He's Attorney James Sokolove

Wherever he goes these days, Sokolove carries two battered folders in his leather shoulder bag. The first folder is for business, the second for everything else. Filed in the latter is a one-page list of goals, typed as dutifully as a high school book report. He prepared it for a life coach he recently hired to help organize his priorities. ("I sort of went through a thing when I turned 64," Sokolove says.)

Turning his mind once again toward retirement, Sokolove has cut back his hours in the office by two-thirds, freeing up his schedule for some more-satisfying pursuits, including spending more time with his 11-year-old daughter and his wife, who in March will open her second restaurant, on Tremont Street in the South End. He’s also working with Stanford Law School to fund a philanthropic project, Roadmap to Justice, that aims to make the civil justice system more accessible to poor people. Sokolove says he’d be surprised if he doesn’t experience a "liquidity event" that would buy him out of his business within the next three years.

Sokolove’s commitment to getting more involved in outside pursuits led him to Manchester, New Hampshire, on a bright afternoon this fall for the second of two days he spent canvassing for Barack Obama. He’d given a good deal of money to Democrats—$250,000 over the past decade—but found a new thrill knocking on doors. Yet he couldn’t seem to prevent his thoughts from sometimes circling back to his business. "I told my wife how many people have front steps where you can fall," he said, as his car rolled into a quiet neighborhood near the river.

Later Sokolove introduced himself to an elderly gentleman who was out walking his dog. "Not the lawyer on television?" the man asked. "I’ll tell my wife—she won’t believe it." Before long, Sokolove had invited himself into the couple’s living room, where they were happy to answer his too-personal questions: What sorts of medications were they taking? Why was their retirement money in stocks and not bonds? (Sokolove has added financial mismanagement to his list of practice areas.) Standing up to leave, he and the man embraced in an awkward hug.

Outside, Sokolove was pleased. "Sitting in houses and talking to people. This is my father," he said. He seemed to feel he’d just made the kind of old-fashioned connection that had always eluded him. Of course, it was something altogether different. What the lawyer from TV had forgotten was that he’d already been in that living room at least a hundred times before.         

Staff writer Francis Storrs detailed the Beacon Hill exploits of con man Clark Rockefeller in the November 2008 issue.