The War of Art — Dan Conway Edition
My book, Confessions of a Crypto Millionaire: My Unlikely Escape from Corporate America, was published in September 2019. By January 2020 I’d largely finished marketing it. I’d appeared on dozens of podcasts and radio stations. The book was covered by a variety of mainstream, tech and investing outlets, including The Hustle, CBS MarketWatch, Forbes, and Hacker Noon. I did a Reddit AMA and filmed a segment for Bloomberg TV. The book was selected for a BookBub deal, which generated more than a thousand sales in a day, sending it to the top of several Amazon best seller category lists. I also sold the film/TV rights.
The book is the crooked capstone on a career that started in 1994 at my first corporate job at a PR firm in San Francisco, and ended with me being fired from my last job and making my crypto windfall. Publishing it was the most satisfying accomplishment over that twenty five year career, which I define as everything that came before the book was published.
While the book was well received by readers, I was roundly considered a reckless maniac by everyone else. The type of person who would certainly blow it all on another high-risk investment. I have zero resentment about this critique. I wasn’t exactly clamoring for privacy by writing a book about myself titled Confessions of a Crypto Millionaire. But that’s not my story. I made the risk in order to earn enough money to do what I wanted with the rest of my life, not to buy a lambo, jewelry or a starter yacht. Unbelievably, it worked out. I’m not the least bit tempted to take more big risks, though I’m still a long-term Ethereum bull and hold a stack (admittedly, that might count as “big risk” for crypto virgins).
I knew I’d have the ability to write full-time with the remaining years of my life. That was the BIG payoff. Unlike versions of this dream in years’ past, it was now plausible. I’d have the time. But more importantly, since quitting drinking in 2012, I’d been fairly prolific. Between 2014 and 2015 I became obsessed with Medium and wrote sixty five essays while holding a full time job and raising three kids with my wife. Then I wrote the book, which was a multi-year process. I’d proven that I was capable of writing, not just talking about writing. During this era, which started in 2014, writing was occasionally hard work, but more often I was in a flow state, or something approaching it. I wrote with the confidence that I had something to say. I knew people would enjoy reading it.
Since January, I’ve been struggling to write. I’ve tried off and on, but it’s like my keyboard is doused in molasses. I set my jaw, type harder, force myself to sit in my seat for thirty minutes, an hour, an hour and a half, whatever arbitrary goal I’ve set the night before. I still haven’t found the path to get motivated and engaged. A variety of mental conditions and thoughts have stopped me in my tracks.
Over the past six years years I’ve spent so much time thinking about myself and writing about it, that I’m sick of me. This is a problem, because first person essays (and a book in the same vein) are literally all that I’ve written, other than corporate nonsense at my jobs. In addition to being fed up with the required introspection, I’ve lost faith that anyone would care what I have to say.
When I was writing to make people laugh — the goal of most of my Medium essays — I was thrilled at the challenge and became addicted to people responding positively. I discovered I had a knack for it, and I wanted more. Then, when the focus shifted to the book, I was motivated to entertain but also to tell a deeper truth about something big I’d lived. Telling my underdog story felt like a public service announcement: “See, a flawed dude like me (and you) can make it!” and “Ethereum is going to turn everything on its head, you should take a look.” I had lived through something amazing and now it was a double blessing because I could lay it out. I was driven to make sense of it all, to find the lessons and the meaning as best I could.
Now I feel like a rich guy whose “made it.” Writing from the perch of someone who doesn’t have to go to work is different. When I was an underdog, I let myself get away with certain vanities because I had the protection of being like most everyone else — just struggling to get by and find some joy in life and work. I was a smaller target because everyone roots for an underdog and allows them their complaints and resentments. But a rich guy who has it all (my meta data, though I’m sure my soul is more complex), is looked at in a different light. Now I have a hard time allowing myself to comment on the human condition.
I also think of Eddie Murphy. I loved his early comedy albums. Then after he got rich, his material changed and he became much less sympathetic. His new routine involved anecdotes about him being fleeced at a hotel as a result of his fame, or him getting rid of hangers-on because they wanted to take too many pictures with him. And it wasn’t funny, because it just sounded like a guy who had transcended normal life and now had to not-hilariously deal with us mortals.
I’m not Eddie Murphy rich and I’m not famous. But my day-to-day life and priorities are different now than they were before the windfall, and also different than most of my friends’. My inner critic tells me I better be damn careful about what I say. This may be true, or it may be a construct in my mind, but it exists.
Desperate to find my muse, I’ve tried to go back to my Medium roots. When I was publishing all of those essays I was mainly gunning for laughs. I recently almost published a Medium story in the voice of 2014 Dan titled “Five things I’ve Noticed about the Penises of the Old Men at my Gym.” Don’t ask. At the time when I was writing this type of stuff, which I don’t regret for a minute, mind you, I was trying to stand out. But now, after the book, am I still at that base level, using clickbait and shock humor to make people respond? Is this the writing I dreamed of spending the rest of my life creating? What’s my goal? And honestly, I didn’t find anything particularly interesting about the variety of shapes and sizes of the penises of the old men at my gym, other than that I could write a funny essay about them.
In moments when I’m determined to forge ahead with a first person essay that actually tries to make a point, when I’m trying to ignore the critic in my head who tells me no one will care or if they do, they will hate me, the content of my current life is still too green and unexamined to write about. Yes, it’s been different now that I don’t have to work. Yes, I’ve been meditating and reading about Buddhism (cliche alert). Yes, I’m turning to some non-profit pursuits. Yes, I’m focused on mortality and optimizing my health. But I have no idea what any of those things mean yet, or whether they fit into a cohesive thesis that I can explain to myself or the reader. Not to mention the lack of plot, although that can always be secondary if the content is true and fearless.
Regarding Buddhism. I’ve been meditating for three years now. And as I said, I’ve been doing a lot of reading on mindfulness and eastern philosophy. I’d recommend Anthony de Mello’s Awareness and Tara Brach’s Radical Acceptance, if you are interested in dipping your toe in. The existential dilemma for me that these books touch upon, is how to master one’s ambition. As I explain in my book, I had (have?) a chip on my shoulder. That’s what led me to go so deep into crypto, because I sensed there was a way to win, to show everyone what I was capable of. I’m not arguing with the short-term outcome of my actions, which led me to the life I have now. But I’m not sure being that driven is the best way to live a life.
Now, at nearly fifty years old, I’m acutely aware of my mortality, the limited number of days I have left on the planet. The thing about a driving ambition is that it sets your mind into the future, to the detriment of your day-to-day existence. A part of me wants to write a kick-ass second book to show that I’m truly a writer, not just the beneficiary of a great story that could have been told by anyone. But why do I need to prove that to anyone? Does anyone even care? And if they do, why should that motivate me? And is it worth projecting myself into the future, departing from my day-to-day for a period of years while I put my nose to the grindstone, to show I can do it?
I’ve always had an artistic motivation to write in its own right. It’s sitting there quietly, as it always has. In the midst of this heated internal conversation between the louder voices of my ego, arguing about how hard I should strive for imagined future glories, it is drowned out. I know my artistic vision will be the wisest voice to listen to. But everytime I sit down to write, the raging macro argument about who I am and who I should be, gives me no peace. As a response, I start thinking about comfort food, like a couple of hot dogs wrapped in tortillas (literally hot dogs, not a metaphor).
Finally, writing is hard work. I’m a lazy bastard. Since one part of me says I don’t have anything else to prove, why shouldn’t I down a pack of M&Ms and put the dishes away rather than grind through another paragraph, which has felt like torture. In other words, run-of-the-mill writer’s procrastination and resistance. COVID hasn’t helped. I used to go to Philz Coffee every morning and write for a couple of hours, away from the sounds and responsibilities of our house, which now contains five of us, all day. Someone always needs to have their lunch made, the dog needs a walk, the TV needs watching to see what crazy shit Trump is up to. It’s a nest of distractions that can suck up my entire day.
Now that I’ve covered the existential and the the tactical challenges, let me end without a flowery close. I’m going to start writing again. Even if I simply write about my writer’s block, like I am now. My goal is to write something every day, to try to build some momentum. Even if it’s a paragraph or two with a wacky headline, maybe I can generate some steam. If I can let my writing-for-writing’s-sake voice back into the driver’s seat after pushing out the blowhards and maniacs in my head, I suspect I can find my rhythm again. Now, I’m going to congratulate myself for writing this modest piece, the longest thing I’ve completed during the shit show that is 2020. At this point, I’m happy with the participation prize.
