Your summer publishing questions answered: Round 3

Why is querying so freaking depressing, are agents okay with small presses, what perspective should a memoir proposal be in, and more subscriber questions...plus a discount code just for subscribers!

Hello and Happy Friday!

If you missed last week’s Wednesday and Friday rounds of Q&As, you might want to revisit them. From the chances of an R&R leading to a book deal to what questions you should ask the first time you meet your publisher, there’s something for everyone!

I’m proceeding through the questions from paid subscribers chronologically. Thank you for your patience, those of you who wrote in—I’ll do my best to get to all of them, but it will take a little while! Without further ado, we’re going to kick off this third round with a difficult question that affects nearly everyone. (You’ll find the full text of all these questions in the footnotes.)

Question 1: Why is querying so freaking depressing?

I’m so glad that Cort had the courage to ask this¹. The only thing worse than being in the query process is—maybe—being on submission, but submission still takes second place on the crapola front because you generally have an agent if you’re on submission, so you’re halfway to your goal.

Querying is such a brutal and unraveling process that back in 2012, when I was still querying myself, I wrote an article for Tin House called “How to Stay Sane While Querying Agents.” I highly suggest reading that article because my advice still stands (try to stay offline, do things with friends, get outside, find people to be nice to you.) But I’d like to share some updates since a lot of time has passed since I wrote that piece. I’m going to start with the hardest pill to swallow and get cheerier from there.

1. Try to bravely consider that your manuscript might not be as ready as you think it is. It is better that you wrestle with this possibility than discover it after you’ve queried every agent on the planet. I myself have been guilty of sending things out that I thought were 100% ready and 100% genius and only in hindsight did I realize they were not. (Generally my problems, and the problems I see with querying writers fall into the categories of either pacing, book length, lack of plot, or a plot that is too complicated in fiction, and in memoir, it’s usually that the story is too personal and specific to the person writing it and needs to be revised for universal appeal OR the theme needs a new take because it relates to a past trend.) After 20 or so rejections, it behooves querying writers to stop, drop, and try to find an honest and trustworthy person to tell them what’s not working. I actually offer this service to people through my Query Doula packages, but I only take on people who are tired of having smoke blown up their a**.

2. Make lists of positive things about your writing that nobody can take away from you no matter what. You want to start reminding yourself of how absolutely freeing and exhilarating it feels to write, and how much you need the practice in your life. Write out everything you love about writing, and your writing in particular. Don’t link these things to anything related to gatekeepers. This list is for you and you should have agency over the things on it. Don’t ever forget that you got into this whole thing because of how it makes you feel. That writing is first and foremost something you do for you. Don’t let the gatekeepers mess up your love of writing. They only have that power if you give that power to them.

3. Try to get excited about alternative forms of publishing. Not because nobody is going to represent you or eventually buy your manuscript, but because if you can buoy yourself with true and honest excitement about all the alternative ways there are out there to publish, you’ll be in a better place if an offer comes in, or if one doesn’t come. After 8 years of trying to get published (and coming super close to getting a book deal that fell apart when my editor quit her job), in my early thirties I—in this order—self published a book of short stories, started writing humor columns for literary magazines, and published a chapbook. I was also doing a ton of reading series and generally having a great time making literary friends. I was meeting editors who were doing exceptional things at their micro presses, which made me feel confident about becoming a guerrilla-publishing kind of girl. Only then, when I started to move in an indie alt direction, did I get my forever agent who was actually able to sell my work and get me a great book deal. But mind you, part of me getting that book deal was that I’d moved on from the manuscript that had broken my heart and was feeling positive about creating new things. The agent that finally got a deal for me is my third literary agent. I parted ways with the first two.

4. Do not (do not do not do not) put all your financial eggs in the agent basket. To me, the number one way to avoid depression and anxiety while querying is to have a source of income outside of your creative writing that will pay your bills. Regarding example number three above, I was working in marketing and advertising at the time that I was doing the alt guerrilla thing, which covered all my bills, making it easier for me to play around with zines and write for magazines that paid me in comped beer and karma. Even now, five books into this adventure, I do not rely on my book deals to keep a roof over my head because I never know when the hell those book deals will come nor how much they will be for. I don’t care if you are working in a laundromat or Starbucks or babysitting or working for JP Morgan Chase, if you don’t have some income coming in outside of this thing you hope to sell, you are going to crash.

5. Identify one friend that you can complain (and cry) endlessly to. Not everyone is going to be able to hold space for all your worries, mostly because if they’re writers, they’re going to have the same worries. So you want to find one neutral friend to whom you can just say, “Hey, I’m really going through it, can I just text and call you from time to time when I need to scream or cry? And will you assure me that you’ll always hear me out?” You’re going to need someone to be kind to you. Kind no matter what. I will try to be one of those kind people here through my Substack, and you have lots of writers in our community who are feeling just as scared as you are.

My dear Substack subscribers, can we send some words of encouragement Cort’s way in the comments below?

Question 2: Do agents balk at book deals with small presses?

Great question, Sarah.² You don’t need to make a pitch because agents have so many examples to draw from of authors who started small and moved to huge, that agents just have to look at their own bookshelves for proof of that. Off the top of my head I can think of Kristin Arnett, Lydia Kiesling, Sarah Rose Etter, Sarah Gerard, Chloe Caldwell, Matthew Salesses, Roxane Gay (!) SO many incredibly talented people who started off small with the backing of agents who just knew that soon enough, their work would draw the attention of the Big Five. (I should say, having published with Indies and the Big 5 myself, that I have had incredible experiences with both parties. The biggest difference is the size of the book advance and the reach that the different publishers have when it comes to marketing and publicity.)

As to how an agent can afford working with a small press author— don’t worry about it! Some agents are just setting out and are eager to acquire and support new talent and establish their own client list, while other agents are veterans who take on raw, exciting voices once in a while because they believe in them and want to help grow their careers. One of the best things you can do if you think your book will go to a micro or indie press is to try and publish nonfiction in flashy outlets (The Cut, Modern Love, Elle...). That’s a surefire way to prove to an agent that you have commercial potential and a voice or story that resonates with readers, and it’s a great way to get a bigger book advance than what you got for your debut.

If you have an agent who doesn’t want to submit to small presses because the money won’t be there, you can get permission to fly solo on the book in question and pitch those editors yourself. There are still lots of publishing houses at the indie and micro level that let (or even encourage) unagented writers to pitch them.

I should mention, just for the sake of disclosure, that I did the reverse of all of this. My first two books were with the Big Fives, and then I wanted to pivot tonally, and my next three books were with Indies. Now I am hoping to swing back to the big guys once again. My agent has stayed with me for each of my five books, partly because she has seen firsthand that I have commercial chops, partly because we trust each other and she knows I like to challenge myself. It’s true that not every agent out there can be that flexible, but them not wanting to accompany you to small presses isn’t necessarily about the modest amount of money involved, it’s more that they don’t want to see your sales track record harmed by going from significant sales (assumed with a Big 5, but that doesn’t always happen) to modest sales (assumed with an Indie, but definitely doesn’t always happen!) Hopefully, you will also find an agent who will stay with you through sickness and through health, through the big advances and the small. Good luck!

Question 3: What POV should a memoir proposal be written in?

Thank you, Wendy, for this question.³ So personally, I’ve never written a memoir proposal with a synopsis in it: in addition to the standard material that goes into a proposal, I include an overview, chapter summaries and 1-2 sample chapters. In terms of “memoir being treated like fiction,” what I can say about that is that memoir should have plot (which successful fiction tends to), and it should have something in it for the reader (either it’s high in entertainment value, the reader is going to learn something or be deeply inspired by the material, or the reader is going to see themselves or their experiences reflected in the work— or all of the above) and these are things we want readers to feel in fiction, too. Memoir is usually written in first person, therefore, to avoid whiplash from changing perspectives too often, I counsel writers to write their memoir proposals in the first person, too.

I’d argue that you’re thinking a little in the weeds here, and would benefit from taking a bird’s eye view to your material. The tense the proposal is in, the perspective you’re writing it from: these questions get answered when you have a crystal clear idea of why people need this book and why you are the only one who can write it and how you are going to communicate with readers before the book comes out. If you go to Amazon and look up the comp titles you’re planning to use for your memoir, you’ll notice that the marketing copy usually summarizes the book in two paragraphs. Paragraph one states the problem (I’ll use my own memoir as an example and I’ll paraphrase, this isn’t the actual marketing copy): “Just shy of 40 with a two year-old and a bustling career, Courtney was more surprised than anyone to find herself severely depressed. The chronic insomnia she’d always dealt with was taking her down physically, and nothing— not talk therapy or pharmaceuticals or exercise or meditation— was getting her to sleep. Enter horses…”

And then paragraph two tells you how the problem will be solved on a structural level in the memoir: “Using reported research, interviews with other women riders and examples from her own life, in the YEAR OF THE HORSES Courtney explores the privileged relationship between women and horses and men’s attempts throughout history to tame both parties, with special attention paid to how horses got Courtney over patriarchal pressures in her own life.” (And then the paragraph would go on to explain what kind of reader would enjoy the book.)

Generally, you want proposal copy (or any public facing copy, really) to sound selling and confident and to take a big picture view of the book’s material.

I’m very passionate about teaching effective book proposal writing. If you all were here last Wednesday, you’ll know I am sharing a special discount code to the online book proposal class that I developed. It’s a short class, it’s online, and it’s totally self-paced through video tutorials you can skip around in. Plus, with the discount, it’s only like ten bucks!

Simply go to this link and then enter the discount code: SUBSTACK

I also suggest listening to my deep dive on proposal writing on the OTHERPPL podcast with Brad Listi where I share everything I know about proposal writing in a super competitive market.

I hope that these resources help you, Wendy, and any other writers who are struggling with how to shape their proposals, and what tone to write them in.

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That’s all for this Friday!

I’ll try to get to more questions next week, try being the operative word as we’re approaching back-to-school time.

Thanks, as always, for being here, my friends. If you have comments or suggestions to any of the above subjects, or simply words of support for the people who posed these questions (I know they will appreciate it!), please comment below.

Commenting is a privilege reserved for paid subscribers. Thanks for your support!

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1. Cort’s question: Hi Courtney! What advice do you have for querying authors who struggle with depression and anxiety? I've found the querying process to be extremely detrimental to my mental health and I'm trying to find a way to reframe my thoughts or manage the process better so it doesn't have such a negative impact. Thanks!

2. Sarah’s question: Thanks for inviting questions. Mine is about publishing with a small press. You've said that even small presses often require an agent -- and I've seen evidence of this. My question is why an agent would be interested in representing an author aspiring to publish with a small press. How could they afford it? How might an aspiring author make such a pitch?

3. Wendy’s question: I feel that whirlpool sucking me down as I'm attacking my memoir NF book proposal and finding conflicting info (what?! on the internet? sacré bleu!). As memoir is treated like fiction for a proposal (synopsis v. chapter summaries), I'm finding little accurate insight as to how a very first person manuscript should read in that synopsis. My memoir is written first person (duh, snicker) in present tense. Best practice = to write my synopsis third person/present like fiction? Or first person/past tense? Or should the synopsis match the manu in tense as well as voice/tone? Taking that further, should the query letter match the tense of the synopsis (if different tense from my manu's first/present configuration)? I'll be twirling over here in the corner waiting for Friday.