Writers On Writing: Ben Wolford, Journalist & Magazine Founder

There’s this feeling I have in my brain that I have appropriately named “perpetual freshman.”

Remember when you were a freshman, brand new to high school and rocking your purple capri pants (No? Just me? Cool.), and while you were intimidated as hell by the seniors — for some reason — the sophomores were the ones who reminded you of your place in the hierarchy? They were in ninth grade only a year ago (or three months ago, if you’re looking back from summer), but those kids seemed so much older and wiser than you. And you couldn’t WAIT to feel that way at the start of the next school year.

But then that next August you arrived, and you side-eyed the freshman class members who just seemed so damn young — only to look up at the now-juniors and have the same feeling of envy.

That’s how Ben Wolford makes me feel.

Now, by all accounts, he’s super nice, smart, and hard-working — all seemingly normal traits I look for in a friend. But I remember being in college and just starting to work at the student paper while he was working at a real! newspaper for a semester, and the advisors and teachers all talked him up in this half-whispered admiration. We all pretty much knew then he was going to be the badass he is now, and I admire him tremendously. (If you couldn’t tell.)

Officially, Ben is a traveling journalist and the founder of the news magazine Latterly, but on a personal level, he’s an open-book who lives all around the world with his adorable family and does really awesome work.

Everyone I’ve talked to for this blog series had their love of writing start with reading, which I assume is the case with you, too, but I’m interested in when you realized you could actually turn this into a career. Do you remember?

My dad was always reading these old paperbacks. Louis L’Amour, Stephen King, Tom Clancy, Elmore Leonard. We had bookshelves up in the attic full of them. So I always had some understanding that writing books was something you could do as a profession. When I got older, I realized that most authors don’t just become John Grisham. Writing for newspapers, on the other hand, seemed more realistic and accessible. I loved reading the sports columns in the Akron Beacon Journal and the Canton Repository, which we got every morning. So I decided to try to get into writing books via this intermediate newspaper step.

It was a total brain-bender for me to switch out of journalism writing, rooted in truth and ethics, and into creative writing, where I essentially just made up 75,000 words. Have you had a similar experience? Any challenges for you?

I’ve tried to write fiction, and I’ve published a short story. But I’m not the novelist I hoped to be. I find it extremely difficult to be creative in fiction. It’s much easier for me to tell a true story because there are parameters (being accurate), and the challenge then becomes framing these facts and scenes as dramatically as possible. Real life is very dramatic. Nonfiction storytelling requires loads of creativity to first excavate the fine details of the truth (reporting, interviewing and researching are arts) and then render them vividly for the reader. You have all the same elements of conflict, character building, suspense, etc. in narrative journalism as you have in fiction. It’s just a different sort of subject matter.

Definitely. I also think back to my days of approaching strangers in the chaos that can sometimes be reporting, and it fueled me in a different way than sitting alone in Starbucks on my computer creating dialogue. What’s you’re preferred setting when you’re writing?

I write best on a tight deadline. Which is another way of saying I procrastinate until I’m almost out of time and then suddenly I feel very inspired. So in terms of the ideal scenario—noisy room, quiet room, music, day, night—it doesn’t much matter. I write best when I have to.

And does that last-minute inspiration carry-over to when you need to think of a new story idea?

Honestly, I’m not that great at coming up with story ideas. I’d much rather get an assignment. But occasionally I’ll come across a story and I’ll know it immediately. The best example of that is when several years ago I was working for the South Florida Sun Sentinel as a general assignment reporter. I was sitting at a bar with a friend thumbing through all these business cards in a fish bowl, some kind of promotion the bar was having. And I picked up one that says R. William Barner III. I read the name out loud and the bartender said the guy was a regular. And he was also a prominent defense attorney who was at that time representing somebody accused of smuggling airplanes into Iran in violation of sanctions. Not your typical Fort Lauderdale crime. So I called him the next day and it turned out to be a great story.

What’s your favorite story you’ve ever written?

Easily this one. It’s about a community of sex offenders who move to a small town in Florida. I’m proud of it because I was able to document a true, Amazing Grace-style change of heart.

You’ve seemed to flawlessly transition between journalist, editor, short-story writer, etc. What advice do you have for those who feel boxed into one area or are even struggling to start writing?

The only thing that works for me is to create a situation for yourself where the writing is “required” in some way. The easiest way to do that is to get a job at a newspaper or somewhere else that’s paying you to write. (That’s also where you can learn the craft at warp speed. Editors, deadlines, the news that needs told and so on are all conspiring to force you to get better. And then the next day you have to come in and do it again.) The second-best situation, I’ve found, is to identify a publication or an award you want to win, and then write for that publication or award. That’s how I got my short story published: I identified an award with a near-immediate deadline (I think it was two or three hours away), and that forced me to put words on paper and file the damn thing.

Ben Wolford is a traveling journalist and the founder of the news magazine Latterly — follow him on Twitter for more updates on what he’s reporting on around the world.