I stood before a dark cave, wanting to go in; and I shuddered at the thought that I might not be able to find my way back. — A psychology patient quoted by Joseph Campbell in The Hero with a Thousand Faces

Nobody asks you about the novel you never finished. They’re too embarrassed for you. They assume the worst, that maybe you spent all that “writing” time binge watching TV shows or day drinking in bars. (I did not.)

From 2014 to 2018, I spent almost five years writing a novel that I haven’t published. Mostly full-time, like a job, like the best job in the world. I risked my successful career as a lawyer and product manager to leap into the unknown, carve a deep gap in my résumé, and live this decades-long dream of writing a book. Life is short after all.

But I put the novel away in 2018 and haven’t touched it since. 

I spent hundreds of thousands of dollars living in San Francisco and New York City without any income to write this book. So it must have been pretty important, right? If it was so important, why do I seem to have nothing to show for it?

It’s a long story. But I would like to tell it.

The novel is the classic tale of man meets woman, man follows woman down the rabbit hole of San Francisco subcultures, man has spiritual crisis, man . . . well . . . you’ll just have to come along for the ride to find out what happens. 

The themes I explored in the novel, and will necessarily explore in this space include:

• Polyamory, sex cults, and other necessarily flawed attempts at creating utopian community 

• Spiritual crisis / spiritual emergency

• Mental illness in a sick society

• What does self actualization in the 21st Century look like?

• Finding love from the inside out

• Moving from control to surrender

It’s not autobiographical but it was certainly inspired by my years living in San Francisco. 

This newsletter is a vulnerable and honest practice in revisiting the novel and answering these questions:

1. Why did I choose to write this novel back in 2014? What was going on with me? As part of this inquiry I am rereading my very comprehensive novel journal that I kept diligently the whole four or five years I was writing it. 

2. Why the above themes? 

3. What do those themes and this story mean for me (and for us) now? 

4. Can I exhume and reanimate this thing? Is it any good? Is there marrow in those bones?

5. Moving beyond failure and disappointment into living freely from the heart.

Even though I haven’t published it yet, writing this novel was nevertheless a valiant and earnest act of life creation for me: Like some kind of Doctor Strange, I carved the shape of a portal with this novel and stepped through it.

Everything that’s beautiful and wonderful about my life now, whether that’s the people I know or my transformational quests in Peru and India, would not exist without it. I also had a hell of a lot of fun writing it! Every minute of the process was pure ecstasy, sometimes wrapped in a film of strife and consternation. But always infused with the bliss of pure creation and play. 

In addition, as an exercise in focus, simplicity, and viability, I am in the process of rewriting the novel as a screenplay to see how the story holds together, before putting the meaty flesh of prose back on those bones. Who knows? Maybe it will work better as a screenplay!

In my next post, we will return to the time and place it all started. Let me set the scene:

In 2013, I left my “dream” job at Twitter in disappointment and disgust and moved to a houseboat in Sausalito to pursue my life-long dream and write full-time. I had my whole life ahead of me. I was finally acting from a space of possibility and creativity instead of fear and safety. I had a lot of ideas…

Next time: Getting started as a full-time writer…