Sara Shepard, the New York Times bestselling author of the Pretty Little Liars series, speaks to guest host Julie Chavez about Penny Draws a Best Friend, a humorous and heartfelt middle-grade series about Penny, a fifth grader who is navigating friendships, finding her people, and lots of worries. Sara reveals she was just like Penny growing up and shares stories of her anxiety, then and now. She also talks about her lifelong love of doodling, which her Pretty Little Liars editors noticed and encouraged her to use in children’s books!


Julie Chavez: Sara, thanks for coming on “Moms Don’t Have Time to Read Books” to talk to me about Penny Draws a Best Friend. I’m so happy you’re here.

Sara Shepard: I’m so excited to be here. Thank you.

Julie: I’m so proud of both of us. We have mounted and surpassed various technological challenges to make this happen. I’m so happy we get to talk about your book. I finished reading it just a couple days ago. I was reading it. It is a middle-grade book. I am so in that wheelhouse right now because I’m an elementary librarian. I loved the book. I’m just thrilled to talk to you about it today because I have tons of questions.

Sara: Great. Yes, it is perfect for elementary, right in that sweet spot of second, third, fourth, fifth grade.

Julie: I was thinking about that on my way home. What I would tell people, too, is if you know, really, any second through fifth grader that is a normal child and tends to have concerns and worries, they should read this book.

Sara: This is every child.

Julie: Exactly. That’s what’s so great about it. Will you just give me the, “What’s Penny Draws a Best Friend about?” spiel to share with everyone?

Sara: Penny Draws a Best Friend is about a fifth grader named Penny. She is, in many ways, just going about her fifth-grade life. She’s just starting school. She has a best friend named Violet. She has a family, a little brother named Juice Box, parents. She has a dog that she adores. She tends to get really anxious about a lot of stuff. Her teacher at school, that she calls her feelings teacher, which is sort of the school counselor, she talks to her feelings teacher about all of her concerns, some of them silly, some of them not so silly. Her feelings teacher is her person that she goes to when she’s worried about stuff. Her feelings teacher told her that some people like writing their thoughts down and their worries down. It makes them a little less scary. She has started to do that. She’s kind of documenting her fifth-grade year. She didn’t want to write, “Dear diary…” That seemed a little just not her style.

She decided to write it to her dog. Cosmo is the name of her dog. All the chapters are letters, essentially, to her dog. She figures her dog isn’t going to judge her. Her dog will love her no matter what, no matter whether she’s super worried about something that seems so silly or she can’t remember math facts or is panicking about something at school. Whatever it is, the dog’s still going to be her best friend. The title, it’s not really — her best friend is not her dog. He’s her animal best friend, but it’s actually about people best friends. It takes her through the beginning of her school year and some things that she’s concerned about. It’s about friendship and meeting new people and getting over those worries and sometimes not getting over those worries. It’s filled with jokes and silliness. It’s not, hopefully, too heavy-handed about mental health or anything like that. It’s just a silly, fun book with a lot of adventures.

Julie: I really cannot say enough good things about this book. Have you ever read the book Alvin Ho, that series?

Sara: Yes.

Julie: This one gave me Alvin Ho vibes.

Sara: That’s so great. I didn’t even think about that. My son read that a couple years ago.

Julie: He has a psychotherapist. He doesn’t like her because psycho is in the name. He’s concerned about that. By the way, Alvin Ho is a go-to recommendation. This will be my next one. I will probably get two or three copies of this for my library. I don’t have a lot of multiple copies because I’m kind of weird about it. I feel like they get lonely on the shelf, which shows, also, that I have weird worries just like Penny.

Sara: I understand.

Julie: I will get multiple copies of this because it’s not too heavy-handed and because every kid worries. I have to tell you, I would read this book, and I cried a little bit. I laughed out loud probably ten times, cackling like a witch. It’s so funny. Even the beginning where you talk about McGruff the Crime Dog, I was dying. I’m like, I’m already going to love this.

Sara: I worried about him. I worried about his messaging.

Julie: What’s funny is I have a book that I wrote in the second grade called The Girls and The Stranger. It was twins. A guy jumped out of a tree with a knife. He was a stranger. I was thinking, strangers were the thing when we were growing up. You had to worry about that.

Sara: Oh, I know. I know. They put that into you very early too.

Julie: That and “Stop, drop, and roll.”

Sara: The strange car rolls up, you don’t talk to that person.

Julie: No, you do not. They do not have puppies in that car for you.

Sara: No, they don’t have anything good.

Julie: No, they don’t. Similar to Alvin Ho, but even more so with this one — I love that book. This is what I love about books, especially for elementary schoolers, they all find their little people, whoever those people are. The thing I like about this one is that I was a lot like Penny. I had a lot of worries when I was younger, and I never had a name for it. I don’t think I needed a name for it. I think that anxiety and a lot of these things that we’re talking about, it’s good our kids are growing up with more tools in their toolbox, with more awareness, but at its core, there is — I didn’t need a name so much as I needed to know when it wasn’t necessarily productive for me and that it was normal, that everybody felt that way. That’s what I loved about this. Penny’s worries go from the everyday to the very unlikely. I used to be a person that would follow those worry trains all the way down the track until we were in a fiery explosion. This book was just so — chef’s kiss. It’s perfect. I can’t wait. I’m so happy there’s going to be a sequel. I really loved it.

Sara: There’s going to be quite a few sequels, actually.

Julie: I’m so excited. That’s good news.

Sara: Lots of Pennys, which is really fun for me. I was a lot like Penny as well.

Julie: Tell me about that.

Sara: I worried about all kinds of things. My mom was also a big worrier, so maybe I got it from her. Besides talking to my mom, who recognized the anxiety but also was able to say, “You can talk about it, but that’s not going to happen,” besides that, I didn’t really talk about it with anybody else. I do feel like kids now are more willing to talk about it. I did sort of think it was a problem inside myself. Everybody else seemed to not worry about anything. Meanwhile, they were probably all worrying. I had no idea. From my perspective, it looked like I was the only one panicking. Then seeing my own kids who have anxieties about different things, which only got exacerbated by COVID and the uncertainty of that, seeing their parents stressed, but also school shutting down and not being able to see their friends, not having their normal schedules and teachers and activities and all of those things, I think a lot of kids are suffering from that still. I think there’s still a heightened awareness of just all the scary things out there in the world. It’s something that’s so near and dear to me anyway. It seems like every child I talk to worries about stuff. We need to normalize that a little bit more and make it okay and show that everybody’s worrying, basically. That’s where I was coming from.

Julie: I was reading this thinking, this just feels so analogous even to my adulthood approach with my worries. That was what was so funny to me as I was reading it. I thought, gosh, I’m still Penny. There are those sides of me that just are there. Learning to be tender with those parts of you, that it’s okay that I’m tuned this way, which we could all maybe argue is a little bit on the tightly wound side, but this idea of, I can accept that — I can get a cell phone so that I can call my mom in Target and track her down as opposed to going down the rabbit hole, which is totally something I would do.

Sara: She’s not trapped under a display .

Julie: That was the one I marked. What could’ve happened? Obviously, she’s trapped under a display.

Sara: There’s been an earthquake. She goes in some interesting directions. This is not a spoiler, but Penny, she’s not cured of her worries. She’s not cured by the end of this book, nor is she cured by the end of the series. That’s not the point. Maybe the things that I worry about are a little different than what I used to worry about as a kid, but the process is still kind of the same. Had I had those coping skills earlier, it would be very interesting to see, when something came up, would I be handling it better now? Maybe. I don’t know. We’re all a work-in-progress.

Julie: That’s something we could worry about. It’s true. That’s what’s so perfect about it. I remember my mom telling me sometime when I was a teenager, “Julie, I don’t feel my age. I still feel young inside like I’m seventeen.” I remember thinking, that is such a weird thing. Don’t say things like that to me, Mom. You just can’t picture your parent as a child. Then now I completely understand that because we’re kind of all those selves. We carry them with us, those early patterns. I think that this would be a really, really great book for parents to read alongside their kids because I think it would be such a conversation-starter. You also write really well about parents. “A prior commitment? My mom is a mom. She doesn’t have prior commitments,” just things like that.

Sara: One of my favorite illustrations about the mom is when she just kind of loses it one day. She can’t get the lid off of a jar. Then she’s like, “If I find one more toy in the stairs, I’m throwing it away.” It just was straight out of things that I say. I was laughing to myself as I was drawing it. I was just like, oh, my gosh. My kids are going to be like, that’s you. That’s the part that’s really fun. My editors, with the drawings, especially with the mom, they said too, “This is exactly what I say to my kids.” It’s one of those fun things. That’s why I think you could read it with a first or second grader too even if it isn’t quite at their reading level. You could read it together. The jokes are funny. It captures younger readers’ attention too because it has all the little drawings. It keeps it fun.

Julie: Absolutely. I’d also put it in the comp land a little bit for Clementine, if you’ve ever read Clementine.

Sara: I know of Clementine, but I have not read Clementine.

Julie: You’ll have to put it on the list. Sara Pennypacker is the author. It’s illustrated by Marla Frazee.

Sara: I know of Clementine.

Julie: She’s just naughty. She cuts her friend’s hair and stuff. It’s awesome. It’s just a great place to start. She’s not naughty. She’s good mischievous. She has a younger brother, but she only calls him vegetable names. That made me think of Juice Box. I was like, this is perfect.

Sara: Juice Box, yeah. Oh, that’s so fun.

Julie: You have been a doodler for your whole life. Let’s just back up a little bit. You are also the author of Pretty Little Liars.

Sara: It’s very different.

Julie: Yes. I was dying. I was looking at everything thinking, is this right? This is the same person?

Sara: It is the same person.

Julie: How has the experience been different? What’s the most fun part of writing Penny? What was the most fun part of writing Pretty Little Liars or those books that are in that genre? You have more.

Sara: You said it before, that we carry these different selves that we were. The humor of Penny and the drawings and all of that is sort of me at that elementary age. Pretty Little Liars, all of the main characters were sort of based on me at other stages of junior high and high school and a little bit beyond. I’m pulling different parts of who I was growing up and different things that I was feeling and different struggles that I was having into each of these book series. I love all the books that I’ve written, but Pretty Little Liars and Penny are the most special to me because they’re the most personal. Pretty Little Liars feels like my true personality, but Penny also seems like my true personality. It’s just a different time period and to different audiences. The most fun thing about Penny, besides just writing a book for kids that are my kids’ age and about a worrier, was definitely the drawing. I just draw little cartoons. I loved art growing up. I took all of the art classes in high school. I actually thought I was going to be a studio art major and go to art school. Then I got really into biology and maybe thought I was going to do that. There were a lot of things that I liked. I didn’t do either of those things. I ended up being an English major because I liked reading too. I always liked art. I always liked drawing. My sister and I were drawing all the time. She’s three years younger than me. We were always drawing characters and illustrating books and making little claymation movies. We were always doing artistic stuff.

In my career, I never thought that I would get an opportunity to draw. I just was like, these are weird little doodles I draw on the margins while taking notes for school or in work meetings or, really, anytime. It’s funny. I work with the editors that I worked with on Pretty Little Liars. They saw me drawing through meetings we would have. They were like, “Your drawings are really cute.” For years they were saying to me, “You should do something with those little drawings. You should write a middle-grade novel with your little drawings.” I was just like, “What? No.” Then I kind of started doing it. At first, I would literally just do it on a piece of paper with a pencil and write the words of Penny around it. I didn’t even have any idea how to lay it out or how it would work. After writing so many books, it was just this new thing. It was so much fun to figure out, this is how it’s going to look. This is how each character’s going to look. This is how the book is going to work with some text and then some art. A lot of the art, there’s three panels, but not all of it. Figure all of that out. It was a new, different thing than just straight writing a book. It’s been a lot of fun. It’s a lot of work. Each book has three hundred or so drawings, or more. It’s a lot, but it’s a lot of fun. I’m able to listen to music while I draw. When I write, I can’t listen to anything. That’s nice. That’s a plus. Sometimes I can listen to reality TV. It just depends. It’s different. It’s been a lot of fun.

Julie: I know for me — I don’t know if this was your experience. When you do something new, especially after having, it seems like, a lot of success in your writing career and you sort of know what you’re doing in that area, then to open it up to something new or this new element with the drawing and things like that, it gives you a weird freedom. You don’t really know what to expect from yourself. You don’t know what the rules are yet, so you don’t have to worry about them as much for a little while.

Sara: Right. My expectations were not very high. To everybody, I say that. No, no, no, I just draw these little comics. Then it was very fun to do it and to realize that I could do it and that kids found it funny. They find Penny cute. Penny and all of her friends, the drawings, they are simple because I want kids to be able to draw her and all the friends. There’s not much to drawing Penny. She has big eyes. Her arms and legs are sticks. There’s not that much to it, but that was for a reason, and also, kind of my artistic ability. It worked out. It’s funny because I have books of other comics that I used to draw, and all of the other characters looked like that too. They had a lot of expression, but the rest of their bodies were just sort of stick-like.

Julie: The way that you do it, though, is amazing. I think my favorite are the mad faces. I just think they’re amazing.

Sara: The mad, yes, oh, my gosh. Again, I drew a lot growing up. I doodled a lot growing up. I do this with my school presentations. I read a lot of different comics growing up. I admired a lot of comic artists. One of my favorite is — she’s not a kids’ author. Well, she did a couple of kids’ books, I think. Roz Chast, who draws for The New Yorker. She doesn’t often draw kids, but her characters are always so worried. They are so funny. She did write one children’s book called Around the Clock. It’s just so strange and very much in the sense of humor of Penny. Beyond that, I read a lot of Calvin and Hobbes and Garfield and all of the really fun comics that every kid read growing up. I loved reading that kind of stuff just for the faces and how you could get a story across in three little panels or whatever.

Julie: Totally. I wish I could go back and read Cathy. I remember reading Cathy growing up. I think to read it now would be such a different experience.

Sara: That would be very interesting.

Julie: I’ll have to see if they have a book of those. Put it on my list.

Sara: I think they do. I bet they do. I feel like Cathy’s struggles were probably a little lost on me back then.

Julie: That’s what I mean. It’s the perennial example, but growing up watching The Sound of Music and finally one year, watching, and I’m like, they were Nazis. I see. I understand now. Cathy, I can picture her with the coffee mug in the office. I bet that would have different resonance for me now.

Sara: Totally. Oh, yeah. We also got a lot of books of The Far Side. I’m sure I didn’t get all those jokes.

Julie: No, but those were so good.

Sara: I’m trying to remember what else. They were always really funny. I’m sure there were other things. I’m trying to think what I show the kids. Mostly, Calvin and Hobbes and Garfield. I’m sure with Cathy, I didn’t really fully appreciate.

Julie: No, but we thought we did. That’s what’s so wonderful about it. We were like, look at me.

Sara: I totally remember what she looks like.

Julie: Pulling it back. Pulling it back, everybody. Come to the late eighties, early nineties with us. It’s going to be great. I have a question for you. This book obviously comes into conversations with mental health, and especially for kids, like we talked about, the ones who are worriers. I think all children worry, but it’s just this spectrum of where your worries — I do want to want to point out, for sure, that in the author’s note to the reader, “If you find that your worries are getting overwhelming or if you find that you can’t stop worrying, please reach out to an adult you trust. Petting a dog or other beloved pet might help too, or doodling and writing, but talking about it with someone and realizing you’re okay just as you are helps best of all.” I have to tell you how beautiful and meaningful and honest that is. I love that you put that in here and that it’s right up at the front for kids to see. There’s so much freedom in that. Talk to someone. What’s mentionable is manageable, letting those things out. I’m so glad you did that. One question about this before I ask you my other question. Was that set for you when you thought about Penny? Did you know where you wanted to start with her in her story?

Sara: I knew what sort of character she would be. I didn’t know, really, what her plot was going to be. I just started drawing. Right off the bat, she was talking to her feelings teacher. I remember the first couple chapters were just talking about her family and getting lost in Target and about her friend. The plot of the friends that she meets and the friend issues that she had came a little later. It was a little bit organic. I just kept going. It’s not how I usually write a book, actually. I’m usually more of an outliner, especially with the Pretty Little Liars books. I outlined, this is where this is going. With Penny, I just was like, who is she? What is she up to? I just kept writing chapters and drawing pictures of her. Then I got to the chapter where — I don’t want to give anything away. She is in this thing called Art Club. I guess I could give this part away. Her friend Violet, who is her best friend, she doesn’t want to do it anymore. I don’t know why I made that happen. I don’t know. From there, it was like, oh, maybe that’s something. For a while, I was just following her. I always knew she was worried about stuff. I always knew that something in her plot would be about figuring out that that was okay, if that makes any sense. I didn’t know what it was going to be or what was going to happen yet, but I knew that that was going to be her lesson, just accepting that about herself and that it’s okay. True friends will accept that in you. Always have somebody to talk to. All of that stuff. She learns different things in different books, but all related to anxiety, mostly. That was the first one. I knew that was something she was going to figure out a little bit. Not all the way.

Julie: Absolutely. That’s how I feel about my own worries, my own anxiety. I’m like, I have it figured out a little bit. Some days are better than others. You can feel that in the book. I think that was a perfect approach for a middle-grade book too because there’s a normalcy to it that really makes it even more relatable. These are things that happen in kids’ lives. It’s something that they will see themselves in and something I saw myself in, which I loved.

Sara: It’s just school stories. It’s about family stuff and science fairs and getting paired in groups that you don’t want to be paired up in and taking your little brother to the emergency room and then having to go to your little brother’s annoying birthday party at the Chuck E. Cheese knockoff that you hate and stuff like that.

Julie: It’s so true. The Chuck E. Cheese knockoff really stuck with me too because even my kids are like, I can’t. At one point, we came out of there, and they were just so grumpy and all messed up because it’s overstimulated, like a toddler or something like that. It was like they had a hangover after leaving Chuck E. Cheese. It’s such a joyful place. I can’t wait to go there again. Get me some tokens. I’m going to send you some in the mail. It’s going to be great. I want to ask you this question. I’m a huge fan of this Esther Perel game, Where Should We Begin? They have all these questions in them. I’m not going to ask you the one about your most irrational fear because I would imagine — it might not be true for you. My husband and I were playing it the other night. I asked him. He tells me his answer. I thought, I don’t even want to bother. I feel like all my fears are my most irrational fear. We could go down that hole forever. To this book, something I grew up thinking was normal but later found out wasn’t, for you, was there a point at which you thought, “I’m worrying too much”? How did you get to that point for you?

Sara: I remember going to summer camp and writing to my mom not about anything that we did at summer camp, but all the things that maybe she should be concerned about. They don’t have us taking showers every day. I haven’t gone to the bathroom yet. Should I be worried about that? I haven’t eaten any fruit. I haven’t slept that well.

Julie: That’s amazing.

Sara: I still think of those letters. I don’t even remember her commenting on them when I got home. She was probably like, did you have fun? I was like, yeah, it was great. I remember writing them. I remember being very aware of, I can’t believe I’m doing this, but I need to do it. I need to get my feelings out here. I need to tell her these things that I’m concerned about. Maybe she wrote me back. It was only a week also. She probably didn’t even have time to write me back. It was enough for me to just write them down and put them on somebody else. You worry about this stuff. That was when I first was like, I bet other kids are not writing about these things. That was the first time I was like, huh, okay. Even that she didn’t comment on it, that made me feel like maybe she either is like, oh, she just worries all the time — she didn’t think it was particularly out of the ordinary. The whole thing was very interesting. That was my first time being like, I have a feeling this is not something other people do. That was my first. I’m sure there are many other examples, but that’s the first one . It was in fourth or fifth grade. Very, very concerned about how I was health-wise. It was a week.

Julie: You needed to outsource those concerns.

Sara: I did.

Julie: Somebody else needs to be concerned about this. I’m going to pass it. That’s hilarious. I wonder if she got them after you got home.

Sara: Probably. I was like, if there’s really alarm bells, she’ll call the camp or something. I just figured she’d — I don’t know. I see that in my kids, though. My son, he has a phone now. He’s in fifth grade. He’ll be in his bedroom, and he will call me while we’re in bed. He’s like, “I have some bumps on my arm.” I’m like, “How many?” thinking there’s a whole bunch. He’s like, “Two.” I’m like, oh, my gosh. I get this a lot. Last night it was, “I drank water, but my mouth is still dry.” I’m like, oh, my god, you’re so me. He just needs someone to be like, you’re all right.

Julie: Is there anything worse than having those moments, though, where you’re like, “I did this to you”? I really have moments where I’m like, I think I did this.

Sara: I know. It’s so true.

Julie: Is your other one like that, though?

Sara: My other son is the same. It comes out in different ways. I think he saw moments of me panicking when he was quite young. He’s gotten better but now as a kid has decided that moments like that need that sort of panic in him as well. I admit I created this problem.

Julie: We’re just doing our best out here.

Sara: I know. He has gotten better, but it is very funny.

Julie: I did tell the boys the other day, I said, “You have to understand that this is the first time I’ve ever parented anyone.” It was one of those situations where there was a bad decision that was made. I said, “Look, everyone makes bad decisions. I made bad decisions. The hope is that I made marginally less than Mimi and Poppy,” your parents. “Hopefully, you will make marginally less bad decisions. Then hopefully, it gets a little better. Then at one point, someone’s going to throw the curve, but we’re going to worry about that later.” It’s such a bizarre experience. How am I in charge? We’re the adults? This feels like a bad plan.

Sara: I know.

Julie: This has been so much fun to talk to you. I’m so excited to share this book. I will be sharing it with kids. I have to say, Alvin Ho, those sorts of books, Clementine, those are my go-to favorites in the library. This will have a place right next to them. I can’t wait to share with them.

Sara: Please stay in touch and let me know what they think.

Julie: I absolutely will.

Sara: There are going to be more Pennys. Actually, by the time you’re back in school, Penny Draws a School Play is out in the fall, so there will be two Pennys.

Julie: I can’t wait.

Sara: There’s going to be more than that. It’s really fun that there’s going to be a second one. Not only will they get to read the one, but they’ll get to read the second one too if they like it.

Julie: They love a series. They will, for sure, fall in love with Penny. I have no doubt.

Sara: Oh, good, and her friends.

Julie: And her friends. It’s so true. Thanks so much for today.

Sara: Of course. This was so much fun. Thank you.


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