All about literary agents: how I became one (and you can too) (although you should know that not all personality types jibe with the job)

I get a lot of questions from aspiring literary agents and the agent-curious, eg: how did I fall into this career? What would I advise someone considering a similar path now? Here's what I say.

• What is it like to be a literary agent?

• Would I be good at doing the work of a literary agent?

• Would I enjoy being a literary agent?

• How does one get started at being a literary agent?

If you’ve ever asked yourself one of these questions, this week’s newsletter is for you.

Even more so, however, it’s for me, me, me.

People email me questions like this about 2-3 times a week. Some are college and MFA students; others are editors, writers, and people from entirely different careers who want to defect to Team Publishing. And I love to see it! It’s an honor to lower the ladder and welcome more people to this line of work.

Yes, and: my clients are my first priority when I’m on the clock. And also, I have three children. And also, I am on the board of two nonprofits I care about deeply. And ha ha ha I’m losing my mind.

Which is all to say that I no longer have the bandwidth to offer individuated informational-interview emails or coffees to aspiring agents. But I CAN write this impersonal newsletter and send it in link form in the future when people come a-knockin’! ::sad jazz hands::

I’m writing this in hopes that it’s interesting to those of you not interested in becoming agents as well — provided you’re at least interested in how we tick.

I’m not going to spend too much time here on what literary agents are.

If you subscribe to this newsletter and/or are at the point of asking agents for informational interviews, I imagine you’re beyond needing to know what a literary agent is.

In case I’m wrong, here in brief is the answer I give my relatives at Thanksgiving when they ask me, “what kind of books do you publish?”

Ha ha, I don’t actually publish anything. I’m more like a talent agent in Hollywood, but not in Hollywood and just for people who write books. I spend most of my time helping my authors put together the most commercial possible permutations of whatever books they want to write. I also pitch them to editors at major publishing houses, solicit deal offers, negotiate contracts, monetize their ancillary rights, troubleshoot their problems, and advise them on long-term career strategy. In exchange, I get 15% of their book income.

OK, so that’s the big-picture job description. Now let’s get into the next-level stuff.

If you answer “yes” to any of the questions below, you might really take to life as a literary agent.

Does the thought of life on a gambler’s income thrill rather than frighten you?

In other words: If you receive your work income in haphazard, erratically-timed blobs, rendering it close to impossible for you to budget in the granular day-to-day manner most type-A people prefer, will you be able to cope?

Do you like being around cool public figures? Do you simultaneously never, ever want to be a public figure yourself?

Are you an extrovert? Do you like cold-contacting, meeting, and befriending interesting strangers? Would you be comfortable doing that a ton? Like multiple times a day, every day? Forever?

Are you good at predicting cultural trends ahead of time? Do the things you like (clothes, music, art, whatever) tend to blow up in mainstream popularity about 1-2 years after you start liking them?

Socially, are you a bit of a stray cat collector? Did teachers or supervisors ever comment that you had a real knack for finding and befriending every brilliant oddball within a 1-mile radius?

Do you have some codependent helper monkey tendencies? Are they healed enough that you won’t have a nervous breakdown if upset, stressed-out people bring their problems to you all day long—appropriately, because it’s your job to listen and help?

Are you aware that this entire career path exists to help authors with the problems they have? So, like, other people’s problems and stress are most of the job?

Are you simultaneously aware on a deep emotional level that other adults’ feelings are not yours to manage, fix, or control?

Can you deal with being rejected and criticized all the time, even (especially) when you’re a success? Can you deal with a job that will in fact involve more and more rejection and criticism the more successful you get at it?

Can you deal with rejecting and criticizing others — not just yourself? When you have to, can you give disappointing news to people whose esteem or feelings you care about?

Do you like hunting for rare items (collectibles, relics, deals, antiques, Pokemon, whatever)? Does the hunt become more vs. less thrilling when you know other people are on the hunt for the same things?

Are you a curious person? Are you curious and observant to the point that it sometimes creeps other people out, so you’ve learned to conceal that part of you behind a carapace of breezy humor and salesmanship?

Do you identify with Cher Horwitz? Emma Woodhouse?

Are you going to be okay with never, ever having a complete to-do list? Are you okay with always being a little behind on deep work? With people sending you “just checking in” emails about your overdue deep work every day?

Do you mind—or can you at least deal with—constant interruptions and distractions? With constantly having to rearrange your priorities and reset deadlines?

Do you have ADHD? Is it the kind that allows you to do 4 things at once, figure out a novel solution to every problem, and live an improvisatory life with relative ease? At the same time, do you have it sufficiently under control that you can also read every word of a contract and negotiate it with care? And also, as necessary, manage corporate finances?

Can you deal with occasionally working for months or years on a project that ends up going nowhere and making you $0?

The questions above get at the quirks and challenges of what it’s like to be a literary agent vs. the many (real!) delights.

Life as a literary agent is not all rejection, stress, overwhelm, and trauma triggers. OMG, OBVIOUSLY. None of us would do it if that were the case.

The good parts of this job are phenomenal. I’ve been working in this field for almost two decades — since I was 20 — yet still often weep for joy after telling a first-time author they’re going to get an amazing book deal.

When I’m able to spot a hugely talented, deserving author in the wild years ahead of the general public and give them the rocket fuel to blast into space….::clawing at face in ecstasy:: what an honor. What meaning. I live for that kind of thing.

Yes, and: I don’t think any of you reading this would struggle with these parts of the job. The general difficulty of being a literary agent is not in the moments of triumph: it’s in the unceasing dynamism, multitasking, unpredictability, and emotional challenge.

Being a literary agent involves a lot of editing, and you have to be very good at editing, but if your idea of serenity is being left the hell alone to edit manuscripts in peace for 5-8 hours a day, this is not the right publishing job for you.

Nor is it the right job if you’re a financial conservative. Editors at publishing houses are for the most part full-time employees. They get predictable (if at least initially underwhelming) salaries with benefits, HR, and all the other normal full-time job things.

Some literary agents make money this way as well, but most do not. Our income comes from commission. We generally work for ourselves or for small companies. We have to save for and pay our own taxes. Support staff at our agencies generally receive W2 salaries and health insurance, but most agents themselves receive income and pay taxes the same way a freelancer and/or small business owner would.

Some of us make much, much more than our approximate seniority counterparts who work for publishing houses full time. Many make much, much less. How much we literary agents make in a given year tends to be a combination of talent, connections, hustle, and—the biggest factor of all—random caprice.

TL DR: chaos clowns tend to love being literary agents. Introverts do not. Intense type-A types do not. Perfectionists not yet on a recovery journey do not.

Growth and success in this career path are improvisatory and individualized in nature. There is no general, set path for a literary agent to follow from entry level to “partner.”

That makes this job a dream for people who hate structure and “being a follower” and a nightmare for those who do.

It also makes this career path exceptionally difficult for those entering the field from marginalized backgrounds and/or socialized not to question authority. This stinks. In a future newsletter, I’ll highlight some of the industry leaders from those communities who are working to make it stink less.

This newsletter is just going to focus on real talk for those of you who want to know what it currently takes to become a successful literary agent. And my real talk is this: it involves making a lot of mistakes as you figure out just how and what to learn from bosses and senior colleagues in the field.

Growing in a literary agent career involves being an apprentice and an entrepreneur at the same time and constantly recalibrating your internal balance between the two. Also occasionally losing your balance altogether in that regard and splatting onto the floor.

This is never not the case, by the way. I’m a partner and agency co-owner myself now, but I still consider myself an apprentice in some ways and an entrepreneur in others. The wisest and most senior agents I know in this field—the people with 20-30 years’ experience on me—are the same.

I’m happy to tell you how I “broke into” my career as an agent—but please read my story less as a road map and more as supporting evidence for why agenting is a Come Up With Your Own Cartography field.

OK, here goes: I’ve always liked English, writing, and championing the work of artists I admire. I majored in English literature in college and got a one-year master’s degree in modernist lit; I was also a big Art Nerd in high school and college.

While these parts of my personality are all genuine, I’ll be honest: so is the one that hates, hates, hates to fail or even look mediocre in public. I have therefore always found myself mysteriously liking pursuits at which I can also be impressive without too much struggle. And for whatever reason, writing and editing are my two biggest natural talents. The fact that they come easily to me is as much a reason why I’m a literary agent now as my love of literature per se.

You know what doesn’t come easily to me? Anything that requires sustained concentration and detail orientation on tasks I find boring.

By focusing mostly on subjects in which I could excel naturally, I was able to get great grades in HS and go to Columbia, a college with strong ties to book publishing. From the moment I entered my first freshman English class there, teachers and fellow students mentioned it as a great potential career path.

I thought publishing sounded fabulous, like the most glamorous and sociable thing I could do with an English degree. I was therefore delighted when the spring of my sophomore year, an upperclassman friend hooked me up with a publicity internship at Grove/Atlantic, the house she’d been interning for downtown.

The internship involved a lot of filing and envelope stuffing, and oh my God, I sucked at it. I sucked at it to a degree my perfectionist ass had no clue I was even capable of sucking. I accidentally misfiled author clippings. I took forever to finish putting mass mailings together. I felt baffled and humiliated by how much I sucked at this job—I was so great at school! I had been an amazing teenage customer service associate at the Bethesda, MD Barnes and Noble! Did this mean I was never going to make it in the real world? But I couldn’t stop sucking for the life of me.

The most pathetic thing is that the people at Grove/Atlantic were super nice to me. I didn’t get fired or even yelled at, ever; they gave me appropriate critical feedback and nothing more. But turns out I wasn’t ready even for that. The first time my supervisor gently rolled her eyes, asking if I could go a little faster on a mass mailing I thought I was doing fast, I lost it. I kept myself together the rest of the day, went back to my dorm, had an actual screamsobbing breakdown, quit the job with no notice via email, and basically took to bed for a week.

I still, uh, had some growing up and simmering down to do.

This was in March of 2005. I turned 20 that April. Still feeling too upset and ashamed to reach for the stars career-wise, I made plans to go back to Barnes and Noble in my hometown of Bethesda, MD that summer.

Alas, I was not quite done being a late-adolescent perfectionist neuroatypical upper middle class lunatic. Come May, I freaked out that maybe I should get A Real Publishing Internship after all, even though I was committed to spending the summer in DC.

My mother worked in TV news with a bunch of people who wrote books. I believe it was one of her coworkers who told me that one “real” publishing thing one could do without having to live in New York was work as a literary agent. I googled what that was, then used whitepages.com to figure out the names of every literary agency in the DC area at the time (there were not many). I then sent my resume and a “can I do a 1-2 day unpaid internship with you” type email to all of them.

Only one person—Jennifer Manguera, the office manager at what was then the Gail Ross Literary Agency—replied, saying sure, I could come in a day or two a week for the next few months. And so I did. And hallelujah: I found myself back in my element, achieving with ease. I loved learning weird new things from the submissions in the unsolicited manuscript pile. I loved putting my curiosity to work on internet deep dives in search of interesting new book ideas and potential authors. And Jennifer Manguera, bless her, took care of the filing as well as the supervision of interns. I had found my people.

I clicked with everyone on the small team at what is now known as the Ross Yoon Agency. And so I stayed. After taking my junior year abroad, I interned in the summer of 2006 at another literary agency in London. I then returned to RYA in the summer of 2007 and full-time after grad school in the summer of 2008. I stayed there full-time for eleven years, only leaving when I was ready to start a proverbial family of my own with Neon in 2019.

For the first few years at RYA, I was a developmental editor and general assistant on a full-time salary. I then added foreign rights representation to my job description and managed that aspect of the agency’s work from I think 2009-2015.

Although I thought about repping clients of my own as early as 2009, I defaulted to my old perfectionist habits and didn’t actually do that until 2012. Instead of take a risk on (gasp!) an author I might “fail,” I waited for years and years until I found The Perfect Project and Client—someone whose work was so transcendent, so obviously necessary in the marketplace, that I knew I could bring home an amazing book deal because, well, just about any agent would have been able to. But my God am I glad Caitlin Doughty chose me.

Caitlin’s iconic debut, Smoke Gets in Your Eyes: And Other Lessons from the Crematory, was the first book deal I ever closed. The book was and is a hit, and Caitlin herself has been a priceless career ally. Through her referrals and people finding me in her acknowledgements and my sending a bunch more cold-introduction emails, I grew my list from there.

So that’s my How I Became an Agent Story: I fired myself from the house side of publishing; I discovered more or less by accident that my talents and psychoses aligned almost perfectly with those required of an agent; I stuck around where I knew I could do excellent work; and I spent a lot of time frozen, refusing take any big leaps whatsoever in my work or life until I knew I could execute them like some kind of Olympian. And also, Columbia. And also, media connections through my mother.

Not exactly replicable or even all that useful. But here’s something that might be: the theme of my story is “my success started in my insecurities.” I found what I was good at (agenting) and went all in on it very early on and forever out of sheer terror and shame. :D Ha ha sob. But then I realized I actually really loved this work, too.

If you have any questions about agents or agenting or whether you too might find yourself falling in love with this line of work some day, feel free to ask ‘em in the comments. I’ll respond to however many I can!