold property and casualty insurance — and went on to work at the New Jersey-based company for 31 years, eventually landing the No. 2 job as vice chairman and chief operating officer.
Then, in 2008, conglomerate Loews Corp., controlled by New York's billionaire Tisch family, came calling. It needed a new CEO to run its Chicago-based CNA Financial subsidiary, which sells property and casualty insurance to businesses.
Motamed took the job and moved into the red tower at 333 S. Wabash Ave. in January 2009. He planned to stay until 2014, but, thanks to a renegotiated contract, will stay through 2016. His total compensation each of the past two years has been more than $10 million.
Under Motamed's leadership, revenues are up as the company has made a bigger effort to serve such industries as technology and financial services, and the company's credit rating has been upgraded. It has resumed its cash dividend and also has made an underwriting profit in four of the past five years, the exception being the year that Superstorm Sandy hit the Northeast.
"It was a great choice by Loews to pick him to run CNA," said Pat Ryan, former CEO of Aon who now heads Ryan Specialty Group.
CNA profits also have been helped by cost cutting. More than 700 Chicago-area jobs have been shed since Motamed, 65, took the helm. That represented about a quarter of its local workforce, many of them information technology jobs that were outsourced.
His early years: The son of an Iranian immigrant father and an Irish mother, his parents married young and divorced when Motamed was only 1.
His father, who got full custody, "was in college all day and would come home at night," Motamed recalled. Then his father went to medical school, worked as an intern and a resident and went on to become a surgeon.
"My grandmother wanted me more than he wanted me," Motamed said. He described his grandmother as "very supportive," and said he was essentially raised by his father's parents in Garden City, N.Y., on Long Island.
Motamed earned a biology degree at Adelphi University in Garden City. He was the captain and most valuable player on the lacrosse team. The athletic field is named for him.
"I had a full college career and didn't spend a lot of time in the library," Motamed said.
That may have derailed his family's expectation of him getting into medical school and to follow in the footsteps of his father, grandfather, who was a surgeon to the shah of Iran in the 1940s, and great grandfather. An aunt was a radiologist.
His career path: Motamed held 14 jobs in his first 18 years at Chubb, many lateral moves, and in departments such as claims, legal, training, field operations and marketing.
"That's how you really learn things," he said. Most people today can't do what he did, he said, because the rise in dual-income couples makes it more difficult to move.
How he became CEO of CNA Financial: Loews CEO Jim Tisch, whose company owns about 90 percent of CNA stock, said Motamed had been on his radar since conducting the search that led to the hiring of the guy Motamed would replace.
"We were ready to go out and hire a headhunter when one director sitting next to Tom" at an industry event "asked Tom if he might be interested in the CNA job," Tisch recalled. Motamed said he met with Tisch on and off for five months.