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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.

It was a reminder that there’s always a grown-up somewhere who knows how to beat the system, and if you can just find that grown-up and ask questions, you can help other people beat it, too. I don’t think of myself as the grown-up, but every week, I still feel like I’m searching for the grown-ups who know the answer to whatever thorny consumer question is bedeviling our readers.

What makes for a good column?

When I think about personal finance, there’s a kind of a Venn diagram of possible topics: things that are really expensive; processes that are really complicated; and decisions where emotions can lead us astray if we aren’t careful. I like to think that when I’m at the center of that diagram, I’ve found the right topic.

And then there’s the matter of voice. The best compliment anyone can pay me is to say that my column sounded like I was there in the room with them, explaining the topic at hand. I want it to feel conversational, and not lecture-y, preachy or didactic. That doesn’t mean it’s always friendly — I try my best to punch up at institutions or entities that can take it and deserve it.

If I can find the right topic, and do it in the right voice, I’ve won the week.

Last month, an article by New York magazine’s financial advice columnist on how she was scammed out of $50,000 went viral. Do you think you would’ve fallen for that scam?

Never say never. I’m constantly telling myself that there’s never a reason to rush to do something right now. There’s pretty much always time to call one or three or five people smarter than you or just calmer than you who will ask you levelheaded questions and try to pull you back from the edge of making a big mistake.

What writers and publications do you read to stay on top of your beat?

I read The Wall Street Journal religiously. I’m a big fan of Ramit Sethi, who’s the author of the book “I Will Teach You to Be Rich” and a newsletter writer. I love reading Michelle Singletary, who writes the personal finance column for The Washington Post. And I also really like the attitude and the message of Tori Dunlap, who most people know from Instagram and TikTok.

What trends are you watching?

All of the people who’ve been in the work force for their entire career without a traditional pension are starting to retire, and a lot of them are going to run out of money. The question of what’s going to happen when that happens is deeply concerning.

I’m also interested in all of the work that Conor Dougherty and other Times colleagues have been doing around our inability to build more housing in a reasonable fashion. It’s not clear where and how people in their 20s and even 30s are going to buy homes.

Anything else you want to add?

If people are seeing things in the world that don’t make sense — whether they think corruption needs to be exposed, or if they just want to say, “I can’t be the only one who doesn’t understand this thing, could you explain it?” — it’s so helpful for me to know. Some of the work I’m most proud of started with a reader comment on one of my columns. We’re all in this together, and none of us are as smart as all of us.