Mr. Glass, this is actually my first time interviewing another interviewer…
(Laughs) Generally when I’m interviewing other reporters it’s somebody who’s appearing on This American Life and we’ve agreed that they’re going to come on and tell this story about this thing that happened — so actually it’s very straightforward.
So you’ve never been in my position?
The one time that I was in the situation that you’re in, I was invited to interview Terry Gross, who does the podcast Fresh Air. And I just revered her as an interviewer! I just think she’s masterful. She gets such incredible answers that these famous people haven’t said to anyone else, which requires this diabolical scheming but also tremendous empathy. It’s a very specific kind of puzzle. I really felt like I was going to play basketball one on one with like Michael Jordan! I totally sweated it; I was frightened the entire time in a way that I’m not used to.
“Interviewing is an art form that so depends on the soul of the other person.”
You once said that being nervous just means you want to win.
I’m ambitious! I want the stories to be special and I want the interviews to be special. The nervousness is my fear that they won’t be, and my awakeness to how hard it might be to get it to work. If you have any ambition, you march into the interview with a battle plan.You have this theory about what’s going to happen with this other person but you really have not the best idea if it’s going to work. Interviewing is an art form that so depends on the soul of the other person and also on how the two of you interact.
I often think about what it would be like to be on the other side trying to answer questions, and I think I would make a terrible interviewee.
Wait, why do you think you would be a terrible interviewee? That’s interesting!
I guess I make a better listener than storyteller. Would you say you have that essential storytelling gene?
I feel the same way about myself! I feel like I’m good at asking questions and I’m good at listening and I’m good at paying attention. On staff and among my friends, like I am definitely a B-level storyteller! On the radio, I can do better because I have time to write it but in real life I’m not, which is one of the reasons why I think I had to study and figure out how to do stories on the radio, I wasn’t naturally good at it.
Would you say that interviewing journalists or writers means that an interview will be better quality because those people have that natural storytelling gene?
Many of them do — but not all. Some people became writers because they don’t like talking to other people. It’s not that uncommon for somebody to become a writer because they’re shy but they’re super expressive!
One of your favourite interviewees was apparently just a regular guy who appeared on the show to talk about babysitting an imaginary family — but he had perfectly broadcastable answers to your questions.
Right, that interviewee, Myron Jones, he was telling a story from his childhood about this family that he and his sister made up in order to get away from their mom. They would just tell her, “We’re going to babysit the McCrearys,” and that way they could get out of the house. It starts off as a comedy plotline: their mom asking them more and more questions, and they’re making up stories and getting more elaborate until the McCreary kids are very, very thoroughly developed characters. But what was wonderful about interviewing him is that I could throw any hypothetical at him.
What do you mean?
Like, the McCrearys were such well thought out characters that I could say, “So where would they live today?” And he would be like, “Here’s where I think they are now.” I could ask something like what do they buy in the grocery store? What kind of car are they driving? You know in improv comedy where you’re supposed to say, “Yes, and” to every suggestion? He would totally “Yes, and” it and do me better! He could tell me what kind of car each one drove and how much each one made and what jobs they had in character for them. He could also do the same about his mom and what was motivating her. He had a really emotional or funny story that he would pull out of a hat for every question.
And those kinds of interviews are rare for you?
To have an entire interview where any place that I point out, they’ll go, and do it so well, that is very rare. It almost never happens that well. Although I will say that if you’re talking to somebody about an incident that really meant a lot to them, almost anyone becomes super articulate, even if they’re not normally a good storyteller. If it’s something that meant something to them or there’s a question that lingers in their mind about it or what to think… All those things lead to really, really beautiful interviews.
Is the intimacy you create in an interview setting as real as it would be if you were talking to a friend or loved one?
Oh absolutely! Yeah. I think in real life, I’m somebody who has a lot of anxiety if I’m spending time with somebody and we don’t have that kind of honesty with each other. If we stay on the surface of things, it makes me anxious and I feel like I’ve failed. I feel most comfortable when we get to that place. The intimacy in an interview, it does very much feel the same. If it goes well, it can be really hard not to fall in love with the person! If it goes really well and they’re being honest with me and I’m responding to them in a heartfelt way, I’m a human being! And it’s hard not to have a feeling that goes with that.
“All you can do really is just make work, make work, make work.”
That’s something you’ve described before in other interviews, and it has since become one of many famous quotes of yours, similar to your very renowned “Nobody tells this to beginners…” quote.
Oh my God, that quote has become more famous than I am!
Can you speak to the strangeness of that experience?
(Laughs) Yeah, I don’t know, that is a case where it was something that was hard fraught knowledge… So I’m glad if it’s helpful to people. I’m genuinely glad and if I’m going to be known for something, at least it’s something that I stand by. The thing that I’m talking about, the struggles of making work when you’re young, is something a lot of people haven’t really talked much about publicly, just this feeling of: before you’re any good at something, it’s just really hard. I wish somebody had told me that that was normal. You’re going to be bad for a while, for a long while sometimes, before you get good. All you can do really is just make work, make work, make work. I say that here and it doesn’t seem very profound!
This American Life has also helped to spawn all these other podcasts… Do you like being an inspirational figure?
I neither like it nor dislike it. I did not aspire to it, and it would be fine with me not to be. I think people who are trying to do creative work are so desperate for any help at all, which I completely relate to, so that if I can be a help to my fellow aspiring creative people in a moment of need then… That’s nice.