I got three messages when I sold my business in 2015. The first two, Change Everything and Decide Nothing, were relatively easy to interpret. The third message took me some time to decipher. On the surface, it made sense; many of the people that I most admire are artists, and I had always wanted to be an “artist”, but I didn’t know what it really meant to be an artist, nor did I have any idea what kind of artist I might try to become—or, most importantly—how to become any kind of artist.
Those mental blocks were still with me when I received this clear message. This glowing headline gave me the freedom to open myself to creativity in a way that I hadn’t experienced since my teens, when writing, painting, and art classes were a normal part of high school. I finally felt free to move forwards.
From there, I explored the idea of what it means to be an artist. I talked with friends who lived creative lives. As an entrepreneur, I explored what it might mean to start a creative business. I took drum lessons, and had an amazingly fun time banging on the cans for a year or two before I concluded that I wasn’t going to spend enough time practicing to get very good, and that most of what I was hearing was in my head.
Finally, in 2018, I began to revisit writing as a craft and an art form. I had always known that I enjoyed writing, and I had gotten some positive feedback along the way, but I hadn’t really considered the possibility of becoming a writer. I did notice that more and more friends were commenting to me that I ‘sounded like a writer’, and that I was often asked, often out of the blue by strangers, whether I was a writer. More than friend even remarked specifically that I should “write a book.”
I began to journal more and more, and to post some bits of writing on my personal site. Since I was no longer drinking alcohol, my intuition had become much more active, and I felt my creativity coming alive. I was enjoying writing more and more, and I began to allow myself to take some writing classes. Surrounding myself with others who were writing and even called themselves writers, I saw that I was amongst peers. I felt that I belonged.
And: I remembered something, something very important. All of my adult life, I had told the story to others and to myself that I “wasn’t one of those people who knew what he wanted to do” in life. I felt resentful of others who did seem to know, and I struggled with the feeling that I might never know what I wanted to do, or who I wanted to be. I felt lost, and disappointed with myself for not having this clarity.
But then, a memory returned. I would have been fifteen, at the beginning of my junior year in high school. We had an early PC computer in the back room of my mother’s flat on Church Street in San Francisco that I would use for homework and assignments in the creative writing class that I had at the time. I remembered sitting at that computer in 1985 and writing to a friend of my mother’s, Betty, who had become an aunt to me, that I would become a writer—and even more specifically that I would become a writer in my fifties. I wrote to her that in the meantime, I needed to acquire experience, to live, so that I’d have something to write about when it came time. I thought then that these experiences would mostly be ‘travel’, and that my writing might take the shape of something like Bruce Chatwin’s In Patagonia, or Coming Into The Country, by John McPhee, two writers that I already admired.
Little did I know then that my ambition and clear vision of becoming a writer in my fifties would be lost, buried by my years as a teenage boozehound, only to resurface just in time, at the age of 49.