Dozens of people every week send e-mails to Michelle Singletary, the Washington Post’s chief personal-finance columnist. They come from CPAs, who pass her columns to clients, from brides, who worry about ballooning wedding budgets, from boyfriends, who fret about free-spending girlfriends. This one launched a book:

A woman wrote that her boyfriend asked for a loan. She dipped into her 401(k) retirement plan for $10,000. They split. She asked for the money back. He got hostile. “Should I pursue it?” she asked Singletary.

Singletary’s response: “What were you thinking when you lent that amount of money to a boyfriend? Of course he’s not going to pay you back. Let it go. Use it as a lesson.”

Singletary has been giving old-school financial advice twice a week in her Color of Money column, begun in 1997. She just won a Best in Business award from the Society of American Business Editors and Writers for her 2007 columns that helped shut down an unlicensed mortgage firm.

Other than Singletary’s award, the Post was shut out in the business awards. The New York Times, LA Times, and USA Today won for overall excellence. The New York Times won ten awards. The Post’s showing can be blamed on lack of attention to financial news and the exodus of experienced writers and columnists in recent years. Singletary’s win and a 2007 Pulitzer for columnist Steven Pearlstein don’t obscure the section’s shortcomings.

Singletary has been a standout since she came to the Post in 1992 from the Baltimore Evening Sun. She has a master’s degree in business from Johns Hopkins but got her wisdom from her grandmother, “Big Mama.”

Singletary’s parents abandoned her and her four siblings when they were all under eight. Grandmother Marie Kelly took them in and raised them on her nurses’-aide salary in a working-class neighborhood in west Baltimore.

“She was a cross between a guardian angel and a drill sergeant,” Singletary says. “She was great with money. She was never late for work or paying a bill. I wouldn’t be where I am today without her. When I write my column, I’m always thinking of her.”

Growing up, Singletary battled rheumatoid arthritis. Some years she was schooled at home. She went to Baltimore’s Western High her last two years, graduated in 1980, and won an academic scholarship to the University of Maryland, awarded then to one minority student in the state by the Baltimore Sun.

Singletary always had an inkling she had a writing future. In sixth grade she wrote Dear Michelle, her first advice column. At the University of Maryland’s school newspaper, the Diamondback, her editor was David Simon, who would go on to the Baltimore Sun, then attack it in his TV show The Wire.

After college, Singletary went to the Evening Sun. She covered zoning, then religion, then business. She learned a lot about bankruptcy.

“Bankruptcy is one of the most fascinating beats out there,” she says. “You get to see everything.”

Like Johnny Unitas’s dirty financial laundry. Checking filings at court in the late 1980s, she came upon the bankruptcy papers for the famous Baltimore Colts quarterback. She broke the story.

The Post hired her in 1992 when many big companies were filing for bankruptcy. She broke the story of the bankruptcy of then Baltimore Orioles owner Eli Jacobs.

The Color of Money column was syndicated in 1999 and now appears in 125 papers. Singletary’s written two books, Spend Well, Live Rich and Your Money and Your Man.

How has the column changed?

“It hasn’t,” she says. “It’s the personal-finance conversation we should be having over the dinner table with our spouses or children or friends.”

And the essence? “Live below your means, for God’s sake.”

Just like Big Mama.

This article appears in the May 2008 issue of Washingtonian. For more articles in the issue, click here. 

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