A Tale of Ten Literary Agents

Sometimes it takes a while to find great representation

A note from Karin: You might be asking, what are you doing in my inbox twice in one week? It’s a new thing at Pitch Your Novel. Occasionally, I’ll be sending out free posts where I collaborate with other publishing pros or do interviews with debut authors.

Onto the story:

They’re called the query trenches for a reason, named after the most brutal type of combat with barbed wired obstacles and bullets of rejection whistling in the air and exploding in writers’ inboxes.

Unlike many soldiers in warfare, you will physically survive the query trenches, but emotionally it’s a treacherous landscape. Many writers stick with the wrong literary agent just to avoid the trenches

But that’s likely a mistake. Sometimes the best move for a writer’s career is to change agents. When author Caroline Madden of Rising Tide Writers confessed to having five literary agents, I immediately thought, kindred spirit. I, too, have had five agents so I invited her to collaborate on this post to trade battle stories and serve up advice.

We’ve both had five agents, which sounds like a lot, but isn’t entirely unusual. How did it happen?

CM: Yes, five agents feels like a lot – I’d much rather be a one-agent woman! However, I know from my writing friends that it is rare to have just one agent over the course of a writing career. Here’s why I’ve had five agents over 14 years:

·My first agent ran her own small agency in London. She signed me in 2012 on the basis of a historical novel inspired by the lives of the playwright Richard Brinsley Sheridan and his wife Eliza. She sent it out to UK editors but it died on submission (just after my first baby was born). I suggested rewriting it based on the feedback we’d gotten from editors, and my agent gave this the thumbs up. After months of working on the agreed rewrites, I sent it back to her but she felt the ending was too downbeat for the book to ever sell, so she wouldn’t send it out. She suggested I move on to another novel.

That was sound advice, but I was too attached to Richard and Eliza’s story. So we parted ways amicably, as the saying goes.

· My second agent worked at a big, prestigious London agency. He signed me in 2014 after reading only the first half of my historical novel (the version I’d rewritten for Agent #1). After a little editing, we went out with it. The book died on submission again (just before my second baby was born). He suggested I move on to another novel.

This time I took the advice, parked the historical novel, and spent three years labouring over a Gothic murder mystery. I sent it to my agent, and he acknowledged receipt, but I never heard from him again after that, despite many, many polite nudges. After four months of being ghosted, I emailed to say that I thought it was best to go our separate ways. He replied briefly, agreeing to waive the contractual waiting period. And… we ‘parted ways amicably’.

I hit a very low point when this happened and almost quit writing for good. I took a long break from trying to get published. But I still could not shake Eliza and Richard’s story. Eventually, I decided to completely rewrite it as a ‘voice-y’ dark comedy, set in modern Dublin. I wrote most of it during lockdown while homeschooling my children. This version became THE MARRIAGE VENDETTA.

· Fast forward to 2023: THE MARRIAGE VENDETTA was finished but I was barely querying. I was losing hope, to be honest. Then a writing friend urged me to query a new agent in the US, Kesia Lupo. I checked out Kesia’s Substack and loved her openness, and I could sense that she was a really down-to-earth, decent person. What did I have to lose? I rolled the dice one last time. And soon after, this life-changing email popped up in my inbox:

I still remember reading that email. I was on my way to have a very difficult, painful conversation with someone and was dreading it. Kesia’s email pinged into my inbox just as I sat into my car to reluctantly drive there – it felt like a sign from the universe and gave me the confidence to get through that tough conversation.

Kesia and I had The Call, and she signed me, becoming agent number 3! She genuinely was everything I could have hoped for in an agent: responsive, easy to talk to, encouraging, always true to her word.

She sent THE MARRIAGE VENDETTA out on submission in the UK and US and, 18 years after I first started writing about Eliza and Richard, I finally got my book deal: it sold at auction in the US to HarperCollins and in a pre-empt in Ireland/UK to Bonnier. It was a blur of editor zooms and conference calls with Hollywood film agents. I barely slept for a month.

But then disaster struck. Kesia was let go from her agency, and it was uncertain whether she would return to agenting. I decided not to look for another agent and hold out for Kesia. Her belief in my story literally changed the trajectory of my life – I wanted to stick by her in return.

And then, months later, by pure coincidence she got a job at my top-choice dream agency, the agency I had been far too intimidated to ever query: the Donald Maass Literary Agency (DMLA) in New York. Donald Maass’s book How to Write a Break-out Novel Workbook had been one of my writing ‘bibles’ for years. What were the chances? I couldn’t believe the serendipity of it.

In 2025, Kesia secured a second book deal for me – THE VILLAGE comes out in April 2027 – but shortly afterwards, she left agenting and returned to the UK to take up an editing job. I am forever indebted to her and anyone who gets to work with her, in any capacity, is incredibly fortunate.

I was once again without an agent.

Just as I thought I’d have to wade back into the query trenches, word came through that the VP of DMLA, Katie Shea Boutillier, was interested in having A Call as her assistant Rachel Saylor loved my new book (forever grateful, Rachel! 🫶🏻) Fortunately The Call went well and Katie explained that I would be represented by both her and Rachel, who is an assistant literary agent: so together they became agents #4 and #5.

I am constantly amazed by their responsiveness, belief in my writing, and proactiveness. Kesia, Katie and Rachel have completely restored my faith in literary agents!

KG:

Agent One (2002-2008)

I had zero connections when I first started querying. Back then, online writing communities were mostly nonexistent. There was no Facebook or Twitter.

Although querying was much more primitive, it was also more civilized and genteel. Agents almost always replied, and often you’d receive personal notes.

Sometimes they’d offer suggestions. One agent wrote to me: “You should write books like Marilyn Keyes. She’s part of a hot new trend!” (He was talking about chick lit, and his prediction was correct.)

I think fewer writers were querying back then so it was possible for agents to occasionally get personal with writers.

I tentatively sent out a few query letters for my first novel, a humorous, smalltown novel and then a miracle happened: An agent called me at work, desperate to read more.

At the time, it felt so cinematic. This is how it’s supposed to happen, I thought. Unknown writer lifted from the slush pile! A star is born!

After I sent the entire manuscript, the agent emailed me breathless updates about how much she loved it: “Page 50, I’m swooning!” “Page 100, I’m on Cloud nine, Cloud ten!” But then the updates abruptly stopped, and she rejected me.

However, she did offer me an R&R (revise and resubmit). Even after my revisions, she was tentative, saying her boss was on the fence, but she finally relented. It was a wise decision for both of us as she sold five novels for me.

Over the years, I got to know my agent fairly well. We had lunch several times and went on a business trip together.

Sadly, we broke up over something petty. But, I will always be grateful to her for taking a chance and giving me one of the most exciting experiences of my life.

Agent Two (2008-2009)

When my first agent and I parted ways, I easily got a second agent as my sales were solid, and my publisher still had the option on my next book. I contacted about five agents, and they all wanted to represent me. But there was a problem: None of those agents had read the book I was pitching; they offered representation on the query and a partial, and guess what? The book sucked!

My agent gave me great revision notes, and I revised twice but still didn’t get it right. I remember her saying the novel was episodic, and I was so inexperienced I had no idea what that meant.

I needed more help than she could give me, so I bowed out of the relationship, but secretly, I was hoping she was wrong about the book.

She wasn’t, of course. I queried the novel, and since my publisher had rejected it, I got many passes. After experiencing so much early success as a novelist, it was an extremely humbling time for me. I also felt tremendous shame over not being “good enough.”

Agent Three (2011-2012)

I realized I didn’t know enough about story structure, so I read a half-dozen screenwriting books and started querying again. Right away, I got five offers, and I remembered thinking, I’m back!

But while it was exciting to have so many offers, it was also overwhelming, and I didn’t choose well. I went with the most inexperienced agent because I liked her the most. Unfortunately, she wasn’t able to sell the book. Would a more experienced agent been able to sell it? Who knows? But because I was in a panic, I probably didn’t make the wisest choice. (She’s also no longer agenting anymore.)

Agent Four (2018-2020)

This relationship was the most heartbreaking. I did a lot of revisions for number four and though we got close to placing it, the novel died on sub. But it was this incredibly, valiant batte, like… Rocky and the astronaut in Hail Mary. We had each other’s backs! We would live to fight another day!

I wrote another novel, and my agent said she didn’t like it—no particular reason given—and she sent me a break-up email on my birthday. BOO!

Agent Five (2022-2023)

Despite agent #4’s dislike of my next novel, my instincts told me it was sound and sellable.

I began to query that novel, and received another agent offer. We went on sub during an extremely tough time for the market.

In a year’s time, my agent heard back from only TWO editors on her sub list. I didn’t understand how much publishing had changed after the pandemic, and that editors were now ghosting agents. I also had reservations about my agent. She wasn’t much for nudging editors, and when she introduced me to members of her private FB page, she said I wrote mystery. (I do not write mystery.)

That sub experience made me want to understand what was going on in publishing and that’s why I started Pitch Your Novel. I have learned so much about the market and have applied that knowledge to my next project which is still in its beginning stages. But, one day, I suppose I will have to…. sigh… query again.

Five agents means five times (or more) in the query trenches. What are some strategies you’ve learned along the way?

CM: Interestingly, although I’ve been in and out of the query trenches more times than I can even count, I only actually got one of my agents through the cold query approach (agent #3). Here are some alternative approaches that worked for me:

• ·I got my first agent after uploading some of my manuscript to an online peer-critique platform launched by HarperCollins called Authonomy. Agents were scouting on the site, and agent #1 approached a friend of mine about his historical novel. He kindly suggested that she might also like my book. Unfortunately, Authonomy is now defunct; the closest thing to it is probably the new Libraro Prize – worth checking out when it reopens next year.

• I got agent #2 through a referral from a kind writing friend. I would encourage aspiring authors to network at their level (even though that’s a horrible phrase!) – in other words, you don’t need a leg-up from a famous bestselling author. Join or start a writing group with other hard-working, determined aspiring authors and lift each other up as you rise.

• ·I also got a lot of agent interest from competitions – that really speeded up the process (though none of them offered in the end). After my book was longlisted for the Blue Pencil Agency’s first novel award, the agent judge requested the full manuscript. Also, Emma Haynes at the Blue Pencil Agency went above and beyond trying to get me representation, introducing me to several of her agent contacts.

KG: Get professional eyes on your query and read recent successful queries. Recent letters are important because requirements have changed. For instance, comps didn’t use to be something you were supposed to include but now they’re a necessity. You can see recent query letters at Querytracker success stories, and author Andrea Bartz keeps a database. Use Querytracker and check an agent’s response rate and make sure you include some agents who actually respond otherwise it can feel as if you’re flushing queries down the toilet. Expect it to take a long time and you might have to query 50 to 100 agents. I did a study of Querytracker success stories and the average number queries sent out was 70.

Querying a lot also means a lot of rejection. How do you cope with that?

CM: The rejections (and the agent break-ups) hit me so hard that I quit writing for long periods over the years. Eventually the memory of that pain fades and you jump back in!

After I parted ways with agent #2, I eventually realised I had to change my mindset: I decided that it no longer mattered how many rejections I got, because I was never going to quit. Even if it took me until I was 90. So my job now was simple: to keep improving until I wrote a book that editors couldn’t say no to. Good enough to get an agent wasn’t good enough. And so I bought every craft book out there and that set me on the path to a book deal.

Rejections and disappointments are an inevitable part of this industry at every stage, though, so I constantly remind myself of this quote: thinking you can avoid rejection as a writer is like being a boxer who thinks they’re never going to get punched. In a way, experiencing so many rejections and set-backs before I got published is an advantage: it has toughened me up.

I also work hard to reduce my ‘wallowing time’, the amount of time I’m allowed to lick my wounds and feel sorry for myself when something doesn’t go my way. Now I bounce back from disappointments very quickly, mainly because I keep reminding myself: my books are simply some words I typed on a page. What people think of those words does not define my inherent worth as a person.

Looking back, I don’t think I would have kept going through all the rejections if I hadn’t started a writing blog, which turned into my newsletter. At least I had ONE creative outlet that was entirely within my control, that wasn’t guarded by gatekeepers. As the newsletter grew and readers seemed to appreciate it, it gave me a confidence boost that counteracted the rejections. I am eternally grateful to all my subscribers.

I recommend that aspiring authors have another outlet beyond their writing, like a podcast or a Substack newsletter – so that your self esteem is not entirely dependent on the success of your writing career and so that you can connect with other writers.

And if all else fails and a rejection sends you off the deep end, rage cleaning helps!

KG: I always tell people to watch this Tedtalk on rejection. Jia Jiang was set out to get rejected 100 times, and he made crazy requests of others to ensure it happened. He asked to be a greeter at Starbucks or to plant flowers in other people’s yards. It made him almost immune to being turned down. I wouldn’t say that I’m immune (and I’ve been rejected an appalling amount of times) but sometimes I feel like an old sailor negotiating the rough waters of publishing, riddled with scars, proudly bragging about them. I’ve been rejected by the best.

What do you think are the most important questions to ask an offering agent?

CM: Apart from the common questions like what happens if my first book doesn’t sell, here are a few questions I never thought of asking and in hindsight it might have been a good idea:

Will you submit my book only in your region? E.g. if you have a UK-based agent, will they or a co-agent submit your book to US editors as well as editors in the UK, or vice versa.

What’s your usual timeframe for reading your existing clients’ new manuscripts and replying with edit notes?

If we get a deal, do you want to be copied in on all emails between me and my publisher? (In my experience, it’s a good sign if the agent wants to be copied in on everything)

However, you’ll never know what an agent is truly like until you’ve signed with them. It’s easy to say the right thing on The Call. I mean, what agent is going to admit that they’ll ghost you if your book doesn’t sell?

Recently, the writer Lauren Kay posted a cautionary tale on Instagram about almost signing with a ‘dream’ agent but luckily she did some digging first. Her advice in this post is brilliant and could save writers from signing with someone who could derail their writing career before it even gets off the ground. Most agents are great, but there are sharks out there!

KG: I would do tons of research on the person to make sure they have some career authors on their rosters and not just a bunch of debut authors that are never heard from again. Also, ask them what their vision is for the book and how they see it in the marketplace. You’ve provided comps but what comps come to mind for them?. I also like to know their sub strategy for the title and reasoning behind it. What’s their nudging policy?

But mostly, do a vibe check during the call. That’s hard as hell because you’re excited but how does the interaction feel? I once had an offer from a superstar agent but I got creepy vibes from the call. I told her I needed some time to think, and she withdrew the offer. My spidey vibes were on point.

Because we’ve both had five agents, there’s been break-ups. When did you know it was time to leave and what advice can you give authors on the process?

In my case, my breaking point was four months of my emails going unanswered. I had come from a corporate background and the lack of professionalism from someone with whom I’d signed a contract genuinely baffled me. Then I had a lightbulb moment: he’s just not that into me.

I had slipped down the list of his priorities. Or off the list completely. And as a result, my writing career had completely stalled. I knew how hard it was to get an agent, but this was worse than having no agent.

In fairness to agent #2, I can now see that the book I sent him was not up to scratch. So I now take much more responsibility for the standard of my writing before even thinking about sending a manuscript, or even a pitch for a new book, to my agents.

If a writer decides to part ways with their agent, I would encourage them to take their emotions out of the situation when sending the parting email (and then rant all you like to your writing friends afterwards!). Keep it short, civil, professional, ‘amicable’. Publishing is a tiny world.

KG: Good advice, Caroline! Don’t throw a grenade over your shoulder on the way out.

Seriously, if you don’t think the relationship is working, they probably don’t either. In fact, if they’re really behaving badly, they might be hoping for the break-up and are wondering what took you so damn long.

My “Dear Jane” emails read like love letters, and they’re not disingenuous. There’s always something I admired about an agent or I wouldn’t have signed with them. And if there’s not been a sale they’ve done a lot of work for free, and I am grateful for the efforts (and also sheepish).

Describe your ideal literary agent.

CM: Kesia, Katie and Rachel (agents #3,4 & 5) have embodied everything a writer could want in an agent: they’ve all been fantastic at responding to messages quickly. They’re enthusiastic, professional, encouraging and amazingly proactive. A pleasure to deal with.

My early experiences left me quite jaded, and with very low expectations, but my recent agents have restored my faith!

I would say the key thing is that the agent matches your enthusiasm, or at the very least that every interaction doesn’t feel like pulling teeth. Personally, for me, that’s even more important than the agent’s experience.

KG: I appreciate candor, professionalism, and mutual respect. The agent/author relationship has a wacky power dynamic, and I think both parties are usually to blame when it goes south. Sometimes writers are guilty of unfairly heaping their dreams and expectations on their agents’ shoulders.

That’s why I’m not crazy about terms like dream agent or agent sibling. Avoid casting literary agents in the role of fairy godmothers or parental figures. They’re our trusted business associates, who sometimes must also give us unpleasant news.

When writers say to their agents, “Don’t send me the passes; I can’t take it,” they’re perpetuating an unfortunate stereotype about artists: We’re fragile and must be protected.

That’s why publishing is often opaque. Some editors and agents think you can’t tell writers the truth because they’ll melt into puddles of goo. Don’t be that writer; separate yourself from your work. Approach publishing like the business that it is and make a point of educating yourself.

Also, agents are now working with more self-published authors who are incredibly business savvy, and you don’t want to be that clueless, hot-house orchid of a client.

As for agents, after years of having writers genuflect in their presence, some can have an inflated sense of their power over authors and that can occasionally extend to clients. Some agents seem to want their clients to be a little afraid of them, so they won’t ask too much of them. I’m a member of several sub groups, and the most common complaint of writers is that they’re terrified of their agents.

My ideal agent still has respect for writers, and, this is old-school of me, I especially appreciate those who give them the courtesy of a form rejection. In the past, I’ve gotten radio silence in response to queries with referrals and to agents I’ve had a connection to. That doesn’t sit well with me. I also don’t like when agents punch down and make patronizing social media posts directed at writers.

Bottom line: In both camps there are problematic personalities, but overall both agents and writers are book people which frankly are the best kind of folk.

Is there some question I didn’t ask that you’d like to add?

CM: One thing I’d like to add is that, over the years, I’ve started to see things from the agent’s perspective a lot more. It’s a very tough job, and certainly in the US, most new agents are not salaried. They’re working on commission. So, if they sign you, they’re putting a lot of work into your book with no guarantee of any return on that work. And they’re most likely working other jobs and doing this on the side.

I think it’s important to bear all of this in mind when dealing with your agent. I also work hard to educate myself on the industry as much as possible, through a subscription to Publisher’s Marketplace, Substacks like yours, Karin, and publishing podcasts. And I try to get my hooks, pitches, and pages as sharp as possible before sending them to my agents.

In other words, I’m trying not to repeat the mistakes I made in the past!

KG: Echo all of that but I will say that authors also work without pay, so many, many years and that they are less likely to make a living at this game than agents, even after a lot of books. So, it’s a big risk for both parties.

Thoughts? Questions? Comments? We’re delighted to weigh in.