Dawn Wotapka’s Media Movers: Kiplinger Retirement Report’s David Crook

David Crook is one cool guy. His journalism resume is supplemented by diverse interests that make for great conversation, including map freak, dog walker and canoeist. (And yes, that’s a two-volume Oxford English Dictionary right behind him in the photo.) Investigations involving soggy nursing home mac and cheese? He’s down for that, too. (Read on.)

He downplays what he’s accomplished as a journalist; he helped launch The Wall Street Journal’s popular Weekend Journal and Sunday Journal back when daily newspapers reigned supreme.

Those are laurels any of us would be proud to rest on. But not David. While some veteran journos struggle to reinvent themselves in a post-print world, David deftly pivoted. Faster than you can say “deadline,” he co-founded DCReport.org, wrote for real-estate site StreetEasy and recently took the reins of Kiplinger’s Retirement Report, an interesting position for a 69-year-old with no plans to retire.

I talked with David about his first job at a trade pub, his accomplished mentors and the advice he’d give my 6-year-old if she shows an interest in journalism:

Dawn Wotapka: Tell me about your new job with Kiplinger’s Retirement Report. What is it and who is the audience?

David Crook: It’s a small operation within the influential and iconic Kiplinger universe, a 70,000-circulation, 24-page monthly print newsletter-magazine hybrid for affluent people 50 and over who are retired or are planning their retirements. As with all Kiplinger publications, the focus is on personal finance, taxes and government policy.

Dawn: What are you changing about it?

David: My emphasis is on real people — stories about real people in various stages of retirement. I want the publication to be “all things retirement,” so I’m trying to broaden the coverage to look at lifestyle and life issues, good and bad – from people launching new careers to stories that explore the financial ramifications of senior marriages and divorces or sibling estrangements. It should have more hard-hitting stories about financial matters pertaining to the readers. I’m also quite interested in how affluent retirees spend their money — not just saving and investing, but spending.

Dawn: For the most part, my generation – and the younger workers – won’t get a pension. How will we ever retire?

David: That’s a question every generation asks. When I was in my 20s, I was skeptical about the future of Social Security. You want to retire comfortably? To paraphrase my old WSJ colleague and friend Jonathan Clements: Spend less than you make, save as much as you can, invest in index funds. Rebalance and repeat for 30 to 40 years.

Dawn: You spent a lot of time as an editor at The Wall Street Journal. What did you learn by launching a new section?

David: I’ve been lucky. I’ve been involved in launching new projects throughout my career, before I was at The Journal and after. The most important thing is knowing that whatever project I’m working on, it’s not just me. Publishing is a collaborative effort. I don’t have all of the ideas. And I certainly don’t have all of the skills required to get a job done. What I do is articulate a vision and a goal, bring in the right people, let them go and, every now and then, steer them back on course. A publication lives and evolves, and the only way it survives is through the efforts of everyone involved — from the newsroom to the IT department.

Dawn: What was it like to end WSJ Sunday after 805 editions? I was so sad to see it go!

David: You, me and 6 million readers. We closed WSJ Sunday after 15 years in 2015. I was glad I got my people placed elsewhere in the company. I was bummed that I was out of a job, but there was just nothing left to do at The Journal that I really wanted to do.

Dawn: Speaking of ending, you mentioned that DC Report will soon sunset. What is it and why is it ending?

David: My partner, the Pulitzer Prize-winning reporter David Cay Johnston, and I are stepping away from it. But the site itself will be around in one form or another, as some people we have worked with are going to take it over. David Cay and I will be listed as founders and we might occasionally post something. Mainly we think the site, as we did it, has run its course. We started out covering the Trump administration because we feared that the traditional press would end up normalizing it and not report on the corruption and venality.  Fortunately, that didn’t happen. Maybe we had something to do with that. Maybe not.

Dawn: You started your career at a trade publication. Would you recommend that to young journalists? The ones I encounter always set their sights on the big brands.

David: Starting out, you get a job wherever you can get a job. Again, I was lucky. My first real job was at Broadcasting magazine in Washington, which, unlike a lot of trade publications, had some actual journalism cred. I was doing stories at the White House and the Hill, covering PBS and NPR, the networks and broadcast news. Sexy stuff. One day, longtime Editor Don West sent me to get to know this “guy down in Atlanta” — Ted Turner — which led me to develop an expertise in cable TV and video that ultimately landed me at The Los Angeles Times. You can start anywhere. Do a good, credible job. Be daring. Break some news. Kick some ass. You’ll get noticed. I was once asked by a young reporter how to get a job at The Journal. My answer: “Scoop us.”

Dawn: What is the future of print journalism?

David: It’s tough. The era of giant newspapers and big national magazines is over. Print will be around a while longer in various niches, but its future is really limited. That’s not a prognosis for written journalism, just written journalism on paper.

Dawn: Who mentored you during your career?

David: I never had a real mentor, but I’ve had some editors who were hugely influential. Paul Steiger and Larry Rout at The Journal; Connie Koenenn and Jean Sharley Taylor at the LA Times. The best single bit of career advice I ever got was from Grant Tinker, the legendary TV producer and CEO of NBC. He clarified failure and success for me. I used to beat myself up trying to make just the right decision every time. But he explained that every call didn’t have to be perfect, didn’t have to be a home run. “Reggie Jackson,” Mr. Tinker said, “only hits one out of three.”  If I make the right call one out of three times, I’m doing OK.

Dawn: If my 6-year-old told you that she wants to be a journalist, would you talk her out of it? Why or why not?

David: Of course not! I can’t imagine a job more fun. Every day is something new. You get to see history firsthand and tell everybody what you heard and saw. And every now and then, you get to do some good in the world.

Dawn: Finally, do you ever plan on retiring? 

David: You mean like take a vacation? Yeah, sure. We’re going to the Caribbean in February. Quit thinking, looking around, listening, writing, editing and publishing? Probably not. I think I’d be able to come up with a pretty good newsletter for my fellow inmates at the nursing home. You know, blow the lid off what’s been happening to the macaroni-and-cheese.

Dawn Wotapka is a former Wall Street Journal reporter who loves to read and write. She lives in Atlanta with her husband and two children. She is a slow runner and an avid Peloton user. To submit tips for her Media Movers column, you can contact her at dwotapka@gmail.com. Be sure to connect with Dawn on LinkedIn.