Notes on Writing CRYBABY: The Beginning

I started writing Crybaby on a warm weekend in September, in 2021, in the guest room of my sister-in-law’s home. My wife, my sister-in-law, and my brother-in-law, along with a few friends all chipped in to buy me a modern word processor after I mentioned a few months earlier wanting to start my second book on a Freewrite. Just to see what it would do for my creativity. The birthday gift came with an ornate card with little sushi rolls on it and it was signed by everyone who contributed to the purchase, despite us all living hours apart.

After some whiskey and mixed drinks—writing after having hard liquor is so typical and I’m not remotely sorry for being a stereotype—the four of us headed to our separate rooms and I stayed up for a few hours typing away thoughts on my new machine. The very first sentence I wrote for my second book, Crybaby, was: “I don’t think you need to be depressed to love emo rap.” I wrote a thousand more words, noncommittal, and then a thousand more the next morning while everyone else was asleep. The ease with which the thoughts spilled out of me told me everything I needed to know about the future of the work.

The Book of Mac: Remembering Mac Miller was coming out in a month, and I was buzzing with excitement about having that project in real life people’s hands, not just as a series of articles online, or a series of chapter drafts in my docs. A short time after the book released, I found myself in Pittsburgh for a small virtual event, where I was asked if I was working on something new. I mentioned being 13,000 words deep in something. That, of course, was Crybaby.

In the winter months, I spent almost every day working on my typewriter. I had this idea of getting away from screens and distractions. I wouldn’t even have my phone in my office, which was at first terrifying but was eventually welcome. I accumulated quite the stack of typewriter scribbles, and tried to transcribe them all onto the computer but quickly gave up. Those thoughts were not meant to live on Docs. They were a series of exercises in gathering myself and clearing my throat. I’m still not sure what I’ll do with them, maybe tuck them into ARCs and mail them out, but one does have a humorous rant about Machine Gun Kelly. That’ll stay with me. 

At the time of writing this note, I’m over 42,000 words in writing Crybaby. I try not to get hung up on word count—the book will have to be written and finished either way, no real sense in giving myself anxiety over numbers—but I’ve been particularly invested in counting every word lately because they all feel so precious, even when I have to fight for hours to get 100 new ones out. And that’s the thing, too. New words. Some days, I’m sitting at this desk and I am in a full written chapter, and I change three words total. Those three changes still feel like a triumph. They feel like more than enough. The micro-decisions of craft mean so much more to me now. The essence of the work undoubtedly lives within them.

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