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First Draft Episode #311: Doree Shafrir
July 1, 2021
Doree Shafrir, co-host of the Forever35 podcast and author of Startup, joins us to talk about her debut memoir, Thanks For Waiting: The Joy (& Weirdness) of Being a Late Bloomer.
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Welcome to First Draft with me, Sarah Enni. This week I'm talking to Doree Shafrir, co-host of the Forever 35 podcast, and author of Startup. Doree joins us to talk about her debut memoir, Thanks For Waiting: The Joy (& Weirdness) of Being a Late Bloomer. I love this conversation. I loved what Doree had to say about learning to live on her own timetable, how podcasts serve a fundamental part of the human experience, showing people that they're not alone, and the counter-intuitive way that Doree found to lower the stakes in her own life.
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Okay, now please sit back, relax and enjoy my conversation with Doree Shafrir.
Sarah Enni: So hi Doree, how are you doing today?
Doree Shafrir: Hi Sarah. I'm good. How are you doing?
Sarah Enni: I'm doing well. I'm so excited to talk today. So excited to ask you about Thanks For Waiting your memoir, which just came out, which was such a pleasure to read.
Doree Shafrir: Thank you.
Sarah Enni: And we're gonna get into your podcasting and your debut novel, all of it. But I do love to start my interviews way back at the very beginning, so I'd love to hear about where you were born and raised.
Doree Shafrir: Sure. I was born in Boston and I was raised outside of Boston. I grew up mostly in Brookline, which is just outside of Boston.
Sarah Enni: I want to ask about how reading and writing was a part of growing up for you. I loved in Thanks For Waiting, there's a special shout out to Harriet The Spy, which is kind of a through line for you. But I'd love to hear that about how that was part of your development.
Doree Shafrir: So reading was just always something that was around. I mean, my parents read to me from the time I was born, essentially, and I was able to read at a really young age. I don't remember learning to read, I don't remember not being able to read. And books were always just such a huge part of my childhood.
I kept books on my bed because I just liked to read them so much. And I would read books multiple times and just always loved books. When I was in kindergarten, this is an anecdote that I share in the book, because I could already read my teacher arranged for me to have special sessions with the school librarian. And at first I was very opposed to this because I was like, "Why am I being taken out of the classroom where I'm just playing with my blocks?"
I didn't like the feeling of being singled out. I just wanted to be inconspicuous and just be another kindergartener. And instead, I was marched to the library, literally kicking and screaming. And then when I got there, the librarian was just this very kindly, older woman who had come with some suggestions for me to read. And she was just so nice and I almost immediately sort of melted.
That began a really nice relationship that I had with our school librarian, my elementary school librarian, for a few years. And writing too, I remember in like first grade we started writing books in school. Once I started reading the Little House on the Prairie books, which I think was around first grade, I started writing these pioneer stories, very similar to Little House on the Prairie.
A few years later my parents got me a typewriter, because I was a kid in the eighties, so I would write on that in my room a lot. And so that was kind of my childhood. It was always something that was very encouraged. My parents had a lot of books.
Sarah Enni: It's interesting to me, you share in the book the love for Harriet The Spy and writing in your journal to yourself a little bit. What came to mind for me was like non-fiction observations, right? Talking about the world around you in that way. So I'm interested in whether creative writing was a part of your life then, or if it was always non-fiction for a while. Because I know you grew up to become a journalist.
Doree Shafrir: When I was a kid, it was kind of a mix of both, but I think it definitely started leaning more towards the non-fiction. I kept a diary starting when I was seven, influenced by Harriet The Spy. Like you said, everything was very observational. At one of the summer camps I went to, like an arts day camp, and they had a newspaper and that was one of the classes that I took. And I helped write the newspaper every day. And that was just always something that I did.
But at the same time, I was actually recently going through some old files and papers and I have all this stuff from when I was a kid, and there's a lot of short stories in there. Now, a lot of them are very similar to things that were going on in my life, but they were made up and there were also ones that had nothing to do with my life. Like there is one about a kid detective agency, you know? There were just a lot of fiction interspersed in there.
Sarah Enni: I'd love for you to lead me to your career in journalism, because you did have a pit stop in history. You were part of this really fascinating new media moment in New York. So I'd love for you to lead me there.
Doree Shafrir: I was in a PhD program for history and I left it to work in media, in Philadelphia, which is where I was living. And then I left that to go to grad school at Columbia for journalism. And when I graduated from Columbia, I didn't have a job, but I did get an offer for an internship at Slate in the culture department.
So I was a culture intern at Slate for the summer, it was a paid internship, which was very rare at the time. And so it sort of felt like I had a job, even though it wasn't especially well-paid, at least I was getting some money. And that experience, I think, started to insert me into a New York media world. And there was some stuff that I wrote for Slate that I think got me noticed a little bit.
And then while I was in grad school, I had done an internship at Radar Magazine, which has not existed for many years, but the person who edited that website, I ended up writing stuff for him on the website. So we became friendly and he forwarded me an email from his friend who ran Gawker, was the managing editor of Gawker. And they were looking for writers, or a new writer, a new editor or something.
And then independent of that, another friend of mine also knew this person and forwarded me the same email. And they were both like, "You'd be great at this" And I was like, "Okay." And you know, Gawker had launched a few years earlier, I was still very much in awe of it. At the time, it was like very cool and seemed very, I don't know, not exclusive exactly, but they were like the cool kids and their take on everything was like the cool take.
And they were snarky and mean, and everyone in New York media read them and was obsessed with them. I was like, "Okay, I'll apply for this job." And so I did, and then I had to do some sample posts and I ended up getting the job. So in 2006, once you worked at Gawker, suddenly everyone in New York media knew who you were. Because when I started, there were only four of us who were writing for the site, and one of them ran it, and he didn't write that much.
So there were really only three of us with bylines. And so you quickly became well-known in that world. And I think, as problematic as Gawker was, and how hard that job was, it really was a springboard in many ways because of the connections that I made while working there. I also did party coverage, which means you're going out every night talking to a million people. So I started to know so many people because I was going to so many parties and, at the time, there were a lot of parties.
So I was doing that and I was also specifically covering media for Gawker. So, getting to know so many people in the industry from the most important people, to the assistants. And that also, I think, just allowed me a very quick entree into that world.
Sarah Enni: I want to just pause on that really quick. There was such an interesting little bit in the book about this that I just wanted to ask you to follow up on. In talking about Gawker at that time, and again, I hope listeners are familiar with it, it was kind of a groundbreaking website. And it was very, as you say, very well-known and really influential.
But, like you said, it had a really snarky tone. I just think that you were sort of on the forefront of getting exhausted by the tone of the internet, right? The hot take life of being online. I think we're all kind of dealing with that, so I would just like to hear you talk about what writing like that consistently did to you? And how you came to understand what you were feeling? Cause now your job is a lot of fighting against that, pretty explicitly, and really being open to nuance and context. And that's like the opposite of what that vibe was.
Doree Shafrir: Totally. I think Gawker, in a lot of ways, played to some of my worst instincts. Gawker was so much about the "in-crowd" and the "out-crowd." And for someone who had always desperately wanted to be part of the in-crowd, I was suddenly part of that crowd. We were the ones who were telling people what to think about everything, and that was very intoxicating for a while.
But we were also supposed to be very critical of pretty much everything. And so that posture started wearing me down, pretty quickly. I think at the time I would have described myself as a cynical person, but I felt like I had to be so cynical. You could never assume that people had good intentions, or everyone is fair game. And it just started to feel kind of icky.
And the pace was also really grueling, like really grueling. We had post quotas and, you know, starting early in the morning, it was just like grind, grind, grind. And I think one or the other might've been okay, you know? If it had been a grind, but not quite so negative, maybe I would have been able to stick it out for longer. Or if I'd be able to be negative and not have to be writing all day every day in this way. But the combination was a lot.
Sarah Enni: I know we're kind of jumping a little bit, but I would love for you to lead me to the opportunity to move to LA. And I think not too long after that, you're dipping a toe into creative writing with Startup and just kind of giving that a shot. Do you mind kind of leading me there?
Doree Shafrir: So when I started working on Startup I was working at Buzzfeed in a management position. I was editing, but mostly managing teams, and not doing very much writing at all. I started realizing I was feeling very creatively unfulfilled, and I was like, "You know what? I just need a project that is just mine. It's just for me."
And so I started waking up early every day before work and basically free writing. But I was like, "I don't want this to be a journal. I'm gonna just make something up and see where it goes." I just kept going. I kept going, I did it for the month. I was like, "I'm gonna do this for the month of January and see what happens. Write every day, see what happens." At the end of January, I had like 40 pages of what we're basically character sketches, but you could see the seeds of a story beginning to form.
And I sent them to my agent, my literary agent, and I was like, "Can you just read these and tell me if there's anything here that you think is worth continuing on?" And she read them and was like, "Yeah, you should keep going." I was like, "Okay. All right. I'll keep going."
It had started as something that was really just trying to get me out of a rut, like a work rut, and then it turned into a whole book.
Sarah Enni: That's amazing. And one thing I think is just so admirable about how you even started writing the novel is that, as you say, you were, at this time, in a job that people would be [pauses], um, how do I want to say it? Like you say in the book a lot, like, "It seems like people's dream jobs, running the culture side at Buzzfeed and being a manager."
But you're beginning to realize that maybe the quote unquote "dream job" was not a dream for you, or it wasn't serving you. And that the inevitable rise through the ranks as a media reporter sort of gets you to this place where it's like, "Wait a second. Why was I on this roller coaster to begin with?"
Doree Shafrir: Yes!
Sarah Enni: I don't know. I'd love to hear you talk about that. A lot of people listening are creative writers themselves, and I think we can all relate to that. Like, "Wait a second, where is this actually going?"
Doree Shafrir: I think working in journalism, the career path seems to be like, start as an assistant, or as a reporter. And then as you kind of work your way up, you become an editor. Then you're overseeing people. Or if you're in digital journalism, running a website. Or in print, being the editor-in-chief of a magazine, or whatever. That was just always held out as like the path.
And I think I was just like, "Okay, that's the path." When I was offered this job at Buzzfeed, I was offered the job as executive editor to launch all these new verticals for Buzzfeed. And it was this period of really rapid growth for the site. They had just gotten a ton of venture capital funding. I started there in 2012, but this was all kind of happening at the end of 2011, the very beginning of 2012.
They got venture capital funding. They decided to launch a news division. They hired Ben Smith (founding editor in chief of Buzzfeed News and now a reporter on the media for the New York Times) to run it and he brought me on. And he was basically like, I mean, he didn't say it in this many words, he was basically like, "You can do whatever you want." And I was like, "Holy shit!" Like, "Great, this is amazing! You never get this opportunity."
And I had just come from Rolling Stone where I was an editor on the website, which was one of those jobs that seems glamorous, and was very much not glamorous. I was sort of desperate for a way out, but I didn't really know how to find one. And then when I started at Buzzfeed, I would say for the first couple years, it was great. And then it started to get really overwhelming.
I was managing teams in New York and Los Angeles. So I was flying back and forth all the time. Managing all these disparate teams. Didn't feel effective as a manager, at all. And I was like, "This is what it is? This is what everyone wants from their careers?" Like, "This kind of sucks."
So I kind of stuck it out for, I don't know, another year or so. And then I gave up most of my management duties and launched an ideas section at Buzzfeed, which was a little bit more gratifying. I was working more directly with writers [sighs], actually, I was still managing a bunch of people but I was at least getting to edit and assign pieces myself.
And I was like, "Oh, I really like doing this. I really like editing. I really like coming up with ideas, and finding writers, and looking at pitches, and editing people's work." That I found really gratifying. It was the like, "Does this person need to be on a performance improvement plan stuff that I was just like, "This is soul sucking. This is awful. I don't want to do this."
It's hard to wrap your head around that because I felt like I'd been conditioned to think that this was the, what is it? The rung of the ladder that I was supposed to be going, up and up and up. And that the logical next step after this would be, "Oh, well, I'll take an editor-in-chief role somewhere." You know? And to be like, "Oh wait, this is not what I want."
Sarah Enni: It reminds me a bit of what you say in Thanks For Waiting about dating. I think this was a reflection on your thought process before you'd had like a really serious relationship. The goal of being with someone it's like, you just want a boyfriend, but you're not thinking in your head like, "What does it actually look like, or feel like? What is the lived experience of being in a committed relationship?"
You're just like, "The goal is someone kisses me and then I guess we're all set?" And then having the scales fall from your eyes about like, in some ways, we are societally led to believe we want some things, but there's not a lot of introspection or understanding of what that entails.
Doree Shafrir: Yes, yes. I often have these thoughts of like, "I mean, it's 2021. I can't believe we're still having these conversations, and these thoughts, and feel these pressures." But we are.
Sarah Enni: And I want to jump back into Startup really quick, because I want to hear about how you wrote it with help, how you got your accountability partner.
Doree Shafrir: So I had met my friend, Kate Spencer, on Tumblr in like 2008, or something. Back when it was this small blogging site, and it seemed like everyone on there was this loose collective of bloggers and writers and we all followed each other. And she was working for VH1 at the time. And her mom had just died and she wrote really powerfully and beautifully about that but also with a sense of dark humor. And I was like, "This person's cool."
And we started following each other on Tumblr but didn't know each other. We both lived in New York, but we were kind of in different worlds in New York. And so our paths never crossed IRL. And then she moved to LA, and then I moved to LA a year or two later. Suddenly we were both New York ex-pats in LA and then it seemed more logical for us to actually hang out.
And so we got drinks and we were both like, "Oh!" I think it was one of those immediate kind of like, "Oh, you're cool. You're cool." And then I didn't see her for almost two years. She had a baby, she lived in the suburbs, we were just leading different lives, but we were in touch. And then when I was working on Startup, when I decided to actually go for it and write it as a book, I remember just emailing Kate and being like, "Would you ever want to do a monthly two-person writing workshop, essentially."
Like, "Be an accountability partner, share pages with each other, give each other feedback, but it would just be the two of us. And I know you're really busy, so, you know, flexible and whatever." And she was like, "Yeah, I'm actually working on this book of essays about my mom and grief and I'd love to share stuff with you." So I was like, "Great!"
And so we started meeting and it was amazing. It was really amazing just getting feedback from her, being able to bounce ideas off of her. We were pretty consistent in our meetings. Like we really did meet pretty much every month, maybe even twice a month, I don't recall. But we both published books out of it. She published a book called The Dead Mom's Club that's a wonderful, wonderful book. And I published Startup. So it worked.
Sarah Enni: I love that. I love that at that pivotal time, you were able to find someone who obviously shared your values, shared some of your background, and also is the right amount of encouragement.
Doree Shafrir: Totally.
Sarah Enni: And a little bit of similar kind of voice. I feel like when you find someone that shares your instincts, it's really a game-changer.
I want to talk about the starting a podcast phase of your creative life, cause that's a little bit of how I was looking at it. The trajectory sort of ended up being, and tell me if I have the timeline right, that Startup came out, I think, in 2017 and that's right around when Forever 35 started, is that right?
Doree Shafrir: So Startup came out in April, 2017 and we started talking about Forever 35 in like October, November. So probably six months later and then it launched in January of 2018.
Sarah Enni: Okay. Well to kind of set the stage for that, I do want to talk about Matt and Doree's Excellent Adventure because that is your sort of origin story in the podcasting world. And that happened, I think it sounds like, while you were writing Startup over a few year period of time. But can you just let us know what that podcast is about? Give us the pitch for that podcast.
Doree Shafrir: Yeah. So Matt and Doree's Excellent Adventure is a story of going through IVF, trying to get pregnant, all of the ups and downs of that whole process, that multi-year process. And we started the podcast in 2016, partly because we didn't see anyone else doing it. Now there are more IVF podcasts, but at the time, the only podcasts that touched on IVF were from either a medical perspective, or a therapist-y perspective. There weren't really any shows that were hosted by people who were going through it, especially in real time.
So that was one thing we were like, "Huh, that's interesting." And I had been a little reticent about talking about it. But Matt, who had been podcasting since 2008 and has done stand-up for a long time, he no longer does stand-up, but he was a stand-up for a long time. And so like sharing very intimate and personal details about his life is like second nature to him. He just doesn't even think about it.
And he asked me if it would be okay for him to talk about it, and I said, "Yeah." But he was like talking about it at his poker game and he came home and was like, "Oh, you know, three of the guys at poker, they all go to our clinic." [Laughs] He found that every time he brought it up, people were like, "Oh yeah, we're going through that too." Or, "We went through that to have our kid." But it wasn't until he raised it that people were like, "Oh yeah, me too."
And then I started noticing people tweeting at him because he talked about it a little bit on a couple of podcasts. And they were like, "Hey, thanks for talking about it. My wife and I are going..." It was a lot of men responding, which I thought was really interesting. I felt like there was such a stigma for women to talk about it, but even more so for men, like men just like did not talk about it. And he was giving them permission to talk about it.
And I was like, "What if we did a podcast about going through IVF?" And he was like, "Who would want to listen to that? That sounds awful." I was like, "I really think people would listen. And there is a need for it." So I was like, "Please do a poll on your Twitter and ask your followers if they would listen to a podcast about IVF." And he was like, "Okay, if it's a majority yes, I will do a podcast." I was like, "Great." And it was 80% in favor, 20% opposed. Or, 80% yes, 20% no. And I was like, "See, they want this."
And so that was the impetus for starting the show, but we were like, "This will be a really short podcast." Because at the time that we started it, we were about to do an embryo transfer. And I was like, "Well, this will work. I'll be pregnant. And then what's the point of doing a podcast about IVF?" Like, "Duh."
But then it didn't work. So it just kept going. And now we still do it, even though we have a two-year-old, because we still get so much contact from listeners who write in with their own problems, and issues, and questions. And a lot of times just want our advice based on our experience. But a lot of times they're asking about things that we have no idea about, but we throw it out to the listeners and, inevitably, there's someone who's like, "I went through that. I dealt with that. This is what happened to me."
And so it's just been really rewarding to be able to bring people together in that way. And also, just this fundamental aspect of the human experience, show people that they're not alone, you know? And I do feel like that's what the podcast has done.
Sarah Enni: You obviously were serving a need cause, as you say, it's created this really vibrant community of people who are sharing information, and really connecting over these things that are so much more widespread than you might even think.
But also, as you say, it was as you were experiencing this, so you kind of give yourself a challenge of, you want to share your story and connect with people, but then that is asking a lot of you to consistently show up and share things that are disappointing, and difficult, and really emotional.
Doree Shafrir: Yes.
Sarah Enni: I'm just curious about what that was like to come back to the mic week after week.
Doree Shafrir: I mean, there were times when it was really hard. There were times when, if we got bad news or something, I would just be like, "I just don't wanna talk about this." Like, "I just want to curl up in a ball and not dissect this for thousands of people." But I did find that every time I did, I got so much empathy from people, and not in a pitying way, but in a, like, "I know it really sucks. I've been through this, this really sucks," kind of way. And I was like, "Yes, this does really suck. You see me, you get it. I see you, and you see me." You know? And so on a very personal level, it did help me through it. Just knowing that, unfortunately, so many people had gone through what I had gone through.
Sarah Enni: There's a great quote from Thanks For Waiting that I'm going to quote back to you, where you were talking about one of those moments when it was hard to go on Excellent Adventure and share. And you were saying, "Did our listeners see us as characters in an ongoing fertility saga and was I disappointing them by not giving them the storybook ending they craved."
And that was just so interesting to me. And it just made me think about how, even though you were sharing something that was so explicitly like, "We're all in the middle of it. This is happening live. There is no expectation of any outcome, or the other." You're still packaging it and presenting it as, in some way shape or form, a narrative. We just, as human beings, consume stories that way.
So, I mean, I feel that as a podcaster myself, who shares a lot of myself personally, it's like, "Well, what are people expecting me to do next? Or for it to go? Or what is being seen as success?" I'm just so interested in what it's been like for you to continue to live on as this character for people to listen to.
Doree Shafrir: I mean, that was really complicated, and I started realizing that after, maybe after like our second transfer that didn't work, people had clearly been so invested in it. And, in a way, I don't want to say it was flattering, but it was also like, "Oh, these people genuinely care. They are invested in our story because we have brought them into our lives." And like, "That's amazing!" And I'm grateful for that.
At the same time, they were hoping, I mean, we were all hoping that the outcome would be different. But they were hoping for it in a way of like, "I want this story to have a happy ending because I care about these characters." And it's like, "Well, I'm not a character. I'm a real person." And like, "This is out of my control. If I were scripting this, sure, the transfer would have worked." But like, "This is my life."
Sometimes we would get emails that would be like, "I had to stop listening to the podcast, it just got too depressing." And I was like, "Okay, well, that's your choice. Obviously, you are by no means under an obligation to keep listening." But it was just interesting that it was like, "Your life's gotten too depressing. I didn't want to hear that part of the story."
And so, simultaneously, I started feeling this weird pressure to resolve the story, and thinking about it in those terms, in addition to actually wanting a child.
Sarah Enni: This is bringing to mind all of these different sort of threads that are kind of coming together with this part of your story it's like, having these moments of subversive thinking about what if life could be different or live life a different way? And that is a push back against the narrative.
You being a late bloomer is kind of flying in the face of the narrative that says, "You should have done this by this time. And you should do this in this way. And that way, your life follows this arc that we all understand."
Narrative is such a human endeavor and people like us who tell stories really rely on it and love it. But that is what kind of hangs over us. And when real life gets in the way of a quick, easy, nice narrative, it's very distressing. But if we could all sort of live in that gray area and deal with that discomfort a little bit more easily, we'd all be a little bit happier, I think.
Doree Shafrir: I think so. I think also because we were doing it in real time, sometimes I didn't have that zooming out that I might've had if we had recorded everything and then took six months and packaged it together in this like 10 episode series, you know what I mean? Where I could have reflected on it. And so there were these certain inflection points where I did zoom out and I was like, "Whoa, what is happening? And how do I feel?"
And then, to your point about envisioning these other possibilities of our lives, that was another thing that really helped me. Because, at first, it kind of seemed counterintuitive, if you really want a child, why would you envision, or even plan out this life, where you don't have a child, where you're childless.
And I resisted it for a long time because I was like, "I don't even want to think about that. That is not the vision of my life that I want. I don't even want to manifest it! Just get it out of my brain." But then after a while, it had probably been about two years that we'd been doing infertility treatments, and it was starting to feel more and more hopeless. And I was just like, "Well, what would my life look like?" Like, "What would our life, as a couple, look like if we never had a child?"
And as I started playing out the scenario more and more, I was like, "Oh, not only would this be fine, this could be kind of great." We already had a dog by that point. I was like, "We could get like four more dogs. We could get like a farmhouse." So, I just had this sort of elaborate child-free fantasy. And then I was so much more at peace with it.
And it let me take some of the stakes that I had placed on the idea of having a child and just kind of lowered them. Because in my head it had been like, "If I don't have a kid, my life is over." I'm like, "In actuality, that is not true. And I would have a really great life with someone I loved and we would figure that out together." And so letting myself picture that was this important mental shift. Um, sorry, I've completely forgotten the question...
Sarah Enni: I love what you're saying because I'm so relating to that. I think it's really applicable in many, many facets of people's lives. I have just been talking about this in therapy, a lot. About many times, and stakes is totally the word that keeps coming up over and over again, in some instances, because we are all playing out the stuff that got hardwired into us when we were so young, then being left behind, or not being cared for, does mean you die.
The stakes are like, "Either I make these friends, or I have social death." There's so much that's just like the other side of it is falling off a cliff. And as you say, in therapy, they often are like, "What's the worst case scenario? Talk me through it, visualize it." And it's so like, "Oh yeah."
And then, on the other side of things, I'm always jaywalking and I'm like, "These are stakes that I'm like literally risking life and death, and I don't even think about it for a second." So it was just such a funny, I'm like, "Okay. Moments to sit and reflect."
Doree Shafrir: That's funny. Yeah, "What's the worst that could happen jaywalking?" Well?
Sarah Enni: "Actual death."
Doree Shafrir: Yeah, "Actual death."
Sarah Enni: "Maybe take that a little bit more seriously, and take the other stuff a little less seriously, and find a good balance." I love that as a takeaway from your long experience. Which then, interestingly, did end in this happy ending. Right?
Doree Shafrir: Yeah.
Sarah Enni: Which is very interesting to have that moment of catharsis. And we'll come back to it, cause I wanted to then talk about the - we're like doing a Russian nesting doll of like - then you write about it in memoir, which inherently is a narrative.
But before we get to that, I want to touch on Forever 35, which is your wonderful podcast with Kate Spencer. I would just love to hear about how it started, if you don't mind.
Doree Shafrir: So picture it, it's 2017. If you can take yourself back to that time.
Sarah Enni: Oh god.
Doree Shafrir: I know, it was a rough year. Donald Trump got inaugurated in January and then I just feel like it was just one thing after another of like, "Wow, we are not in Kansas anymore." Like, "This is fucking real and terrifying."
Sarah Enni: Yeah, talk about living in real time and not knowing.
Doree Shafrir: Yes. And I found that I, and many of my friends, were kind of like retreating into skincare. Suddenly all anyone wanted to talk about was like, "What serum are you using?" Or, "What's your favorite shade of red lipstick?" I would see women who were publishing executives, posting on their Facebook being like, "Hey, anyone have some great eye cream recs?"
It was just like, "People just need this refuge. Everyone is just retreating into this world." And I would text with friends about it. And we all just became obsessed with our skin because it felt like the one thing we had some semblance of control over. And then Kate texted me one day in the fall of 2017, and she was like, "Do you want to start a podcast about skincare?" And I was like, "Yes, I do."
And at that point, we'd already been doing Excellent Adventure for a little over a year. And so I was like, "I think I can get us off the ground." We hired a producer and just hit the ground running. I was like, "We can do this ourselves. We can do this independently. We don't need to join a podcast network. We can just do this."
And we didn't sell our own ads on Excellent Adventure, but I knew through having ads on Excellent Adventure, I kind of had gleaned enough about the industry that I just kind of knew some stuff. And so we started getting inquiries on ads and I was like, "Yes, we can do that." And so that was how it launched, and then it just kind of took off from there.
Sarah Enni: And you had already had experience with this from Matt and Doree's Excellent Adventure, but now, ostensibly, Forever 35 is about skincare, quote unquote, but really you and Kate share so much about yourselves. You really give a lot to your listeners, you give feedback to them, and you hear back from them, and there's a big community that's formed around Forever 35.
So it's been another way for you to give people an alternative narrative and interrogate what is expected, especially of women, after 35, which is kind of the point of the title. But again, you are a character in people's lives and someone who they're following. I'm just interested in what it's been like, as the podcast has exponentially grown, how that's been for you as a person staying sane behind the mic.
It's funny, sometimes I forget that we are talking to thousands of people and some of them have turned us into characters. And I'm reminded of that because I'm in a bunch of Forever 35 Facebook groups and I'll periodically comment or post. And sometimes people will be like, "OMG, I can't believe Doree Shafrir responded to my comment!"
And I'm like, "I'm just a person. What are you talking about?" But then I'm like, "Oh yeah, I do host this podcast. This is the community that Kate and I have created." So it's like this weird thing where I'm suddenly reminded, "Oh yeah. These people are all here because of me...right."
Sarah Enni: It reminds me of you being in that manager position, right? Where that's not always a comfortable fit. I find that I'm less comfortable with maintaining a community around First Draft as I am just creating First Draft. So it's interesting to me.
Doree Shafrir: Yes, that's a really good point. We've handed off control of the Facebook group to a team of admins and mods. We pay our admins, this is a part-time job for them, they take it really seriously, which I really appreciate. And that was the thing that I was like, "We can't manage this on a regular basis."
I think that's one thing that I've come to realize when you're running your own thing, you just really have to prioritize and think about like, "What is the core of this endeavor?" Well, the core of it is the podcast. Without the podcast, the rest of it does not exist. So is my time best spent moderating the Facebook group, or booking guests? You know what I mean? Or recording? Or whatever.
And that's been an interesting learning process and we had that same thing come up with selling ads. Because for the first year, I sold all our ads and managed that. And then I was like, "This is insane. This is so much work. It's kind of fun, but it's also exhausting and just an administrative headache."
And so we decided to join a podcast network, Acast, and we have to give them a percentage of our revenue, but it is so worth it to just not have to deal with all that stuff. And that's been a good learning process for me.
Sarah Enni: There's a lot of navigating. "What am I really good at? What can only I do? And how do I make sure that that's where I'm putting my time?"
Doree Shafrir: Yeah, I mean, there's one more example of that, that actually connects to writing. Which is, within six months of launching the show, we got close to, I think, 10 editors approached us about writing a Forever 35 book. It felt like every other day we were getting an editor being like, "Have you guys thought about writing a Forever 35 book?"
And we actually tried to write a proposal. And then we were like, "What are we doing?" First of all, the podcast has only been around for six months. So for us to come out with a book felt very premature. And then we were also like, "What are we saying? Is this a self-care handbook? Is this like a memoir? What is this?"
And third of all, the podcast is our main thing. And we should be growing the podcast and focusing on the podcast, especially in the first year. So that was another thing where, at first, we were like, "This is so cool. People want us to write a book. Wow!" And then we kind of pumped the brakes and we're like, "This is not what we should be doing right now."
Sarah Enni: That's so interesting and an intriguing process to have to go through and then to talk about with a partner as well. It's not just you chugging along, you have to make sure that you're both in it, and in it the right way, and for the right reasons, and at the pace that you can maintain. Sustainability is a word I've been using a lot lately for all this stuff. It's a tough balance to find.
But, you led me perfectly to Thanks For Waiting. Before I ask specifics about the book, I would love for you to actually give us the official pitch for Thanks For Waiting.
Doree Shafrir: Thanks For Waiting is a book about living life on your own timetable. And how the things that you thought you wanted, might not turn out to happen at the time that you wanted them. And they might not turn out to be the things that you wanted, in the end, after all. It's about having empathy for your past selves and your present self.
It's about navigating a career in a rapidly changing industry. It's about moving across the country as a single woman at 35 and kind of starting over. It's about infertility, and dealing with infertility, and all of the craziness that comes along with that. Gosh, I could go on, but that's longer than an elevator pitch, but those are the main themes.
Sarah Enni: I mean, it's a memoir, so it's about your life and experience. But I understand that it started as a collection of essays.
Doree Shafrir: Yes.
Sarah Enni: Can you talk about the origin story of this?
Doree Shafrir: For sure. I've always written personal essays, from the time I was a teenager. And it was always a form that I felt really comfortable in. And I think in my mind, a book of essays just made sense to me. It was sort of weird, actually, that I had written a novel because my whole career had been in journalism or creative non-fiction. And I just always assumed that my first real book would be a collection of essays and then it was a novel.
So then after the novel, I was like, "Okay, I'm ready for my essay collection." And I wrote up a proposal, it sold, which was amazing. And then two months later I had a baby and then I didn't work on it for like seven months. And then when I came back to it, I kind of struggled to write a couple more essays and sent stuff to my editor who was like, "Okay." I was like, "This is not complete, but let me know what you think."
And she had a lot of thoughts. I just had a lot of work to do. And then I felt very paralyzed. Like I was just like, "This was a mistake. What was I thinking? This is so hard. How does anyone write essay collections that aren't just like collections of things they've already published?" You know what I mean? I was like, "What was I thinking? This was so dumb."
I was having so many regrets and I was like, "Can I give back my advance and rip up my contract?" I was really like, "I don't think I can do this." So finally, as a kind of Hail Mary, I reached out to a woman named Carrie Frye. She's like an independent book editor, who I knew some people who had used her to either develop book proposals, or they worked with her on writing their books, or she had edited their books. She'd been involved in some way.
And I reached out to her and I was like, "I'm supposed to turn in this essay collection," this was in May or June of 2020. I was like, "I'm supposed to turn this essay collection in, in September. And it's a disaster. Could we work together?" And she was like, "I have this window of time from like July 15th to September 15th where I could work with you." And I was like, "Okay, great." Or ,actually, no, I think the book was due in June and she was like, "I can work with you from July to September."
And I was like, "Let me see if I can get an extension." And I did. And then I sent her my pages and I was legitimately like, "She's gonna tell me these are so bad that like, just pack up and go home." But instead she was like, "This is not a book of essays. This is a memoir. And here's how you're gonna restructure it." And she really held my hand through the course of like eight weeks or something.
And we basically tore up the book and started from scratch. And I would send her pages every week, and she would get me notes, and it was super-fast. It was like a crash course in writing a memoir. I was on deadlines all the time. But I was like, "This is my last chance. I have no other options."
Sarah Enni: How do you feel about the end product and putting a book in the world that is, I mean, as you say, it is really personal. It's a lot about your dating life and a lot about your struggle to make choices that feel right for you. But then it does come to the end here, where you do feel like you have found a better place. I mean, that was kind of the journey that I went on with the book, but how does it feel to have this out in the world?
Doree Shafrir: Good and scary, you know? Because people are reading it. To me, it's like they're reading it as a book, but it's also like they're reading my life, you know? So it's interesting. It got reviewed in two of the trades and one of them loved it, and I felt like, really got it. And then the other one was basically like, "This person's life is boring and she's not a late bloomer." Like they were basically like, "It's well-written, but the events of the book are pretty ho-hum."
And I was like, "Okay, you've just really honed in on the exact insecurity I had around this book. So thank you for that." And they also got some details wrong, and I was just kind of like, "Okay." So, what I'm trying to say is, everything they wrote in that review were things that I'd already thought to myself. And so to see that someone else had that same impression just was sort of like, "Oh my God. Well, who am I to think I can write a memoir?"
And that is my anxiety surrounding having a memoir versus writing a novel, because it's so personal. They are basically saying like, "Your life is not interesting enough to write a memoir." And that's like, "Ugh!"
Sarah Enni: A whole different kind of feedback than a fiction review.
Doree Shafrir: Right. So I don't know. And obviously some people are going to have that response. It's not going to speak to everyone. The people who it speaks to, I think it really speaks to, and then there's gonna be some people who are just like, "Eh." And I know that.
So to answer your question, I'm really excited. I'm thrilled to have it out in the world. I feel like it is the best version of the book it could have been. And just based on conversations with people that I've already had, who have read it and liked it, they felt very seen by it. That has been really rewarding [sighs]. I'm nervous and excited.
Sarah Enni: I mean, just to kind of put a cherry on that point, I do appreciate you sharing that particular insecurity. Because with non-fiction writing, and memoir writing, and personal writing and essays, I think what you're touching on is that you have to have some sort of inherent belief in your self-worth. And that you have something to say and that what you have to say deserves to be heard.
And that's hard to find as a woman. That's hard to find as a writer. That's hard to find by anybody in the world right now. And that sort of reflects the journey you go on in the book, I think, to find what feels right to you. And, "Is carving my own path... how can I come to a place that feels good with that?" So, anyway, I obviously did connect with it. I loved it a lot. I think it's sort of the proof of concept, for you to have gotten that review, and to be able to be like, "Well, that's fine. That is over there. And we're just moving on this way with the people who get it."
Doree Shafrir: Totally, totally.
Sarah Enni: Okay. One last thing and then I'll wrap up by asking you for advice. But I love that you and Kate are writing for InStyle now, which feels like Doree's triumphant return to writing for the internet.
Doree Shafrir: I know! Yeah, an editor from InStyle reached out to us a few weeks ago and asked if we were interested in writing a column focusing on beauty and skincare for women over 40. And we were like, "This sounds amazing." Like, "Yes!"
So I think by the time this comes out, the column will have officially launched. It's just funny to me because we open every podcast by saying we're not experts. We're two friends who like to talk a lot about serum. So we've very consciously positioned ourselves as kind of amateur enthusiasts in this world.
And that is sort of still the posture that we have adopted for the column. But we are more experts than we used to be. And so it's just interesting now, for me, especially to bring it back to the book as someone who always felt like she was a little like catching up, or clueless. Especially about beauty and grooming and all of those things. To now have a column in InStyle?
Sarah Enni: The great irony.
Doree Shafrir: Yeah, exactly. But also, it's kind of sweet, right? It's kind of like, "Well, you know, I stuck it out and here we are." So it does feel really nice to be able to do that.
Sarah Enni: That's so great. Irony is not the right word, but it does feel like a sweet cherry on top.
Doree Shafrir: Yes, totally.
Sarah Enni: Well, I'm really excited about the column. So congrats to you guys on that. And good on InStyle for thinking of that.
Doree Shafrir: I know, I was like, "Sure! Awesome."
Sarah Enni: This has been such a joy. I do love to wrap up by asking my guests to give advice. So I would really love, and this is kind of a selfish question cause I am interested in writing personal essay and non-fiction in the future, but I'd love to hear from you about someone that might be interested in writing non-fiction based on their own life, and memoir style. Where should people get started? What do you think about how people should approach that kind of writing?
Doree Shafrir: So I think what's so important to remember is that there are so many stories that we tell about ourselves, that we've been telling, for years and years. And they seem so familiar and commonplace to us, but other people haven't heard them. And I think that was something that I had to keep reminding myself when I'd be like, "Oh, everyone's so bored of this." And I was like, "Well, no. You're bored of this because you lived it and you've thought about it for decades. But everyone else has no idea."
So that's one thing, feeling like you do have the right to take up this space and tell this story. So that's one thing. The other thing I would say is just starting to free-write, when it comes to memoir, is really important. Just writing any memories that you have, just jotting them down, not trying to form a cohesive narrative or story at this point. Like, "Oh, the time we went to grandma's." And just any story that you have, might not end up in the book, but you might start to see patterns. You'll make connections. And so I think just having all of that stuff in a notebook is really important. I mean, I would think of stuff so randomly and just jot it down on any piece of paper that I had handy.
And sometimes, several come to me in the middle of the night, even when I was almost done with the book, I'd be like, "Oh my God, I can't believe I didn't talk about that thing!" And just scribble it down. And there's so much stuff like that, that's in our brains, you just have to kind of dislodge it.
And then the third thing I would say is, as I mentioned before, having Carrie to be like, "That's interesting." I do think it's helpful to have another person who you can kind of bounce things off of. Whether it's at a point where you're just developing your ideas, or reading or whatever. I do think that that is really helpful.
Sarah Enni: Well, it's kind of sweet that you had Kate for that for your fiction and then Carrie kind of swept in to help you with that with your second book. So, that's a great thing for people to be able to try, having an accountability buddy, who can kind of cheer you on and help you parse things as you go
Doree Shafrir: Agreed. Yes.
Sarah Enni: Well, thank you for giving me so much time today, Doree. This was such a pleasure to chat with you and congrats on Thanks for Waiting. It was really a pleasure to read.
Doree Shafrir: Oh my gosh. Thank you so much, Sarah. This was so fun.
Thank you so much to Doree. Follow her on Twitter and Instagram @Doree. Follow me on both (Twitter and Instagram) @SarahEnni, and the show @FirstDraftPod (Twitter and Instagram).
And thank you again to our sponsor, The Great Godden, the new perfect beach read from National Book Award finalist, Meg Rossof, out from Candlewick Press now.
First Draft is produced by me, Sarah Enni. Today's episode was produced sound designed by Callie Wright. The theme music is by Dan Bailey and the logo was designed by Collin Keith. Thanks to social media director, Jennifer Nkosi and transcriptionist-at-large Julie Anderson.
And, as ever, thanks to you bloomers of all seasons for listening.
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