Episode 70 – Jessica Ewing, Founder and CEO at Literati

How does a promising tech. wiz go from surviving alone in the wilderness (for a long time!) to starting the incredible children’s book company, Literati? Well, her story and her path will surprise you and give you the courage to do things you’ve never done before.

Today, Jessica and Jessica sit down in the Noonday office to discuss life, courage, entrepreneurship, and – wait for it – fishing!


Jessica H: Hey everyone! Welcome back to the Going Scared podcast. This is your host, Jessica Honegger, founder of the socially conscious fashion brand Noonday Collection. Are you ready for honest and vulnerable conversations that will inspire you towards action? Join me here, every week for conversations on living lives of purpose by leaving comfort and going scared.

Today I am sitting down with probably one of the most fascinating people that I know, Jessica Ewing. Jessica is in my EO Group. That is a small business group that I am a part of—it’s part of a larger organization called EO that helps support and grow entrepreneurs. Jessica is a trained survivalist. Yes, those exist. She’s also the CEO and co-founder of Literati books. She also spent five years building consumer products at Google after graduating from Stanford. She was featured in Fast Company magazine as one of Google’s twelve most innovative minds. She’s instructor at the Boulder Outdoor Survival School which is the most intensive civilian survival training school in the world. I’m telling you, today’s podcast is such a treat.

In fact, a lot of what we talked about—some of the survival skills we talked about—I was able to use this summer. For those of you who follow me on Instagram, Jack and I—my son Jack—we traveled to Rwanda—Jack is from Rwanda—and we wanted to go back for his ten-year birthday. And on the last two days, we are leaving the country, and it’s a 48-hour trip home, and Jack got food poisoning. Jack had diarrhea and vomit coming out all sides, all the ends, all the places, guys. For two days while we are traveling home on multiple flights, multiple layovers. It was so horrible. It was horrible. But I recalled this conversation that I had with Jessica, and I did her whole Compare Down trick with Jack. And it works, guys. I’m really excited for you to give this show a listen.

Also, Jessica is being super generous, and she is offering a gift certificate to Literati for one of our listeners. Literati is the premier children’s book subscription service in the U.S. for kids ages 0-9. They send a child five age-appropriate books a month based on a theme like “the golden rule” or “this is magic.” The child enjoys the book at home for up to a week, and at the end of that week, they only keep the books they love, and then they send the rest back. So, she’s offering a gift certificate to us for those of you guys that repost this episode. So, if you guys either want to link to it through Facebook, tell your friends “Hey, go listen to this episode,” if you want to screenshot this episode and put it in your Insta stories, then you will be entered to win a full year’s subscription to Literati as well as my book, Imperfect Courage. If you do the contest via Facebook, make sure you go ahead and DM us over on Instagram to let us know, because that’s where we’ll be tracking the contest. Otherwise, just share the episode today. It’s really interesting, and it’s just, I love fascinating people, I love multifaceted people, and it’s been really fun to get to know Jess. So, enjoy our conversation.

Jess, thanks so much for coming in today.

Jess: Happy to be here.

Jessica H: OK. So, I’ve got Jess with me. Jess is the second person from the entrepreneurial organization I’m a part of called EO, Adelle was on the show with Eterneva a few months ago. So, Adelle, you can go check out that episode. Now, I’ve got Jess with me, and as I already told you, Jess runs the coolest company, it’s called Literati, and it’s a subscription-based box of books for children. And we’re gonna get more into that, but I want to start off with your story, before the story of Literati, because it’s pretty wild. We are gonna talk about surviving in the wilderness. Jess.

Jessica Ewing: Wilderness Survival Pro

Jess: That’s right. I mean, I don’t know where you wanna start. It was just… OK. So, the background was, I was working my way up the chain of command at Google, I was a product manager, I was maybe three years in, and my friend, Nakheel, came up to me one evening at a bar in San Francisco and just said, “I’m doing this crazy thing. You need to do it with me.” And I was intrigued. And he’s like, “There’s this crazy school, it’s in Southern Utah, it’s 20 people, it’s this tiny little school, and they take people out into the wild for 28 days with just a knife, a blanket, and a poncho.”

Jessica H: A knife, a blanket, and a poncho.

Jess: Yeah. And he’s like, “Oh, but…” And then added, “But you don’t get the blanket and a poncho for a few days. You just start out with just the knife.”

Jessica H: So, no food?

Jess: There is food after a certain stage. So, it’s not all living off the land. There’s just too many courses that they run through to do that sustainably.

Jessica H: But it’s educational in nature?

Jess: Correct. That’s right. And so, I was just intrigued, I was like, “This is crazy. I wanna…” It just, immediately, was appealing to me, I don’t know why. I have no outdoor skills, I’m not particularly fit, I wasn’t at the time. It just sounded appealing to me.

Jessica H: Like, how many hours a week are you working at this point, at Google?

Jess: A lot. At least 60, generally, yeah, 60 to 70, probably. And there was just something about this that was so intriguing to me. And so, Nakheel had been trying to get a bunch of people to sign up, but I was the only one that was, like…

Jessica H: Remotely interested.

Jess: Remotely interested. So, he started telling me about the structure of the course, and he was like, “All right. First, there’s this impact phase where you just get … you don’t eat, you just get a knife and the clothes on your back.” And I’m asking him these questions, and I was like, “Do they do shorter courses?” And Nakheel, and he hesitated for a second, and he was just like, “Oh, yeah, they do. They do a 7-day and a 14-day course. But here’s the thing,” he’s like, “We have to do the 28-day.” And I was like, “Why?” And he goes, “Because anyone can survive anything for seven days, and anyone can survive anything for 14 days.” He goes, “But to live and survive for 28 days, and to do this, you’re gonna have to adjust to the lifestyle.”

Jessica H: That’s legit.

Jess: And that’s the only way. And he was, “And that’s where all the learning is gonna take place, so we have to do it for 28 days.” So, he’s like, “Are you gonna sign up?” I was like, “I’m gonna sign up.” So, we both signed up.

Jessica H: Did you have to quit your job to do it?

Jess: No, I didn’t. So, I had accrued enough, five weeks accrued vacation that I just decided to burn on this experience. So, I was just like, “I’m gonna go.”

Jessica H: You’re not gonna go to the beach, you’re not gonna go to Mexico and drink margaritas, you are going to go live for 28 days with a poncho, a knife…

Jess: That’s right.

Jessica H: And what was the last thing?

Jess: A knife, a blanket, and a poncho.

Jessica H: And a blanket, a blanket.

Jess: Yeah. And I think, if you’re a certain type of person … like many entrepreneurs, I’m constantly thinking, and constantly in my head, I’m a workaholic, all these things. And so, for me, ironically, doing something crazy and extreme that forces me to get out of my head is almost more of a vacation than relaxing on a beach, because I don’t have to totally think about work.

“For me, ironically, doing something crazy and extreme that forces me to get out of my head is almost more of a vacation than relaxing on a beach.” Jessica Ewing

Jessica H: I can totally relate. I have had beach vacations with my husband, who is my exact opposite. His national natural bent is to be very present and in the moment, and my natural bent is to be in the future and in my mind. And I have looked over at him during a beach vacation and been like, “Babe, what are you thinking about right now?” You know? Expecting this … just inspiring conversation to ensue. And he looks at me, and he’s like, “Babe, I’m not thinking about anything.” And I’m like, “I don’t even know what that’s like.” What is it like to not think about anything? But perhaps, what it’s like to be in survival for 28 days, where you’re just thinking about the moment.

Jess: That’s the thing. For me … And that was so much of the learning, really just to get into it. I mean, it was one of the hardest things I have ever ever done. But yeah, it’s just … there is no room to think about anything, but just your basic mammalian existence, and like, OK, you figure…

Jessica H: Had you spent much time in reflection before? Was there an emotional element of “Oh my gosh, I’m about to go and be alone with my thoughts now.” And had you … I feel like … Did you go straight from Stanford to Google?

Jess: Yeah. I went from Stanford to Google, and I was on that path, you know? And high-tech…

Jessica H: Yeah. So, pretty high-achieving, high-tech.

Jess: Super high-achieving. And, I mean, everyone thought it was crazy, right? Nakheel had been known for being a little bit of a weirdo, and he was in the process of leaving the company and getting a PhD in neuroscience. I found him fascinating. And so, I aligned myself with him from the beginning, and we were always these, like, kind of weirdos. But he was a known weirdo, I was, sort of, a believed-to-be, like…

Jessica H: Somewhat normal, but inside you’re crazy.

Finding Creativity and Authenticity in the Wild

Jess: Yeah. I’m just nuts. And so, I think that this was the first signal anyone had that was like, “Whoa, maybe we’re dealing with someone who’s just not rank-and-file tech employee.” We’re gonna do something weird here. So, it was great, but … Yeah. I mean, you go out there … And, I mean, I had no … to be honest with you, I had no reflections going into this, I had no idea what to expect. I just thought it was gonna be in the wild badassery, and it was gonna be great, and I was gonna take on mountains, I had no idea, to be honest. And it was just a really cool experience, but it’s a very humbling experience. And so, I think, we’ve talked about this before, but I really think that, to tie into entrepreneurship and those sort of things, I really think creativity comes from … we don’t really know where creativity comes from. But for me, getting out of my head, being in the moment, getting past my ego, all these things which are really, really hard to do, often yields just an incredible gift of creative insight. And so, that was the thing I wasn’t expecting. You go into the woods, you think you’re doing this, sort of, like, masculine survival thing, and then the bizarre thing is that it makes you softer. It made me more feminine, actually. It made me more authentic, more…

“It was just a really cool experience, but it’s a very humbling experience. … we don’t really know where creativity comes from. But for me, getting out of my head, being in the moment, getting past my ego, all these things which are really, really hard to do, often yields just an incredible gift of creative insight.” Jessica Ewing

Jessica H: Tell us about that.

Jess: Yeah. Definitely. So, one of the cool things that made me feel more comfortable right when I arrived was that my head instructor was female, and I wasn’t expecting that, I was expecting a bunch of commando … I didn’t know what to expect, really…

Jessica H: Did you go to scout out men? Like, was that a little bit in there?

Jess: No, that was that was not it for me, but I was mostly thinking about how much weight am I gonna lose. To add to your point about, “Was this a very reflective thing?” I was like, “No.” For the first couple days I was like, “Well, I’m not eating.” And I was like, “I’m walking 12 to 20 miles a day, so I’m calculating the number of calories in my head,” I’m a very analytical person. And I was like, “If this doesn’t work, then I just can’t lose weight at all. This has got to work.”

Jessica H: So, there were some ulterior motivations at work there.

Jess: There were definitely ulterior motives, but I think it’s almost better to go in with stupid motivations, than…

Jessica H: No, I love that, I love it.

Jess: …and then be pleasantly surprised with the spiritual benefits, than to go in with some crazy, mystical assumptions, and then be, like, “All I ended up doing was losing weight.”

Jessica H: Yeah. Right.

Jess: I get there, Laurel, is her name, and she’s this fascinating … She’s Chinese-American, right? So, I wasn’t expecting a woman, I wasn’t expecting someone Asian at all. And she’s got a bullet pendant around her neck, and she’s a hunter, she hunts elk, and has a philosophy degree from Berkeley. And just all these things that had just seemed so…

Jessica H: They don’t seem like they go together.

Jess: They don’t seem like they go together. And what struck me about her was, she … I love that when you meet someone that isn’t a stereotype and not an archetype, and they’re such a hodgepodge of so many interesting, incongruent things, that you know that this is just an authentic, sort of, fully-actualized being.

Jessica H: Which by the way, I feel like authenticity, somehow, has to do with being incongruent. We all are multifaceted and multi-passionate, and I think we have this expectation that you’re supposed to fit into this stereotype. But maybe, perhaps, the more we embrace our authenticity, the more we embrace our multifaceted nature. So, that’s super cool. I love that.

“I feel like authenticity, somehow, has to do with being incongruent. We all are multifaceted and multi-passionate, and I think we have this expectation that you’re supposed to fit into this stereotype. But maybe, perhaps, the more we embrace our authenticity, the more we embrace our multifaceted nature.” Jessica Honegger

Jess: Absolutely. And she was that way, which I think, sort of, gives everyone else a license to be a little bit more that way, you know?

Jessica H: So true.

Jess: When someone is their authentic self, then other people see, “Oh, I have all these congruencies.” And that’s OK, and that’s actually beautiful, incredibly beautiful, because she was just stunningly beautiful. And she had this bullet pendant around her neck, and then these silver bracelets with this safari shirt, and this cowboy hat, so incongruent, but so beautiful. So, she barely speaks, you know? Had barely spoken to us before we all piled into a van and got dropped off in the middle of this hauntingly, beautiful desert in Southern Utah, and she just … we’ve all got out of the van, we had spent like a few hours learning how to make packs out of our blankets, but then they took all the blanket packs away, and then we just walked off into no trail. The van just stopped, and I’m like, “How does she even know where we’re going? What is she doing?” The van just stops, it’s this beautiful sunset in this desert, and there’s just sand and stone, and she just starts walking off the side of the road, like, out there, right? No trail, no nothing. And I’m just like, “All right, I guess we’re going into the desert.” So, I had no idea what I was doing, and all my puffed up ego from being a tech executive and all this stuff didn’t help, in fact, that was counterproductive, and a disaster, but I was there to learn, so that was good. And we just start walking off into this desert, and then she just turns around and says, “Goodnight,” after a few hours of walking through the dark.

Jessica H: Oh my gosh.

Jess: And we’re just like, “OK.” And she just says goodnight, and then we all sort of, like, scurry away, and that’s their way of letting people follow their natural instincts about how to sleep in the wild, and what to do.

Jessica H: With no blanket still?

Comparing Down and Embracing Softness

Jess: Yeah. Nothing. No, I just laid down on the sand, which was fine and warm for a minute, and then the desert gets very, very cold at night, and the sand starts to cool down. And so, my comfortable, warm mattress quickly turned into the world’s iciest bed sheet, and I couldn’t sleep, and I was just tossing and turning. And I don’t think I slept the first night, maybe I drifted off for a second.

Jessica H: How could you?

Jess: But it felt so alive. You’re just like, “I’m just sleeping out in the middle of nowhere.” One of the psychological tools that they teach you is a technique called Compare Down. And so, we’re always so used to, as people, comparing up, meaning, “What’s the next thing for me? What’s the bigger house? What’s the bigger pool? The nicer fridge.” You know, we’re always trying to trade up and keep up with the Joneses, this is kind of our nature. But that’s actually really a poor survival tactic. So, if you’re in the wild and you’re thinking about what you don’t have, you’re not gonna make it, because it’s honestly more of a psychological challenge than a physical challenge, it’s physically demanding, but it’s psychologically brutal. And so, you’re laying there, and if you’re sitting there thinking about your warm bed at home, that’s not gonna help you. So, they teach you this technique of, sort of, compare down, which is, “All right. This isn’t perfect, but it could be worse. It’s a lovely night out, at least it’s not raining, at least it’s not hailing, I’m cold but I’m not wet, you know?” And those are just the things that you have to tell yourself to put your mind at peace. And it’s so counter…

“One of the psychological tools that they teach you is a technique called Compare Down. … If you’re in the wild and you’re thinking about what you don’t have, you’re not gonna make it, because it’s honestly more of a psychological challenge than a physical challenge. … So, they teach you this technique of, sort of, compare down, which is, ‘All right. This isn’t perfect, but it could be worse…. It’s a lovely night out, at least it’s not raining, at least it’s not hailing, I’m cold but I’m not wet.’ … And those are just the things that you have to tell yourself to put your mind at peace.” Jessica Ewing

Jessica H: To what you your mind, naturally, is doing in that situation.

Jess: Absolutely. And that’s really the first psychological trick that they teach you, and it’s an important one.

Jessica H: OK. Wow. It’s so simple, and you’ve shared this before. And so, I’ve done this before, compare down, when I’m in a place of … really, it’s discontentment, you know? And it helps you access contentment and gratitude.

Jess: Absolutely. And if you just think about the entrepreneurial journey, it’s like we get so caught up in…

Jessica H: More.

Jess: Yeah, in more. I mean, it’s the word.

Jessica H: How we didn’t meet the sales, or how we didn’t get that investor to close the deal, or how … Yeah.

Jess: Totally. And even though I’m a trained survivalist, and now an instructor at the school, believe it or not, which we’ll get into that story. But I still have to remind myself of this, this compare down, it’s a technique for survival, but I think it’s a good technique for life too.

Jessica H: So, you wake up the next morning, you didn’t sleep a wink, and…

Jess: And they just say to us, “Who wants to learn about building a shelter?” And we’re like, “And if I wasn’t interested the night before, I was real interesting the next morning.” And you can better believe, despite the fact that I hadn’t slept a wink, I was paying attention to that lesson. And so, they start to teach you, and it’s this fascinating school where, I mean, everything is a teaching moment for them. And so, what they do is, the instructors are fabulous, but they let you barrel off and do what feels most natural to you, and they let you make mistakes. And they’re always there to protect you and make sure you don’t do anything, you know…

Jessica H: Life-risking.

Jess: …life-risking, yeah, of course. But they let you…

Jessica H: Go to a cave where there’s snakes hanging out.

Jess: They let you suffer.

Jessica H: Let you fail.

Jess: They let you fail. They let you confront your ego, your demons, they hold back, they don’t say a whole lot, but they’re always there to teach, right? As soon as you have a moment where there’s a teaching moment, they’d step in. And probably the fascinating teaching moment that I had with Laurel, which gets your original question about being softer and more feminine, came around, I think it was maybe day 18. I had been in there a long time at that point. And we were at the section of the course where we were learning how to fish with our hands. And they use a technique where you basically take your hands and you put them in the weeds, and you feel along the bank for a fish. It’s called tickling, is the technique, OK? So, you kind of feel along the fish, if you move your hands very slowly, the fish don’t know that you’re anything other than…

Jessica H: Another fish.

Jess: Or weeds, or whatever, because there’s so much weeds in there. So, you reach along the sides of the bank until you feel a fish, and then you put both your hands around the fish once you can feel its body, and you sort of tickle it, and you’re touching it for a minute, and then you grab it, squeeze it, and pull it out. OK. So that’s…

Jessica H: That’s pretty hardcore.

Jess: Yeah. That’s the technique, OK? So, I’m sitting there and I’m watching all of these other people have success with this technique. I’m watching all these guys, in particular, catch their second, third, fourth fish, and I’m hungry, I wanna bring back food for the group, and I wanna be successful with this. You know, my ego is just, sort of, like, “I can’t do it, I can kill a fish.” And here’s the funny thing, and these are the things that you sometimes encounter in the wild, which is why it’s fascinating and interesting to me. So, Laurel is being very patient with me, she’s in the weeds with me, literally. So, we’re sitting in the weeds, and she’s teaching me, very patiently, how to move my hand along the banks and to feel a fish. So, I put my hand along the banks, I feel a fish, I’ve got it. I’m moving my hand under its slimy underbelly, and I’ve got it, and so, I move my other hand in, and it’s kind of perfectly positioned, and I have this moment of hesitation. And Laurel is just like, “OK,” she’s like, “Time to go,” and she’s trying to give me encouragement.

And I grasp my hands around this fish, and it immediately starts ringing in my hands, it starts flailing back and forth, and back and forth, and back and forth. And so, it’s struggling for life in my hands, you know? And I’m struggling for life in the wild, so it’s this complex confrontation, you know? And I couldn’t do it. I just, something in me just let it go, because it was struggling in such a fierce way, that I just couldn’t do it. And my face got all red, I just was brimming with tears, I was just so frustrated and angry at myself, “Why can’t I do this?” And I just was so mad, and I went and stormed down the river and sat by myself on this bank. And Laurel caught the fish, and she brought it to me, and she killed the fish. She brought it to me, and she handed it to me in a bandana, and she was just like, “It’s your fish.” And I was like, “It’s not my fish, I didn’t catch it. You caught it,” and all that stuff. And she just sat there very patiently, and she said, “You know what? You can learn this, you absolutely can learn this. But why didn’t you kill a fish?” I said, “I don’t know, I’m weak I don’t know.” And she just sat there very patiently, and she said, “You know, Jessica, you can learn this, but I would be lying to you if I said that this came as naturally to women as it does to men.” And she just paused, and she said, “You know, you are a protector of life, and I just want you to know that there’s just as much value in that as hunting, as killing.” And she framed it in such a way that, all of a sudden I felt so different. I felt like this total failure that I had…

Jessica H: Was actually a gift.

Jess: Was actually a gift, and it was just I softened in that moment, because she saw value in it. And the fact that she could be as strong as she was, as competent as she was, as capable as she was in the woods, and yet still see the value and what I was bringing to the table, which was not wanting to kill, was a tremendous moment of grace. And that single moment, I think, changed my life, because it helped me understand the kind of person I wanted to be, which was someone who was super strong, and was super competent, and was capable of doing all these stereotypically masculine things, and being in the world, but yet, someone who didn’t lose perspective of the other side, and could appreciate, you know, what that feminine core really is about.

“I felt like this total failure that I had was actually a gift. … I softened in that moment. …  [seeing] the value and what I was bringing to the table, which was not wanting to kill, was a tremendous moment of grace. And that single moment, I think, changed my life,” Jessica Ewing

Jessica H: Wow, that’s so beautiful. And here you went just thinking, maybe it all is a little weight and, like, learn a few things…

Jess: I know, it’s so stupid.

Jessica H: …and, like, prove my badassery.

Jess: Yeah. It was like I changed.

Jessica H: Yeah. So, then you go back to Google…

Jess: Oh, yeah.

New Perspective, New Career

Jessica H: Had you been thinking about a career shift before that, or did that open you up to a whole new future?

Jess: I think it really did. I mean, I just didn’t even have time to think about it. You know, I was working so many hours, that I just didn’t have space to reflect at all. But after 28 days in the wild, it’s hard, it’s grueling, but it also fills you with this injection of courage to go do something else. Because you just, sort of, think, “If I can do this, I can do anything.” You know, we worry so much about our finances, and taking risks, and it’s really hard, I think, because our default mode is to just be full of fear. And after having this experience, I was just, sort of, like, “I can get by on… I don’t need…”

Jessica H: I can get by with a knife and a poncho, apparently.

Jess: Yeah. I mean, you were just, sort of … And be fairly content, right? I was just like, “I don’t need a lot here.” You know what I mean? You would have a cup of lentils for dinner, or something, and … It was just a bag of lentils, a bag of rice. It really changes your perspective. And you’re just, like, “I can’t believe I think I needed all this stuff to go follow my dream, or my pursuit,” which was to be a writer, that’s what I always had wanted to be. And so, I left the survival course and I just kept thinking, “I need to do this, I need to go do something else, I need to follow my childhood dream.” And really, it shouldn’t be that hard, if I can do this, I can do anything, and I think that that’s, really, what it instills in people, along with a return to your heart and your essence, and putting you in touch with, “OK, well, what is that thing?” You know? Because I didn’t … The truth is, I didn’t have either thing. I didn’t know what I wanted to do, and I didn’t have the courage to go do it even if I knew.

Jessica H: Although people would look from the outside … I mean, weren’t you one of the youngest people in your position at Google?

Jess: Yeah. I mean, I was doing well, I really was doing well, but it just … It was a phenomenal position, and it’s a phenomenal company. But speaking from a more spiritual standpoint, you just know when you’re off your path, you know?

“It was a phenomenal position [at Google], and it’s a phenomenal company. But speaking from a more spiritual standpoint, you just know when you’re off your path.” Jessica Ewing

Jessica H: Yeah. Yeah.

Jess: And it’s like you can sit there and go, “Oh, it’s because of my boss. Oh, it’s because of my salary. Oh, it’s because of this or that,” or, “That person that I don’t like in the office,” or whatever. You can tell yourself all these stories. And sure, there were things to love and things to not love, but at the end of the day, you know when you’re on your path, and you know when you’re off your path. And when you’re on your path, none of those things really seem to matter, but when you’re off your path, you know. And I was off it.

Jessica H: You were off of it. It’s so interesting because you were like a math genius, right? You were in…

Jess: I don’t know about math genius.

Jessica H: Well, no, but didn’t you enter MathCON in high school?

Jess: Mm-hmm.

Jessica H: I remember you sharing this, one time, that you were … and yet, you’re wanting to be a writer. I mean, you obviously have one of those rare unicorn right-left brains so it’s, like, super congruent with the other. So, I think that’s so interesting that you’re in this very tech role, this analytical role, but then your desire is to be this writer. So, you come back, and you’re at Google, and now you’re having this reality of, “I’m not on my path.” And so, how do you go about getting off that path and on to a different one?

Jess: Yeah, it’s hard. The uncomfortable answer is that it’s real hard. It took me a year and a half to extricate myself, because I just didn’t wanna let down my team, and I wanted to vest another year of stock, because I just … Suddenly, the fear set in again, you know? And I was like, “Well, if I leave now, I won’t vest, maybe, for my financial future if I wanna be a writer, it’s not a very lucrative job. I should probably save more money.” And so, suddenly, you lose…

Jessica H: You go the logical self.

Jess: Yeah. I had been planning on quitting by Thanksgiving, and maybe a few months after, and it ended up taking me taking me like a year and a half, it just took me a much longer period of time. Suddenly, Google was offering me more stock, it was almost as if they … I don’t know if they knew, they probably didn’t, but it suddenly became much harder to leave. And that opened up an interesting period of questioning too, which was that if you are thinking of making a move or making a career shift, you’re asking other people in the company, “What do you wanna do? Is this your end-all-be-all?” And it’s funny because, there’s this book called Your Money Or Your Life, and there’s this fascinating study, I believe, from that book, where they ask people, “How much money do you need to go take a risk?” Right? To start a company, or to be a writer, just follow your artistic dreams, or just do whatever you wanna do. And the funny thing is that, the answer is always twice as much as they already have.

Jessica H: Really? Every time? So, if you have $20,000, it’s like, “Well, I need $40,000 to start my dream.”

Jess: Clearly $40,000.

Jessica H: But if you’re at, $100,000, “Well I need $200,000.”

Jess: Yeah. And if you’re at $1 million, you’re like, “I would need $2 million to feel safe.” It’s all relative.

Jessica H: It’s the comparing up thing.

Jess: Its the comparing up thing, that’s absolutely what it is. But the problem is, if it’s always relative, then it’s like, “OK.” Then, maybe, you get your $2 million, or whatever. But then suddenly, you’re like, “Maybe I should hold out for $4 million.” I mean, it becomes this treadmill, right? And you just never feel safe. And the ironic thing is, for me, the more I had, the more I had to lose. And so, I just had to draw a line in the sand. So, what I finally did after months of my brother and everyone else and me just constantly talking about this and not making a move, I’m sure it was frustrating…

Jessica H: People are probably tired about this at point, they’re like, “Jess.”

Taking Time to Find Your Path

Jess: So tired. I mean, everyone was super gracious about it, but my brother was just like, “Here,” he’s like, “You need to just need to put a date on a piece of paper, or a number, or something, and just put it in a drawer, and agree that the moment that you reach this goal, you know it’s time, you know you’re gonna walk.” And that’s what I did. And so…

Jessica H: You made a contract with yourself.

Jess: I made a contract with myself, and then I was like, “I have to do this, like, I have to go do this.” And then I did, and it was hard, and it ended up being super weird timing, and it was awkward, but the funny thing is that, as awkward and as weird as it was, I instantly felt like, “OK, I don’t know exactly what I’m doing, I don’t know exactly where I’m going, but at least I felt like I was figuring it out, and I was, sort of, on my path again.” And the first thing I did after I left my job was, I just drove back to that desert, I just drove back to the survival school, because I just wanted to go back to the cradle of civilization where it all began. And I just showed up, just to hang out, they were having a week of just teaching, where you could come make primitive pots, and learn how to make medicines from plants, so they were having like a workshop. And so, I just drove there, I sold my stuff, I drove back to the desert, and I showed up for this workshop, and my dad called, he’s like, “What are you doing with your life post-Google?” And I’m like, “I’m in the desert making some pots.” And he’s like…

“The first thing I did after I left my job was, I just drove back to that desert, I just drove back to the survival school, because I just wanted to go back to the cradle of civilization where it all began.” Jessica Ewing

Jessica H: “It makes perfect sense.”

Jess: “It makes perfect sense.” He said like, “Glad that Stanford Engineering degree really panned about.” And I was just like, “All right, whatever, dad. Just deal with this phase. You’re gonna have to deal with this phase.” So, I was making pots of clay, and hanging out, and then Laurel asked me, she said, “Would you like to become an apprentice?”

Jessica H: Wow.

Jess: And I said, “Yeah.” I mean, I was surprised because I was so awful at the initial course that it didn’t even occur to me that she would…

Jessica H: She would see potential in you.

Jess: Yeah. You know? I mean, the fish thing was…

Jessica H: One of many.

Jess: …just one of many, like, sort of, uncomfortable, disastrous, non-intuitive things for me. But I think I grew a lot, I think that the worse you are at, the more growth and opportunity there is for you. And so, for me, when she asked me to do that, I was like, “Wow.” I was like, “These are my heroes, all these people are my heroes, and I wanna be like them.” And so, “Sure, I’m totally gonna become an apprentice.” So, thus began years of training, and summers of just being an apprentice, being unpaid, and learning the ropes of this experience, and how to become an instructor. And, yeah. I mean, and I was usually … In the beginning, I wanted to stay close to that experience, you know? Even if it just meant getting out for one course, or a year. I wasn’t doing this full-time, by any stretch of imagination, I was trying to be a writer most of the year. But I knew that staying close to that experience and those people would be crucial for me as I was figuring out my path, to keep close to that courage, and to that authenticity that I needed to make my next move.

Jessica H: That’s powerful. And you’ve made many next moves since then. So, you explore becoming a writer, I know you eventually wrote a book, did you publish that book yet?

Jess: Not yet. No.

Jessica H: So, you wrote the book, I know you moved, you made some moves, what actually brought you to Literati?

Jess: Yeah. I mean, that’s a great question. So, it can be a winding path, and for me, I just knew that I love books and literature. And so, I thought that I always was ” OK, I’m gonna be a writer.” And so, I did against everyone’s better judgment I wanted to write a novel. And it was probably harder than survival school, but I finished it, and I was brought into the world of New York, meeting with literary agents and publishers, who are trying to figure out, “Is this viable? Can I publish this?” And I haven’t yet, I’m in the process…

Jessica H: You need to write a contract to yourself, Jess, it’s time

Surviving as a Writer and Birthing Literati

Jess: Yeah. I know, I know. I know. It’s hard. What was great about it was that, it put me in this world of books, which gave me so many insights into things that I could do to provide meaning, and to do meaningful things in that space, you know? It’s not an area where tons of entrepreneurs go, it’s not an area where tons of people from tech are interested at all.

Jessica H: That’s so true.

Jess: And so…

Jessica H: The publishing world is notoriously known for being stuck in another century.

Jess: Yeah. And that means that, for me, it’s ripe with opportunity, and I saw so many opportunities to do cool things in the publishing space. And Literati was just, sort of, a brainchild of my best friend and I. Let’s go backwards for a second. I left Google, I became an apprentice, I started working for the survival school, and the first thing I did after I went back for a year was, I just started writing, and I moved to the island of Kauai. So, I moved to Hawaii.

Jessica H: Because that’s what you do. When you decide to become a writer, you move to Hawaii.

Jess: Well, I was just like, “I can write anywhere. Where am I gonna go?” And I was like, “I might as well go to Kauai, right? And so, I went to Kauai, a I met this girl who was living downstairs for me, and her name was Kelly, and she just was such a passionate person about books and literature. She was also writing on the island, she was a poet. So, she was working on her poetry downstairs and I was writing upstairs, and we just became instant friends, phenomenal friends, like, within a second. And so, a few years later, after I had painstakingly finished this novel and was trying to publish it, Kelly and I had always had this friendship around books, and I was kicking around entrepreneurial ideas, and she’d gotten married, and she’d gotten pregnant, and she was a new mom, a brand new mom. And I called her, and I was like, “Hang on, I have all these ideas in the book space. Would you wanna do some design work?” She’s a phenomenal designer. And she hesitated a little bit because she was just, like, “I don’t know, I’ve got this…” Her son was just a few months old at that time, and she’s like, “But I wish…” And she was home, but at the same time, she just felt like she wanted to do something with her brain, something creative. And so, she agreed to step on just for a few hours a week. And we loved working together, and we got going … You have those relationships where they just … the people who just create energy in you, you know?

Jessica H: Totally.

Jess: And she created so much energy in me, so much passion for books and literature. And I was like, “Do you wanna move to Austin and do this company with me?” And she said, “Yeah, I do. that’s so exciting.” And so, we’ve been best friends for 10 years now, and doing this partnership. Where Literati really began was … we had all these ideas, and we were like, “Where are we gonna get started?” You know, we’re sitting in her house, and her newborn is screaming, and she’s tending to him and hustling and bustling around the kitchen, and she’s just, sort of, like, “You know, I’ve got to tell you, even though…” she’s like, “Children’s books,” is what she said to me. She’s like, “Children’s books….” I can’t even tell you, she’s like … Despite having an MFA … She’s an MFA in fiction from Brown, she’s one of the most literary people I know, one of most educated people I’ve ever met about literature. But suddenly, you have a child, and you’re thrown into this world of children’s books and literature. And she just said to me, she goes, “I don’t know what’s good. I have no idea. And I know reading is important, and I want my son to be a reader, but this is literally the worst time in my life to start researching this space. I don’t even have time to take a shower.” And she just said, “You know, if it weren’t for Halley,” who’s a good friend of her. She’s like, “If it weren’t for Halley, I would have no idea what to buy my son, I would have no idea what books were good.” She’s like, “Thank goodness for Halley.” And we were suddenly really intrigued, because we wanted to build this book club platform. And she was like, “Honestly,” she’s like, “We should start with children’s books, we should just focus on that that area because I,” she’s like, “Let me just tell you, it is so hard to find good stuff, and you just don’t know what’s good, you don’t have any time, and it’s a very hit-or-miss process.” And I was like, “That’s so fascinating,” because you’re not buying books for yourself when it comes to kids, you’re buying books for someone else. It’s not like you’re shopping for books yourself, your shopping to try to create and spark, intellectual curiosity, and insight into someone whose brain is rapidly developing.

“When it comes to kids, you’re buying books for someone else. It’s not like you’re shopping for books yourself, your shopping to try to create and spark, intellectual curiosity, and insight into someone whose brain is rapidly developing.” Jessica Ewing

Jessica H: That’s so true.

Jess: And so, that was really the brainchild of Literati, was that moment of just her being like, “Honestly, I can’t predict what my son’s gonna like. The books end up becoming favorites are totally random. All I can do is introduce him to things and hope that he takes an interest.” But that’s kind of expensive if you’re buying those books online, or it could be frustrating if you don’t have a good children’s bookstore, or a good library, or you go to the library and all the good stuff’s taken out, or these babies are putting books in their mouth. There’s just a lot of problems that parents have.

Jessica H: So, tell us, what is Literati? You have this aha moment of there is a hole in the marketplace, this is a need. And what is it now?

Jess: Yeah. I mean, we start looking around, and we just…there were a lot of people doing book boxes for kids, but no one was solving, really, what we considered to be the core problem, which is that I don’t know if my child will take to these books. And I just don’t want more stuff sitting around my house that is just taking up space, and I’ve got enough kids stuff in my house, you know? That’s what most parents are thinking, and I don’t need more stuff. I only really want books that are really connecting. So, that allowed us to go back to the drawing board and design a totally different product, which was the impetus for how our children’s book clubs work. It’s a little bit different than how an adult book club would work. In an adult book club it’s like, “OK, here’s the book of the month, we’re all gonna read it, we’re all gonna discuss it.” Our kids book clubs operate in a very different way, which is “Here’s five books to try, you get to keep them for a week.” It costs $10 a month for the service, and then you can buy the books at … We’ll match or beat the best price on the web. So, we’ll match or beat the Amazon list price, or whatever, so you’re buying the books at a good rate.

Jessica H: How often do you get a subscription box?

Jess: You can set the frequency. So, it defaults to monthly, but you can switch to every other month, or quarterly. And it’s funny, because one of the features that parents like the most … they get this box, and we really really really put a lot of thought and effort into, like, “OK, what is the theme of the month? Is it science? Is it art? Is it friendship?” And then kids get these personalized letters and personalized book plates and they get stickers that they can peel off with their name on it and put it there in their book, like “This book belongs to Jess,” or whatever. And so, we’ve put a lot of thought and effort into creating a very high-quality, very thoughtful experience, but you know what is funny, which is one of the number one features of the product? You’re gonna laugh, because going back to that point that I was making about a lot of parents feeling like they have just too much stuff. So, we decided three months into the product launch that we would let people send old books back to us as donations, and we would pay the shipping, right?

Jessica H: My gosh.

Jess: And we were like, “That might be a nice way … just a nice feature to give back, and also just to clean house.” Because it’s like, “If I’m buying two or three new books a month from this box, maybe I wanna get rid of a couple books as well.” And we just offered it, and then we can take all those books and we can find good uses for them, you know? We can get them to kids who can’t afford books, or libraries, or other ways. There’s lots of things that we do with our donations, but that’s not the point. The point is that we just started seeing, parents would keep a couple of books, but they started having these really meaningful moments with their kids, where they would say, “OK, what are the two books, or the three books, we’re gonna keep this month? OK, that’s great. Now, we’ll buy these, but what are the three books that we feel we’ve outgrown here and we’re gonna give?” And so, people just started sending any books they wanted to return, along this phenomenal number of donations, and creating moments of meaning with their kids, where, “Hey, it’s not just about buying stuff here. For every book we keep, we’re also gonna give back to someone who can’t afford a book.” And it ended up being one of parents’ favorite features, because they could just feel like they were building a library of favorites, but at the same time, they are cleaning out.

Jessica H: Cleaning out. That’s so fascinating. And then suddenly, you’re having to figure out how to systematize these donations.

Jess: Oh, we get so many donations, we get so many donations, it’s just crazy. And it’s fascinating for us, because we can see the need for people to feel like they’re really giving back. And people don’t wanna throw out books, and I get it, I get it.

Growing Through Entrepreneurial Shifts

Jessica H: So, survival, writing, being a writer, now being an entrepreneur…

Jess: Yeah. You got it.

Jessica H: … what is, sort of, this through line through all of this?

Jess: Yeah. I mean, I think the answer is growth.

Jessica H: Growth?

Jess: Yeah. Because you’re an entrepreneur, and you know the pressure to grow, but, for me, it’s just having a growth mindset. I didn’t know I would end up an entrepreneur, I didn’t set out to be an entrepreneur, I didn’t leave Google and, “Oh, I’m gonna, you know…”

Jessica H: Start a business.

Jess: Not even at all, not even remotely. I now interact with a lot of people that I once interacted with at Google, and it’s come full circle, because we’re women in this entrepreneurial world now, this business world. Some of my friends from Google, or colleagues from Google, have become investors in the company. And so, it has thrown me back into that world, but it’s funny, because you go back home after a long journey, and you go back home with a completely different perspective, and home is just as fresh and interesting as it… You know what I mean?

“It’s funny, because you go back home after a long journey, and you go back home with a completely different perspective, and home is just as fresh and interesting.” Jessica Ewing

Jessica H: Right.

Jess: As it was, but then suddenly, everything’s different now. And so…

Jessica H: Yeah. And to see, to me, how God, sort of, used all of these pieces too. Your time at Google has now come full circle, because you’re VC-backed, and I’m sure a lot of those connections came from having been from that world.

Jess: Definitely. And it gave me a start, and a few people that believe in me. I mean, it all ended up being super useful, but I think that’s the funny thing about the path looking back at it now, talking to you, it looks like a very well crafted novel, you know? But at the time, when you’re in it, it just looks like a mess. I mean, you’re just plotting one foot in front of the other, just saying, “Where is this going? This isn’t coming together. This, in fact, just seems to get increasingly random and weird.”

Jessica H: Yeah. And there even could be a shame story there, about like, “Do people perceive me as being someone who’s just all over the place?” Am I wasting my Stanford engineering degree?”

Jess: Yeah. You know, it’s funny, I never had those kinds of thoughts, because … No, I really never did, and I’ll tell you why, because I knew I was on my path. It was just an intuitive thing, and I wasn’t sure where it was going, it just kept unraveling. It was years of just knots unraveling, and just things getting more and more weird, and seemingly disparate things, but it all ended up being useful, to your point, you just … And so, I think the only unifying thread to answer your questions is growth, and deeply personal growth, you know? And anything more … I went to the desert because some part of me really wanted to grow. I mean, some part of me just wanted to lose a few pounds too, but there had to be something going on in the subconscious that was a little bit deeper, to do that. But, yeah, I think entrepreneurship too, it’s gonna test you. But I think that, the worst days, to be honest, the worst days of running a company are better than some of the best days when you feel like you’re not on your path. You know what I mean?

Jessica H: Yeah, that’s true.

Jess: Even the hardest days is like … the worst days, they still feel authentically yours.

Jessica H: Right. Because you’re like, “I’m still growing what I meant to grow, and creating what I meant to create in the world no matter how hard it is.”

Jess: That’s right. And suddenly, it’s not as outcome-driven. I mean, we all wanna be successful, but you’re in it for the adventure.

Jessica H: For the journey.

Jess: Yeah.

Jessica H: Well, that’s the journey I am on continuing right now, is loving it for the journey of it, for the practice of it, for the joy of it, and not for the outcome of it. I mean, I feel like I’m diving in, almost afresh, to that lesson right now. And, yeah.

Jess: Yeah. To just love the challenge, I think, that’s what it is. And I think the survival stuff can teach you that, just to … It’s like you’re not going anywhere, I mean, you’re just wandering, you’re just trying to survive. I mean, it couldn’t be…

Jessica H: There’s not a big purpose. You’re right. You’re not even summoning a mountain. You’re in the desert. Walk around.

Jess: You’re literally trying not to make a fool of yourself, and you’re just trying to survive on a basic level. Yeah. I think it’s a really great exercise for someone who is very Type A, and who is very achievement-oriented, who is trying to tackle that question. We all know, intellectually “Oh, just be in love with the journey and not the outcome, not the goal, or whatever,” But it’s hard. It’s really hard. And so, I think we all understand that on an intellectual level, but I needed to experience that on a bodily level, on an experiential level.

Jessica H: So, could we ever go to the wilderness together? Could I go on this? Could you be my instructor?

Jess: You can go. I mean, the school’s still, I’m still an instructor at school. The school converted into a non-profit actually, and I’m on the board. So, I’m now helping the school more on the logistics side, and whatever. But it’s still a tiny school. Laurel still works there, and she … So, not all the courses are 28 days. There’s a 7-day, a 14-day, but there’s also short custom courses. So, I could take you out, and we could do a 3-day or something, and go fishing, or whatever.

Jessica H: Wow, that’s cool. Oh my gosh. I don’t know. I have to write a contract to myself for this one. Well, listen, Jess. Thanks so much. I love your story. I’m gonna have you write a contract to yourself about publishing your novel, because you’re such a good storyteller. You are captivating. I mean, you’re such … I mean, I can see why you’ve been able to raise so much money, because you’re good. You’re good at storytelling, and this was such a great conversation. So, we wanna follow along. So, Literati is it literati.com?

Jess: It’s literatibooks.com.

Jessica H: OK. And then Insta, Facebook?

Jess: Yup, Insta, Facebook, you can find us, you can just Google Literati, or Literati children’s books, and you’ll find us.

Jessica H: Awesome. Awesome.

Jess: Yeah. It’s pretty easy to find, hopefully.

Jessica H: Well, thanks for coming into the office today.

Jess: Absolutely. Thank you so much for having me.

Jessica H: Alright, so one of her tips is, in a situation, instead of comparing up, like you’re in a hard place and you’re like “Oh, I wish I had it like that person,” there’s actually a time when comparison can be helpful. Which, y’all know me, I’m all about “Never compare! Run your race! Get in your lane!”  But comparing down is helpful. And so, when Jack was like … Oh my god, he was moaning “I’m going to die.” I mean, he truly thought he was going to die. And so, we would just do some compare downs. “Well, at least you’re not in this situation, at least you’re not in that situation.” And, in fact … well, I’m not even going to get into this whole other story. I’ll save that for another episode. But I’m just telling you that that one works. So, if there’s anything you got from today, I hope that that is what you got.

Remember Jess is offering to a Going Scared listener a full year’s subscription to Literati via a gift certificate, and I’m giving away a book of Imperfect Courage to one of you. To enter to win that contest, all you need to do is share this episode. So easy. So, go onto Facebook and put the clickable link to tell your friends to go listen to this episode, or go onto Instagram and screenshot the episode and share it in your stories. If you do share on Facebook, make sure you let me know in your DM to me on Instagram so that you can be entered. And you can be entered twice. So, whichever way you do it, we want to know. We want to hook you up. So, thank you so much for listening to the show, and thank you especially for also for sharing the show so that we can grow our listener base.

Our wonderful music for today’s show is by my good friend Ellie Holcomb. Going Scared is produced by Eddie Kaufholz, and I’m Jessica Honegger. Until next time, let’s take each other by the hand and keep going scared.