Ann Friedman Had the Bestseller and the Followers. It Still Wasn’t Enough.

One editor said, “We would literally buy anything else from you.”

Anti-viral is presented in partnership with Sublime, a creative thinking tool and communal search engine designed to help you collect, connect, and create from what inspires you — away from infinite feeds and AI slop. Sublime is my favorite kind of business — the small kind! — and they’re building my favorite kind of tool: thoughtful, single-focused, centered around what is distinctively human.

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This is the fourth installment of Anti-viral, a new series presented in partnership with Sublime, where I talk to creatives about the meaningful work that algorithms overlook, and what they would do more of if attention was no object.

Today I’m excited to share a conversation with Ann Friedman, a journalist and essayist who thinks about questions of community, technology, and why the world is the way it is. Together with Aminatou Sow, Ann co-hosted the trailblazing podcast Call Your Girlfriend and co-authored the book Big Friendship: How We Keep Each Other Close. She also teaches writing workshops with Jade Chang. You can keep up with her work by subscribing to The Ann Friedman Weekly.

In this series, I’m interested in any and all forces that influence whether things get made and find an audience, whether or not they use the canvas of code. I’m thrilled that Ann took the bait and agreed to chat with me about a book project that nobody wanted to buy. Our wonderful conversation touches on creative hauntings, confronting external markers of success, and what’s wrong with traditional publishing.

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Photo by Ryan Schude

Tell me about your book project that never came to be.

I went back and reread the proposal in advance of this conversation and had to stop because I was like, this is good. I was so mad all over again. In 2020, a book that I co-wrote with my friend and collaborator Aminatou Sow, Big Friendship, was released, and I spent most of 2021 on a quest for what book I was going to try to write by and for myself. This also coincided with becoming a homeowner in 2021.

I think a lot of the best work comes from a place of wanting to read something meaty and satisfying about an experience I’m having. And I wondered, where is the book about transitioning from renter to homeowner, and everything that entails—financially, culturally, emotionally, socially? There are definitely some books that nibble at different aspects of this, but there wasn’t anything like what I wanted to read.

So I spent many months working on a book proposal about the less tangible aspects of owning a home. I think my agent’s exact quote was, “That sounds very commercial,” which in agent-speak is ding, ding, ding.

So I was feeling confident about being able to write this book. It felt rich to me because it was rooted in my personal experience, but there was a lot of fun reporting to do. And it mirrored conversations I was having with friends and in my personal life, which is also a good tell for me that I want to write about something: if I want to keep talking about it.

Then the book first went out to Simon & Schuster, which published Big Friendship, because many authors have a clause in their contract that gives their publisher the right to either bite on or refuse their next book. They passed very quickly on this, which I was fine with. But then my agent sent this proposal to lots of other editors. And every single one of them was like, hell no.

Sometimes if an editor is kind of interested, they’ll ask a few more questions, or they’ll kind of push back and be like, “What if we framed it this way?” And this proposal received none of that. It just received a hard pass. The general reasoning was: we don’t think there’s an audience for this book. If publishing thinks there’s an audience for a nonfiction book, they buy it. It’s all about presumed sales, it’s all about presumed audience, and this book had none of those things, to their eyes.

[Editor’s note: nonfiction books are typically sold “on proposal,” meaning that rather than write the full manuscript, authors draft a long document that makes the case for what the book will be and why it will sell.]

What is it about this particular project that is still haunting you after all these years?

Here’s what’s so good about it. The topic is actually pretty narrow: owning a home. But it touches so many contentious, emotional, unresolved issues of this moment: how I feel about the modern state of America, what it means to be in middle-aged adulthood right now. It touches really big stuff while still being specific.

And it’s quite serious. Where do you live? How do you put a roof over your head? Questions of land ownership. But also, it’s kind of superficial and fun. There was a real throughline of this book that was about design, aesthetics, and the funhouse mirror of social media when it comes to the home. I know every topic that’s deep also has its lightness, but it had a really nice mix of those features.

In the idealized version of this book that will truly never be—because no idealized version of a book ever really comes to fruition—it was satisfying because it was all of those things. I still might write a version of it, but it will disappoint me in the act of writing. I will disappoint myself.

Was the rejection more about whether the book had a built-in audience, or about whether you were positioned to sell to that audience?

The feedback was twofold. One was: people don’t buy books about buying houses. Homeownership is not a topic that sells in this more reported, essayistic category. People only want to know how to do it, the mechanics of saving for it. And I wasn’t pitching a practical guide to becoming a homeowner.

The other problem was: you are not a housing market reporter. You write about friendship and “women’s stuff.” If you wanted to pivot and position yourself as a housing expert with a talking-head gig on MSNBC, maybe we would buy a book about homeownership from you. One editor said, “We would literally buy anything else from you.” So it was really quite universally negative feedback. Most things in life are more mixed than that. Most things in writing are more mixed than that. And this was just a hard pass from all corners, for reasons of perceived audience.

What story do you think those publishers are telling about why this project wouldn’t draw readers?

I’ll tell you something that my agent frequently says, which is that people pick up a book either to be entertained—swept away by a story—or to learn something to solve a very concrete problem in their lives. I would like to believe that my work, and some of the best essayistic reporting in this category, do both of those things. It’s not pick a lane: there are juicy stories, and you’re going to learn something about how you approach the world.

Maybe it’s not solving a problem in the sense of, how do I buy a house? But figuring out how to ask the right questions is why I read a lot of things. And that seems to be universally acknowledged as a bad way to sell books right now.

I’m content to acknowledge that maybe you and I are weirdos. Maybe we read in a way that most people don’t. I do sometimes read purely for story, or purely to get concrete advice about something. But I would say all of my favorite books, and most things I pick up, are a combination.

The other thread I’m hearing is this idea of personal brand. You had a popular podcast with your best friend, so now your brand is “friend,” and you’re allowed to write a book about friendship. But you hadn’t yet built your brand as a homeowner. It feels like an inherently internet-age logic.

Totally. Maybe I could have found some loophole if I were assiduously documenting a home renovation on Instagram, or if I freelanced for Architectural Digest. Maybe there would be a side door I could get in, with something approaching the career I have now, as opposed to being a market analyst. The appeal of that is less than zero.

Ann Friedman and her co-author, Aminatou Sow. Photo by Milan Zrnic.

What is your relationship with attention in general—with being perceived as a public figure?

I feel fine about being perceived. I like to have a say in which aspects of my life are perceived. When I used Instagram or Twitter, I was not showing the interior of my home. I have a robust quilting practice, but you will never catch me posting any quilts, because it’s protected. Texting friends, yes, but documenting for the internet, no. My child will never be on the internet posted by me. I spend a lot of time unchecking boxes from daycare that are like, can we post photos of your child? Are you kidding me?

Did the rejection change how you felt about the value of the project?

I thought it was a great idea, and I still do. My reaction was: something is wrong with publishing. Maybe if I had gotten feedback that was like, look, we agree that there’s a space for this book, but the way you approached it wasn’t quite right, or we need to add this angle, then I would have done a little bit more soul-searching. But my feeling was, it’s not my job to convince you to want this.

I think it’s a fool’s errand to try to convince a huge system like publishing or Hollywood that something is inherently valuable. I was obviously not going to become a talking-head commentator on cable news about the housing market. So my options were: sell it to a really tiny press, where I wouldn’t be making any money up front, which was not a financial possibility for me; or set it aside and think about what else I might want to do.

I work as a journalist. My job is selling words. So these words didn’t sell; I’m going to find new words to sell. I feel quite practical about it in a lot of ways. Maybe after another project, if no one has beaten me to this, I can come back around to it.

And I’m fully aware that maybe one viral Atlantic article about homeownership hitting right before I pitched this idea would have changed everything. It’s not logical. As much as it seems like there’s a formula, what editors want to acquire is subject to whims that I don’t control.

What do you think is wrong with publishing?

Every big industry that produces creative work, or funds creative work, has a risk-taking problem. They do not want to take a risk on something unless they are absolutely certain there will be an audience for it. And that’s doomed to fail from the start.

How many things have you personally loved in your life where you’re like, wow, I never would have thought I would love this, but it was great? That is the way we consume things. From an investment perspective, any industry that is investing in creative work is so small-c conservative. Finding a way to cater to that conservatism while still making things that you want to make is the trick.

The other option is to not expect any payment upfront, fund for yourself the making of exactly what you want to make, and then, once you demonstrate an audience for it, say, “Haha, now you can pay me.”

Time for you to launch your homeownership Substack.

If I were to time travel back to late 2021 and talk to the version of Ann who didn’t want to give up this project, that is exactly what I would advise her to do. I would say: start a really juicy, journally, bloggiest-personal-Substack-you-can-think-of newsletter about your experience as a non-homeowner → maybe-I’ll-be-a-homeowner → trying-to-be-a-homeowner → being-a-homeowner trajectory.

She didn’t want to do that. And that’s fine.

Given that you are so haunted by this idea, why have you never written about homeownership in your newsletter?

There is a sweet spot for when to write about something personal for me, and it is when I feel a little bit of resolution—when I feel like I’m starting to come to some language for what has happened to me, but I’m not quite there yet. In 2021, as I was working on this book proposal, it was still pretty fresh.

Then there was a period of time where I was like, okay, it’s all going in the proposal. I’m going to save it for that. I don’t want to burn this publicly. And I do think a book is the right venue for a lot of this. I don’t actually think a 1,500-word essay is how I want to talk about becoming a homeowner. It doesn’t feel like enough space for everything I want to tease apart.

Then there was honestly a period of grieving this book proposal, where I was like, I don’t want to touch it now. It feels tainted. A proposal takes months and months. It takes effort, reporting, revision. I was done for a while.

The question of what books get made feels so cosmically important. And at the same time, the way those decisions actually happen feels so cosmically random. On an individual level, everyone I’ve met in publishing is passionate and acting in good faith and genuinely loves the book as an artifact. But on the level of the machine, it feels so tragic to think about all the books that aren’t written based on such an imperfect measure of value.

The counter to that is small and independent presses, which do not have the budget to fund reporting work upfront, but do publish things that are more driven by a logic of “I like this and so someone else will too” as opposed to: “What is the exact market niche? What table will this be featured on? Which celebrity book club is likely to pick this up? Will BookTok like it?”

I think that once you let go of major publishing buy-in equals value, or equals this is a good idea, and accept that it is just random, you’ll be better oriented towards publishing.

What’s an example of a book that the publishing industry would not have predicted you would like, but that changed you?

Maggie Nelson’s The Argonauts is a great example. A book that’s not going to light any marketing person’s loins on fire. It’s a book that is a little academic, a little personal, and frankly a little journalistic. She’s talking about a moment in time, what it was like to be in a specific place, in a specific relationship, with the politics of the moment. That book was riveting to me. I actually drooled on myself while reading the final third of The Argonauts.

I read it as someone who was not queer, not interested in having children—demographically, other than being a woman of words in California, not aligning with what a marketing professional might have said was the demo of that book. And I know so many people who just had their views of family, self, and relationships rocked by that piece of writing. A friend of mine always keeps a copy on her table because that book is the reason she decided to have children. That book has it all.

That book changed me, too. It was one of the first things my partner and I talked about when we met, and it’s quoted in our marriage vows.

Green flag. Talking about The Argonauts on an early date: green flag.

I can’t imagine that book was sold on proposal.

Exactly. And granted, I don’t know what number book that was for her. She’s a prolific, experienced writer with serious-writer, faculty-type accolades appended to her name, so maybe she was a safe bet to do what she wanted. And I don’t know who published it, was it Graywolf? [We both run to grab our copies]. It was published by Graywolf, so it’s a small press. That is no coincidence to me: a Big Five publisher was not “boi-oi-yoing” to that idea.

Maggie Nelson’s The Argonauts.

There’s a throughline between homeownership and publishing, where these innate human needs—shelter, groundedness, expression, connection—are co-opted into financial instruments, which in turn corrupts those initial human needs: People end up without shelter. People can’t publish books. As someone who has thought about ownership a lot, how do you think turning both books and homes into financial instruments changes what those things are?

We don’t think or talk about it enough. That was one reason I was excited to write about it at book length. It is not only people who are shut out from having a home or owning a home who experience the warping effects of turning where you live into a financial product. In the same way, it is not just people who are shut out of traditional publishing who are affected. It’s also people who do get published traditionally, and who bend their work to fit into that space.

Maybe more than anything, it’s just talking about it and acknowledging it. I don’t think the homeownership book would have ended with a call to abolish private ownership of homes or anything like that. I think it would be: What are we really talking about when we talk about this? What are we really craving when we say we want it? What are we really feeling shut out of?

What do you think a publishing economy would look like that valued this kind of work more highly?

I think it would empower individuals with considered, but probably flawed, taste to make decisions based on what they wanted to read and what they wanted to see in the world. That is why I say that if someone had read that proposal and been like, “Ugh, not for me,” I would have been like, “I get it.” But the idea that it’s outsourced to some nebulous idea of the crowd makes me not respect the feedback.

I don’t have close friends who are editors at Big Five publishers. And I do wonder sometimes about the toll of not being able to just leap at something because you like it, even though it seems like there is no “market value.” Much like turning a home into a financial product also hurts homeowners, it’s probably not great for your soul to be in it for the love of words and then cater to the abstractions of a market.

It’s interesting to have this conversation as someone who has a general, documented following, because you hear this over and over: publishers want someone who can demonstrate that they can sell a book. I’ve known many writers who pitched really worthy books and were told, you don’t have enough of a following. Come back to us when you have a magic number of Instagram followers. I’ve advised people to just buy followers while their book is out on submission. This is how stupid the whole system is.

The publishing police are going to come for you.

[Laughs] My God, are they? What’s the worst they can do? Cancel the contract for this book I’m working on? At this point that would be a blessing. Come for me.

But what I think is worthwhile about telling this story is that I don’t have that problem. I have Instagram followers. I have newsletter subscribers. I have people who are familiar with my work because I’ve been working for so long. And still, it wasn’t enough to just do what I wanted.

We spent a lot of time and effort trying to make Big Friendship a bestseller. And one reason was that I thought it would mint me for the next project. I thought it would be this silver bullet—she’s published a bestseller. Sure, we wouldn’t normally greenlight this, but you go ahead, girl! I thought I wouldn’t be in the position I was in because we had just barely crested that bestseller status. And it wasn’t enough.

Understanding that it doesn’t matter, it’s quite liberating. Not that I’m not going to try to sell the next book. I’ll try to get people to read it; I will have spent years of my life on it. But the idea that there’s any kind of reward from the system for becoming a bestseller, I’m over it. There’s none. That’s not part of my calculus anymore. In that way, I guess it was a very worthy experiment in whether I care about external markers of success from the publishing industry. Who cares about a bestseller if you can’t do the thing you want?

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You can keep up with Ann’s work by subscribing to The Ann Friedman Weekly.

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