1019. This week, Jonathan Small, author of "Write About Now," shares what he's learned about the common struggles writers face throughout their careers. His book highlights stories from bestselling authors about their beginnings, the risks they took, and how they handled early rejection. I was especially surprised by the stories of shockingly bold decisions that launched more than one successful author's career. If you've ever wondered how authors get a foot in the door or get through failure, this episode is for you.
1019. This week, Jonathan Small, author of "Write About Now," shares what he's learned about the common struggles writers face throughout their careers. His book highlights stories from bestselling authors about their beginnings, the risks they took, and how they handled early rejection. I was especially surprised by the stories of shockingly bold decisions that launched more than one successful author's career. If you've ever wondered how authors get a foot in the door or get through failure, this episode is for you.
Find out more about Jonathan and his books at WriteAboutNowMedia.com.
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LIGHTLY PROOFED TRANSCRIPT
Mignon: Grammar Girl here. I'm Mignon Fogarty. And today I'm here with Jonathan Small, an award winning author, journalist, producer, and podcast host. For 25 years he's worked as a sought after storyteller for such top media companies as The New York Times, Hearst, and Condé Nast. He's held executive roles at just a whole bunch of magazines. He is the former Jake advice columnist for "Glamour" magazine, if you remember that, and the Guy Guru at "Cosmo." His podcast is "Write About Now" and gives a glimpse into the lives and stories of successful writers, how they got there, what they learned, and what you need to succeed.
And we are here today talking about his new book "Write About Now: Successful Authors on Overcoming Obstacles, Finding Inspiration and the Birth of Their Careers." Jonathan Small, welcome to the Grammar Girl podcast.
Jonathan: Mignon, it is so great to be here. A big fan of yours and your show.Â
Mignon: Yeah, and I was on your show a while ago, like mutual admiration society here.
Jonathan: Good. Yeah. Lots of love to go around.Â
Mignon: So you have this fabulous book about, you know, these successful authors and a few other creative people, and it's all about their origin stories. You know, what do you think it is? Why are we so interested in people's origin stories?
Jonathan: You know, when I came up with the idea for this book, I thought the same question because like, I am always really interested in people's origin stories, from movie characters to real people. And I think it's that first of all, they're just inspirational, right? They show oftentimes, especially when the origin stories of people you really admire that the possible, the impossible can be possible and in this particular book, we're talking to writers, and I think a lot of people reading this book might have fantasies or aspirations to be a successful writer.
So it's kind of exciting to see how somebody who you admire got to where they are. I think they also make us not feel alone. Like other people have gone through the same challenges in the same obstacles that you're facing. And it's kind of nice, especially when you're in a creative endeavor to know that you're not alone.
Because a lot of times creative people can feel like they're the only person in the world writing this book and you know that they're all alone in this kind of journey. And it's nice to know that there's a lot of people that came before you and that will come after you that are struggling in the same way.
And you know, one thing is, every origin story is kind of unique to the person who has the origin story. Like there's no origin story that is the same. And I think it's one thing about us that is truly unique. I mean, there's many things about us that are unique, but it is one thing that when you start to think about your own origin story, nobody else is going to have that exact origin story.
AI is not going to be able to tell your origin story, right? It is your story, it belongs to you. And I think that's something that really appeals to people is just how kind of unique and authentic it can be.
Mignon: So how did you choose, you've interviewed many people. How did you choose the particular stories to put in this book?
Jonathan: That was kind of almost impossible. I mean, cause I always ask people to give me their origin stories. And so when I decided to do this idea, I was like, “Oh God, now I've got to look through 320 transcripts.” But you know, I tried to find stories that were relatable, that were inspirational, that were moving and touching at times, that were sort of unbelievable and tried to kind of find people who did different kinds of books from nonfiction writers, journalists, to fiction writers.
We even have Betsy Johnson in there, who's not really a writer, but wrote a memoir, and I had her on my show, and she's obviously, she's a famous fashion designer. We even have a musician in there, Chris Franz, who is part of The Talking Heads, who also wrote a memoir. I had him on my show. So I tried to kind of mix it up.
Different people with different types of backgrounds and different types of career trajectories.
Mignon: And I know they're all unique. They are. But as you went through them, as you put together this book, this collection, did you come away with any universals, any big-picture advice or ideas that would be applicable to a lot of writers?Â
Jonathan: Yeah. I mean, I think, again, they're all different. Everybody has their own different journey, but there were common themes that kept kind of coming up like, and I was like, “Oh, okay, I'm going to write this down because this seems like maybe this is true for a lot of people and it's something that we can use as we kind of approach our own lives and our own careers can kind of use as maybe some inspiration.” One of the things was just being open to the unexpected opportunities that are going to come along in your career. And I think a lot of times, we have a plan, like, “This is what we're going to do. I'm going to write a book, I'm going to get it published, I'm going to send it to an agent.”
And yet a lot of the people who are very successful, it didn't really happen in a linear way like that. Like it was, unexpected things happened. I have one writer in the book, Max Brooks, who wrote "World War Z" and wrote "The Zombie Survival Guide."
He was on this total path. He's the son of Mel Brooks, right? So there was always this expectation that he'd be this really, and he is, he's a very funny guy, but that he would basically be his father. And he was on this path that he didn't really want to be on, which was to be this comedy writer working in comedy writing rooms, which was really not his thing.
And he even got a job at SNL. And he was miserable. I mean he thought he was living the dream that he wanted. And then all of a sudden he had this idea to write something he was really interested in, which was a book about zombies, about how to survive a zombie apocalypse.
And he wasn't going to write this in a funny way. This was going to actually be a real book about what somebody would do if there was an actual zombie apocalypse. And at the beginning all the people were like, “Oh, this is funny.” Even his agent was like, “Oh, this is great. We’ll market this as a joke.”
And it turned out it wasn't a joke. So when they released the book, and they kind of positioned it as a joke book, it didn't find anybody to read it. Like, it was kind of a little bit of a flop because they had kind of marketed the wrong way. So Max took it upon himself.
So, he was listening to Dee Snyder, who is a rock and roll star. I think he's like from a big hair metal band, but Dee Snyder is very into zombie stuff and comics and stuff like that. And he was listening to a podcast once that Dee was doing and said, “You know, I'm going to call Dee and see if I can be on a show. Cause that's the audience that I want to be in front of. And that's the audience that will really respond to it.”Â
He was on Dee Snyder’s show, and the book just completely took off. It was like an unexpected, it wasn't the path. It was a different route that he decided to take, and it paid off.
So that's one thing that I noticed, sort of the, maybe a little more obvious, but sort of one that kind of follows the, almost the trajectory of a hero's journey tale and that you see, but it really is true in real life too. It's really taking a leap into the unknown, that the good origin stories are people who were planning to do one thing, and were sort of in their ordinary world, and were kind of in a safe place, and then they just decided to completely take a risk and do something that was way out of their comfort zone, like write a book, and sometimes it pays off.
And in these cases, it really did pay off. But I think we forget that even the greatest writers that we love, they were terrified to write their first book. Like, they had no confidence that this was going to be a big success. And so that is something that really struck a chord with me is like, you got to take a risk.
You've got to leap off the deep end.Â
Mignon: That was one thing that jumped out at me, too, is that people were saying, so many people in your book said, “I had no idea what I was doing.”Â
Jonathan: Yeah, I mean, we had this guy J. Todd Scott, who's become this huge bestselling kind of crime… He was a DEA agent. I mean, he had no business being a writer. He just had this incredible experience as being a DEA agent and going undercover and busting all these drug dealers and stuff.
And so he did that, what is that called? The yearly writing competition.Â
Mignon: Oh, NaNoWriMo.
Jonathan: Yeah, he did a NaNoWriMo.
Mignon: For people, that's National Novel Writing Month, where you write 50,000 words in one month on your novel.Â
Jonathan: Right. And you have a community that's sort of supporting you, but there's really no motivation other than yourself to get this thing done. And he just went to a completely different place in his career and in his life, a place that he wasn't comfortable with being a writer.
He had so many stories that he wanted to tell. And he did this month of writing this novel and what came out of it was his first novel, and then he went on to have a very prolific sort of second career as a crime novelist. So yeah, that leap into the unknown is so important. Also just not letting rejection get in your way.
I think a lot of us are so scared of rejection that we won't even take that first move just because the fear of actually what might happen. And most of the writers that are in this book that are successful got terribly rejected. I mean, Kristen Hannah, who wrote "The Nightingale," one of my favorite books and now has a bestseller called "The Women" out, she wrote a book and this agent told her, “Well, you don't really know how to write a novel. So, come back when you really understand how to write a novel. And then we'll talk.”
And I mean, that might've sidelined a lot of people, like an agent telling you “You don't really know what you're doing.”
And it didn't, like she went, she got that note, she said, “Okay, well, if I don't know how to write a novel, then I'm going to read all my favorite novels, and I'm going to study their structure and see what they have in common.” And she bought all these kinds of bestselling novels and kind of cobbled together this kind of what she thought was a formula that would work.
And now she's one of the most prolific bestsellers working today.Â
Mignon: Yeah.Â
Jonathan: And then the last. Go ahead…
Mignon: I don't remember which author it was that you featured. I don't remember the name, but there was one who had been rejected hundreds of times, and I was impressed because she was like, “It never occurred to me that it wouldn't work out.” And I was like, how could you… an astonishing confidence.
Jonathan: I know. I think just knowing that other people have been rejected is enough and it can be enough sometimes in some cases just kind of keep you motivated because listen, I have been rejected so many times in my own career. I mean, my first book idea we went out with, it was rejected 50 times.
I didn't even sell that book. So it was a great book idea that I thought was a great book idea. I had a really good agent. We went out and I got 50 rejections from every major publishing company in the world. And I just said, “You know what, okay, maybe this idea wasn't ready yet, or it's just, it's not my time yet.”
And I went out and wrote another book. And honestly, that book, that experience of writing that first book, I've used a lot of that on my Substack. I've repurposed that content and it's worked in other ways. I just got that one of the stories that I wrote for that book that got rejected was just sort of re-Substacked on a major Substack guy, this guy, Rob Henderson.
He put it as recommended, and I got thousands of views. So it wasn't really a waste of time and I didn't let…. I'm not going to lie. When I got those rejections, that was hard, that was hard to take, but I just, I kept going and I think you just got to do that and know that there have been many rejections. And the other thing is just luck. I think we discount luck in all of this. You're going to have, and hopefully, knock on wood, you're going to have some luck, right? You're going to have some bad breaks, but you're also going to have some lucky breaks.
And I mean, I think a lot of people just, you can't discount the sort of role of luck in your career and in the success of your career. I mean, I had mentioned David Frantz, The Talking Heads drummer, Chris Frantz. And basically The Talking Heads were great.
We all, we liked them, but they didn't really have any big hits. But when they moved to New York City, they got a job opening up for The Ramones and as sort of openers for The Ramones, this is a lucky break. Like The Ramones actually wanted them to open it because they thought the band wasn't that good, so they wouldn't steal that much thunder from their own act. Right. And look at what that got them. Just opening up for the Ramones, all these people started to see them and know about The Talking Heads, and they became this, it also happened to be that the club across the street that they ended up where they lived, it was just across the street with CBGBs, which ended up being the sort of most famous iconic, punk rock, rock and roll club of the seventies and the eighties. So all this luck was involved in their success too. Don't discount luck. You're going to have some luck.
It's going to be there.
Mignon: That was another theme throughout the book that it actually surprised me is how many people seemed motivated by this strong desire to get to New York City. And I was wondering if that was like a generational thing.
It doesn't seem to me like that's such a, I mean, New York's cool. I love New York but…
Jonathan: I do too. But us WestC. Yeah. I mean, I'm actually from New York. I have a lot of, most of my career I spent in New York. I grew up in the time, or the beginning of my career was all the publishing industry. And that's where everything was. And I think there was a time when New York meant publishing. And that meant that was the big leagues, the sort of "Mad Men" days for advertising, and I think there was a sort of glamorous association with New York. And I don't think that's true anymore. I don't think it matters where you live. A lot of the agents are still in New York, but by the way, they all work from home anyway.
So it's not like there's some big avenue somewhere where all the publishers were like there was back in the old days.Â
Mignon: Yeah.Â
Jonathan: But it is interesting. But I think that idea of aspiring to go or be somewhere that where you aren't is just kind of, I think that's very motivational for people. You know, people used to say, I'm going to come to Hollywood to make it as an actor.
But again, you don't have to really go to Hollywood anymore to be an actor. You can make a really amazing TikTok video or do a YouTube channel and find your success that way. So, I think there is something, maybe there's a psychology behind setting up a destination for your goals.
Mignon: Yeah. Yeah. The book is just filled with wonderful anecdotes, like The Talking Heads one and the Max Brooks one. Another sort of big picture thing, maybe you can think of an anecdote that goes with this one. I was struck by how bold they all were, how just audacious that they would just, the people in your book, they would just call up and ask for jobs, pitch not like their local paper, but The New York Times.
Jonathan: Yeah. Or I think of, one of the stories that really resonated with me was this or just really made me think and wow, this woman was really bold. And it's funny because I had worked for this woman by the name of Lori Majewski, who really early in my career, Lori Majewski and I knew each other because she was an editor at "YM" magazine, which I don't know if you remember was like a teen, a magazine for teens in the sort of nineties and "Young and Modern Magazine."
And I had written for, but I didn't know her story. And this woman, she was basically from a kind of poor, working-class neighborhood in New Jersey, her parents had no sort of connection to writing. She loved Duran Duran, she had this love affair with Duran Duran, and she decided that she was going to be Duran Duran's scribe like she was going to write everything about Duran Duran, and she was going to be their biggest fan. And nobody was going to stop her, and so when she basically would set up and like or not she would set up camp like outside of Duran Duran's hotel room, and they would come out, and she would explain that she was a journalist, and you know I think she was like 19 or 20 at the time and just say "Hey, can I get a few quotes?" And then sort of maybe feeling a little bit bad for her, they would give her some quotes. She would get some good quotes.Â
And then she would write it in, I think she went to Fordham University local newspaper, and she just was fearless. Like she would just go up to them, and then once he started writing these things in Fordham, then she started a fanzine, and it all kind of just started blowing up to the point where now she's like good friends with Duran Duran.
But it was kind of like this, she didn't care if they were like, “Yeah, get out of my way, kid.” But she was one that really impressed me. Also, people who started their career really, really late, like Sue Monk Kidd, I think was, I don't know, she was in her 50s when she first started writing.
Now, she's the person who wrote The Bee. Oh, God, like, sorry, I'm like spacing the bee. Um, the Sue Monk Kidd wrote, Sorry, this is edited, right? I'llÂ
Mignon: on that.Â
Jonathan: Yeah, we'll just do a little re secret life of bees. So Sue Monk Kidd, right? Who wrote "The Secret Life of Bees," like a classic book that was made into a movie.
She was a nurse. She didn't start writing until she was 50 years old. And I think that idea that you know, “Nobody's going to tell me I can't be a writer. I don't care how old I am. I'm going to start writing books.” And not only did she start writing books, but she wrote books that are beloved and considered some of the great books of her generation.
I think that's really cool.
Mignon: Yeah. What are some of your other favorite anecdotes from the book?Â
Jonathan: Well, I mean, one of the anecdotes that it's just kind of an incredible story is the story of Joyce Maynard. Now, Joyce Maynard, I don't know if you're familiar with her, but when she was 18 years old, she was going to Yale University, and she was asked by The New York Times to write an article on what it means to be an 18 year old in 1967, and she wrote this , and it ended up being on the cover of "The New York Times Magazine" and she ended up overnight …This is a time when if you were on the cover of "The New York Times Magazine," that was like there was, there's really no equivalent today because there were only a few places where people got their media at that time, and The New York Times being one of the prominent ones. So she became an instant overnight star writer. And she got all these fan letters, but one of the fan letters was from J.D. Salinger, the writer of "Catcher in the Rye." And he said, “I see a lot of you in my writing. I would love to meet you. I think you're going to be an amazing writer.”
And of course she's starstruck. This is like one of her favorite writers in the world. She went up and met him up in New Hampshire, and ended up being in a one-year affair with this man. Now she was 18, and he was in his late fifties, completely inappropriate. And we'll say to this day, she didn't know what she was doing.
She was just a kid. She was totally influenced by this man. And of course, nowadays, this would have been a very real “me too” situation. But you know, this was in the sixties when apparently it was more glamorous to date older men and have those kinds of relationships, which seems crazy now.
But back then it was different times. And he just one day just dumped her just without any fanfare, just said, “It's time for you to move out,” and just absolutely broke her heart and crushed her dreams, right? She suddenly felt like everything that she had worked for as being a , and she really thought this man really respected her as a writer and all these things, but really turned out to just be to be nothing for her.Â
And she kind of went into this real funk and this real depression, and she was at Yale, didn't go back to Yale, didn't go back to her dream city of New York that she wanted to live in, just got married. But at one point she's decided, “You know what, I'm not going to let this guy dictate my future here. I'm going to pick myself up and really make something of myself” and she started writing stories and she started getting attention. And she was able to kind of push through all the doubts, all the rejection, and also being associated with J.D. Salinger in a kind of a negative way.
And it got even worse because eventually she would write a memoir sort of talking about her life with J.D. Salinger and in a not so positive way. And you would think that people would be like, “Wow, that's really brave that you would finally confess what happened to you and then how inappropriate the nature of the relationship was.”
But no, the media completely turned on her. And for the second time in her career, she was considered to be a pariah. She was considered to be somebody you couldn't trust with secrets, somebody trying to take down one of our greatest writers of all time. And she was considered to be, I think Maureen Dowd called her a predator or something like it was awful, and this is her origin story of constantly facing cancel culture. Again before this is cancel culture. This is in the '90s, constantly facing, and then turned it around and is now one of the more successful novelists working today, but I love her story because it’s about coming up on top in the face of adversity and really following your dreams.
So I always found her story quite inspiring.
Mignon: Inspirational. Yeah. And I thought it was so interesting that she decided to do it when her daughter was the age that she was when she met J.D. Salinger.
Jonathan: Right, exactly. I thought that was …Â
Mignon: Like suddenly she …Â
Jonathan: It's like you kept this secret until she's like, “You know what, now that my daughter's 18, I can really see how incredibly inappropriate that relationship was.”
Mignon: Yeah, she felt like it was her fault until she saw her daughter at that age. And it's like, “Of course it's not my fault.”Â
Jonathan: Exactly.Â
Mignon: Yeah.
Jonathan: Another guy that I was really inspired by was Andy Weir, who wrote "The Martian."
Mignon: Love that book.Â
Jonathan: And it's such a great book. And he's the sort of self-publishing hero because he couldn't find anybody to buy that book. And so he just started publishing it on his own, kind of like in a time when people weren't really doing that on Amazon.
And just basically people started finding it and discovering it and say, you know, actually he published it as a blog, right? And then people were saying, “Well, it's hard for me to read it as a blog. Is there any way that you can put it on Amazon? So at least I can read it more as a book?”
And so he did that, and he said, “Well, I'll do that if you can maybe give me like a dollar” and he did that and people were giving him more than a dollar, and so basically he took something that he was really super passionate about and just kind of almost gave it away for free.
But as a result of that experience, he built this huge fan base of people who just respected him as a writer. And now he's not putting his stuff on Amazon for $1.99. Now he's considered one of the better science fiction writers working, but I love that he’s basically one of those guys that got rejected forever.
I mean, he was not a writer when he wrote "The Martian." I think he was working as an engineer somewhere. And "The Martian" just changed his whole life.
Mignon: Such a fun story. I love those “change his whole life stories.”
Jonathan: I know
Mignon: What else?Â
Jonathan: I want to change my life.
Mignon: Well, give me one or two more of your favorite anecdotes.Â
Jonathan: Some of my favorites. Let's see here. I loved Elizabeth George was not in the book, but I'm just going to tell you her story. She's a little bit like Kristin Hannah where Elizabeth George is a big mystery writer. And she decided she wanted to write mysteries. So she wrote a mystery, and it was the agent read it and said, “You write mysteries. You have a good voice. You write mysteries like Agatha Christie writes mysteries. Nobody writes mysteries like this anymore. If you really want to be a mystery writer, you got to figure out what's happening in the mystery world.”
And so she did what Kristen Hannah did, she went out. So a lot of times it's just like researching and really like she went out. She didn't let that rejection put her down. She read all the mystery books she'd get her hands on and kind of got more of a handle on what was working today. And not only that, she decided that she was most comfortable writing mysteries that took place in England. So here's this American, I think this is really brave, this American who's maybe been to England a few times in her life, writing mysteries with British characters, with British plot lines, all about sort of British society.
And she's an American. And I just find that really interesting, considering that we know that the British can be a little snobby sometimes. I would be a little bit nervous to get it wrong, getting all the kind of the language differences and the cultural differences.
I was really impressed by that story.Â
Mignon: Yeah. We have another guest this season who has a whole book about “writing an identity not your own,” and that's not one we talked about, but there are many cultural differences that you have to get right or you'll get called out for getting it wrong.
Jonathan: Right? It's incredible. Let me think of another one that I really, really liked.Â
Mignon: You have to do a lot of extra research when you do cross-cultural things like that.Â
Jonathan: I know. I mean, I've always wanted to write a history. I love historical fiction, but I'm just in awe of the people who write it because it's like to not only learn so much about a different period of time, but to be able to sort of recreate it for your readers through the language and the images.
I'm always blown away by that. I'm reading "Centennial" right now, James Michener. I'd never [read] a Michener book before, and it's called "Centennial." And not only does he recreate history, but he recreates it in different eras from a thousand years ago up to current time.
So it's like he's basically talking about the way people talked in the 1840s. And then he's talking about what the world looked like in 1910. I can't even imagine. It's just an incredible story.Â
Mignon: Yeah. My mom liked Michener. I read a lot of that growing up. And I have to say, the conversation has moved on, but my brain is still stuck on someone using Agatha Christie as essentially an insult. Like one of the best selling writers of all time and saying, “I don't know, you're a little bit too much like Christie.”Â
Jonathan: Right, right. Another story that, I tend to sometimes gravitate towards the stories of people who really faced great adversity or tragedy in their life that were able to overcome it. But there's a writer by the name of Claire Pooley also from the U.K., and she was an advertising executive, and she was also a mom, but she had a terrible drinking problem.
And it was really manifesting itself in terrible ways and her life was falling apart. And she started as a sort of form of therapy. She started writing a blog called "Confessions of an Alcoholic Mother." And she just put it out there. First, she wrote it anonymously and this was a time when blogs were still picking up steam and maybe now would have been a Substack or whatever, but she did it as a blog at this time.Â
And it really resonated with a ton of, she found an audience of people who could completely relate to everything that she was going through. And she just got thousands and thousands and thousands of comments and realized that writing, she says at this point, “Writing saved my life,” that experience and that support that she got basically healed her. It got her sober, and she transitioned into being a full-time writer. So I always thought that was a really amazing story.Â
Mignon: Yeah. It was the story of what sort of shook her to take that action. She was drinking wine from a coffee cup in the morning, and she looked down and saw it had, I think it said "world's greatest mom." And that was when she realized.Â
Jonathan: So depressing.Â
Mignon: She had a problem.Â
Jonathan: Yeah, Sometimes it takes moments like that. Exactly.
Mignon: Yeah, that's quite a moment. Yeah, well we're gonna wrap up here for our regular listeners, but we have bonus content now.
If you're a premium subscriber on Apple Podcasts or you're a Grammarpalooza subscriber, we're gonna continue this conversation, and we're gonna hear about, Jonathan Small, his own origin story, which is a pretty good one, and his…Â
Jonathan: It is?Â
Mignon: It is. I loved it. And his book recommendations. So, if you're a subscriber like that, stick around.
If not, we're going to wrap up and thank you for being here today. Jonathan Small, your book is "Write About Now." It's an inspirational story of really great bestselling authors and their origin stories.
Tell people where they can find you.Â
Jonathan: You can find me, I have writeaboutnowmedia.com is my website. The book is available in all places you can buy books. It's available at Amazon. And you can also check out my podcast, which is called "Write About Now." I'm staying very on brand. I just decided, I had all these fancy titles for my book and I was like, “You know what? I'm just going to keep it to 'Write About Now' because it kind of works with the subject matter anyway.”Â
Mignon: It does. And it's a great book. So, thanks for being here today.
Jonathan: That means a lot coming from you, from the Grammar Girl herself.
Mignon: Thank you.