Good Prose Month: Dan Wilbur on What to Expect When You’re Expecting Your First Humor Book

Editor's Note: In conjunction with his publication of his new book, "Good Prose," Pulitzer Prize winner and bestselling author Tracy Kidder and editor Richard Todd will host “Good Prose Month” on Signature.com, with the goal of bringing together the strongest voices in nonfiction to share insight into the writing and editing process with the next generation of authors. Every day during the month of January, visit Signature.com for a new Good Prose tip, lesson, or story from bestselling authors, award-winning journalists, acclaimed editors, and favorite storytellers. The conversation will continue on Twitter with a weekly #GoodProse chat about the craft of writing, hosted by selected authors from a range of nonfiction genres.

Dan Wilbur is a 10.  That is, a 10 after adding up his three best features: Physique (3), Face (5), Personality (2). Dan is a comedian, writer, and avid video game player living in Brooklyn, NY. He only eats fast food on weekends and occasionally exercises by accident (police, fire).  He has read nearly half of nearly half of all the books he owns. If you like Dan, even a little, it’s probably because you’ve seen his writing or you’re his parents.  His writing is featured on Collegehumor.com, McSweeney’s, the Onion News Network. Dan is the creator and editor of Better Book Titles. His first humor book “How Not to Read” is available now from Perigee (Penguin).

If there’s one good tip a stand-up comic can give a writer, here it is: it’s never as good or as bad as you think. Don’t sweat it if you bomb or people hate your latest Huffington Post blog. More importantly, though, don’t get an inflated ego over something you know is mediocre (after listening to hours of my sets on the train ride home from a show, I know the applause breaks will always sound softer, the laughs always lighter than what I heard in my head onstage. The tape knows best!). Even when your book wins the Pulitzer, remember that when you wrote it, it wasn’t perfect. It was a draft.

The joy of having your own project to work on is that the usual envy a writer feels toward his or her peers goes away. It goes away for exactly ten seconds. In that ten seconds, you’ll spend five bursting with ideas about the success/genius of what you’re writing, followed by five seconds dreading that your name will appear on the cover of the garbage you just put on paper. But, take heart! When those ten seconds are over, you’re back to being your normal self (for better or worse). The bad part of having your own project is that it’s YOUR PROJECT to sweat over and worry about.

The month before my book came out, I suddenly lost weight. Don’t worry, male models. You can all breathe a sigh of relief that I put this weight back on. It was not a good weight drop either, although I was actively trying to cut out cake for breakfast. This weight drop was an anxiety-filled, alcohol free (which I would never recommend), sleepless month spent brooding over something I could not change: my book. I had spent a year toiling over a manuscript. I had sent e-mails to my editor begging to have certain dirty jokes appear unrevised. I responded to messages within minutes of receiving them about what pages I’d like to cut, and I answered most with the glibness of The Queen of Hearts. Cut, cut, cut. After all that, I had a book in my hands, and when I was supposed to be excited and happy and bragging on Facebook, I felt fury and disappointment toward myself for not trying harder.

The fun part about writing a stand-up that’s different from writing a book is not the instant gratification of making someone laugh at a thought you had a few minutes prior to telling it. The fun part of stand-up is when you’re working on a joke you found in a year-old notebook, and with a few revisions you make the joke new again. Live theater is malleable. Print media feels set in stone. The good news is that print media is on paper so if you really were super-embarrassed you could always burn all the copies, right?

The funniest and rightest statement made about my book prior to its release came from my boss at Community Bookstore. In an effort to keep me from worrying as the release date neared, she told me: “No one cares about your release date except for you and your mom.” The day the book is released is not the end of the world, nor is it the day they hand you said world (by “they,” I mean the Illuminate). Your release date is special because your book is in the world, but there’s still work you can do, ways to consider why the book is still worth reading. There are still people who will be reading it after that one day, and now that the book is out, you can (or should already be) working on the next book!

Of course, this terrible month wasn’t all bad. I had a supportive editor with a terrific sense of humor to write me notes of congratulation. My parents told me they were proud of me before (and after) they read the book. And I did some stand-up while I waited for the dreaded release date.

It’s never as bad or as good as you think.