How I got my book deal (and how it is going so far)

A peak behind the curtain

Readers may know that I am writing a book. The book has quite a few working titles right now, but I’ll refer to it with the title we used in Publishers Marketplace: The Intellectual Life. It is an autodidact’s guide to leading the life of the mind in the age of distraction, and it covers topics like:

• The vita contemplativa in the history of philosophy

• The virtues of reading old and difficult books

• Strategies for reading

• Note-taking methods

• The value of going on long walks

So far, I’m quite happy with what I’m writing. This book represents a synthesis of the project I’ve been carrying out here and on YouTube for several years now.

But today’s post isn’t about the book itself — it is about the process of getting a book deal. This is not a guide on how you can get a book deal yourself; as we’ll see, my process was a bit out of the ordinary. I believe that writers and readers all benefit from transparency; that’s why I’m writing this.

Topics we’ll cover (in no particular order):

1. The origins of the book idea

2. The failed book idea I had to discard

3. Finding an agent

4. Selling the book

5. Living while writing the book

6. How things stand now

The majority of this will be free, but I am going to talk about some more personal details at the end, and that will be behind the paywall.

How it started

Last June, an editor from Penguin Random House, B., emailed me. She had been recommended some of my work and thought that I had interesting things to say, and she asked if I had any book ideas. As it happened, I did have one: I had outlined a book about the concept of meaningful work (working title: The Grind), and I thought maybe she’d be interested. We set up a time to meet and talk about things via Teams.

Readers of this newsletter might know that last June was not a very good time for me. My son had just turned 1, and I wasn’t yet settled in my new house, and I had just lost my job. I was trying to figure out if I could make it as a writer and YouTuber. This made for a very anxious few months, though the upside was that it gave me a strong sense of hustle: I was writing constantly and felt like I was on the verge of making it. So, I felt ready to have a meeting with an editor, even if it wasn’t completely fleshed out yet.

As an aside, this has always been the way I do things. I tend to present ideas before they are fully formed. The result is that many bad ideas make it out into the world — but the other result is that I get to see what people are interested in. When I was choosing a dissertation topic, I proposed three topics to the man who would go on to be my advisor. He listened attentively (as he always would) and then, after I had finished describing the third topic, said something to the effect of ‘Any of those would be good topics. Which would you like to pursue?’

Good question, Keith, and it took me the rest of the summer to decide.

The meeting with B. went well. She liked the idea, though she didn’t seem to think that it was quite ready. She suggested that I flesh it out a bit more and find an agent. She offered to make some introductions, though I was encouraged to go and find an agent on my own.

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I’ll acknowledge here that this is not the normal way one gets a book deal. The usual scheme, as countless blogs and books will tell you, is:

1. You craft a perfect proposal

2. You query agents and eventually find one

3. You work with your agent to refine the proposal even further

4. You submit to editors and, finally, secure a book deal

I was doing things out of order. Part of this was because of my public profile. Last June, I had approximately 250,000 subscribers on YouTube. (I now have about 550,000.) My Substack was starting to grow. It isn’t true that you have to have a public platform to secure a book deal, but I would be lying if I did not say that it helped. The fact that people already cared about what I had to say about books, philosophy, etc. was a draw for editors and agents.

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Around the same time last summer, I started attending a writers’ group in Austin. It’s a very business-oriented meeting with mostly journalists in attendance. (I was invited after making connections with a feature writer at Texas Monthly.) There are at least a few big names that you would recognize who attend, though they don’t come every month. We monthly attendees are mostly younger writers who need to make connections and like free wine. (There is a tip jar, and people do donate!)

Because of this, I now had a few connections with writers, and if I needed an agent I figured the best thing I could do was ask for referrals. Through B. and the writers in Austin, I received approximately six referrals.

1. Some were Austin-based literary agents, mostly people who had moved out of New York in 2020/2021. None of these agents thought my ideas were worth much, though they passed along their best wishes.

2. One was the agent of a very famous New York Times bestseller in Austin. He told me he was too busy to read anything, but he passed along another agent I might want to query. (He did not make an introduction, to be clear, though I didn’t expect one.)

3. One was a New York-based agent who specialized in popular nonfiction and what I started calling in my head ‘conversational Big Idea books.’ (I would eventually choose this agent, but we’re not there yet.)

4. One was a very accomplished New York-based agent who was at the same agency as a writer from my writers’ group. He read a draft, didn’t love it, and offered to read a substantive revision. (In the world of agents, this is a good sign.)

I also queried 10 agents without referrals. During the query process, you produce a proposal, a substantive writing sample, and a cover letter. I was told to lead with my platform: here are my subscribers, here are my growth projections, etc.

Of those 10 agents, I received one response. I mention this here not to complain – as you’ll see, things worked out for me! – but to note that even if you have a big platform, many agents won’t respond. 90% of the agents I emailed did not even send an automated rejection. This is the norm. If you don’t have a platform, I imagine the numbers are even more skewed. Many good writers query many agents, sometimes hundreds, and receive no response.

This is the part of the story where I am supposed to say that this is evil, wrong, vile, etc. Unfortunately, I think it is a product of that most dreadful of technologies: email. Because email makes pitching books so much easier, agents are overwhelmed. I suspect that soon a SaaS company will pitch an AI editorial assistant to sort through your slush.

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I believe that some of these rejections or non-responses were due to the fact that my idea wasn’t unique enough. The Grind was about the problems of American work culture, heavily influenced by David Graeber and Byung-Chul Han with a heavy dose of Aristotle and William Morris. I don’t think this exact book has been written but, frankly, I think that many similar books have been. This wasn’t the right idea to put forward. And as one agent told me, books about work tend to be labelled as career books, put on the business shelves, and flounder.

If things hadn’t gone well, I was going to start from scratch with a brand new idea.

However, the responses I did receive all had some things in common: they liked the conversational tone, the storytelling, the way philosophers were woven into the narrative. So, I knew that at least as a matter of style, I was on the right track.

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Eventually, I picked an agent: Daniel Greenberg. I liked Daniel’s approach in our conversations, I liked that he liked the work book idea, and I liked that he had worked with Chuck Klosterman.

So, Daniel and I now had a contract, and we’d need to work on refining the proposal.

A Digression about Agent Economics

Agents get 15% of your money. Considering that as a self-employed writer you’re already giving 25-30% of your money to the government (we pay our own payroll taxes), an additional 15% cut feels pretty severe. Common advice in the smaller publishing world is that you don’t need an agent, that all they’ll ever do is take their check.

This is not true in my experience.

I am a bad negotiator. When I finally got to the point of selling the book, I was inclined to take the very first offer — or even suggest that, maybe, they had offered too much. Daniel’s job in that moment was, as another writer once put it to me, to be my bastard: to be the guy who had the uncomfortable conversations that I didn’t want to have.

(This ended up being less severe, though, because Daniel has a good reputation in the literary world and my editorial team likes me.)

If you’re asking ‘Is an agent worth it?’ you need to break this up into two separate questions:

1. Is an agent necessary? For some presses, the answer is yes. For others, it is no. Do your research and act accordingly.

2. Is an agent going to pay for himself? You need to get to the point where the agent is securing you a deal that is roughly 17.7% higher than you would otherwise get.

Revising the Proposal

Despite the fact that he liked the idea, Daniel thought the proposal needed substantial work. A good agent can help you with this. They know the market, they know the tastes of various editors, and they know what makes for a readable book. Since I was aiming to write broad nonfiction, I knew I had to take this sort of feedback into account.

This part of the process was a slog, and it was mostly uninteresting. At the time, we were still working under the assumption that the book was going to be about work. The working title had changed several times, but the subject matter was the same.

This took about six months. We now thought we were ready to sell the book.

Selling the Book

If you are selling your book to publishing houses, your agent has to make some strategic decisions. Do you send it out to every person who might be interested? This can lead to a bidding war if you’re lucky, but it has the feeling of swiping right on Tinder on the profile of every woman in a 25-mile radius: there’s no romance, and who knows what matches you’ll make.

We decided to do an exclusive submission to B. at Penguin Random House. Given that she had been the one to initially encourage me to write a book, and given that she and Daniel knew each other, it felt like the right call. (Looking back, it was clearly the right call.) So, we sent it off.

And B. did not like the book. It didn’t feel like the right book for me to write. Looking back, I can see the point. I don’t think I had a unique angle fully developed, nor do I think my readers would have been eagerly anticipating this particular book. (But one day I want to write some version of this book. One day.)

But, given that I had a prior relationship with B. and that she was interested in my writing, we decided to have a meeting. She had floated the idea of a book that was a bit closer to what I was doing on Substack — which at that point was a flourishing enterprise. Daniel and I decided to come to the meeting with some new ideas to brainstorm. I decided not to sleep all weekend and write a brand new proposal.

Here was the thought. My book about work was not really about work. It was about all the things we should do when we aren’t working. It was really a book about leisure and idleness. So, I crafted a new proposal on that topic. Working title: Reclaiming Leisure. I wrote this proposal, and Daniel sent it to B. and her team a day before our meeting.

I believe this was a critical decision because everyone liked this idea a lot more. And while they all had feedback about the idea, and the idea did transform a bit more over the next two weeks, I feel comfortable saying that this is the book I sold. Though by that time it had a new title: The Intellectual Life.

That was the book. How to live the life of the mind in a world of productivity and distraction. That may not be the title – we have a few floating around – but that is still the idea.

We then entered a period of negotiations, which I’ll discuss below, but the short version of the story is this: I sold my first book. As Publishers Marketplace printed:

YouTube creator and author of Commonplace Philosophy on Substack Jared Henderson's THE INTELLECTUAL LIFE, an autodidact's guide to developing the life of the mind, to Bria Sandford at Portfolio, with Megan Wenerstrom editing, by Daniel Greenberg at Levine Greenberg Rostan (world).

To parse this: Bria Sandford was the purchasing editor, though Megan Wenerstrom (a younger editor) would handle most of the early edits. The book would be published through Portfolio, an imprint of Penguin Random House, and they had purchased world rights, meaning it was their responsibility to find international publishers and translations.

Currently, I have written one-third of the book. The book is projected to be 60,000 words, with chapters ranging from 5,000-8,000 words. Overall, I am happy with the book. I think everyone who reads Commonplace Philosophy will enjoy it and, hopefully, benefit from it.

We are also making good progress on international rights for the book. Details will come later, but so far it seems that it will be available internationally in English and in translation in at least a few major markets. We’re still working on other markets, but my hope is (obviously) that it will be available as widely as possible.

Exact publication date: TBD.

Reflecting on the experience

My experience was far from typical — though, as I talk to other writers, I’m beginning to question if there is a typical experience. I made my name on YouTube; others make their names in academia, in The New Yorker, or as a podcaster. The media ecosystem is increasingly diverse and chaotic, and so the ordinary paths to success (and failure) are becoming less and less ordinary.