Making It Big in 30 Minutes

Transcript: Episode 6, Janice O'Leary

Making It Big in 30 Minutes

Transcript: Episode 6

Janice O'Leary


Terri:
What does it mean to make it big? Having money, fame, worldwide acclaim, climbing the corporate ladder, or crushing it in your business? One thing's for sure. There isn't just one way to do it. Welcome to "Making It Big in 30 Minutes," a podcast for, by, and about the Emerson community.

Terri:
You're about to meet an Emersonian who's making it. Making a living, making a difference, and sometimes making it up as they go along. As far as we're concerned, if you're making something, you've made it big time. I'm your host and Emerson alumni, Terri Trespicio, and we've got 30 minutes. So let's get started.

Terri:
The Emerson alum you're about to meet is one of the most delightfully curious people I know. I can say that because unlike many of the guests I've introduced to you and to myself on this podcast, I've known Janice O'Leary for, oh, it must be 15 years now, back when we were editors at Body and Soul Magazine. When she left there, I cried my eyes out. Then she was hired as the editor-in-chief of Boston Common Magazine. And I quickly had to find something to wear, so I could plus one at her fancy parties.

Terri:
Janice earned her MFA in creative writing in fiction from Emerson in 1996. And for the past 20 years has worked on or with just about every kind of publication you can think of. Book publishing, lit journals, alumni mags, big glossy newsstand titles. She's tried on editorial roles the way you and I try on pants, and she has worn them all well. Now curiosity is a human trait, right? Not a character trait. But I say she's delightfully curious, because you actually want to watch the wheels of her brain as they turn. That's what makes her a great storyteller, which is what a good editor must be.

Terri:
Today, Janice is executive editor at Robb Report and lives in Malibu. Unless you think writing about whiskey isn't real journalism, you'll find her insights on the role of editor compelling, because that job isn't going away anytime soon. I give you my dear friend, Janice O'Leary on how to make it big in publishing. You have one of the sunniest voices I think I've ever heard in my life.

Janice O'Leary:
That's great. How can I capitalize on that?

Terri:
You already have. Do you not know that you have a charming, sunny voice?

Janice O'Leary:
I don't.

Terri:
Oh, well now, you know.

Janice O'Leary:
It doesn't sound that way to myself.

Terri:
I don't know. I mean, look, the truth is when you interviewed at Body and Soul with the executive editor at the time, and they told me you're really going to love her. And I said, "Oh good." And she said, "The best way I can describe Janice is, she's sparkly."

Janice O'Leary:
Awe.

Terri:
And when I met you, I was like, "You know what? She is sort of the human version of champagne, this woman."

Janice O'Leary:
It's really no wonder that I love that beverage.

Terri:
Well, you are a woman of exceptional taste. Since I didn't know you when you were getting your MFA, and I don't know what you went into it thinking, put me in the mind of Janice O'Leary two decades ago, when she was considering getting an MFA.

Janice O'Leary:
Well, first of all, I had already been working. I had worked for a year or more in Manhattan in book publishing. And all I was thinking every day at that job was get me out of here.

Terri:
Why?

Janice O'Leary:
Because New York was miserable.

Terri:
But was it about the job, or was it just the city?

Janice O'Leary:
It was both. It was the city and also the job. The job that I was doing, I was in the kind of promotions end of publishing. They wouldn't hire me as an editorial assistant at the time. So I took whatever I could get. I was making pens to give away at the ABA, at the American Booksellers Association.

Terri:
What do you mean you were making pens? You were designing pens?

Janice O'Leary:
I was designing pens. You clicked it and a different book title from the Little Brown Book List popped up in the window of the pen.

Terri:
Wait, that's actually really genius. I don't even understand how I never heard this story... And that was your idea?

Janice O'Leary:
No, it wasn't even my idea. I was just the one who had to create the text.

Terri:
So you were like, "This is not my life right now."

Janice O'Leary:
Exactly. I'm like, "I don't think I want to make pens."

Terri:
So then what happened?

Janice O'Leary:
I had always wanted to do creative writing. And somehow I thought that book publishing would get me close to that. What you learn in those kinds of jobs is that, "Okay, well, this is actually a business. It's not the creative end of things, necessarily." I kind of got that wake up call and it just solidified how much I wanted to live a creative life.

Janice O'Leary:
I thought for sure that going and getting an MFA in fiction writing specifically, that's what I was most interested in, would be really the key. The key piece I needed to living a creative life. And I wanted to write books. I wanted to tell stories for a living.

Terri:
So you applied. You got in to the MFA program. And you knew you wanted to focus on fiction? Or did you kind of, like I did... I kind of dabbled around. I didn't know.

Janice O'Leary:
I actually think that when you dabble, it's a better thing for you. But I was focused and driven. I wanted fiction. I wanted to write novels. Well, I still haven't written a novel. But I did at least graduate.

Terri:
But being in the program itself does something to your brain and your skills, it really does. Whether you write a novel or not.

Janice O'Leary:
100%.

Terri:
Tell me what it did for you.

Janice O'Leary:
One of the most interesting things I did while I was there, I had read an essay I think by Rosella and Brown, that had said one of the most important skills for a writer to have is to be fluent in multiple genres. I'm like, "Well, I'm not. I need to do something about that." So I took a poetry for prose writers class with john Squeals.

Terri:
Oh, he's wonderful.

Janice O'Leary:
I know. I love John Squeals. That class kind of changed my life. And it did for everyone else in the class. We were all a bunch of fiction writers and most of us were afraid of poetry in some way or another. Either afraid we weren't going to understand it, or we didn't know how to make a rhyme, or that's all we knew how to do. It was this crazy synergy in that class. And I felt like this happened over and over again, in my experience at Emerson. Where you would get this synergy among the students. Everyone was kind of in it together. We all created unbelievable poetry that semester. And some of us won awards for the poetry. All of us had our poems published. It was prolific and magical.

Terri:
And you might not have normally signed up for a poetry workshop?

Janice O'Leary:
Definitely not.

Terri:
It's something about, and I love that you said the fluency of language. Now, looking back, that switched to seeing what is transferable as a writing skill, how do you think that has served you to this day even?

Janice O'Leary:
Well, that articular skill I'd say it's serves me on a daily basis, because it creates a rhythm of language in your mind. I am looking at the rhythm of language with every single sentence I edit, every day that I work my current job.

Terri:
And your job is, of course, you're the executive at Robb Report. So you are pumping out content all the time.

Janice O'Leary:
Yes, that's true. Right.

Terri:
That is a very specific skill and a way of seeing language. There's a thing that people think about, when they think about like what a life, or career in journalism, or writing is. And I think there's a disconnect between what people think it is and what it actually is. Now that you've been in the industry for what, 20 years, what do you think is one of the biggest misunderstandings about what people think a career is, or as journalist, or as a writer, or editor even is or means?

Janice O'Leary:
I think one of the things about it is that most of the time we tell ourselves a story, in fact, that we are this one thing, or that person is that one thing. But, especially if you've tried a few different things, that's just much too narrow. You can broaden your perspective and say that you are a storyteller, or you are a creator.

Janice O'Leary:
As you've talked about in your intro, we are makers. And in that broader sense, it gives a little bit more unity with the rest of the world, I think. I never thought that I would go into journalism.

Terri:
Really?

Janice O'Leary:
Yeah. Never did. Even though I did some of it in college. I hadn't thought that it was a very creative profession, or a creative kind of writing.

Terri:
What do you think it would be? The idea of journalism, did it sound like factory work in a way?

Janice O'Leary:
A little bit. Yep. There's a lead, it's an inverted pyramid.

Terri:
You knew too much, you thought. [crosstalk 00:09:23].

Janice O'Leary:
I knew too much, but I actually didn't know anything at all. I felt like it was kind of the more mechanical version of writing.

Terri:
Oh. And you're still in journalism. So I know you too well to know that if anything felt mechanical or purely functional, you really wouldn't do it.

Janice O'Leary:
I wouldn't, you're right.

Terri:
So what is it that keeps you hooked into this work?

Janice O'Leary:
What keeps me here is the creative process. Every time I sit down to write a story, I might be writing about a private jet. I might be writing about a bottle of wine. I might be writing about a really interesting person. But it doesn't matter what it is, I still have to come up with a way to tell that story. And tell it in the most compelling way possible, that's going to make someone else want to read it, and bring this person or this thing to life. So that is still a challenge every day. And I love meeting that challenge. I actually also love the creative process of putting together an entire magazine.

Terri:
Ah, there's the zoom out, right? The zoom in is when you're writing the pieces. But you're not just sitting there writing pieces, you're the executive editor. So you're overseeing. So when you zoom out, that higher level editorial strategy and thinking through, you find that satisfying also?

Janice O'Leary:
Completely. It's another kind of creation, "Oh, what are we going to make next year? Let's make an issue devoted to fine art. Let's make an issue devoted to becoming superhuman." Whatever you can think up, and we get to do that. Then there's the greater, and this has become something I've thought about more and more as I've gotten deeper into the field, and been in it long enough. I like to think also, and no one's really solved this problem, what's next in journalism? We've gone from print medium to digital medium, we have social, what are the other platforms that are coming next? I love to spend time envisioning that and potentially trying to make it happen.

Terri:
Yeah. Because what the heck do we know what's going to happen? We think, "Oh, now..." When web content came up, it was like, "Oh, cut paste. Take what's in the print, put it on the web." And then we realized that people read things online differently. But what do we think, that we've reached the end of that evolution? That's where we are now. But if we think it's still just a matter of writing for a website, that isn't it. And we really don't know. But it doesn't ever mean that content's going away. I can't imagine that it ever would.

Janice O'Leary:
No, it can't. What would we do when the world shuts down?

Terri:
People are reading more than ever now.

Janice O'Leary:
Who would tell us about it? What would we use to distract ourselves? And they are reading. People are reading more than ever now. Our print subscriptions have gone up since the shutdown, and our digital traffic has gone through the roof.

Terri:
Now that might be because our lifestyles have changed very dramatically. But that's [crosstalk 00:12:48] just about Robb Report. People who know Robb Report associated with luxury, Jetset lifestyle. But how do you explain if someone says to you, who's never heard of Robb Report, and they go, "What do you do Janice?" So say, "I'm an editor with Robb Report." "Well, what is that? What do you write about?" How do you describe it to people?

Janice O'Leary:
Well, I tell them I'm a storyteller and a cleaning lady. I'm telling stories, but I'm also cleaning up other people's stories and making them sparkle.

Terri:
And what's it about? Do you say, "Well, I write about high end stuff?" How do you talk about it?

Janice O'Leary:
A lot of our magazine focuses on men's interests. So I'll say, "Oh, we write about toys that guys love. Yachts, and watches, and cars, and whiskey." And then people get it.

Terri:
And it is mainly male readership your thing?

Janice O'Leary:
Yeah. We say we have a pass along rate where the guys, their spouses read it.

Terri:
Oh, I see. I see what you're saying.

Janice O'Leary:
So women read it too, but we are mainly focused on men for the magazine.

Terri:
Well, it is named after dude, right? Robb.

Janice O'Leary:
It began as a magazine about Rolls Royces, by the way.

Terri:
Oh really?

Janice O'Leary:
As a newsletter about Rolls Royces. Yeah.

Terri:
Oh. I didn't know that. And tell me this though, there is something to be said about this, because there's not everyone who reads the Robb Report has a luxury jet setting lifestyle, and no one has jet setting anywhere right now. It's very interesting to me to hear that the readership is up across platform, because we're in kind of a downward spiral of economic despair, when people are really worried about money. Where untold millions and millions of people are unemployed and don't have money. Isn't it kind of interesting that people are reading something? How do you attribute that gap there, between what's real and what's happening, and this kind of luxury lifestyle that's so few can afford?

Janice O'Leary:
We talked about this as an editorial staff. When everything was happening we said, "Okay, well, what's our mission during this crisis?" And our mission was twofold. We decided one, to inform as much as we can within our sector. We're not the New York Times, we're not the Washington Post. So the stories we're going to focus on are going to be a little bit different. But there's still stories there to tell. And then our other role is to entertain and give people a means to escape.

Terri:
Escape. That is it.

Janice O'Leary:
So, we can't get on a plane, but they can read about someone's private jet.

Terri:
How does it change what you guys write about? Because since people aren't jetsetting, or maybe actually the only safe way to do it is with their own jet.

Janice O'Leary:
Private aviation. That's exactly right. Those are the people who are still flying around the world right now. They're flying from their second home to their third home on their private airstrip.

Terri:
You know your audience. It isn't meant to be for everyone.

Janice O'Leary:
It's not meant to be for everyone. This is one of those things I actually feel kind of strongly about. Luxury journalism is often sniffed at, that it's not actually journalism, because we're writing about fancy things. Hey, I'm a journalist. I'm actually not one of the fancy people. But that doesn't mean that when I'm writing for that audience, I give them any less respect than I would give someone who is unemployed or doesn't have the money to even buy a week's worth of groceries right now, just because they have money.

Janice O'Leary:
I see this kind of bias in journalists over and over again. And part of it is a problem within the media itself. But beyond the media, just other normal people are like, "Oh, that's not real journalism. Is it?" And I'm like, "Well, it is actually and I'm at the moment very grateful for it." So I think every audience deserves respect, and that's one of the first roles of a journalist.

Terri:
That is really pretty potent. In fact, I don't know that I hear that a lot or enough. Because it would be easy to blow off what you do and say, "Well, whatever. You write about whiskey, and we can do that." Actually, no, every audience deserves and can have content. Truth is, if you're not interested in whiskey and private jets, then you don't need to read the Robb Report and that's fine. They're fine. They have their audience.

Terri:
So you bring up a point here about content and about the role of the editor too. Because you're a journalist and you're also an editor. And to my mind, the way I've always defined editor was as a curator of ideas. That job doesn't go away. We need someone that... We can't just go all to primary sources all the time. We need editors, and we'll always need them. They are our barometers for tastes, for interest, for what matters to specific groups. Do you see yourself that way?

Janice O'Leary:
Absolutely. And the more expertise you have in a particular subject, the better barometer and curator you can be.

Terri:
Now, I know you to be a wonderful kind of charming person to meet in person. You're great at parties. You have no problems socializing. But you and I both define ourselves as introverts. We get drained by a lot of people and a lot of attention. And years ago, when you left Body and Soul, and you went and became the editor in chief of Boston Common Magazine, in Boston, you became a very public face in a way that I think you hadn't before.

Janice O'Leary:
Yes.

Terri:
I'm curious about that, because the irony is that the editors usually want to go read and write. And yet there you are having to spend more time out at nightly events, and cocktail parties, and book launches, and product launches, when you might have rather have been at home reading.

Janice O'Leary:
100%.

Terri:
This isn't an interesting workplace hazard. Talk to us about that and what that was like for you.

Janice O'Leary:
And it was very much a workplace hazard. And it was absolutely part of the job. I took that job knowing I was going to have to do those things, and knowing that I probably wouldn't like it very much.

Terri:
You knew it and you took it anyway.

Janice O'Leary:
I did, because I wanted the experience of being the ones making the decisions to say, "This is what this magazine is going to be like." I wanted the experience of crafting something from the ground up. But I will say that the social aspect of the job was hell.

Terri:
You hated it. You had so many great outfits and you hated putting them on. You had to like get messed up almost every night of the week.

Janice O'Leary:
Every night of the week. I had to wear heels all the time. It was hell.

Terri:
Well, I didn't feel like that part of it was not necessarily a natural fit. Didn't it get easier?

Janice O'Leary:
It got easier, but it also got more trying in some ways, too. It eventually got so old. I surprised myself by how good I was at it.

Terri:
Really. I was going to say, did you learn something when you were forced to be in a part? Everyone has multiple roles in their job, but not all of them feel great, but this one you did do. What happened?

Janice O'Leary:
Different group of people than I would normally have met. And since I didn't come across those people in my regular life, this was a first for me. And I wasn't sure if I was going to like those people, but I really did. I learned about so many other different kinds of jobs and activities. Things that people did for fun, for charity, for business in the world that kind of made an entire city tick. It gave me this insight into an entire city.

Terri:
See, you got to see the workings of a city that you hadn't before.

Janice O'Leary:
I did.

Terri:
And it took a little discomfort to get there. And you knew you'd have to go socialize and be nice to people, and that might've felt uncomfortable, but there is a trade off. And my fear is now that people think they have to find a custom fit job that suits exactly what they care about, exactly what they're comfortable doing. And the fact is every job has its trade offs. You knew going in that this would have things in it that you didn't love. When, in your opinion and your advice, is it worth a trade off? When you think that a job you might take could be uncomfortable.

Janice O'Leary:
If there's a more compelling reason to take the job, if the good outweighs the bad, then definitely take that job. Even if you're looking at a job and you think, "This is perfect for me," you have to know there will always be some imperfect aspect of it, something you're not going to love.

Terri:
Yeah. That goes for jobs and people. We're never going to love everything about everyone. It doesn't make me don't have friendships or relationships and it doesn't mean you don't take jobs. Ultimately, of course, you did leave Boston Common and you were recruited by Robb Report to launch a publication. And you got to go and do something totally different. I'm interested, because a lot of people, especially in journalism, they jump around. Right? Jobs begin and things close. People get laid off. What kind of instinct do you listen to when you feel that it's time to go? And it's not always our choice, but it's scary to let go of something that we're comfortable with.

Janice O'Leary:
And sometimes there's a reason to stay in something that's a little comfortable also. Just going to say that. The thing I start paying attention to, in myself, is that I lose a little bit of that sparkle.

Terri:
Oh no, we can't have the human sparkler lose more sparkle!

Janice O'Leary:
The stories all kind of seem tinged and gray, or this is kind of boring, I don't want to do it. I just lose interest in it. My curiosity starts to die. And once my curiosity dies, and I can't find a creative path forward, then I'm done.

Terri:
Now, curiosity, I know you to have that as a... It is sort of your barometer for how connected you are to your work. I think anyone whose job it is to be a storyteller. If you're not interested in the story, it's real hard to get someone else interested.

Janice O'Leary:
That's true.

Terri:
So the kind of litmus test, it sounds like, for how we know if there's a future in the particular role or work we're doing is, is there something to still be curious about? You've been at Robb Report for years. You know more about whiskey than the average person. You know more about the Learjets than the average person. But if you're able to still find something interesting or to hold your curiosity, but that's not the jobs job, right? That's our job to cultivate that. Not everyone is as curious. How did you do that? If someone goes, "Well, I'm bored. How do I get curious?"

Janice O'Leary:
If there's nothing in there that you're interested in, then it's not the place for you. But you do go through valleys and peaks, even within one role at a job. And you have to find that thing that makes you curious. So I have been editing and writing for a long time, even though I've done other kinds of journalism and other kinds of writing, I have been in the luxury sector for a long time.

Janice O'Leary:
There are days when editing a copy about another 21 white wines does not seem all that appealing. But then there are other new projects that come along. It's not like I'm learning new editing skills at this point. In fact, I think I learned all of my top editing skills at Emerson. So instead I need to make it a little more interesting for myself at this point, and start trying to learn new skills in creative ways. So I've recently started working with our business development team on creating product collaborations between Robb Report and other brands. I've never done that before.

Terri:
That was a new skill?

Janice O'Leary:
Totally new skill. I'm loving it. It's so much fun.

Terri:
Did you say, "Hey, I want to learn about this." Or how did that happen? Because that is how you discover a thing that you didn't know was part of the job and might not be, if you weren't curious about it.

Janice O'Leary:
Right. It doesn't have to be part of my job, but I can probably make it part of my job, because I am curious about it. For me I've always been a big idea person. I have tons of ideas. I have more ideas than I have time to execute them. Sometimes my ideas don't fit into the track of storytelling exactly, or in what I'm writing about, or even about my own magazine. I have ideas constantly for other magazines and I'll send them to friends who work at those magazines. "You should write this story, by the way."

Terri:
What a wonderful way to serve. You're brimming over and you give them away.

Janice O'Leary:
Yes. I do end up having to give them away. I just can't write about these things. I don't have any more time left in my day. But because of that kind of thinking that I ended up doing, I come up with product ideas. "Why don't we make something like this?"

Terri:
Like, "What about a pen that every time you click it, the name of a another book tittle?"

Janice O'Leary:
It's so funny you say it, Terri. This is one of those things that I always think about when I talk to students in classes that I've taught, or graduates. I'll say, "You think you're going on a linear path. You think you know where you want to go. But it is not at all linear. Your jobs will take you all over the place, and it's not sequential, and sometime it's circular."

Terri:
Now, you said that you learned your editing skills at Emerson. What would you say is that skill? You learned to transfer skills and not get worried about one genre or another. But what about the editing part you feel was refined for you?

Janice O'Leary:
Right. I went in kind of thinking I was just going there to write. But one of the things that happens during an MFA program is a lot of workshopping. There's a lot of workshopping. What workshops essentially are, is an editing session. I didn't know that until then I went on to get a journalism degree. And in my journalism classes, nobody knew how to edit anything.

Terri:
Really?

Janice O'Leary:
Yeah. And these are people who are going to become editors at newspapers, or magazines, or something. And no one knew how to edit. And I knew how to edit, because I had gone through Emerson's workshopping.

Terri:
That's really interesting. I don't think I've ever heard anyone say that, that the workshopping process helped refined their editing skills. And what do you think is at the heart?

Janice O'Leary:
I think it's creative, but I do think it's a different part of the brain. You use a little bit more of an analytical brain while you're reading that piece. I always sit down, I read whatever I'm reading to absorb it, and whatever it has to say, and enjoy it. But then my second pass is an analytical read, where I'm asking questions of it. Do we need that word? What do you mean? Is that true? What's your proof?

Janice O'Leary:
So I'm always kind of querying the copy itself. But then I'm also taking it apart and saying, "Okay, well that beginning wasn't very interesting, but ooh, this is very interesting. Let me move that third paragraph up to the start, and how can we make that work?" And that I have to attribute to Pam Painter. Did you ever take a class with Pam?

Terri:
Yes! Flash fiction.

Janice O'Leary:
I can't remember how many stories I had cut up and laid out all over my bed, and my kitchen table, at Pam's advice. She forced you to look at a story mechanically, at its different parts. And that is editing, essentially.

Terri:
So lastly, Janice, what does it mean for you to make it in the way that we use that term? We throw it around. What does it mean to you to make it as a journalist, as a writer, as an editor? And how will you know when you get there?

Janice O'Leary:
It's a great question and it's kind of an interesting answer. At least for me, it's fluid. I had once thought, "Oh, I knew I would make it when I was writing about food. Well, I'm going to start writing about food. Okay." And I'm like, "I'm still just Janice. Don't feel like anything special."

Terri:
How about whiskey?

Janice O'Leary:
Right.

Terri:
We're hooking into subject.

Janice O'Leary:
Well, I was hooking into whatever it was that was pulling me forward. And I thought, "Okay, when I'm editor in chief of a magazine, yes, then I will have made it."

Terri:
Well, you've done that.

Janice O'Leary:
Yeah. I've done that now. Okay. So what now? And I've always thought that writing and publishing a book would certainly be a marker for having made it. But then I know once I did that, then I'd want another one. Or I'd want the book to have won a prize.

Terri:
Always a moving goalpost. But it sounds like what you're saying is that there is no before and after making it. There's just making it. Which sounds, in a way, true to even the title of this podcast, because it's meant to be an ongoing thing.

Janice O'Leary:
It is ever evolving and ongoing. And if it wasn't, what do you do, just lay down and die?

Terri:
I guess you do, I guess you do. But the fact is, Janice, you remain not only a dear friend, but really one of my most glamorous friends. So I think you've made it many, many times over. And I can't tell you how much I appreciate you being on.

Janice O'Leary:
Thank you, Terri. This is a lot of fun.

Terri:
"Making It Big in 30 Minutes" as a production of Emerson College, bringing innovation to communication and the arts. Sponsored by the Emerson College office of alumni engagement and supported by the alumni board of directors. Our theme music was written by Phantoms and Avocado Junkie.

Terri:
For more information about the alumni association, please visit emerson.edu/alumni, where you can also find bonus material from the show. I'm Terri Trespicio. Thanks for listening.