(Mission) The Art & Business of Digital Writing: How To Master Your Craft & Earn A Living Online

An Evergreen Book: The Introduction

“No one makes a living as a writer.”

It was the last class of college, and one of my professors gave us ambitious students these parting words of wisdom.

He was one of my favorite professors (although I was not the archetype of what I assume were his favorite students). He was the one whose class I’d waited five semesters to join. Whose third book had become a local best-seller—and made him a Chicago literary star. Every student in the Columbia College Chicago fiction writing department wanted to take his class, and right before my last semester as a senior someone had dropped out.

I was a last-minute addition—a spice thrown in the chili.

I looked nothing like my peers.

They wore flannel shirts. Skin-tight jeans. Brown satchels strung over right shoulder to left hip. Studded belts. Pink and blue and yellow highlighted hair. The song “Thrift Shop” by Macklemore & Ryan Lewis was about them. They looked like “writers”: rusty wire-rimmed glasses treading water above their animé comic books and David Foster Wallace or Virginia Woolf novels. They talked like “writers,” quick to swap simple adjectives for their verbose older siblings. And they ate like “writers,” scurrying to the hallway vending machines during our fifteen-minute breaks for Snickers bars and Flamin’ Hot Cheetos, or the community microwave in the teacher’s lounge to reheat a half-eaten cup of ramen noodles.

As the room emptied, I zipped open my backpack and pulled out my next container of cold brown rice, chicken, and broccoli.

When people ask what I studied in college, I like to say I majored in Fiction Writing and minored in Bodybuilding. I started college weighing a little over 120 pounds, malnourished from a childhood spent undiagnosed with Celiac Disease. I had a concave chest, an S-curve in my spine, and enough insecurities to fill a lifetime of navel-gazing memoirs. But by the time I graduated, I carried around nearly 180 pounds of pure muscle. I wore tight-fitting Nike t-shirts with big, fluorescent letters on the front screaming JUST DO IT. I walked, waddled, swaggered in my black, swishy sweatpants and giant white Air Jordan sneakers. The insecurities were still there, but now I had a layer of armor. And in this small, liberal arts classroom, sardined in a semi-circle of hipster “writers,” I was the eyesore statue in front of a government building only a few appreciated. Everyone else could have done without.

Some people find their place easily in the world.

They just fit.

But the puzzle pieces of my personality have never seemed to fit anywhere.

The dilemma started at a young age. I was too artsy for the athletes, too competitive for the dramatic—a combination of my parents: my dad, a successful spine surgeon and driven achiever; my mom, a singing teacher committed to untethering the artistic soul of each student she shepherded. My childhood was a montage of hockey practices and Show Choir camps. If you don’t know what Show Choir is, it’s when you and a gymnasium of pitch-perfect glitterati sing Broadway songs in four-part harmony while dancing—usually in a vest or dress that shimmers. To the hockey kids, I was weird for singing on key and in tempo. And to the Show Choir kids, I was weird for putting on pads and willingly throwing myself face-first into the boards. And I wasn’t just the wrong fit for them. They were the wrong fit for me. The music kids only cared about “expression,” whereas I wanted to win. And the hockey kids only wanted to talk about winning, when I so desperately wanted to express myself.

Which is why all my closest friends lived on the Internet.

I don’t have many memories of high school. I didn’t attend any school dances aside from senior prom. I never ran for class president, or participated in any of the after-school programs. I tried Speech Club for a semester, and won third place in the Original Comedy category at my first (and only) competition. But I would hardly call the kids there “competitive,” running from classroom to classroom to cheer each other on, pat each other on the back, and eat bologna sandwiches (wheat) in semi-circles of laughter. Meanwhile, I roamed the hallways alone, same as I did before any hockey game, mentally preparing myself to dominate. They judged my expression. I judged their threshold for pain. So we just sort of left each other alone.

Instead, my fondest high school memories took place in the World of Warcraft: a massive multiplayer online role-playing game. It was the first world, the only world, where I met people just like me: fiercely competitive, but unfiltered and vulnerable. Obsessed with achievement, but only in the name of imagination, creative freedom, and magic. My guild became my after-school club. My battleground teammates became my best friends. And the words I typed into the chat box of my character became “my voice.” This is where I created myself. The Internet was my high school, my online character, my first set of armor—and just like high school, any fame and fortune I achieved was wildly overrated and short-lived.

But this is where my journey as a Digital Writer began.

Back to my professor.

Columbia’s fiction writing program was known for its workshop method. Small classes, twelve to twenty students at most. No tests. No “grades.” When people ask me if I learned to write in college, I say no. Columbia didn’t teach me how to write. Columbia, and it’s many talented professors, taught me how to read my writing out loud. “What did you notice?” was the golden question. No right, no wrong. Just the splashing sound of your words high diving off the tip of your tongue and onto the concrete floor of the classroom. The teachers didn’t need to critique our sentences or stories. We learned what was wrong just by hearing ourselves outside ourselves, bellyflopping around.

But graduation was coming up. Swim lessons were over. And it was time for us “writers” to be let loose to the ocean of agents, publishing houses, and opinionated readers.

“Pull out your notebooks,” my professor said. “Today, I’m going to give you the recipe for becoming a successful, published writer.”

I’d waited three years for this.

I rummaged through my backpack of stacked Tupperware containers, clicking my pen at the ready.

He started slow: “Work on a short story.”

And that made sense. Start small.

Then he said to walk down to the bookstore, any bookstore would do, and find a magazine with short stories inside. Like The New Yorker. Flip to the back. There, you’ll find a list of agents. Write that list down and take it home with you. He said no need to buy the magazine, which I found ironic. Then look each agent up online and find their mailing address. Print off your short story, a few short stories, eventually your novel-in-progress, stick it in a manilla envelope and mail it to them. Then wait. Just leave them be. “They’re persnickety.” Six months with no response is common. Get used to it. One day, you’ll receive a letter in the mail. It will be a rejection letter. It just will. But don’t get discouraged! This rejection letter is a symbol of your commitment to the craft. Hang it above your desk, along with the others. And repeat this process until you’re grey and bitter and on the verge of becoming an alcoholic.

The half-moon of students around me scribbled down these instructions. But my page stayed blank. The year was 2013: Facebook was taking over the world, Twitter was democratizing journalism, Instagram was giving birth to “influencers” with millions of followers by the day, and my professor’s advice for becoming a successful writer in the digital age was bookstores, manilla envelopes, and Post Offices? I didn’t even own a printer! I had grown up on the Internet. Writing online was clearly the future. I just didn’t know how—yet.

The girl next to me raised her hand and started talking. “But how do you pay your bills while you’re waiting to be published? How do you make a living as a writer?” Thank you. That’s what I want to know.

And that’s when he said it.

The sentence that started all of this.

“You work at a coffee shop. Or you get your MFA and you teach, like me.”

A pause.

“Nobody makes a living as a writer.”

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I don’t know how else to say this, so I’m just going to say it:

10 years later, and writing online has made me a millionaire.

I’ve tried searching for where my classmates ended up—like a soldier years after an explosion trying to reconnect with members of his platoon. But best I can tell, none of them survived. Their writing never went anywhere. They took those words, “Nobody makes a living as a writer,” to heart.

Whereas I took them as a challenge.

“If James Patterson can be worth hundreds of millions of dollars, and J.K. Rowling can become a billionaire from writing, why can’t I make a measly million?” That was my thought process. And there’s a large percentage of the world who would call that “grandiose.” But what was the alternative? Bookstores, manilla envelopes, and Post Offices? What would you tell an aspiring writer to do? Accept their place in the world, learn to love the steady stream of rejection letters, and drink up?

The thought of graduating college terrified me. I was about to enter the real world with arguably the least valuable degree on planet earth: Fiction Writing. My parents had made it very clear moving back in with them wasn’t an option—and to tell you the truth, I didn’t want that either. And here my professor, my guide, the one I was counting on to give me any sort of map forward, was stopping us at the 1 yard line and saying just kidding, this is all a pipe dream, enjoy working at a coffee shop for the rest of your life (not that there’s anything wrong with that).

Which meant I had three options.

1. I could give up and admit to my father I was wrong, he was right, and find a different dream, a different identity to reach for.

2. I could get a job as a barista, take my first crack at The Next Great American Novel, load up on manilla envelopes, and start acclimating to a life of grocery store coupons, fire sale airline tickets, and hand-me-down flannel shirts.

3. Or, I could figure it out; trust my intuition that writing online was the future, and dedicate the next decade of my life to practicing my craft and doing whatever I had to do to make a fortune doing it.

I went with Option 3, but I’d like to explain why.

Psychologically.

There’s a famous Seinfeld episode where Jerry and Elaine are debating over who should get to fly first class. When Jerry claims the free upgrade for himself, Elaine asks why she can’t take the free first class ticket. Jerry says, “Elaine, have you ever flown first class?” She says no, and he responds, “Alright then. See, you won’t know what you’re missing. I’ve flown first class, Elaine. I can’t go back to coach.”

It has taken a long time to admit this because the purist in me wants to believe a true “artist” doesn’t care about money. They’ll suck down cheap liquor and sleep on a straw cot and work the graveyard shift at a trash factory if it means dedicating their life to their art (the Charles Bukowski blueprint). I observed this same mentality in a lot of my professors—a nobility in poverty, as if a dirtier pipe led to cleaner water.

Well that’s not me, and I don’t believe that to be true.

I grew up in a wealthy family in a wealthy suburb. I already knew the feeling of being well-off—which many white and privileged people who argue against things like affirmative action don’t seem to realize is the greatest privilege of all. Because even though my parents didn’t give me any money after graduation, didn’t pull strings and help me get a job, I was still advantaged because becoming wealthy didn’t intimidate me. And knowing it’s possible is half the battle.

Second, I knew I wanted a family one day. I knew I wanted kids. And the thought of being a poor, struggling writer—baby crying in the next room while I’m fiddling with the description of a doorknob in my next novel—was unbearable. If not for myself, then for the poor partner who would have to try to love me through it. Writing is hard enough. And I couldn’t imagine the stress of trying to write from the heart knowing your heart better sell otherwise the pantry would be empty and, maybe soon, the spot in your bed beside you.

Being a broke artist my whole life wasn’t an option.

But neither was not-writing.

I tried, many times as a young adult, to pursue something other than words.

My father encouraged medical school, but my inadequacies in math and science were painfully obvious to the both of us. My mother encouraged music, and for a while that made the most sense. I had been playing Mozart and Beethoven since I was five years old. One semester in college, I tried a few piano performance classes. The next, I tried music production. But as much as I loved music, I loved writing more. And when I discovered the creative writing department, I was hooked.

Every successful writer I’ve ever looked up to, in every interview I’ve watched, every On Writing book I’ve studied, has always said: “If you are meant are meant to write, you just will. You won’t be able to stop yourself.” And that’s true. When I go more than a day without writing—even if it’s just journaling—I get antsy. Itchy. Like I’m uncomfortable in my own skin, eager to shed my next layer.

But this is different from what many of my college professors told us, which is, “Not everyone has what it takes to become a writer.” This, I disagree with. The skill of writing is no different than the skill of playing piano, cooking eggs, or matching your belt with your shoes. It’s not some magical gift you’re either born with or you’re not. Anyone can learn it. But just like music or cooking or fashion, some people build the habit easier than others. Some people enjoy it more—and whatever you enjoy most, you will do the most. And whatever you do the most, you will be the most successful at. This is personal growth 101.

Which is why I pushed all my chips into the center of the table and chose to study creative writing. I knew, even though the odds were against me, I had a better chance of becoming successful doing something I enjoyed than doing something more “guaranteed” and safe but that I hated.

Here’s where I’ve netted-out:

I don’t believe writers or artists of any kind enjoy being poor.

And I think the ones who say, “I don’t care about making money,” simply don’t know how to make it.

It’s a logical fallacy to think caring about making money somehow means not-caring about the quality of your work—as if the more money something makes, the less “artistic” or “good” it is. Fifteen seconds of critical thinking reveals that’s not true.

I see so many creative individuals stuck in this faulty belief system, and I believe the reason is because the worlds of art and business are often kept separate. When you study art, of any kind, there is almost no education around how to make a living doing it (and not just “a living,” but how to get wildly rich while staying true to yourself). And the inverse is also true: when you study business or marketing, there is almost no education around how to make your work something more than just a creative exercise in pocket picking; how to be Andy Warhol straddling the canyon between what is timeless but also lucrative.

The false remedy for this faulty belief is that many artists, creative individuals, and writers defer responsibility. They either condemn it—like a child on the playground who loses at kickball and shouts, “Who cares! Kickball is stupid anyways!” Or, they put “money” on a pedestal, idolize it, and tell themselves it’s more difficult to obtain than it actually is—and then avoid putting in the hours required to gain the skill, unconsciously thinking making money is something that just “happens.” I fell in this camp. Since no one explained to me how to make a living as a writer, I just thought the name of the game was to write something “great.” I couldn’t tell you what “great” meant, which made it all the more difficult to strive for. The hope was just that someone would recognize my talents, buy my manuscript, write me a huge cheque, and I would spend my days reflecting on my great success from a castle in the countryside of London until the setting of my final sun.

Which is basically like saying my strategy is to win the lottery.

Over the past 10 years, the biggest lesson I’ve learned is that writing and making money as a writer are two completely different skills.

If you want to become a better writer, you have to practice the skill of writing. But if you also want to make money as a writer, then you need to also practice the skill of monetizing your writing. And from what I can tell, the vast majority of writers who struggle to make end’s meat rarely, if ever, practice the other half of their careers: the business side, the money side. They read Ernest Hemingway, but don’t read Gary Halbert (one of the greatest sales copywriters of all time). They study Stephen King’s On Writing, but don’t study David Ogilvy’s On Advertising. They join book clubs to discuss Anaïs Nin, James Baldwin, Maya Angelou, but don’t join communities or mastermind groups to discuss marketing funnels, pricing strategies, and business models.

These two worlds are kept separate. And worse, you are often condemned for reaching across the aisle and showing your interest in the other. If you are a marketer or entrepreneur, and you admit you want to invest hundreds of hours into writing something from your heart, your business friends will look at you like you’re crazy—wasting precious time that could otherwise be spent making money. And if you are an artist, and you admit you want to start choosing projects that will allow you to afford nice meals, new clothes, or God forbid a nicer apartment or house, your artistic friends will look at you like you’ve decided to “sell out.”

But innovation always happens at unlikely intersections: art and business, show choir and hockey. And in order to become a successful writer in the digital age, I believe you must untrain the human desire to “fit in” to either extreme. Because creative and financial freedom rarely come from following the crowd.

They’re byproducts of standing out.

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My teacher wasn’t wrong when he said, “Nobody makes a living as a writer.”

I see now he just forgot to specify which category of writer.

You see, in today’s digital-first world, not all writers are playing the same game. There are “legacy” writers, and there are Digital Writers.

Here’s a metaphor to help you understand: World of Warcraft has been around for nearly twenty years. Since the game first launched in 2004, it has released over a dozen expansions—each one changing the rules of the game, so much so that the World of Warcraft today looks nothing like it used to. That original version is now known as “Vanilla” or “Classic,” and there are a sub-set of players who continue to play together on small, private servers because they much prefer that original version of the game. Meanwhile, the players competing in tournaments, landing large sponsorship deals, amassing hundreds of thousands of followers on social media and making millions of dollars are all playing the newest version of the game. They are at the cutting-edge, and they are rewarded for it.

Well the publishing world is no different.

30 years ago, the game of “writing” was analog. And success meant getting published by an analog magazine, or landing a book deal with an analog publisher. You couldn’t share your thoughts, stories, perspectives, and insights with millions of people without someone else’s approval. It wasn’t even an option. The “game” had rules, and many writers still play by those rules today. Said more explicitly, they prefer playing a legacy, outdated version of the game.

But fast-forward, and “writing” is no longer just analog. It’s also digital. And the digital version of the game is one anyone can play, and anyone can win. The only barriers to entry are an Internet connection and some sort of typing device (even your phone will do). This is radically empowering, and radically different from the legacy writing & publishing world where “only a select handful” of writers are chosen and amplified, and historically marginalized communities and voices tend to be underrepresented. According to a New York Times opinion piece titled, “Just How White Is The Book Industry?” 95% of American fiction books published between 1950 and 2018 were written by white people—and just 11 percent of fiction books in 2018 were written by people of color. For many talented writers, it’s a rigged game from the start. And the truth is, even if you land that celebrated book deal, the numbers still aren’t in your favor.

The average advance is shockingly low. On average, first-time authors are offered five figures for their book—ranging anywhere from $5,000 to $50,000. The writer then receives an 8% to 15% royalty on each book sold after their advance has been earned out. Or, said differently, in exchange for a paltry five figures, you give up 85% or more ownership in your product. In the preface to A Heartbreaking Work of Staggering Genius (one of my favorite memoirs), author Dave Eggers shares he received a $100,000 advance for his book—which, after agent fees and taxes netted him $39,567.68. Divided by the number of hours it took him to write this masterpiece, it’s no wonder so many people think “Nobody earns a living as a writer.”

This is The Big Publishing Lie, passed down from publishers to agents to creative writing teachers in liberal arts colleges—a multi-level marketing campaign that trains talented writers to believe there is no money in writing. Instead, the reward of becoming a published writer is recognition. Bookstores. Prizes. Spotlight interviews in small, literary, analog magazines. Accolades your mother can hang on the refrigerator in the kitchen and tell her friends about. Never mind the fact you can barely pay your rent—you’re “published!” And this lie is how the Big Five publishing houses (Penguin Random House, Hachette, HarperCollins, Simon & Schuster, and Macmillan) have a monopoly on the United States’ publishing industry, generating 64% of the revenue accounting for over $12 billion per year (2021).

Clearly someone is making a living.

It’s just not you.

As an artist, I understand wanting this approval for your work. I really do. Even today, when I receive promotional emails from Columbia College Chicago’s creative writing department celebrating an alumni’s short story being published in a literary magazine, or novel being purchased by a Big Five publisher, I have a moment of jealousy. It seems so “official,” like they are the real writer and I’m the lousy phony. But this is how deeply embedded The Big Publishing Lie is in the psyche of every writer, every artist. And I have to remind myself these writers are playing a different version of the game. They are living in the past, collecting trophies and achievements that mattered thirty years ago, and choosing to trade financial and creative freedom for acceptance, validation, and approval from the “legacy” writing community.

“Nobody makes a living as a writer” is misleading.

I would clarify and say, “Nobody makes a living as a legacy writer.”

Because if you’re a Digital Writer, sitting at the intersection of Art & Business, you can make a killing.

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A few years ago, I reached out to Columbia College Chicago.

I wanted to share some of the things I’d learned amassing half a billion views on my writing, attracting hundreds of thousands of followers and email subscribers, selling tens of thousands of copies of self-published books, ghostwriting for hundreds of industry leaders, building multiple 7-figure writing-based companies, and achieving a level of creative and financial freedom less than 1% of writers and artists achieve in their lives—all before the age of 32. I am a big believer in throwing down a rope and helping the next person, and considering I had to learn many of these lessons the hard way, I wanted to return to where it all started and pay it forward.

But no one was interested.

My story of becoming a “successful writer” doesn’t fit the mold. It’s not the sort of thing you’d find in a literary magazine, or hear about on a creative writing podcast. If what you’re looking for is motivation to “write, just write, pour your heart out, reach for that book deal,” pat pat pat on the back and reassurance that keeping your eyes closed and letting your agent take the wheel is sound advice for your writing career, you won’t find that here. The artist in me is too competitive, and the entrepreneur in me knows the value of owning the expression (and not selling majority ownership for pennies on the dollar).

However, if you are willing to consider a new and different way forward as a writer, and if you are willing to let go of acceptance and approval from the “legacy” writing world and play a different version of the game, I’d like to give you the blueprint. More importantly, I am on a mission to break down the wall that separates Art & Business.

And to start, here’s my first piece of advice:

Whenever you find yourself listening to a fellow writer complain about how difficult it is to pay the bills, how ruthless the industry is, how tired they are of stacking rejection letters, and how “nobody makes a living as a writer,” walk away. Remind yourself they are playing a different version of the game. They are stuck in the past. And an alternative game exists—all you have to do is start playing.

Now is the greatest time in history to make a living as a writer.

So long as you’re a Digital Writer.

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