Life as a freelance business journalist

Ken Otterbourg left the traditional journalism world of daily newspapers in early 2010 and hasn’t looked back.

For nearly four years, Otterbourg has made a living as a freelance business journalist, publishing his work in national publications such as Fortune, The New York Times and The Wall Street Journal. His work can be found at www.kenotterbourg.com.

Prior to his freelancing, Otterbourg had been managing editor of the Winston-Salem Journal, a Media General newspaper in North Carolina, since 2005.

Otterbourg, a native of New York, graduated in 1983 from Bowdoin College in Brunswick, Maine, with a bachelor’s degree in economics. He worked as a news assistant at The Wall Street Journal and a reporter at The Register-Citizen in Torrington, Conn., before coming to the Journal in 1986 as a business reporter.

Otterbourg left the Journal in 1988 to take a job at the St. Petersburg Times in Florida, but returned to Winston-Salem two years later to report from the General Assembly in Raleigh. He was later promoted to assistant metro editor and became the newspaper’s metro editor in 1996.

In 2002, he was named the Journal’s assistant managing editor for news, and in December 2004, he was promoted to managing editor.

Otterbourg spoke Wednesday morning by email with Talking Biz News about his life as a freelance business journalist. What follows is an edited transcript.

How did you decide to leave the daily newspaper world and go into freelancing?

A little background. I became managing editor of the Winston-Salem Journal in 2005, so I was watching the water drain out of the pool for a long time. We were shrinking the staff, cutting the news hole, etc. In addition, many of our most talented journalists were leaving for other publications or other careers. I had always prided myself on being able to make good hires and trade up, and that was no longer the case. So we were not just a smaller staff, but a less capable one.

In 2009, Media General began developing a plan to consolidate the copy-editing and layout of our paper at a satellite location. I thought it was a bad idea that compromised the independence of our newsroom, and when it was clear that I couldn’t win the fight, I realized it was a deal breaker on my values. So I voted with my feet and resigned. That was in January 2010. At the time, freelancing was not on my plate. I wanted to do public-policy work, but Winston-Salem isn’t exactly the public-policy center of the world, so here we are.

How hard was it to build up a list of publications to write for?

It was extremely hard and continues to be so. Editors are very busy people and as a freelancer you have very little negotiating power over the relationship with the folks in charge. It’s frustrating, but that’s the world we live in. That said, if you deliver stories that editors wouldn’t have gotten otherwise, they can be very appreciative and supportive of your work.

What was the hardest part about making the switch to freelancing?

First is the lack of a steady paycheck. I won’t lie. It was nice getting five weeks of vacation and coming back from a trip and finding you had been paid for not being at work. Second is the endless hustle. I have had to learn to sell myself, which is something I’m not naturally wired to do.

How have you kept yourself focused when there is no office to go into every day?

I’ve always been a pretty disciplined person and understand that work is called work for a reason. I try to plan out each day with what I want to accomplish, whether writing, research or just cogitating an approach to something. Having met deadlines for 25 years helps. Usually, I am toggling between projects.

There’s the stereotype of the freelancer typing away in his pajamas, and while I get dressed every day, I don’t always shave. Within the framework of going to work every day, I also try to take advantage of my freedom. You can get a lot done without the distractions of a conventional office. I’ll take the dog for a walk to clear my head, and I often write on weekends or at nights. I probably work the same amount as I did when I was managing editor, but it is different work spread over a different flow.

You’ve been writing regularly for Fortune. How did that relationship develop?

I went to college with Andy Serwer, and we’ve stayed in touch. I’m not saying this because he’s the managing editor there, but he has a great sense of story. After I left the paper, I was doing a couple of consulting projects and trying to figure out what I wanted to do with my life and I sent him an email suggesting he have someone write a story about the controversy in North Carolina regarding Alcoa and its dams on the Yadkin River. He asked me if I wanted to do it.

I know that sounds fishy, but it was not my intent to get back into journalism. I was still a little burned out. Anyway, I did the story, and they liked it, and for me it was a lot of fun to be a reporter again after all those years in the management grind. So I’ve kept at it with them. The editor I work with most often is a guy named Tim Smith. I call him the reporter whisperer. He can be alternately cryptic and blunt, but his editing skills are really pretty stunning, and he’s been a big advocate of my work.

And you’ve also written for The New York Times and The Wall Street Journal. How did you get those?

One of my former reporters, Valerie Bauerlein, is a reporter at the Journal. I’m really proud of her. I knew she was a star way back when. She reached out to me and put me in touch with their editors for a couple of short-term assignments. One of those was covering part of the trial of Sen. John Edwards. At that trial, I met a couple of folks from the Times and then contacted  them during the controversy over the Duke-Progress merger. I knew they were interested in the story but might need a more efficient solution than putting a staffer on a plane to Raleigh.

Are you pitching ideas more now, or are these publications coming to you with ideas in the region?

Both. I don’t think you ever stop pitching — which is a good thing — but it is gratifying when editors recognize your value. My last piece for Fortune was on the TVA, and they assigned it to me because I had written for them about other energy issues and also about the barge industry, which supplies a lot of the TVA power plants with coal. So often it comes full circle.

Have you turned down anything that you felt uncomfortable doing?

No. Usually when I turn something down, it’s not for ethical reasons but more that the money/topic balance is out of whack. For example, I write for Business North Carolina magazine. It’s a really well-edited regional business publication in an era when most of its peers have fallen by the wayside. They don’t pay all that well, but I do stories for them because the assignments are good and I believe in their mission. If your name is on the story, you want it to be something you’re proud of.

What about non-journalism writing? You’re doing some work for some non-profits, right?

I work for a company called Capital Development Services, which is based in Winston-Salem. They help nonprofits raise money, and I do case studies for them. It isn’t journalism, but you use a lot of the same muscles, and I enjoy learning about these organizations and their challenges. I’ve also done grant writing, report writing and contract editing. One key to freelancing is to try to diversify your income stream and create a bit of stability in an unpredictable world.

Do you ever see yourself getting back into a full-time journalism job where you went into a newsroom?

I loved the energy of a newsroom and many of the most important moments of my life were spent gathered around a table or a computer trying to hash out projects and stories, often on deadline. So, it’s not out of the question, but it’s not top of my mind. That said, I would never want to return so I could be the guy in the newsroom telling everybody about how great and noble everything was back in the day. That would be totally obnoxious, and I would hate that guy.

What do you like the most about freelancing?

I’ve been very fortunate on my assignments. I’ve gotten to travel to some incredible parts of the country and spend time with interesting people doing outrageous things. That’s a privilege, and when I am working on a story I try to keep that front and center, that someone is paying me to write and ask questions and think. I don’t want to let them down.

What’s been fun for me is to learn/relearn the craft of narrative writing. All long-form journalism, but particularly financial journalism, has gotten very difficult because of the Web. It’s very rare that an article is completely revelatory. So the challenge is to tell a story and to tell it well.

What do you like the least?

The unpredictability. You are only as good as your next assignment.