For quite some time, I’ve been struggling to explain the rationale behind what appears to be the most glaringly hypocritical aspect of my life: I’m the CEO of a tech company that makes an app, and yet I refuse to use a smartphone. Instead, I have a flip phone.

Most people’s eyes glaze over when I try to clarify that, first of all, Readup isn’t just an app, it’s a platform. (Note to self: This is a horrible way to start a conversation.) Then I’ll mumble some stuff about minimalism, digital simplicity, the old iPad I hacked to be a Readup-only device, and finally, the fact that constant connectivity is causing the downfall of society. Trying to connect all of those threads, quickly, is a lesson in frustration, especially for a long-winded person like me. I’m out of breath just thinking about it.

Now, as I journey across America’s heartland, trying – and often failing, sometimes quite fantastically – to explain to everyday people what it is exactly that I do for a living, I have some new perspectives on this problem.

For one thing, buzzwords are useless out here. Terms like attention economy, surveillance capitalism, and clickbait might as well be in a foreign language. As a self-proclaimed hater of buzzwords, this has been a humbling wake-up call. As much as I hate to shelf it until futher notice, “panopticon,” will have to wait.

And since flip phones aren’t so rare in western Michigan, brandishing mine doesn’t have the same performative effect it had in Oakland or Brooklyn, where it literally caused jaws to drop.

All things considered, folks in Middle America might move and talk a lot slower than their coastal peers, but what they lack in speed they make up for with enhanced intuition, a spidey sense that sometimes puts me on edge. For example, “Not profitable yet,” gets the sideways glance it completely, utterly deserves.

It’s a hell of a feeling to get sized up and dressed down, quickly and accurately, and I think it’s knocking some of the bullshit out of me, which I’m thankful for. Lord knows I need it, having been groomed in Silicon Valley where grifters reign supreme.

And lastly, there’s one thing that people here don’t need to be lectured about (especially from the guy who taps into the library wifi from the sidewalk after hours) and that’s screen time. This is the land of no connection, where everyone knows full well that fresh air is good for you and there’s plenty of it to go around. And where work, unless otherwise noted, means real work, not desk work. Still though, unlike many other digital media buzzwords, screen time has permeated the rural conciousness and everyone has a story to tell.

But since the issue at hand is my own fraught relationship with screens, it’s time for a trip down memory lane.

So, rewind.

September 2011. I’m twenty-four. My undergrad days at Stanford feel like ancient history even though I’m barely a year out and never even graduated. I’ll sort that out later. For now, I’m living the Silicon Valley dream: solid job, apartment in Pac Heights with sweeping views of the Golden Gate and Alcatraz, the whole nine yards. But something isn’t right and that something seems to be emanating from my phone. So I do what a lot of people do when they need to figure things out; I enroll in a yoga teacher training course. For ten weekends in a row, I’m in yoga mode from Friday afternoon to Sunday night. To kick it up a notch, I leave my phone at the office and sleep the nights under the stars in the Berkeley foothills. It’s a charade inspired by a book I just finished, Dharma Bums by Jack Kerouac, but in hindsight, I can see that I was pioneering something that would soon become a widespread cultural phenomenon: the digital detox.

Spring 2014. “Product management” turns out to have been a wise career path, because it’s a lot of smoke and mirrors, which I can be good at, as long as I don’t let my heart into the work. The work is growth because growth is dollar signs. Period. God knows how I’m pulling it off, but I’m still managing a relatively conventional up-and-to-the-right career trajectory despite living a sailboat and spending huge chunks of time travelling, including all over Malaysia, India, and Nepal. Also, somewhat begrudgingly, I’ve actually graduated from Stanford by this time. With all of that out of the way – and, most importantly, having fallen in love in a big, scary way – I find myself in New York City, wondering why my startup career hasn’t imploded just yet, and still thinking that the problem is merely “I don’t like having a boss” and not “I can’t keep looking at screens.” I accept another job, reporting to another CEO, at a startup that has a Joan Didion quote on the Careers page and portraits of famous writers on the walls of the office: Virginia Woolf, Toni Morrison, John Steinbeck, and, of course, David Foster Wallace. This could work, I think. I interviewed in a closet-like room with no windows and bookshelf wallpaper. It should have been a tip-off that the secret room known as “the library” is actually a complete facade and that the only real bookshelf in the office is stocked with content marketing books. I’m in for a wild ride. For now I’ll just say this: I saw the how the internet-sausage is made. I helped make it. Also, I know what’s happening to writers and journalists right now, and I know why.

Fall 2017. I’m part-time dairy man at a rural, family-run general store in central Vermont that’s been in business for generations. I applied for the job without a resume (obviously; I’ll never have one of those again) and was hired on the spot, despite the one, strict condition I discussed with the owner at the onset: I don’t want an email address or a virtual calendar. No screens. He looked at me in a perfectly absurd way, like, “What are you even talking about?” I keep track of milk inventory on a clipboard and call in orders at the crack of dawn on a landline phone with one of those long spiraly cords that always tangles. When I’m lucky, I spend some of the day outside, pumping gas or shoveling snow. I know my customers by name and they have no idea that I’m running two startup tech companies in my spare time. I still have a lot to figure out, but finally I know this: It’s never been about getting away from bosses. It’s about getting away from screens.

January 2018. On a cold winter night in New Hampshire, Jeff and I are in the woods with shovels and flashlights. We’re stomping through a foot of snow and ice, trying to figure out where I buried my iPhone the previous fall. The following morning, we’re set to kick off an iOS project with a team of eight Dartmouth undergraduates. Needless to say, it won’t look good if I don’t have a device. The technical aspects of this project are complicated enough, I can’t imagine how confused these students will be if I try to explain how the flip phone fits in with the larger vision: We’re building an entirely new medium. A better way to use the internet. Time well spent. Screen time that’s good for you! Reading! Besides, at this point, that vision is still blurry even to me. What I know is that I hate my iPhone. I like having it underground. And, sure enough, we can’t find it anyway. After digging a few holes, we give up and call it a night.

Today. Right now. Luther, Michigan. I just had a beer at North Bar that cost a dollar fifty and the bartender told me where I can sleep tonight - behind the ball fields on the edge of the village. In search of an end, an answer, I grab my copy of The Shallows: What the Internet Is Doing to Our Brains, the screen time magnus opus by David Carr, published in 2010, long before social media came to dominate our lives. I open directly to a page with a quote surrounded by stars and checkmarks and a little hand-drawn brain:

The form that writing came to take on a page of parchment or paper enabled us to become deep readers, to turn our attention, and our brain power, to the interpretation of meaning. With writing on the screen, we’re still able to decode text quickly — we read, if anything, faster than ever — but we’re no longer guided toward a deep, personally constructed understanding of the text’s connotations. Instead, we’re hurried off toward another bit of related information, and then another, and another. The strip-mining of “relevant content” replaces the slow excavation of meaning.

And then, just as fortuitously, I find this, from Neil Postman in Technopoly, The Surrender of Culture to Technology:

“We are driven to fill our lives with the quest to ‘access’ information. For what purpose or with what limitation it is not for us to ask; and we are not accustomed to asking, since the problem is unprecedented.”

That’s it; that’s the thing: I have decided to ask.

I have decided to stare that question in the face, to knock on every door and chase down every lead in pursuit of more information about that “purpose,” that “limitation,” and I’m prepared - for now at least - to let my life revolve around this quest. That’s why I use a flip phone. That’s why Readup exists. It’s a crusade to save complexity, nuance, abstraction, critical thinking. A crusade against our growing obsession with easy-to-digest nuggets of information, binaries, bullet-points, trumping one another. Of course I can’t quickly explain my “work,” why I do what I do, how it all fits together. In a way, that’s the point. That’s why this blog post is long. And that’s why you’re still reading it.

The only way I know how to get closer to an answer is to keep digging deeper. To read more and write more. But don’t be surprised if we’re talking about Readup, or my flip phone, and then all of the sudden we’re talking about Infinite Jest, about what happened to me when I read that book, where I was, who I was with, and about the Infinite Jest within Infinite Jest, the film, the thing that plays on a screen and is referred to as “The Entertainment,” that which sucks the characters in, addicts them, renders them useless, unable to do anything but sit there, borderline-comatose, watching, forever, unable to get up to eat, to sleep, to go to the bathroom, unable to look clearly, ever again, at anything except that movie, including the people they love.

And don’t be surprised if we’re talking about this, in circles, for hours, and then I say, “I’m trying to figure out what David Foster Wallace was trying to figure out,” and if you strangely feel the urge to take me seriously. You should and you shouldn’t.

People fear the downfall of print. I do too. I read about it, write about it, and think about it constantly. But what really keeps me awake at night is something even scarier, more nefarious, more subtle: the end of language. Or at least the long, slow deterioration of it. We can’t let reading slip away. But it will happen if we let it happen. So let’s not.