The only books that ever really helped me in business were books about art. The War of Art by Steven Pressfield. Real Artists Don’t Starve by Jeff Goins. Steal Like An Artist by Austin Kleon. Over the years I came to accept that the workflow of an entrepreneur is identical to the workflow of an artist. We do the same things, different mediums, at different times.
This led me, in my mid 20s, to take an interest in art as a viewer. I’d go to museums when I got the chance, follow a few artists on social media, and sort of care what was going on in the art world. I’d read more books about artists, and so on.
Then I went to Barcelona and a shift started to occur. More specifically, I went to the Museu Picasso in Barcelona. That’s when everything changed for me. I found myself in tears that I could not explain halfway through his Blue Period and tried to avoid the girl I was with so that I wouldn’t be asked to.
It all made sense to me in an instant. I didn’t want to be a fan of Picasso; I wanted to be Picasso.
His museum showed me the way. It opens at the beginning of his career, his earliest works, and proceeds through the years and his growing body of work. You see trends, problems he was working on solving internally, moods that lingered. You see him get better. You see the student become the master.
How did Picasso become Picasso? Thousands of paintings and a devotion to getting better at them. I could do that. I spent a few days alone afterwards in my hotel room contemplating the sheer foolishness of imagining any hypothetical future in which I was an artist of any renown, let alone at the stature of one of the great masters.
Then I remembered Art Prize. As you either know or soon shall, I’m from Michigan. A few years back there started to be this thing once a year in Grand Rapids called Art Prize. It was an art festival, where people voted on the art, and the winner got a bunch of money, 6 figures I think. I wasn’t into art but I was into girls and girls were into Art Prize and so I went to Art Prize.
Some of the stuff was cool, but I found that my reaction to art in person was always, “What would I do as art?” My answers were always tending towards the audacious, over-the-top, impossible to ignore (I hoped) variety. At my first art prize I thought, “What about like a series of 15-25 foot tall portraits of myself, just doing mundane things like washing a dish, or putting on a shoe?”
That idea never left me. I’d come back to it every few months. I’d fantasize about learning how to paint and painting it. About standing next to it at a gallery and answering people’s questions about it. My secret life as a wannabe artist. This was in 2007 and another decade would need to pass before I’d touch paint.
As the years passed and I began my career as a professional adult the ideas for paintings kept coming, but I’d mostly ignore them. I was not an artist. I was a serious businessperson.
Until Barcelona. The thing inside me was set on fire. Ignoring it longer became problematic. One cannot unsee Guernica, which happened to be in Madrid where I’d visit a few days later.
As the months rolled on painting began more and more to consume my thoughts, but my identity wasn’t there yet. I was 28 now, far too old to learn something new. Plus, painting is really hard probably, I’d need to take classes or get an instructor and I’m busy. I can’t even draw.
I’d bought a book called How To Draw, and I’d made a few sketches, struggled, and quit. If I couldn’t make a decent drawing how on earth was I going to paint.
And then, summer 2018, I found myself once again alone, this time at the Museum of Modern Art in San Francisco. Staring into the face of The Son Of Man. Reading about how it was thought to be a self portrait and everything inside of me died and was reborn. I saw the painting in my head. The Son Of Man, but instead of the man in the bowler hat, me, and instead of the green apple, an iPhone. So obvious, so clear.
Two more months were spent trying to ignore it. I was on the road. Once I got back home and was settled I’d be able to paint. But then I had company for a month and couldn’t paint. And then i was in Europe for a few weeks.
The fury inside of me was becoming unbearable. I spent the flight from Budapest back to Bangkok taking notes of ideas for paintings, all self portraits.
Taking generic Instagram updates from my feed and painting them as fine art. Portraits of myself doing mundane things. Break down the great art movements in a single self portrait. The surrealist self portrait. The abstract self portrait. The impressionist self portrait. The pop art self portrait.
Or I could summarize the work of major artists in a single portrait. Condense Picasso’s life’s work onto a 50 x 60cm portrait that’s a picture of me, now we were getting somewhere.
Then I could recreate great masterpieces but swap out the subjects for me. The Last Supper but Jordan and his twelve Jordan’s. Jordan with a Pearl Earring. Finally, Mona Jordan.
I saw my whole career flash before my eyes and didn’t want anything else anymore.
The plane landed, I slept, and then bought everything on every beginner’s checklist for oil painting: Paint in a handful of colors, canvas, a selection of brushes, medium, paint thinner/cleaner, a palette, some paper towels, an easel. Three days later I painted Self Portrait 001.