Personal finance reporting can be funny

Brian O’Connor is the syndicated Funny Money columnist from The Detroit News, a Knight-Bagehot fellow from the class of 2001, founding managing editor of Bankrate.com and author of the new humorous personal finance book, “The $1,000 Challenge: How One Family Slashed Its Budget Without Moving Under a Bridge or Living on Government Cheese.”

The book is selling well and garnering good reviews, including one from Go Banking Rates that called it “a hilarious and savvy guide.”

Publishers Weekly said the book’s advice and approach is better than Suze Orman and concluded that, “This funny, pragmatic guide will have you laughing all the way to the bank.”

O’Connort is the winner of the inaugural Christopher H. Welles Memorial Prize for business writing from Columbia University, as well as a winner of the Best in Business award from the Society of American Business Editors and Writers.

O’Connor also is a two-time winner of the award for humor writing from the National Society of Newspaper columnists. A native Detroiter, he is a graduate of The Roeper School in Bloomfield Hills, Sarah Lawrence College and Columbia University’s Graduate School of Journalism

How did you start writing about personal finance topics?

In the 1980s, as a copy editor and assistant business editor at two South Florida dailies, I edited the Monday business tab sections, so I handled a lot of personal finance copy. When I became the founding managing editor of Bankrate.com, my focus shifted to all personal finance, all the time. After moving back home to Detroit to work at The News, the personal finance job opened up here and it was a perfect fit.

How do you come up with your ideas?

Usually in desperation. There are about three topics in personal finance at any one time that everyone is covering, so you read the same story over and over again. I try to avoid those, while looking for something that can be personal. And, because my column is a humor column, too, it has to be something where I can find a funny angle.

Do you find yourself writing about the same topics over and over again? In other words, how do you keep it fresh and new?

When I was running Bankrate, every Wednesday we released our new mortgage stats, so the main feature had to tie into home loans. I thought it would be impossible to get a new story every week, but if you dig deep enough and look broadly, there is always some new angle you can explore. If not, there is always some news event that makes it a good time to take a new look at an old topic. I saw a good feature last week on emergency savings that was tied to the government shutdown. That is a basic bread-and-butter personal finance feature, and advice that people widely ignore. But if the writer makes it timely, it could be that learning moment for some readers to finally take action.

You use a lot of your own personal situations in your writing. When did you decide to do that and how does that help you with your readers?

When I got the Your Money gig at The News in 2007, the column came with the job. Now, I’d read a lot of personal finance columns between 1985 and then, and many of them were just as dry as dust. Editing them was murder, and I can’t imagine the readers felt any more enthusiastic about 850 words on “selling short against the box” to avoid taxes on stocks. (By the time I actually understood what that was, by the way, it was illegal.) When I sat down to do my first column, I just couldn’t be “that guy” so, being a naturally born smart aleck, I tried humor. And to find any humor in most financial topics, I had to personalize the situations.

My wife was less than enthusiastic about becoming a central figure in the column, so I refer to her as Mrs. Your Money, which creates enough distance to keep the peace at home. When someone asks, she says, “I’m not Mrs. Your Money, but she’s a character based on me.” It’s basically the same thing Erma Bombeck and Mike Royko did with their families and alter egos, plus my wife is much more attractive than Slats Grobnik.

What’s the hardest thing about personal finance writing?

First, for me, it’s finding humor, and finding the right situations that can be addressed through humor. That can be very, very difficult during a bad economy, as I found out. When the economic meltdown was confined to a credit crisis in 2007, I wrote a Q&A that was one of my funniest columns, and readers love it. I had dozens of phone calls from non-traditional business readers, saying they laughed out loud. A year later, I reprised it about the recession, and the phone calls were all bitter, angry or obscene (except for the ones that were bitter AND angry AND obscene). When it was happening to them, readers didn’t find the recession to be the least bit amusing.

The other hard part for me is getting down to a real answer for readers. Every column poses some kind of question or problem, and I want to lead my readers to making the decision that works best for their situation. Because I was a Knight-Bagehot fellow at Columbia University, my first impulse is to run the numbers and do the math, to see what gives the best return, or the lowest cost, or the best outcome. Going from writing about basic personal finance concepts into doing the actual math can be a challenge, especially in finding data and constructing good, accurate scenarios. But I just can’t write a column about whether it’s better to buy or lease a car without looking at the long-term best outcome for the buyers, then discussing the individual situations where buying or leasing makes sense.

My own hard-and-fast rule is that every column I write – and pretty much every story, too – absolutely must contain dollar signs. Otherwise, you’re just not giving readers the bottom line.

What do you do when you write something that you later regret?

Besides trying to blame someone else? The only thing to do is ’fess up, admit the mistake, apologize if that’s called for, and get the right information out there. I had a disastrous column about flood insurance a year ago, and I had to write another entire column just to correct the misinformation I was given by some pretty big insurance companies. But it’s my column, so it’s my mistake. I just try to focus on what is going to make things right for my reader, to tell them where I went wrong, and make sure it doesn’t happen again.

Of course, with humor, someone always gets offended. I did a column based on the last pope’s retirement, and I referred to him once as “Bennie.” Now, my two aunts in the convent and my cousin the priest were OK with it, but I got a rash of complaints from around Detroit.  (Oddly, the syndicated column that goes through Tribune Content Agency got a total of zero gripes.) My bosses apologized to callers, but I refused. Going into a family newspaper, my jokes already are pretty tame, and unless I’ve been purposely mean spirited, my attitude is, “(Screw) ’em if they can’t take a joke.” Especially since I’m the butt of nearly all the humor in my column.

How did you decide to put this into book form?

I did 10 columns in late 2009 where I aimed to cut $100 from my family’s top 10 monthly budget categories, and they formed the basis of the book. I was hoping it would be a big enough gimmick that it could be the basis for a book, since there were all these stunt books coming out at the time, such as “My Year Without Toilet Paper” or “My Year Without Spending” of the woman who made love to her husband every day for 365 days straight. One of the things that’s said about writing a newspaper column is that it’s like being married to a nymphomaniac — as soon as your done, you just have to start all over again — but I’ve never wanted to take it THAT literally.

Fortunately, I did manage to save $1,000 — barely — which wasn’t a given going into the project. The columns were a big hit with readers, and they won the Christopher Welles Memorial Prize from Columbia, as well as a SABEW Best In Business award. But the book proposal languished for three years until I happened to link up with the right book agent, just by pure accident, and then the book wound up going to auction. But it wasn’t ever guaranteed to be a book project.

Did you change or update any of the columns for the book?

All told, the original 10 columns, plus a first-week introductory piece, came to about 5,000 words, and the folks at Portfolio-Penguin wanted at least 50,000 words for the book. My original plan was to open up the columns by expanding the advice, which is the bulk of the book. But since it’s also first-person, it’s got a bit of a memoir approach, too, and that required writing a first chapter to set up the characters of my family, and our situation of having moved to Detroit — which was basically Ground Zero for the economic meltdown — to take a newspaper job at the outset of the Great Recession.

How did you organize the book’s content?

The hardest part to write was the first chapter, setting up my whole family situation. First you’ve got to know these people well enough to care about them, then you’ve got to understand how they got to this situation, and what they want. It was daunting, but fortunately my fifth-grade girlfriend is a writing teacher in New York, and she’s married to a guy who teaches screenwriting and wrote for “Seinfeld.” They pointed my in the right direction for what originally was the first two chapters, but my editor, Maria Gagliano, was smart enough to ask me condense it into one chapter, which took three different attempts.

After that, the book followed the order of the columns, since each chapter ended with a running tab of what savings I’d found and how much more I needed to cut to get to the $1,000 goal. My strategy for expanding the chapters was that I divided all the savings strategies into three categories, ranging from how much people need to cut to how desperate they were to find savings. So we had three different approaches in each chapter: “Freeing Up Cash;” “Making Ends Meet;” and “Pinching Pennies So Hard That Lincoln Gets a Headache.”

What do you like, and dislike, about the current state of personal finance writing?

I think there’s a really good crop of columnists that I see out there doing good work, from Liz Weston, to Gail Marks Jarvis, Al Lewis, Jean Chatzky and Pamela Yip, plus some smart, fun stuff from my buddy Charles Passy and the whole crowd of staffers at Marketwatch.com. I also like that we seem to have gotten away from constantly covering the hot investment of the moment and are looking to topics that are more basic concerns for readers.

What really, really bothers me about personal finance writing is two things.

First, the lack of hard, investigative approaches to consumer finance. As we saw after the mortgage bubble, a lot of the agencies and boards that are supposed to protect consumers and investors do a lousy job, or have rules that aren’t up to the task, and a lot of our readers have taken a major, life-changing hit because of those failures. And those failures are OUR failures to watch the watchdogs.

I’ve done stories on foreclosure abuses that are still going on in Michigan — and in every other state, too, I’ll wager — that amount to judicially sanctioned thefts of people’s homes, where the foreclosure laws are not fairly enforced but routinely violated and abused. Everything that comes out of the CFPB is a story that personal finance writers should be digging into on a long-term basis, from abuses by credit-card issuers to debt collectors and more. We need to turn some of our resources away from telling comfortable, well-off people which credit card gives them the most frequent-flyer points to protecting people’s basic assets and rights under the law. And that isn’t happening, even at the biggest, strongest papers or Web publications.

Second, is that we need to start covering the personal finance aspects of poverty and people who’ve taken major setbacks. There is a very self-satisfied, ignorant strain of thought that says anybody can cutback or save or work and be able to provide for themselves and their families, and that is simply not true. I even say in my book that saving $1,000 a month isn’t realistic for many people in this country, and that there are plenty who’d be lucky to find savings of $1,000 a year. We’ve got a huge wave of people who are going to retire with nearly nothing but Social Security to depend on, and another big chunk of wage-earners who are seeing their real earnings shrink and their costs soar. We need to start writing about the financially vulnerable and the personal finance realities of not being able to make it in the U.S.A.

Why don’t more media have personal finance content? It would seem to have widespread appeal.

I think it’s because a lot of personal finance stories come off as very generic, don’t involve real people, and don’t address the big, hard topics that make some people squirm, but would really engage readers. And a lot of what passes for personal finance coverage is aimed at the top earners in our country, who not only don’t need the advice, but already pay advisers to tell them all that.

But there aren’t a lot of religion writers anymore, either, because newspapers can’t seem to find the right way to talk about the huge moral questions of the day, including right, wrong, evil and the meaning of life. You can’t really grapple with that stuff in the inverted pyramid. It should be a challenge to us because we know people care about big life issues such as their financial security and morality, but we have to find ways to engage them on all those topics.

What do you enjoy about your job?

Hearing from real people who are finding ways to create financial security. And hearing from people who normally wouldn’t read the personal finance or business section, who get engaged through the different approach of a humorous personal finance column.

Plus, getting off a good joke every once in a while. If my wife reads my column and I hear her laugh, I know it’s been a good week.