In March 2013, I quit my job at Twitter to see if I could make it as a full-time writer, risking my career and professional reputation by taking a hard left turn. Robin Sloan, one of my colleagues at Twitter, had done it successfully and I desperately wanted to make that transition. 

I also broke up with my girlfriend. I moved out of our cute craftsmen house in Berkeley and into an even cuter houseboat in Sausalito. It was the top floor of a two-story houseboat owned by an eccentric artist couple who drank and yelled a lot. They were old-school Sausalito—1960s renegade houseboat people. I loved it. That was exactly the vibe I was looking for. I wanted to marinate in the vapors left by the likes of Alan Watts and the rest of Bay Area counterculture. I loved San Francisco then, had ever since my early twenties when I went through the Beat Writer phase every sensitive young man goes through.

It was a modest houseboat dock next to the seaplanes. The Grateful Dead used to play in the small building at the end of the dock.  

Houseboats are not boats; with few exceptions, they’re not seaworthy. This one was a shabby warehouse-type space built on top of a floating slab, with a one-bedroom apartment plopped on top. You haven’t lived until you’ve woken up in a bedroom with the entire San Francisco Bay quietly glistening outside your window. I loved how the house gently rocked, almost imperceptibly. Sometimes I would forget I was on water until I would see the skyline slowly sliding back and forth out the living room window, or feel the shower floor moving slightly beneath my feet. It was perfect.

It had a giant deck, where I spent most of my time—writing and doing yoga (see above). 

I gave myself at least a year to write and do nothing else. I would get up around dawn, meditate, and then write all morning. Afternoons were for reading, hiking, seeing friends, and yoga. That was my life in 2013–2014.  

I had never been so excited in my life. I had finally started living. 

As I embarked on the path of a full-time writer, I did experience some doubt arising from the fact that I wasn’t a “classically trained” writer—I did not have an MFA in literature or creative writing. Back in 2000, I had briefly considered an MFA in creative writing after making a small amount from the dot.com bubble, when I was casting about for a new direction and wanting to fulfill my dreams. But I got scared. It felt too impractical. My blue-collar upbringing and the practical voice of my parents trumped any sense of creative possibility I might have had. So I went to law school out of a combination of a desire for financial security and a moderate intellectual interest in constitutional law, environmental law, and intellectual property law and tech policy. 

To assuage my concerns about having no formal training, I came up with many counterexamples of successful writers without any classical training and decided to become an autodidact: Hermann Hesse, one of my idols (more on him later). Jorges Luis Borges. Rabindranath Tagore. William Blake. Maya Angelou. Charles Dickens. Jack London. Joseph Conrad. Faulkner. Melville. Hemingway. Capote. Bradbury. And Henry Miller, who started writing in earnest when he was 50, just a decade older than me at the time. (More on him later too.) Not that I was aspiring to be on par with any of those luminaries or win the Nobel Prize in Literature like many of them had. It was a comfort just to know that it could be done, that a living could be made.

Also, not only had I read literature my whole life but I had been published as a lawyer fairly consistently. I knew how to put a few words together at least. And I had always had a wild imagination. 

I would teach myself; I would read the best books about writing. And I did. Dozens. More on that in a later missive too.

And I read fiction, lots of it. Short, long, literate, trashy.

But I really fell in love with the writing of Richard Yates, most famous for his novel Revolutionary Road. There was an economy and a weary wisdom to his prose. And he was exposing the hypocrisy and emptiness of modern American life way back in the late 1950s. I wanted to do that.

Of course I knew better than to tackle a novel right away. Instead, I would write a short story. I read The Art of the Short Story. And Creating Short Fiction by Damon Knight. 

I jotted down three story ideas in quick succession. Because I had been steeped in the culture of Silicon Valley since at least 2004, my first two ideas were about technology culture. One was to be a critique of Silicon Valley and the harms of techno-utopianism — the idea that technology is the solution to every challenge, inspired largely by this New Yorker article by George Packer. I was thinking a lot about Bay Area economic disparity at the time. And trendy, superficial “mindfulness” symbolized by conferences like Wisdom 2.0. I can’t remember what the theme was. It was something about how the mind of Silicon Valley needed more heart. I was thinking a lot about how the Valley needed more leaders with heart and real wisdom rather than the egotistical, Aspy males that were in charge at the time (and still are to some extent). One working title was, “Myopic Valley.”

The other short story was more specific: a story inspired by the tragic death of Aaron Swartz, an idealistic hacktivist with a passion for reforming technology and information policy. He had hung himself just a few months prior because he was facing an absurd federal criminal prosecution for illegally downloading thousands of copies of academic journal articles through MIT’s computer network as an act of protest (he never distributed them further). According to his 2008 manifesto, like many idealistic technologists, he believed that information is power and that academic research should not be proprietary, especially when so much of it is funded by taxpayer money. He was right about how much public research is inaccessible to the masses. It was tragic, especially given how easily criminals had gotten off in the 2008 mortgage crisis. 

I knew people who were friends with Aaron. I believe the same things that Aaron did when I was in my twenties. I had been a sensitive, idealistic technophile like him. Something about his story fascinated me. His idealism, rebellion, and suicide touched me deeply. Tying back to my other story idea, I wanted to tell a sort of David and Goliath story that would do justice to the devastatingly short and influential life of Aaron. 

I’m sure it would have turned out to be a jeremiad. Nobody wants to read a jeremiad.

Then I had an idea that blazed with intensity and excitement in my mind: An uptight corporate lawyer new to San Francisco falls in love with a wild, polyamorous woman deeply steeped in wild, old, Cacophony Society San Francisco, and tries to possess her. Everyone loves an Alice in Wonderland story. And monogamy vs. polyamory has a built-in friction. And, like all juicy story ideas, contained an entire microcosm of themes that were percolating in my subconscious. I didn’t know it then but this story was the vehicle I was building for myself to sort out a whole host of questions that were and still are central to my quest to carve out the most authentic and relevant life that I can. 

Like any curious man back then who had his eyes open and his ear to the ground, I had had some brushes with the burning, throbbing, gyrating underbelly of San Francisco in various ways, almost always through women. As my mind became more still there on those long, languid days of reading and writing on the waters of the Bay, these brief glimpses of another world started to fill my consciousness. 

I would have to do a lot of research. It might be too big for a short story, I thought. 

I don’t recall when I decided to scrap the whole short story thing and just go for a novel. As I started to do research and invent the first few characters, intuitively and instinctively I could see that I had far too much to say for a short story. Fuck it, I thought. Let’s just write a novel. 

But, despite my curiosity and experiential research, I was too removed from it, judging it all a bit too much. I wanted to have my cake of celebrating polyamory and witchcraft and all the rest while at the same time eating my cake of satire and arch observations. The story would need to do its work on me first.

I didn’t think I was risking my entire professional career at the time. I was only giving myself a year off at first. But I also didn’t care. If you had asked me at the time if I was worried about this I would responded, “Not a bit.” In fact, at one point a few years later, I promised myself I would spend all of my savings to finish the novel if that’s what it takes. And I did.