This is an excerpt from my latest book Dear Hannah: 70 Methods I Used and Abused to Change Who I Am.

How I Finished Writing My First Non-Fiction Book

Date: August 8, 2011

Age: 29

Location: Austin, TX

Subject: “Table of Contents” Method

Hi Hannah! I think I’ve finally figured out how to write a book. For the past 10 years, I’ve struggled to eke out anything more than a blog post, and now I think I’ve got something.

It was past 2 a.m., Alana was asleep in my bedroom, and I was just bored, noodling on my computer in the living room. I then thought about my aspiration to “Do something with my writing.” So I posed a question on MetaFilter, asking for suggestions for books that have unique formats, books like Flatland, The Gay Science, and The Devil’s Dictionary (all three of which are on my list of favorite books). One user suggested Alphabetical Africa, a book where the first chapter only contains words that start with “a,” and the second chapter contains only words with “a” and “b,” and so on. Another suggested that I look into epistolary books, ones written as a series of letters, like C.S. Lewis’s The Screwtape Letters, which really got me thinking.

When I was 14, I was half-joking when I said to keep my emails because I might turn them into a book later, but I think we might have something here. If we select the 50 or so letters that focus just on my reaction to a specific self-improvement book or some crazy method I’ve applied to myself, I think it would paint a nice progression.

I already wrote down a quick table of contents, starting with when you gave me How to Win Friends and Influence People. Then I listed every significant experiment I’ve tried on myself in the past 16 years, and then cross-referenced them with emails I wrote to you. I picked one at random, and tried to flesh it out, and I couldn’t stop writing. I finished one letter, then another one, then another one, and then I started breathing heavily. I couldn’t believe what was happening.

I knew I wouldn’t be able to sleep with this idea on my mind, and I was especially scared that I was confusing over-excitement with inspiration again. That’s all Philosophistry has ever been for the past 10 years, just me writing in the midst of these intense emotions. If I’m going to write a full book, I need to also write it when I’m relaxed. So I pushed away from my computer, and did my 30-minute meditation at night, instead of the morning like I normally do.

As I sat there, the fireworks of “OMG, I have a book on my hands!” smoldered into something more like cautious optimism. I could see the rapid-fire fantasies of receiving a Pulitzer or being on NPR march through my mind, like a parade, only to see them gradually whisk out of my field-of-attention. At the end of the 30 minutes, my whole body just felt nice, and then I curled up into bed with Alana.

The next day, I resisted writing. And the next day, I resisted again. I knew I had to get out of the wave of initial excitement, and see if was still interested in the table of contents method.

And lo and behold, I still am. I can’t believe it. I’ve been writing for three weeks now, and I’m pretty sure I’m going to finish this. None of my other writing methods for making a book have ever lasted for more than 10 pages or so. And now I’m a third of the way through the first draft of this entire book!

I guess everybody’s got to find out what works for them, and for me, it’s the table of contents. If someone gives me a table of contents that I believe in, then I’ll write them a book. The medium is what drives the message for me.

- Phil

My first attempt to write this book was probably in 2005, when I tried to make a dictionary explaining all my weird self-improvement jargon. My second attempt was in 2008, when I tried to condense all my concrete, re-usable lessons from self-improvement into a vanilla self-help book about how to calm your mind. My third attempt was the PubPost (a.k.a. “Publish Posthumously”) method in 2009. My fourth attempt was just before this letter was written and was inspired by the film Source Code. It has me taking the same Caltrain from Palo Alto to San Francisco 50x over, each time bumping into the same woman in a blue dress. Each instance would show me acting differently according to a different self-improvement experiment I was under. The book you’re reading, based on the epistolary approach, is probably my fifth attempt.

These letters to Hannah won out because they represent what has been consistently helpful in my journey: having someone to talk to. As much as I claim to be Mr. Do-it-yourself, writing to someone has become a cathartic lens for my self-improvement. It’s helped in ways that a mountain of private texts — whether in spreadsheets or diaries — never could have.