The Midcareer Query

[This article originally appeared in the September/October 2025 issue of Writer's Digest magazine.]

“Who’s your agent?”  

I winced. But the question was innocent enough, if not obvious enough: In the wake of two other books over the past decade, I had just released a new title in Bloomsbury’s cult-favorite 33⅓ music series. And by “cult-favorite,” I mean a line of books with the nichest of niche readerships—and thus the most modest of modest advances.  

“I don’t have one,” I said, playing it cool. “All of the books I’ve done have had small advances, so I’ve never really tried to get one.” 

My friend—a fellow writer with a dozen books under her belt—stared at me, eyebrow raised.  

“You know,” she said, “there might be a reason your advances have been small …” 

I laughed and changed the topic, as I tend to do when confronted with (uncomfortable!) truths … especially when said uncomfortable truth concerns something I’ve spent the better part of the past 15 or so years avoiding. No matter where you’re at in your publishing journey, agents can be a daunting part of the industry—yet another hurdle to clear, in an ecosystem already beset with hurdles. There’s the exhaustion factor: I know I can write this—how many more gatekeepers do I need to convince?! The (seemingly) practical factor: Are my deals even enough to be able to share 15 percent of them?! The rejection factor: I’ve been working in this industry for a while—what if they think I’m a charlatan?! 

Rather than deal with it all, I just dealt with publishers directly, in various ways. But in the process, I’ve long wondered how much money, rights, and all things beyond I’ve been leaving on the table by staying solo. 

So, for this annual issue of WD, I decided to ask a trio of stellar agents just that. More specifically: Should unagented midcareer writers with a book or two under their belts, or a bio filled with short stories, articles, etc., be working with a rep? And if so, how should they go about getting one?  

Ray Bradbury famously said, “You’ve got to jump off the cliff all the time and build your wings on the way down.” Which is what I’ve been doing. 

But guess who (obviously) had an agent?  

Ray Bradbury. 

Unsurprisingly, the agents interviewed for this piece champion their profession of championing writers—and largely agree that an agent can be a boon for any experienced unrepresented author looking to take their career to new heights. Here’s why. 

When you get an offer on a book, it’ll come with a contract of varying quality. And no matter how savvy you are with contracts, there’s someone savvier: an agent. 

“The contract! Oh my gosh, so much can go wrong with the contract,” says Jessica Sinsheimer, agent at Context Literary and co-creator of Manuscript Wish List. Specifically, she cites subsidiary rights—e.g., translations, adaptations, audiobooks, and so on. “It’s incredibly difficult for a writer to broker those deals.” 

To that end, Michael Bourret, partner at Dystel, Goderich & Bourret LLC, says that even attorneys can fall short of the finer points of a solid deal. 

“Unless those are very specific publishing lawyers who know publishing contracts very well, those lawyers honestly don’t know the right questions to ask,” he says. “Having that breadth of experience is what allows us to have a different look at things than what an author can have on their own.” 

Moreover, to Bourret, what an agent truly offers is perspective. Having done so many deals over the years, they know what’s possible in a negotiation. “For a writer who doesn’t have that information, you can very easily be underselling yourself—or, on the other hand, maybe overselling yourself.” 

As writers, we do what we do for myriad reasons, and a career in publishing ain’t all about money. But if you’ve ever had to unexpectedly repair a faulty foundation on your house, it sure as hell might suddenly seem like it is. Bourret says that, in general, writers with agents get higher advances. In fact, he adds, publishers implicitly understand that they have to pay a bit more when an agent is involved: “When I go into those negotiations, even with a smaller publisher, I’m looking to hopefully pay for myself, right? I’m hoping to extract enough out of the situation where my author is actually making more money in the end, while also having the benefit of my skills and expertise.” 

Afraid your deal is too small to warrant handing over 15 percent of it to an agent, as I have been in the past? “Getting it up enough to cover the agent’s commission is typically not that difficult,” Bourret says.  

As a self-employed solo writer, I’m my own literary rep, accountant, financial advisor (or lack thereof), and janitor. And when I’m doing any one of those tasks, the one thing I’m not doing is writing. When I haven’t been paid a royalty that’s due, it is thus on me to sort it out—and Bourret says agents carry extra weight in such crucial conversations. Even though a publisher may not care if they ever work with a given writer again, they don’t want to lose an entire agency’s portfolio, so that response is likely to come sooner rather than later (which is great when you’re trying to stop your house from quite literally sinking into the ground).  

Sinsheimer adds that editors’ time is finite and often stretched thin—and repped writers tend to have more leverage within that space. 

Katharine Sands, an agent at Sarah Jane Freymann Literary Agency, represented herself on a book deal. And, well, she likely regrets it. “You know, the level of emotional reaction, it almost surprised me. I mean, I worried about everything I ever told a writer not to worry about,” she says. “I was wailing half the time.” Agents offer a buffer—one that even a career agent can benefit from. As much as we might pretend we can divorce the practical from the personal, writing is a deeply human craft, and it’s easy to lose the plot (even when it’s yours). 

Of course, all of the other benefits of having an agent apply regardless of what you’ve published. Bad at conflict? An agent conflicts for you. Need thoughts and advice on your manuscript? An agent is there with a red—or green, if that seems less scary—pen. Need help sorting your next career move? An agent careers with you. Bad at touting yourself? Agents aren’t. And ultimately, they are there exclusively for you—something you don’t have when working a deal yourself. 

“What I really like about the agent-author relationship is that you have two people who are working towards the same goals and who are on the same side,” Bourret says. “Your editor is working for the publishing company. As much as they might like you, as much as they might champion your work within that company, in the end, they answer to somebody. Agents answer to their clients.” 

If you’re seeking an agent, there’s a good chance you’re looking to level your career up—with a bigger book, a bigger authorial presence, and so on. As Sands notes, an anthology or poetry collection does not face the same scrutiny as a front-list book. The events. The PR. Are you truly prepared for the job and everything that comes with it?  

“You have to be ready for each level of publishing,” Sands says. “And I can’t stress how much it is a job.” 

Bourret adds that experienced writers who have not worked with an agent before should take an honest look at the prospective relationship—“to be able to articulate to the agent what it is that they need, what sort of support they’re looking to get, what changes they’re looking to make, and to have an idea of why they think bringing an agent on is the thing that is going to help them get to that point.” 

If you’ve pondered that progression and are ready to take the plunge, here are a few things to know. 

Just because you’ve published a few things doesn’t mean that you get to skip the line and escape the query process entirely—but it does add some compelling bonus points to your pitch. Notably, “What you have is something to point to, to say, ‘hey, I can write a book because I’ve already written one’—which automatically puts you in a different category,” Bourret says. “I do take a closer look, because I have at least some belief that they have the skills necessary to get it done.” 

For Sinsheimer, it means that you’re not starting from zero with your publishing education—and that matters in an industry with a steep learning curve.  

Of course, there is indeed a potential downside to having already been published … 

If your pitch is compelling, the first thing an agent is likely to do is pop your name into BookScan and check how your past books have sold. And that can be a highly determinative factor for a publishing house. Sands recalls a conference dinner where she debated with an editor that an author might hit on their third or fourth book instead of their first for various reasons—how many copies were printed, the political climate at the publishing house, and so on. 

Per Bourret, there are ways for an agent to create a narrative around lower numbers. For instance, that an author was with a smaller publishing house with limited resources, and for that publisher, their book in fact did well. With better distribution and better resources, the possibilities are that much greater for said author. 

Sands made a similar point during our interview—and perhaps struck at the heart of publishing at large. 

“From an agent point of view, I have a tremendous hunger to discover new voices, new talents. And yes, a book can come out and sink like a stone, but if the writer has something special … it could be their wordsmithing, or their imagination, or their ability to create a world or to bring a character to life … I have to absolutely believe, if I’m in play, that that writer’s got something and somebody’s going to see that.” 

Ultimately, the agents interviewed for this piece noted that numbers aren’t the only deciding factor—they also take into account reviews, platform and reach, awards, speaking gigs, if a book is positioned to reach a larger audience, and more. 

Another crucial factor: “Personality, of course,” Sinsheimer says. “We need to be able to collaborate creatively, which is actually a pretty rare dynamic—the editorial process is full of abstract concepts you can only talk around, and you need to have someone who speaks almost the language between the words with you. Plus, they have to have a growth mindset, be open to edits (or alternatives to edits that accomplish the same thing), take well-meant criticism gracefully, be kind to editors, and generally be good human beings.” 

You may be tempted, as I admittedly once was, to reach out to an agent with a deal in progress that you worked on your own, seeing it as, A) a way to get some professional eyes on a contract, and, moreover, B) a lazy hack to land an agent. But Sands says that’s tricky, because an agent is a bit handcuffed in terms of how effective they can be when the architecture of the deal is already in place. 

Bourret adds that the timing can be tough—having to do a sizable internal download of the book, the contract, the author and more in a tight turnaround—but the key is that he and the client would not only be a good pair for the particular book in hand, but books beyond.  

“We’re not looking to negotiate one deal. We’re hoping that this is a long-term relationship across several books.” 

Around 15 years ago, I commissioned a short piece from Sherman Alexie for this magazine. To take a quote from it completely out of context, he wrote, “Writing is a lonely business. Do your best to make it a little less lonely.” 

Ultimately, as Sinsheimer put it, “The author-agent relationship is so complicated. You’re trusting someone not only with your career and contracts and future partnerships but also to help navigate the many creative choices you have as a writer. You’ll always do your best creative work if you feel safe. You’ll take more risks, try new things, follow what inspires you—even if you can’t ‘prove’ it’ll work before you try.” 

And, well, that is utterly appealing after years of toiling away at my desk with nothing more than my greyhound looking on.  

“Who’s your agent?” I don’t know. But it’s probably time I found out.