When I first arrived in New York for my job at BuzzFeed, everyone and everything was intimidating. My coworkers knew how to do things like effortlessly swipe their metrocards without holding up the entire line. They could wear heels and pull off cool haircuts and make elaborate meals from the snack closet. They knew how to make GIFs. I turned 33 on my second day and deleted my birthday on Facebook so no one would try to awkwardly celebrate or, you know, actually know the number. I liked my age then and I like my age now but I don’t like my age defining me, which is what it felt like it would do in those early days.
Then I went to the Los Angeles office for the first time, ostensibly to write an oral history of Empire Records and report out an investigative piece on TMZ. The Hollywood office was quieter, sunnier, less anxiety-filled, which I guess is just a way of describing a certain sliver of Los Angeles, but the median age of employees was also about ten years older. I felt like I could exhale. Especially after I met Doree Shafrir, whose Generation Catalano piece had been part of my personal canon for years.
At that point, Doree had been part of New York media long enough to get really fucking sick of it. I liked that, as someone who could already telegraph the point in my future where I, too, would get really fucking sick of it. As an editor, she would take a paragraph, ball up the sentences, throw it against the wall, and have it bounce back refined. She could spot throat clearing and BS-ing and rhetorical windmilling from miles away. She taught me how to turn a sentence into a small dagger. Some of this skill came from her time at the New York Observer and Gawker. And some of it, I’d later realize, came from navigating the intransigent bro management spaces of Rolling Stone and, in many cases, BuzzFeed.
I don’t know if L.A. softens New York media people so much as literally and figuratively warms them. When Doree decided she wanted to stop being executive editor — and start writing on the Culture desk — I got to see a lot more of that, because when someone’s not editing you anymore you get to actually cultivate a friendship. When she launched Forever35 and left BuzzFeed, it felt like watching a career trajectory click into place.
Now, she’s probably the person in my life who, when people find out that I know her in real life, prompts the most mini freak-outs. YOU KNOW DOREE????? That’s a testament to the incredibly loyal communities she’s built over the last few years, and but also an expression of a desire to just know more Doree, because she manages to emanate an aura of having-seen-some-shit and having-figured-out-some-shit while also modeling a real openness and curiosity. That’s rare, and that’s magnetic, and I’m thrilled to be talking to her today about all of that and her new memoir, Thanks for Waiting: The Joy (and Weirdness) of Being a Late Bloomer.
Brief Programming Note: I’m taking the next week off the newsletter — the first time I’ve done so since December. Thank you, as always, for your support.
This book has gone through a lot of conceptual and formal shifts — and I know you worked with our mutual pal Carrie Frye to help shape it. Can you get writing nerdy and detailed about how it went from book proposal to final project?
I always wanted to write a book of essays. I’d been writing personal essays pretty much all my life, and it was a surprise (to me!) that my first book (Startup, which came out in 2017) was a novel and not non-fiction. So I put together a book proposal during the winter of 2018-2019, and thought, this will be fun! I’ll write that book of essays I always thought was in me, and it will just flow out of me.
It… did not do that. Two months after I sold the book, I had my son, Henry, and then I went into a black hole writing-wise and didn’t come out for months. When I finally resurfaced, I submitted around 100 pages of essays to my editor, whose response was basically, “So there’s a lot of great stuff here, but…” You know, the words that begin any editorial note that you know is going to just be brutal.
I went through another few months of barely being able to write anything and was getting despondent, to the point where I seriously considered ripping up my contract and sending back my advance. Then, in what seemed to be a total Hail Mary, I emailed Carrie Frye, the former Awl editor who now runs her own independent editorial company, and asked if she would be willing to help me resuscitate this book. She said she’d love to, but that she only had something like six weeks over the summer to work on it with me. So we devised a plan: I would send her the whole manuscript, she would read it and send me an editorial memo, and then I would revise it in chunks and send them to her and she would respond with additional editorial memos on the revision chunks, and we had a call every week about her memos and what I was working on.
And it was… ridiculous? I do not recommend it. I basically rewrote the entire book in six weeks, then did another revision on my own, and sent it to my editor, Sara Weiss. Then Sara and I went through three, or maybe four, rounds of revisions, which was also a grueling process because by this point I was extremely late. Sara really pushed me to be more vulnerable and open in the book, and also had some really smart structure suggestions, and I had to turn in the draft that was going to go to copy edits in mid-January, and then my husband got COVID.
Anyway, this is all to say, it turned out that I needed Carrie’s handholding to get a complete draft to send to my editor, and I learned that that’s okay! As someone who has typically not been great at asking for help when it comes to work stuff, this was a really good lesson for me to learn.
Reading Thanks for Waiting is a trip for me because I was paralleling a lot of these experiences at BuzzFeed, even if across the coast, and when you talk about quitting BuzzFeed and our then-editor-in-chief’s reaction (“Huh”) I laughed out loud, it was just so precisely what he’d say. But this isn’t a tell-all, or a memoir of, like, a massive historic moment, but how did you conceive of narrativizing life at public-facing company, filled with other public-facing writers?
Telling the BuzzFeed part of my story was interesting, because I had so many mixed emotions around it, and it’s all still relatively new. I realized as I was writing that I hadn’t fully processed a lot of the things that happened at BuzzFeed, or how I felt about them, until I started writing. And I had to really think about how BuzzFeed fit into the bigger picture narrative that I was trying to tell. So what I realized was that, in the context of being a late bloomer, BuzzFeed was the thing that I had been conditioned to want, career-wise, but that actually was not right for me. Besides Ben, no one else from BuzzFeed, except for Jonah Peretti (the founder and CEO), is named in the book, and that was a deliberate choice.
In the book, your podcasts and the communities around them serve as sort of a (current) culmination of your larger professional trajectory, and I feel like I was just a few years behind you in realizing that I wanted to own and run my own thing. But like you, I was also terrified of it — we had both internalized that the other (digital publishing) shoe was always about to drop, that the internet was fickle and deeply assholeish, but also that truly, what the fuck do you do without health insurance???
Can you talk through a bit about what it means to own your own brand, for lack of a better word, and the fear and joy that accompanies both that stewardship and the community that’s sprung from it?
This is one of the things I think about a LOT, especially as a woman who is now in her mid-forties, a time when a lot of women are kind of quietly put out to pasture in the media industry. So for me personally, part of owning my own brand also means owning my age, and owning the fact that so much of what I produce — podcasts, writing, social media — is speaking to people, mostly women, who are around my age. Which, in our youth-obsessed culture, can feel almost subversive! And another part of it is speaking openly and honestly about the experiences I’ve had, whether in my career or dealing with infertility or dating woes. People want to feel seen, and I’ve tried to foster community around both of my podcasts (Forever35 and Matt & Doree’s Eggcellent Adventure) that show people that they’re not alone.
But as you say, there is both fear and joy around that stewardship. We have a team of admins and moderators for the main Forever35 Facebook group that approve posts and monitor comment threads around the clock, because I’ve seen so many large Facebook groups just go off the rails. Still, I’ll occasionally get an email from someone who’s indignant that a moderator rejected their post, or blocked them from the group because of their behavior, and they threaten that it’s a reflection on me — which of course, it is! But also, I have a responsibility to the thousands of other people in the main group and the spinoff groups, and that’s why there are rules in place to protect not just them, but also Kate (my Forever35 co-host) and me.
All that said, I would not trade the professional life I have now for anything. I’m incredibly lucky that I get to do this and that people have put their trust in me, and I’m well aware that it’s not going to last forever. Part of being your own “brand” in media is that you have to constantly be pushing and looking for the next thing, whether it’s writing another book or launching another podcast or doing a paid newsletter or whatever the next iteration of The Thing that everyone else who is their own brand is doing right now. It’s a grind and it can be overwhelming and exhausting, but ultimately, it’s mine.
I love the point in the book where you’re like, there is no way to be “chill” about infertility. It is not an accessible posture. That acknowledgment — plus the description of buying the black linen jumpsuit, and rejecting the male gaze on our own bodies that so many of us have internalized — felt at once familiar and revelatory to me. Do you think women are able to access these revelations earlier now, or is it still something that just takes decades?
I was just having a conversation with someone about how deeply fucked the ‘90s were in terms of the messages that we were all forced to internalize, and how someone growing up today really cannot understand just how pervasive and insidious they were. Or, not even insidious — they were right fucking there, in our faces, all the time.
So I think the women of our (roughly; I’m a few years older than you, but I think the general conclusion still stands) generation don’t even KNOW the amount of unlearning we have to do, and then every so often we get confronted by something in the culture where it’s suddenly clear that women in their twenties have grown up thinking VERY differently about things like the male gaze and body autonomy and consent than we did. I think that’s often a source of tension between women our age and younger women: we don’t understand that they don’t feel the same way we did, and they don’t understand how we could possibly still have so much internalized misogyny.
In the last few years I’ve been forced to confront some of my own internalized misogyny and hoo boy, it is a hell of a drug, but once you get sober (am I taking the metaphor too far?) you start to notice it EVERYWHERE, like how our boomer parents can’t not comment constantly on people’s appearance and what they’re eating, which I did not even NOTICE until like, three years ago and now I’m like: what the FUCK? Also, yes I am still hungry!
And as a fun ridiculous closing note, you were one of my first editors at BuzzFeed, back when I really did not know how to write like a journalist. If you have any memory of me doing something weird in my writing, I’d love to get lovingly razzed.
HAHAHA. Well, as a dropout from academia myself, I can say (lovingly!) that you had a habit that I think most academics have, which is: showing your work. I remember sometimes reading your pieces and being like, okay, we don’t need to know about EVERY single document you consulted for this story! There are no footnotes in a celebrity profile, unless you fancy yourself the next David Foster Wallace! (I say this WITH LOVE) (AHP NOTE: Yes, very guilty)
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