CNN anchor, law student, and now author Poppy Harlow joins Zibby to discuss her children’s book, The Biggest Little Boy, which was inspired by a real Christmas memory with her son. The two talk about the problems with dedicating books to just one child, what prompted Poppy to go to law school in the middle of her career, and how they’re learning to embrace the mess in life as mothers. Poppy also shares the piece of advice that has been changing her self-perception and the two connect over the discomfort of owning up to their achievements.


Zibby Owens: Welcome, Poppy. I’m so excited to discuss The Biggest Little Boy: A Christmas Story, your new children’s book.

Poppy Harlow: I’m so happy to be here, Zibby. Thank you. Hero mom of four.

Zibby: Hero mom who works at CNN, commutes to Yale to go to law school, two kids. Please, seriously.

Poppy: I’m thrilled to be here. Thank you for having me. I’ve had this interesting, uncomfortable feeling this week because people say things like that to be nice, which I appreciate and I love, but if they saw how it really is — people say, what can’t you do? You can do everything. I’m like, no. I’m just trying. At almost forty, I’m experimenting and trying different things in my life. It’s really messy. I’m not great at all of them. I’m just trying them. It feels really good for someone who has tried for a lot of my life to — none of us are ever perfect — to strive to be close to perfection, which I never achieved. To finally allow myself to not even get close to it and to just embrace the messy and be okay with just being okay, is the way that I’ve been putting it, feels really good. I’m genuinely smiling and happy. Yes, I commute to New Haven to go to school where you went to school, but I am going to be lucky if I pass. I’m just like, graduate. Do not try to be top of your class because it is not happening this year.

Zibby: I love that. I saw you said something similar with Savannah Guthrie on your Today Show appearance, which was amazing, by the way. You were like, I don’t have to be top of my class. I just have to pass. I have to pass my finals.

Poppy: Savannah was valedictorian, I will tell you, at Georgetown Law School. I will not be that. I’m going to law school to learn, to get better at my job that I love. To work, by the way Zibby, for this incredible — I’ve been at CNN since 2008, so many years — this incredible employer, my boss Jeff Zucker, who not only said, “Yes, you can go. We’re encouraging you. We will make this work. You don’t have to anchor your show for the next nine months. You can go do this and make it happen. Just work every holiday –” which is the deal. I’m working every holiday. I don’t have class. That’s remarkable. I think it’s a message to other employers right now. If you can make the seemingly impossible happen for your employees, if you can make that possible, do it because they’ll be forever loyal to you, forever loyal to you. There are things that you can do to help build someone in ways that they couldn’t do without your support. That’s why I feel so, so lucky.

Zibby: That’s really amazing. That’s so great. I went to business school, by the way. While I was there, I lost my best friend on 9/11, which I talk about a lot on this show. It was the first time in my life where I was like, okay, I am not even going to try to get good grades. I have to pass. I actually tried to drop out, but I was not allowed to drop out. The deans convinced me to stay. I was like, I can’t fail, which is such a different approach for a perfectionist, the way I’ve grown up, which is always to try to do my best every minute. Not that I didn’t try, but it’s a different mindset. Even with all this stuff I’m doing now too, people are like, how do you do it? I’m like, well, I make a ton of mistakes. I make mistakes all the time. I don’t know. It’s not perfect. I just forgot my kid’s dentist appointment. There’s always stuff. There’s just always stuff dropping. I don’t know. Why not?

Poppy: It’s okay to let it drop and not catch all the balls. Glennon Doyle, who says and writes so beautifully, we can do hard things, that really impacted me. I was like, this might be the hardest thing I ever try to do, but I’m going to try. I’ve had so many moments of second-guessing myself. I remember, oh, my gosh, near the beginning of the semester — it’s a two-and-a-half-hour commute from Brooklyn where we live, almost three hours. I take the subway from Brooklyn to Penn Station and then the Amtrack up to New Haven and then have walk about twenty, twenty-five minutes to class and have my backpack. That really bad storm in New York a few months ago, all the trains were obviously canceled. I went to Penn Station. Train was canceled. I’m trudging through Times Square with my backpack on in my Birkenstocks. My brother, my savior, calls me. He’s like, “I figured your train was canceled. Do you want me to drive you to New Haven?” He did. I was like, what am I doing? I could be at CNN doing the job I love, going to sit in hair and makeup, but I’m trudging through Times Square after a storm with a heavy backpack in my Birkenstocks. I’m not home nearly as much for my kids as I used to be because I don’t get home until late evening. I used to be home all afternoon after my show. I was like, what am I doing? That was a moment where I was like, should I quit? Should I not do this? Then I was like, I just have to try. I just have to get through graduation in May and remind myself we can do hard things. What a privilege and blessing it is for me to be able to do this. Most people do not have this kind of leeway with their employer. I have to embrace that privilege and make the most of it.

Zibby: I’m so fascinated by this decision of yours. I could talk about this all day because I want to know why. I also want to find out about your children’s book and why you wrote it. I loved, also, not to keep quoting your other interview, which I hate to do, what it was like to write about one child and not the other. I have my own children’s book coming out. I dedicated it to one of my kids. I have four kids, as you mentioned. My other daughter who didn’t get the dedication just found out when I showed her the printout. She called me crying. She was at her dad’s sobbing. “What? Why not me? Oh, my gosh.” Now I feel terrible. I’m like, “Maybe the next one.” Then my son — you can’t do anything right.

Poppy: At least it’s only your dedication. I wrote this whole book about Luca, my son, and not about Sienna. By the way, I looked at your children’s book that’s coming. I know it’s coming, Princess Charming. What I loved about it is the message of what I’m good at, what she’s good at is keeping trying, is being persistent. It’s great. That’s like ninety percent of the battle in life, is persistence. Just be persistent. I love that message. I did dedicate this book to both Sienna and Luca, my two kids, but this is my way for trying to make up for only writing a book about Luca. By the way, Sienna’s book is very in the works. It’s coming.

Zibby: Good.

Poppy: The reason I wrote it was — it just happened. It was a true story. I was carrying Luca about — you know how children’s books go. It takes a long time to get them illustrated, and COVID delays of shipping and everything. I was walking through the Christmas tree market in Brooklyn on Court Street with Luca in the BabyBjörn or holding him or something. He reached out to grab a Christmas tree and almost pulled the big Christmas tree over. I was like, this would be a great book. I wrote the idea down in my to-do task list, as I do everything. Then I just started writing it. It took months. Then I got in touch with Tina Dubois, who’s my fabulous book agent at ICM, and Tamar, my publisher at Penguin. We made some tweaks to it and then found this great illustrator, Ramona Kaulitzki, who has just brought it to life, really brought it life. The idea was, do I teach my kids — yeah, there’s her beautiful art.

Zibby: It’s so great. People on the podcast, I’m holding up the book to show Poppy. It’s just so gorgeous.

Poppy: She even added sparkles. Look at the sparkles.

Zibby: I know. I can feel it if you run your hand over it. They pop out.

Poppy: The message in the book is it’s not all about big things. It’s not just big things that are special. I was trying to bring a little bit of my Minnesota roots and values to trying to raise normal kids in New York City where there’s so much excess and so many big things and so much going on, to remind them that the little things in front of us are the beautiful things and often the most perfect things.

Zibby: It’s so true. It’s such a good message. It’s such a good story, even the size. Taking life from somebody else’s perspective, particularly our kids, it must be scary going through this big, crowded world so little, and just remembering that you don’t need the biggest things. You don’t need the biggest trees. You need what’s right for you. That’s okay. That’s good.

Poppy: Having a heart for things big and small is the message. Sienna’s not happy that this book is not about her. I get it. I wouldn’t be happy either. I’m begging for her patience for the one about her to come out.

Zibby: What’s that going to be about?

Poppy: I can’t disclose all of it yet. Let’s just say it’s about superpower that she has inside of her. To be honest, reading both my kids this book, they didn’t want any of it. They jumped out of the chair when I tried to film a video for social media. They’re like, we’re over it, we want the dinosaur book. Then Luca told me this week, “Mom, actually, I don’t like little trees. I want my tree to touch the clouds.” I’m not sure the message resonated with him.

Zibby: That’s okay. They’re not your audience. They’re built in.

Poppy: I hope your kids like it more than my kids did.

Zibby: My kids loved it. Thank you.

Poppy: I’m so glad.

Zibby: How did you end up at CNN, by the way? Could we go back to that for two seconds? I’m sure you talk about it all the time. You were from Minnesota. You went to Columbia, or no?

Poppy: Yeah, I went to Columbia where my dad went to school. It was a lot about following in his footsteps. He died when I was young. I was fifteen. By the way, he was a lawyer, so this is a big reason why I’m going to law school.

Zibby: How did he pass away? Can I ask? You don’t have to tell me.

Poppy: Of course. He had cancer. It was pretty fast, four months in the hospital, never came out. He was forty-nine. He was everything. He is everything. He’s so with me in my job that I do. He’s on my walls. I’m looking up at something from him now. He went to Columbia, so I wanted to follow in his footsteps. I went to school in New York City. I was going to go to law school right out of college. Then I started working in news while I was in college at CBS News in an internship. I ended up interning there for three years and loved it so much that I was like, okay, I’m going to do this news thing and try. I started working my way up in local news here. I was just blessed to learn so much here from CBS and my colleagues at CBS Newspath. I would transcribe interviews, run tapes from across the street to the studio and all that stuff. Then I was very fortunate to get hired by New York 1, amazing New York news station. They really taught me so much, to film all of my own footage, to edit it. We did everything. I was a Staten Island and New Jersey Now local reporter. I drove the little station car out to Staten Island and New Jersey and would film my own segments and edit them. It teaches you so much. Then from there, I went to Forbes.com video network, which is where I learned so much about business news and economic news. That’s where I got my specialty. From there, CNN hired me. This great guy named Caleb Silver, who is still such a close friend, hired me. I was very lucky he took a chance on me. I’d never been on live television in my life.

I remember I went to the interview at CNN. I was so excited. I’d go to his office. I still give him grief about this today. He was busy. He’s like, “I have to leave.” I was like, “But it’s our interview. Where are you going?” He’s like, “I have to go to Time Inc.,” which was part of Time Warner at the time, which owned CNN, part of our company before the spinoff. I was like, “I’ll come with you.” I did my interview with him on the subway. So, persistence, your messaging in your book. I was just like, “I’m not leaving. This is my interview. Let’s go. I can talk to you on the subway.” He hired me. I started at CNN. I’ve never left. I never want to leave. I love it so much. Then the market crashed, remember? 2008 financial crisis, here I am a business and economics reporter. I’m down at the stock exchange. I was a junior, junior reporter only hired to do the website. Atlanta, our headquarters, called. They needed someone on in the middle of the day. I was at the Nasdaq stock exchange. The market was tanking. They’re like, “Put Poppy on.” I was like, “I don’t know how to do this. I’ve never done live TV. I can’t do this.” They were like, “Just try.” I think Caleb’s words were, “Don’t F it up.” I tried not to. Then they wanted me next hour. I was like, okay, I guess I was okay. That was the beginning.

Zibby: Wow, that’s amazing. Now you’re going back to school. It’s wild. It’s great. What is this show, by the way, that you’re doing on the side, the CNN+?

Poppy: This is exciting. I can’t tell you what the show is. Sorry. I can tell you we launch in the first quarter. It is a show that I travel for. Basically, every Friday, I don’t have class. Fridays, I travel with this great team of producers. We get to talk to some really fascinating people about their journey and their stories. It’s long form, which is what I love. No commercial breaks. It will stream on CNN+ in the first quarter. That’s been a real highlight and joy for me to get to do.

Zibby: What else is on your big to-do list? I want a peak at the list. What else is on it?

Poppy: Here’s my to-do list of all the people to write thank you notes to today. That’s my immediate to-do list. I, for one of the first times in my life, don’t really know what’s next. I’m really happy and fine with that. Meaning, I’m going to stay at CNN. I love CNN. I have a contract here. I hope to be here for a very long time. I will go back to our show, the show that I get to co-anchor with my friend Jim every morning. I’ll go back to that at the end of May, maybe June first. Maybe I’ll try to sneak in a week off after finals in May. I’d love to keep doing stuff with CNN+, whether it’s a different iteration of this new show or we continue this new show. I’d love to do that. The reason I’m going to school — it’s not a full law degree. It’s a master’s in law. It’s me and the 1Ls, me and the twenty-five-year-olds, who are all so flipping smart. They just blow me away.

Zibby: Did you read One L by Scott Turow?

Poppy: Of course, I did. It completely terrified me. That book is about Harvard Law School.

Zibby: I know, but still. Close enough.

Poppy: Very different than Yale Law School, believe it or not. Yes, I read that book. It was terrifying, but so well-written. I want to find a way to use what I learn this year. Obviously, I will apply it to my job. A big reason I went was to learn more especially about constitutional law and criminal law, the things that we cover so much, and civil procedure. Beyond just informing me for the interviews we do and giving me a better base knowledge, I hope that it will in some way tie into some other work that I can do to help people. Next semester, I’m hoping I get in, there’s a class called Capital Punishment that I really, really, really want to take by Professor Stephen Bright who has argued the most death penalty cases and won the most death penalty cases before the Supreme Court of anyone in history. Bryan Stevenson of Equal Justice Initiative was a student of his. I hope I get in. I bid for the class. We’ll see if I get in. I filmed quite a few times in prisons and reported on the criminal justice system. I hope that there’s something I can take from that course and from my peers in school that can be helpful to society. I just don’t know what that is yet.

Zibby: That’s okay. It’ll all unfold organically, as my husband says.

Poppy: I’ll have time to figure it out, exactly.

Zibby: Do you have any time to read?

Poppy: Little, which is why your podcast is so great. Moms don’t have time to read. Little. I just read this book that changed me in a great way called The Second Mountain by David Brooks.

Zibby: I have not read that yet.

Poppy: Really love it. I think the subhead is The Quest for a Moral Life. Even in the first few pages, he talks about how many of us climb this professional mountain. Then we get to the top and then we’re like, oh, is that it? There’s got to be more meaning of substance in what I have achieved or what we as a team have achieved. It’s about that second mountain that we all climb to what a moral life is for us. There’s a lot of spirituality in the book. I really, really would recommend that to people. I think I may be at the base of my second mountain in life as a parent, as a wife, as a friend, as a colleague, as a professional. I have no idea what is going to be at the top of that mountain.

Zibby: It’s exciting.

Poppy: Books sit on my bedside table constantly and don’t get read, constantly. I’m trying to read my law school stuff on the train. That’s what the train’s for.

Zibby: You do that every day?

Poppy: Four days a week. Monday through Thursday. This week, I’m out skipping class.

Zibby: Don’t you want to just stay up there?

Poppy: I could, but I got these two little munchkins. I like to tuck them in at night.

Zibby: That’s true. I guess I would probably do that too. All right, I won’t try to change your whole commuting schedule. That is something I would do.

Poppy: Next semester, if I get into this class, it’s an evening class, so I think I will try to stay one night up there. I’ve been calling my husband lately, the miracle man, which of course, he loves. I was just thinking, he’s got a super demanding job and lots of people that report to him. He works in consulting at Ernst & Young. Sienna was home from school this week and doing virtual school. He did that with her all day last week or whatever it was while he was doing his job because I was in New Haven. He’s never questioned or thought that any part of parenting was more my job than his, which is the only way that I could do this and is a testament to him and to his parents who raised him that way, both working as well. My miracle man, he’ll get that title until I get mad at him again.

Zibby: How did you meet him?

Poppy: Sinisa’s his name. I met him in Minnesota at our favorite restaurant — it’s not there anymore — called Figlio in Calhoun Square in 2005, long time ago, right after college. We did long distance for five-plus years, Minnesota, New York. I was working in news. He was trying to build his career in Minneapolis. We made no money. I think I made $28,000 a year as a journalist, I was an entry-level, and saved every penny to go on to buy a flight or to get home to Minnesota on what was then Northwest Airlines. The same thing for him. Everyone says, how did you do long distance for so long? It was actually great for us because we really got to know each other slowly and become friends first and then work on our own careers so that when we were in the same city, we had sort of established ourselves more and could start building a life together.

Zibby: Aw, that’s so nice. I love it. You’re lucky to have him. That’s awesome.

Poppy: I think it was Sheryl Sandberg at Facebook who wrote in her book a long time ago, the most important decision you’ll ever make in life is who your partner is. Her husband Dave passed away so young. I think that’s definitely, definitely true because you got to have someone who’s supportive of many different aspects of your life if you’re going to try different, crazy things.

Zibby: It’s hard to get everything right, including, perhaps —

Poppy: — By the way, can I just say one thing, Zibby?

Zibby: Yes, of course.

Poppy: I listened to a bunch of your podcasts. You did one with this guy whose book I loved, Matthew Barzun. His book is The Power of Giving Away Power. You said something in it. You said, at one point, that you’re not a leader. He was talking about the presidents and queens. You talked about yourself. The reason I bring that up is because you are such a leader. I have always said that about myself. I’m in this fellowship group, the Henry Crown Fellowship, with all these amazing businesspeople and CEOs. They’re all the boss. They’re way more powerful than me. I was like, “Yeah, but you guys are the leaders. I’m not a leader. I feel like I’m a worker.” Then Tim Noonan, who’s one of our teachers in this fellowship, said, “No, you’re a leader.” No one had ever talked to me like that. Now I try to tell myself I’m a leader. When I heard you say that, I wanted to tell you that you’re a leader for all of us, not just mothers, parents, entrepreneurs trying things, missing dentist appointments, making the messy work. This is me passing on my Tim Noonan advice to you, Zibby Owens. You’re a leader.

Zibby: Aw, Poppy. That’s literally making me cry. That’s so nice. Thank you. Thank you for taking the time to listen to my podcast.

Poppy: It’s great.

Zibby: Oh, my gosh, thank you. It means so much to me, especially coming from you. It’s hard to own up to anything we’re doing. We’re just so busy and trying and this and that and the other thing. Thank you.

Poppy: You’re welcome. I mean it.

Zibby: It made my day.

Poppy: Good.

Zibby: I am so happy that we got a chance to talk, particularly today. I know this will come out later, but today is the day after your book came out. It is the day before Thanksgiving. It is already craziness with kids, so thank you for letting me have this half an hour to be with you, be inspired by you, have a great adult conversation, and connect.

Poppy: Thank you, Zibby. I hope I can take you for a cup of coffee one of these days when we’re both back in New York. Not that we have time, but you know.

Zibby: Not that we have time, but I would love it. Yes, that would be really fun. Thank you. Bye. Have a great Thanksgiving.

Poppy: See you. Bye.



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