The Trouble with Being an Entrepreneur

Until recently, I enjoyed calling myself an entrepreneur. Publishing on my own terms felt liberating. It also seemed realistic. In 2007, when my son went to kindergarten and I headed back into magazine journalism, I discovered that I had to figure out digital media or change professions. So, I started blogging. By 2010, I’d cofounded an online magazine.

With wonder in my voice, I would tell friends that I never could have imagined being an entrepreneur just a few years before—but I was! I embraced Twitter. I made very little money, but I spent entire days hustling on social media.

By the summer of 2014, when I first began drafting this piece about money, I even found myself blaming authors who complained about losing out in the digital economy. I wrote that concerns about not getting paid “were beside the point, even ridiculous.” I emphasized that I write because I love to write, just as poets and quilt makers are driven to create regardless of financing.

Then came a morning about a month ago, when I suddenly felt my stomach clench. As I studied the draft on my laptop screen, it hit me that I was reading an argument worthy of Donald Trump: The money you make is based on the demand you create, and all the whining about society supporting artists because “art matters” is bullshit.

Not only was I reading it—I’d written this self-sabotaging screed. I’d taken the anger I’d been feeling all year, fueled by my father’s death but also by ominous trends in the publishing industry, and flung it in the wrong direction. The mindset I’d grown so leery of during my time in the 1990s at the Harvard Business Review had wriggled into my brain. It had invaded my own thinking like a creeping little alien, outwardly cuddly, but with sharp teeth.

I still believe in the power of an online magazine like Talking Writing to expand the audience for literature, but I’ve stopped chirping about the joy of being an entrepreneur. Yes, the Internet has leveled the playing field, allowing writers to compete in a virtual landscape no longer bounded by nations or an insular gang of New York graybeards. But that means everyone is competing—all the time, against legions of other hopefuls—and the constant competition can be soul deadening.

Let’s see what business thinking looks like in a typical 2014 article directed at writers. In “Why Every Writer Needs an Author Brand,” Writer’s Relief puts it this way:

You’re promising your audience a particular kind of reading experience, and you shouldn’t let them down. From project to project, maintaining continuity in your voice as a writer is vital to building a successful author brand and establishing a strong fan base.

Such advice has proliferated all over the Web in writers’ blogs, trade journals, and writing coach sites (there’s even an Author Entrepreneurship magazine). Phrases like “reader experience,” “fan base,” and “author brand” are rooted in business talk about customer satisfaction.

While the entrepreneurship model works for high-tech startups, grafting it to what creative writers and journalists do is like sticking a brick on an apple tree. And yet, I now hear business jargon issuing from literary publishers, indie authors, and my own mouth: the need for buy-in, value propositions, takeaways, economies of scale, branding. This stuff is in our collective head, and it’s messing with it.

After spending the past seven years promoting myself online, I’ve realized that a business focus creates a basic conflict of interest for writers like me. In order to pitch and sell, I need to shape my content to the audience out there. As a journalist, however, I’m uncomfortable with being told not to “let down” my audience. That puts me on the road to click bait. Maintaining “continuity in your voice” is even more problematic. Nonfiction writers, in particular, need a trustworthy voice, but that voice may change over time and depending on the topic of a story.

This year, the stories I want to tell have changed with the recent deaths of my parents. I’d like to delve into my life with them and write a full-length memoir, an impulse that has nothing to do with author branding. The trouble is, my writing has now been influenced by years of crafting 1,000-word blog posts and opinion pieces. It’s almost kneejerk, the way I think in terms of headlines and blurbs, of what I can pitch, of what types of openings drive reader traffic.

This summer, when I tried to jam together memoir scenes from previous blog posts, I felt frustrated. I knew part of what blocked me was the freshness of my grief. But I also suspected that switching so often between marketing and writing gears had affected my ability to tap the unconscious material that fuels my best work.

The thought chilled me—and continues to chill me. At the very least, it takes longer to find the necessary creative flow, and my impatience has become a barrier. I can’t tell you what material is left untapped, only that I feel pressure to stay on the surface, producing fast and loose regardless of quality.

This is my personal struggle, but I’m revealing some of it here to convey why such a conflict is tricky for writers. Lately, I’ve heard too much nostalgic fatalism among older authors about the loss of print, as if the battle is over, so there’s no point in creating a digital alternative. I don’t believe that for a second. At the same time, I’m intimately wound up in the new online technology I use and not altogether comfortable with its impact on my thinking and writing. I won’t say I’ve been co-opted by the companies that own the technology, but I still wonder if I’m being swayed by the entrepreneurial drumbeat of Silicon Valley.

In July, I laughed when I saw an iPhone, with no apparent irony, displayed in the “Gorgeous” exhibit at San Francisco’s Asian Art Museum—along with Hindu sculpture, a sixteenth-century Persian Qu’ran, and a Mark Rothko painting. Then I thought harder about why a popular digital consumer product had wormed its way into rooms full of art and sacred texts.

Would the iPhone be considered a “gorgeous” work of art if it hadn’t made such a market splash? I doubt it. I like my iPhone, but I found combining it with that genuinely gorgeous Rothko not only absurd but recklessly obtuse. Last January, I was lucky enough to go to David Hockney’s “A Bigger Exhibition” at the de Young Museum in San Francisco, which included drawings he’d done on an iPad and smart phone—a fabulous use of new technology by a great artist. But sticking the equivalent of a blank sketchbook on the wall? That’s a whole other kettle of pixels.

It’s easy to be seduced into thinking that writers, artists, and entrepreneurs are kindred spirits. Like writers and artists, entrepreneurs must be dreamers, ignited by ideas, willing to put in “sweat equity” and perhaps work for nothing for years because they believe in their products. Maybe that makes them sexy rebels—James Dean “thinking different” on an Apple billboard. But it doesn’t make them artists. Entrepreneurs look for market openings: what will sell and become popular, what customers want. The goal is payoff on all that sweat, no matter how beautiful the product. If the product doesn’t sell, it’s a failure—not a work of artistic genius that may be understood only years after its creator has died unheralded and penniless.

I sympathize with the ever-present need for creative people to make money. I feel it myself, and I have to be entrepreneurial, or Talking Writing wouldn’t be here. But I’m worried about more than my own magazine. Despite the rebellious artistic stance—“Here’s to the crazy ones. The misfits. The rebels”—what today’s digital companies really want is this: cheap content to sell Kindles, iPads, apps, Web ads, and customer data. The people behind these for-profit corporations are highly motivated to say “nobody pays for content” because they know the payoff is in the technology—not the gorgeous words filling screens.

That’s the bottom line. It needs to trouble us all more.

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Publishing Information

• “Why Every Writer Needs an Author Brand” by the staff of Writer’s Relief, Huffington Post, April 30, 2014.
• “Gorgeous,” Asian Art Museum (a joint exhibit with SFMOMA), San Francisco, June 20 to September 14, 2014.
• “David Hockney: A Bigger Exhibition,”  de Young Museum, San Francisco, October 26, 2013 to January 20, 2014.

Art Information

• "Entrepreneurs Under the Water - 10" © Aurora Chisté; used by permission.
• "Mirroring" © Aurora Chisté; used by permission.
• "Entrepreneurs Under the Water - 13" © Aurora Chisté; used by permission.