My last post began a series of posts in which I’ve decided, upon setting out to find an agent for my new YA novel, The Elusive Black Truffle, to recount my writing journey and how I came to be where I’m at. I described my half decade spent in my early 20s writing and rewriting a junk drawer novel Barcelona and how, when I abandoned that, I moved to writing and publishing stories and poems to literary magazines. I chronicled how, knowing that to get where I wanted to be, I would need to write a novel, so I wrote an autofiction day-in-the life account of transitioning into marriage and fatherhood that I felt was too personal to publish called, rather unironically, Personal Time, and how once I got to the point where I felt I might be able to publish it, the business had seemed to move on from its autofiction craze to something else and I may have missed my moment (we’ll never know because I didn’t send it out). So now that those who didn’t read that post are all caught up, we’re in the year 2016. I’m tinkering with Personal Time and whittling it down, cutting it from its original 120,000 words to about 85,000, learning to edit text of that size, but I have to come up with another idea, and I’m hoping at this point, it’s an idea that will sell.

Personal Time taught me that I could write a book. It taught me that I could write a good book, a book I was ultimately satisfied with, but it was based on my life so it didn’t feel like a stretch. It was hard to do, but would it be quite as hard as doing straight fiction? I didn’t know and I wouldn’t find out for sometime, because the next project that really got me going was a memoir of my youth. Like a lot of people, I had a best friend growing up. Like a lot of people, we were close, more like siblings at times than friends. But unlike a lot of people, my best friend and I had fallen out somewhere around the end of college, stopped speaking for several years and then revived the relationship at a distance, but it was never the same, we were never as close. To some extent, this bothered me. I didn’t spend a lot of time thinking about and reexamining my youth. To a large extent, I took Don Henley’s advice to heart: “Don’t look back, you should never look back.” But who are we kidding? Even if you try not looking back, you don’t actually control where you mind wanders. And if you work an office job and you’re sitting in a cube, you have a lot of time to think. And sometimes when I would think, I would think about him, my friend, and sometimes, yes, I’ll admit it, I’d wish I could talk to him, I’d come to start missing him.

Before this, I’d never considered that time in my life as the stuff of drama. I grew up in the suburbs. My family was middle-middle class. We never had enough money to take vacations or anything, and my parents were living paycheck-to-paycheck mostly, but we always had food and a roof over our heads, and the school district where I lived was considered good and I got a solid education. Yet, the suburb was also unique in that it was on the cusp of a big city. Our schools were racially diverse while at the same time different populations still lived in unofficially segregated enclaves. Beyond that, my best friend had two older sisters, and so while I was attempting to assume the standard trappings of masculinity, my meeting him changes that. He encouraged me to be myself, to allow qualities of sensitivity, emotion and artistic inclinations to come to the fore. I was never the most traditionally masculine guy to begin with, so this felt refreshing. I had learned, early on, to play guitar, and I taught him how to play, too, and we started a journey together to become musicians that didn’t pan out, but then, how often is it that dreams like that do? We were unique in the type of relationship we had, but we also weren’t. Could I write about that? About having to navigate the masculine world while adhering to and honoring the parts of myself that didn’t fit in with what we consider traditionally masculine?

I decided to do it online, on this very site. Some of you might remember it? I drafted a chapter each week, posted it here, and then provide the link to that post on Facebook, inviting readers to comment and participate, allowing the audience to influence and direct the flow of the book. I thought this was a unique idea. Social media was still in its adolescence, and I thought that the resulting work might sell. The Crowd Sourced Memoir! And the response rate was good. I got a lot of comments on a lot of sections. I decided to call the book Both Cruel and Kind: An American Boyhood, because that dichotomy to me defines American boyhood. I spent a great deal of elementary school getting bullied, and in turn, that made it so that I could sometimes also be cruel to other kids, yet as I matured and realized we were, as adolescents and teens, all going through the same confusing shit, trying to fit in, trying to get to know who we were as people, trying to develop, I became a lot kinder to others, which doesn’t mean I didn’t still have the ability to wound someone who’d offended me. So there were lots of contradictions in that I was sometimes the bullied and sometimes the bully but sometimes neither.

In any case, I finished the book in the course of that year, beginning in May 2016 and finishing…somewhere in October? I’d have to look at the dates on my posts. And when I finished the first draft, the plan was to return to the online text, use the posts as chapters, and then write new and interstitial chapters based on audience comments to chronicle the experience of writing the memoir online. Like Personal Time, the first draft was a mess, a bit less messy than Personal Time because I didn’t start in third person, move to second person midway through and then only move to first person in my revision. Both Cruel and Kind was all first person. And I spent another six months carrying out my plan, writing the interstitials, trying to shape it into something I was satisfied with, and though I was close, it never felt right. I used the same approach on editing I used with Personal Time, which was writing more than I was going to use and cutting it back, sculpting the final draft out of the overwritten first draft, but Both Cruel and Kind wasn’t cohering in the way I wanted it to. As a writer, I rely often on my intuition to tell me whether something is working or not. That’s one of the gifts you develop over time as you spend many many years writing, the gift to discern whether what you’re doing is working or not. And it wasn’t working. It wasn’t bad. But it wasn’t where I wanted it to be to stand by it if it were out in the world as a final statement with my name on it.

So what do you do at that point?

You shelve it for a later date, write something else, and hope that when you come back to it with fresh eyes, you see what isn’t working and can fix it. So that’s what I did. I moved on to writing another book. I didn’t test the waters, at least not then, of whether there was an audience for Both Cruel and Kind by sending it to agents. I might have submitted it two or three times to independent publishers myself once I got it in shape…but that all happened a few years later, and by then, the industry had changed again. But we’ll get to that in a future post. For now, this one is getting long again, I’ve covered the second step in my journey toward finally writing a book I felt ready to put out into the world, so until next time…see ya soon!