I took a seminar at Northwestern this spring about the practicalities of the business of freelancing, and today's interviewee spoke for half of it. I was seriously impressed by his breadth of work, including work for GQ, Harper's and This American Life. Oh and he also works for a documentary film company. So I thought he would have some interesting things to say on the writing life.

What has been your most difficult writing assignment of late and how did you deal with it?
The most difficult of the last few years was probably a piece I did on dog fighting. It ran in the New York Times magazine, but it was originally a story for GQ, something I pitched and started to report, only to have a long succession of dog-fighting insiders flake on my interviews. That's the way it goes, I guess, when you're reporting on illegal activities and there's an obvious fear, among your contacts, of getting caught. Anyway, eventually all those flake-outs wound up killing my assignment. I kept trying to get back in, though, and after a number of months I got hooked up with some new contacts and a new assignment.

The reporting was scary. I wasn't undercover, exactly. But, at times, I wound up in situations where only one person in a group of assembling dog fighters (some armed and some stoned) knew I was there to report. So there were some tense moments when I was challenged about being a cop and had to answer with the not-exactly-helpful response of, "No, I'm actually a reporter."

What have you learned about what makes a good writing teacher versus an average or bad one?
I think a good writing teacher probably shares a lot of the same characteristics of any good teacher: patience, high standards, a love of the material and an ability to communicate that love to the students. When I've had the chance to teach, I think the qualities that have served me best go back to all the difficulties I had with reading and writing while growing up. I didn't learn to read until 4th grade. I had some sort of undiagnosed learning disability (I still can't spell). When I finally started reading, I was slow and it took a lot of concentration. Each syllable was a hurdle to get over. So I think those kinds of struggles have put me in touch with some of the ways a student might struggle.

As for the bad writing teachers, I think there are a lot of them out there just cashing their pay-checks and giving as little as possible--all the better to save time and energy for their own writing. In the mid 90's I did a year in an MFA fiction program in New York, but I dropped out before year number two. I felt a lot of the professors were dialing it in, and I didn't need to pay big money for that. I also took a writing class once where the first thing the teacher said was, "I don't like teaching, but I need the money." There's this sense you get, from some of the bad writing teachers, that teaching is beneath them.

Do you think that certain people have a knack for investigative journalism, or that any writer can become adept at it?
I think certain people have a knack in the sense that certain people are more fearless. But I don't necessarily mean fearless as in hiking into rebel territory to interview the head guerilla fighter in some terrible civil war. I mean, it can be hard enough to work up the courage to just pick up the phone and call someone who might make you feel stupid. I also think certain people are more adept at certain kinds of research. I don't know a lot about how to follow the money or dig up hard-to-find paperwork. I have had fairly good luck when it comes to dealing with people and making them feel comfortable enough to talk. So that's been a help when it comes to trying to get access and/or deeply personal information. If you're going after someone's personal story, it's also helpful to share a little of your own, because that encourages sharing in general. And it never hurts to go out for drinks.

What else? A mild obsessive streak can serve you well. I once called the FBI field office in just about every major US city trying to find an agent, any agent, who'd give me some straight answers about bank robberies. In the end I found some very helpful FBI folks, but it took a while and this was before long distance phone calls were so cheap. I think my phone bill that month was $800. It's also helpful to take it personally when you think people are giving you the run-around. Makes you dig harder.

Can anyone do it? I think so. But you have to be prepared for the scary stuff (I had to take a break from it when I found myself studying the parked cars on my street for bad guys waiting to get me) and for the stuff that is just tedious and demoralizing (like trying to deal with the military and feeling like your interview requests are being constantly thwarted).

How is writing a piece to be published different from working on one for the radio?
No offense to the radio people (especially all my good friends at This American Life), but I've found writing articles to be a lot more work. For example, I've struggled a lot more with my prose when writing articles. And that's not to say that there's not a whole special type of prose that you have to dial into to write good radio. It's just that the radio stuff is much more direct--it actually sounds better if you don’t try to get too fancy. That's not always the case with magazine articles.

With your work at Towers, do you get to select your projects, or are they assigned to you? If the latter, is it difficult to write a script on something you might have little interest in, or is each subject equally of interest?
Most of my work at Towers is assigned and most of what I do involves acting as a sort of script doctor on projects produced by others. There are always some scripts that seem more interesting than others, but in general I'm able to get fired up about improving the prose (and the structure) no matter the subject.

As for projects that are more my own, I have managed to hook on to a couple of documentaries where I've also done the producing (in addition to some of the camera and sound work) and these shows, and these scripts, can spark a much more personal sense of investment. It has as much to do with fear as anything. The more you're responsible for a show's success or failure, the more you're likely to give. But television (unlike magazine writing) is such a collaborative medium, there are plenty of times when no matter how much you give, you'll only have a certain (relatively small) impact on the final product. It's a visual medium and a lot of the time the visuals rule.