August 9, 2006

Anonymous Lawyer: From Blog to Book

Anonymous Lawyer: From Blog To Book

In March 2004, I was a second-year student at Harvard Law School, preparing for finals and then a summer job at a corporate law firm in New York. On a whim, I started writing the Anonymous Lawyer weblog, from the point of view of a hiring partner, like the ones I’d met that fall in the interview process. Like most of my classmates, I’d interviewed with 15 or 20 firms, met a few dozen lawyers, and they’d all seemed pretty much the same. For obvious reasons, there weren’t any real blogs written by hiring partners, so I thought I’d play around, see if I had anything funny to say in the voice of a partner, and whether anyone would bother to read it. I thought it would last perhaps a week. But the website gathered momentum I never expected. By that fall, I was getting over a thousand unique visitors a day, and hearing from readers who thought I was real and wanted to share their own stories. The more over the top I thought my posts were getting, the more feedback I’d receive from lawyers saying I was describing their lives. I even received a handful of resumes from law students.

That December, The New York Times wrote an article about the blog, and I immediately started hearing from agents and publishers who wanted to know if I’d thought about turning the blog into a novel. The truth is that I hadn’t – but this, quite clearly, was my chance to actually get to write for real. My agent had me put together a short book proposal that she attached to a printout of the 50,000 words I’d written on the blog – basically, a plot synopsis of the book I hadn’t yet written, pretending I actually knew what I was doing.

There’s an easy way to turn blog to book, and, in a way, part of me was hoping someone would say, “You know what, it’s a successful blog, people like it, let’s just pick some of the best posts, clean them up a little bit, put it in between two covers and there’s our book.” No one said that. As I started meeting with publishers, the first thing they all asked me was if I realized it was going to be a lot harder than that. And since my agent had told me to expect the question, I was prepared. Fundamentally, I knew there were four big issues I needed to solve:

1. The Plot

If someone had asked me, “what has happened to Anonymous Lawyer over the life of the blog?” the answer would have been, “nothing.” I’d written each entry as a stand-alone anecdote, with few exceptions. On Monday he might be taking the summer associates out to a $100/person sushi dinner, complaining about the one country bumpkin who’d never tried sea urchin. On Tuesday, he’d be firing yet another housekeeper for forgetting to straighten the fringes on his rug. And on Wednesday, he’d be venting his frustrations about an associate who wants to take a few days off and doesn’t realize that some things are more important than a honeymoon.

There really wasn’t a thread in the blog that connected the entries together in any sort of sequence. In that way, it was more like an episodic sitcom than a novel. You can watch the episodes of “Everybody Loves Raymond” in any order, and still follow what’s going on. That’s why it works so well in syndication, and, for a blog, it works because people can find it six months in and don’t have to read the archives to know what it’s about, or they can read from front to back or back to front, and either way they’re getting the same experience.

But I realized that the expectations would be different with a book. People pick up a book and expect a story, not just a set of posts. There needed to be more to keep the reader turning the pages. Suspense. Action. I didn’t realize until I went back and read my entire set of archives that Anonymous Lawyer wasn’t a very active character. He was reactive. People around him did things he didn’t like, and he commented on them. In a blog, that was all he needed to do. But for a book, I knew it wouldn’t be. I needed to give Anonymous Lawyer a goal, and have him take a set of actions to get there. The book needed a dramatic structure the blog simply didn’t have. Anonymous Lawyer needed to be a protagonist. He needed to get up from his desk and do something.

2. Anonymous Lawyer’s Character Development

Similarly, Anonymous Lawyer needed to somehow grow as a character between the first page of the book and the last. On the blog, as in a sitcom, in each episode the characters may learn a lesson or have a change of heart, but by the next episode, they’ve forgotten it, and are the same people they’ve been all along.

There wasn’t very much character development in the blog for Anonymous Lawyer, at least not intentionally. He’d certainly become a richer character after I spent time at a law firm and developed real feelings about the world of corporate law that I was trying to express through the character. There were moments of self-reflection – real posts about real issues lawyers were thinking about, and reacted to in the comments and through e-mails – but there were also weeks where he was a heartless jerk without much nuance, simply getting off on being wickedly cruel to those around him. These could both be elements of the character, but whereas in the blog the only rhyme or reason to how Anonymous Lawyer would be on a given day was whatever inspiration I had when writing the post, in the book it needed to be more rational.

My editor pushed me to start the book with Anonymous Lawyer as a fairly one-dimensional character, without much in the way of self-reflection, and gradually introduce the other side of his personality as the story proceeded and he reached a crisis. This way there would be some emotional build, and he would change over the course of the book. I struggled with how to make him evil at times, but still sympathetic, and whether or not to redeem him at the end and give him a change of heart about his job and the way he acts in the world. Beyond the external actions that form the plot, there’s an internal struggle that the blog teased a little bit but never really developed. Merely thinking about Anonymous Lawyer’s inner life was something I wasn’t forced to do much when it was just a weblog, but I had to pay a lot more attention as I developed it into the novel.

3. The Supporting Cast of Characters

On the weblog, it’s the Anonymous Lawyer show. He would occasionally mention another character for convenience – Anonymous Wife, Anonymous Secretary, “A Summer Associate” – but with the exception of his wife, they’d never come back, and there was an inexhaustible supply of these random associates and partners at the firm who I would use in his stories, without any repeat players from one day to the next. If the summer associate he talked about one day seemed like the same one he talked about a week later, it was an accident. The world of the law firm, outside Anonymous Lawyer’s office, simply wasn’t fleshed out.

For the book, I needed to change that. The first thing I wanted to do was give Anonymous Lawyer a rival. Someone worse than he is, without the moments of reflection – someone truly evil and irredeemable. I called him The Jerk.

It wasn’t my plan all along not to give any of the characters real names. Anonymous Lawyer didn’t have one because he couldn’t tell the world who he really was. But once I had The Jerk, and Anonymous Wife, I realized I could have fun with the naming convention, and play around with the idea that, at work, sometimes people really are just one characteristic. There’s The Guy With The Giant Mole, and The Girl Who Dresses Like A Slut, and The Musician, and The Woman Who Missed Her Kid’s Funeral. They’re all in the book, along with about two dozen more of Anonymous Lawyer’s colleagues. On a scrap of paper, I created a world of these people, and pulled from that list when I needed to as I was writing, trying to use some of them enough that they developed as real characters, and weren’t just one-off jokes. At one point I thought it would be fun to have the seven dwarves of law firm life – Sleepy, Drinky, Ditzy, Dopey, Stinky, Lazy, and Doc, the summer associate who, before law school, graduated from medical school. Some of them survived the editing process, some didn’t.

And on the homefront, Anonymous Lawyer needed a family – his wife, two kids, parents, a niece and nephew… all to create a world the blog didn’t need. For the blog, Anonymous Lawyer was enough. But for the book, Anonymous Lawyer needed to develop relationships, interact with other characters, and give the world the richness of a full cast – or readers wouldn’t be able to spend 270 pages at the law firm without getting bored.

4. The Form of the Book

At my first meeting with an editor, someone mentioned that the blog was like a modern-day epistolary novel, and I nodded my head, wrote the word down, and as soon as we left I asked my agent what the editor was talking about. I didn’t know what an epistolary novel was, let alone understand what it meant to try and write one. There haven’t been any novels (that I’m aware of) written in the form of a blog, and, to be honest, I expected when I started pitching the book to publishers that it wouldn’t be staying in blog form. But they all seemed to agree that the blog form was working, and why experiment with something else when the form was successful as it was? “The only challenge,” they said, lightly, “was incorporating the plot.”

But that was a real challenge – one I didn’t completely realize at first. At one point, I thought there’d be an actual physical fight between Anonymous Lawyer and The Jerk. And then I tried to write it. And discovered that a weblog is a terrible way to convey action, because there’s the fiction that someone is sitting at a computer writing it, and that it’s all in the past tense.

He punched me, and I've come back to my office to get ready to attack him again.
Posted by Anonymous @ 3:35 pm.

I just went back to his office and stabbed him with a letter opener. Uh oh. I see him coming down the hall. I’d better log off.
Posted by Anonymous @ 3:40 pm.

The fight's over now. I won. It was very exciting.
Posted by Anonymous @ 3:48 pm.

I cut the fight.

But even a traditional epistolary novel written in diary form has to deal with that same struggle. The added difference that a weblog introduces is in the notion of private thought versus public thought. In an epistolary novel, the diary entries are the character’s private thoughts, and they can be contrasted with the public persona he or she presents to the world. But a weblog isn’t quite private, because it’s being shared with the world, but it isn’t quite public either, especially when it’s anonymous. The persona that Anonymous Lawyer presents to his weblog readers is absolutely different from how he presents himself to the people he encounters in real life, but it’s also different from the private thoughts he has in his head.

At first, this seemed like it created a ridiculous challenge: how to convey what he’s really feeling, how to convey what he’s writing on the weblog, and how to convey what’s really happening – all without confusing the reader. When I started writing the novel, I wrote in three voices: the weblog, Anonymous Lawyer’s e-mails, and a traditional narrative, written by Anonymous Lawyer in the present tense, explaining the blog posts, and explaining what was in his head as he was writing them. I got about 30 pages into that draft and realized the present tense narration was ruining all of the suspense. The fun of a blog is that even the writer doesn’t know how things are going to unfold. From one day to the next, it’s a surprise. Everything feels fresh and current. Once there was a voice in the book that knew everything that was coming, the blog became a lot less interesting.

And then I realized that the public-private nature of the blog could actually add another level of depth to the book, and that I could use the book to not just satirize corporate law firm life but also comment on blogging itself, and how you never know the degree of truth in what you read on a weblog. The blog isn’t like a diary in an epistolary novel – a diary is a reliable narrator, a reliable indication of the voice inside the character’s head, but a blog is not. The blog allows the character to present one image of himself, even if that’s not exactly true. And so part of the fun of the book is figuring out what the truth is, and how reliable the blog narrator turns out to be. This develops over the course of the book – at first, everything on the blog seems true, but then we start to see distinctions and places where Anonymous Lawyer is telling his readers one thing, but we know from his e-mail conversations that his blog readers aren’t getting the entire truth. And the e-mails and blog entries play off each other to create a richer story – and a different experience for the reader than merely reading a weblog.

In the book, I ultimately decided to mix weblog entries with an e-mail thread between Anonymous Lawyer and a number of correspondents, some part of his real life and some merely blog readers e-mailing him reactions to his posts. The e-mail threads serve a number of purposes:

  • First, they break up the monotony of the blog voice – 270 pages inside Anonymous Lawyer’s head, all in blog voice, would get boring.
  • Second, they let us get a glimpse of the private thoughts of Anonymous Lawyer, when he can’t blog them. I created a character who never appeared in the blog at all – Anonymous Niece, about to go to law school, and the person who told Anonymous Lawyer about weblogs in the first place. At first she’s the only one who knows about the blog, and that he’s the author, and she becomes his “secret sharer” – his e-mails to her are the only place he can confide his anxieties and fears that he wouldn’t feel comfortable telling his readers.
  • Third, the e-mails let us get inside the heads of some of the other characters, like Anonymous Niece, but also the characters who start to discover the blog as the novel proceeds.
  • Fourth, the e-mails let the reader get deeper into the world of the blog, in a way the weblog itself doesn’t – book readers get to see responses from the fictional weblog readers, and Anonymous Lawyer’s replies to those responses. The form let me explore a bunch of blog-related things that I otherwise wouldn’t have had a way to, if the book was written entirely as a blog – people trying to guess Anonymous Lawyer’s identity, law students sending in their resumes to work at the firm, and the relationships that can sometimes develop between bloggers and readers, even when both parties are anonymous to each other.

When I started thinking about how to translate blog to book, I expected I would end up using a lot of the blog entries I’d already written, and simply incorporate a plot thread in between the recycled material. And that simply turned out not to be the case. As I started piecing things together, I found I had to rewrite more and more of the blog entries, and develop much of the material from scratch. Each draft, more old material would be cut, and more new material would be written. To create a book that worked on its own merits – that had forward motion, a dramatic arc, plot and character development – the blog entries I’d been writing for more than a year ended up acting mostly as 50,000 words of character work, background material that informed the novel but didn’t fit inside of it. By the end, I’d say probably 90% of the book is new material, and even the material I took from the blog has been tweaked enough to be mostly unrecognizable.

Not just because it would be silly to expect readers to pay for a book when they could get the content for free online, but also because the material on the blog as it was just wouldn’t work as a novel, I felt like I’d have failed if readers who’d been reading the blog all along felt cheated by the book. Early reactions to the book, even from long-time blog readers, have been gratifying in that way. And, to some degree, a relief, to be honest.

If you pick up a copy of the book, I'd love to know your thoughts. Shoot me an e-mail. Thanks for reading.

Contact: © 2006 Henry Holt and Company.