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When Ron Lieber arrived at The Wall Street Journal’s office in 2002 for a job interview, a couple of editors immediately sized him up.

“They said, ‘We know what your beat is: beating the system,’” said Mr. Lieber, who had last worked as a senior writer for Fast Company covering management, design and careers. “And now you’re going to come here and do that for us.”

After cofounding the Personal Journal section of The Wall Street Journal and writing a separate money management column, he was hired by The New York Times in 2008 to take over Your Money, a personal finance column. Sixteen years later, he has gained a reputation for offering readers advice — often tinged with his own experience — on headache-inducing issues, like how to navigate the maze of paying for college or prepare for life after a layoff.

“I love introducing readers to characters who they might not think would be the subject of money columns, but who are actually perfectly suited to teach us a thing or three about how the world works,” said Mr. Lieber, whose column appears online and most Saturdays in the Business section.

As a columnist for The Times, he has witnessed two recessions and a pandemic. (In 2009, he even wrote about how his own financial planner had been charged with fraud.) In a recent conversation, he shared the unexpected lessons he had learned in writing the column and the topics he thought might soon dominate the world of personal finance. These are edited excerpts from the conversation.

How did you first become interested in finance?

When I was a high school senior in Chicago applying for financial aid for college, I found my way to Roger Koester, who was an associate director of financial aid at Northwestern University. He had an after-hours side gig in his office; in exchange for $45, he’d explain the whole financial aid system to local families who were trying to understand it. He knew exactly what he was talking about and gave me terrific advice.

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