[The Biz] Writer Career Paths: 9 Ways To Make $1M With Words (Part II)

If you want to get rich as a writer, you better pick the right game (over the right time horizon).

Jul 28, 2023

I was going to put this post behind the paywall, but I feel it’s important to share this with the writing world—so I’m going to make it free. If you have a writer friend who you think would benefit from reading this, please send it their way & pay it forward.

In my last post, I talked about the 3 ways you should think about measuring your financial success as a writer:

Financial success relative to Industry.
Financial success relative to Vehicle.
Financial success relative to Time.

But the follow-up question, of course, is, “Well that all sounds great, Cole, but what Vehicle should I pick then? What’s going to make me the most money?”

And again, it comes back to the question of Time Horizon: how long are you willing to give yourself?

Writer Career Paths

I will never forget taking a class in college called “Writer Career Paths.”

I was a sophomore, and had recently transferred from The University of Missouri to a small liberal arts school downtown Chicago called Columbia College Chicago.

For the first year or so, I bounced between all sorts of different majors: poetry, music production, classical piano (yes, I grew up playing classical piano for almost 20 years), until eventually finding my way to the Fiction department.

One of the classes they had both Fiction & Non-fiction writing majors take was this class called “Writer Career Paths.” The purpose of the class was to give you some insight into how you could monetize your craft after graduation, and educate you on what jobs would be available. (It’s worth keeping in mind this was back in 2011—and for context, Instagram was launched in 2010.)

Well, my teacher, educated as he was, didn’t have very many recommendations. The only options presented to us aspiring writers were:

Get a job at a newspaper
Get a job at a magazine
Get a job as a barista—and hope your novel-at-night becomes the next Harry Potter.

That was it.

How discouraging!

9 Ways To Make $1M With Words

Since that fateful day, and after much experimentation over the past 10 years (I graduated in 2013), I have spent a SIGNIFICANT amount of time thinking about this problem:

When someone says they want to become a writer, what does that really mean?

First of all, going back to my previous post, “success” can be defined in all sorts of different ways.

But more importantly, saying you want to “become a writer” is, again, lazy language. There is not one universal definition of what it means to become a “writer.” I have lived all sorts of different lives as a writer, and I know plenty of people who have achieved massive success in their lives, through writing, but you probably wouldn’t think to call “a writer.”

I’ll give you an example:

The Pulitzer Prize Winner & The Copywriter

A few years ago, when I was living in LA, I went to an event up in the Hollywood Hills.

If you aren’t familiar with the area, the Hollywood Hills are where a lot of famous actors, musicians, startup founders, movie producers, and investors live. The first time I drove up there, twisting and turning up the winding roads and admiring all the houses nestled into the mountain, I thought, “I have to live here.” My whole life, I had only ever lived in Chicago (and a short year in Missouri). The Hills were a wake-up call to how much bigger the world was than I had ever realized.

Anyways.

While in LA, I had become friends with one of the most successful copywriters in the world. We bonded over writing, and one day he invited me to an event he was having at his house.

Not this house exactly, but something like this:

He threw these events often, and invited leaders in a wide range of industries to come connect, have drinks & dinner, and then usually listen to a few speakers. That night, I remember listening to a Disney executive give a talk about cultural representation in movies that I found really fascinating.

Anyways.

As I was making my rounds (easily one of the youngest people there—I was only 28 years old), this mentor of mine called me over to meet someone. He seemed ecstatic to make the introduction. “Cole, this guy just won a Pulitzer!” he said, facilitating a handshake between the two of us.

The guy whose hand I was shaking looked disheveled: old jeans, a wrinkled button-down shirt that was unenthusiastically tucked in, held together with a brown belt that had lost so much of its color through wear and tear. And he had on New Balance sneakers that used to be white, but had turned grey with age.

I had never met a writer who had won a Pulitzer before. A Pulitzer is one of the highest peaks you can reach as a writer. And in that moment, I observed two very different reactions happen at the same time. This mentor of mine was thrilled, and so was I, to be talking to such an esteemed writer. And meanwhile, this Pulitzer Prize-winning writer could barely maintain eye contact with me. He just kept looking around at the sky-high ceilings and the modern art on the walls and the sprawling view of the city through the windows.

When the event started a few minutes later, I ended up walking over to the seating area in the living room with this writer. We sat next to each other. And while people shuffled in and the first speaker got ready, he turned to me and said, “Whose house is this? Do you know?”

I was a little confused by the question, but I told him it was the guy who had introduced us.

“Oh,” he said. “That makes sense.”

I nodded.

Then he leaned in a little closer, as if to ask the un-askable:

“What does he do? Do you know?”

Without even thinking about it, I said, “He’s a writer too.”

And that was true. This mentor of mine had generated hundreds of millions of dollars in revenue directly from words (sales scripts) he had written. He was a world-class copywriter.

But hearing those words clearly broke this man’s brain.

He tilted his head, as if to let the thought roll around for a second. And then he whispered, “I didn’t know you could own a house like this as a writer.”

I didn’t either.

Until I started to meet more and more writers, and study more and more career paths, and begin to understand which ones lead to Fame & Fortune.

Let’s dive in.

Disclaimers:

But first, a few quick things.

What I am about to share with you is not a perfect science. But it’s directionally right.
There are always outliers—success stories that defy any specific framework. However, studying outliers rarely gives you an actionable path forward. My goal here is not to be “all-inclusive” and cover every possible “yea-but-this-worked-for-so-and-so.” My goal is to give you potential paths forward that are actionable & reasonable.
Every single Career Path laid out here benefits tremendously from: a) creating & dominating your own niche/category (if you want extra reading here, check out Snow Leopard), and b) building a niche library of content (and organic audience for yourself) online (and if you want extra reading here, check out The Art & Business of Online Writing).
Every single Career Path laid out here can earn you over $1,000,000 as a writer. That’s my goal of compiling these all together in one place for you—so you understand the different paths that are available if you want to BOTH do what you love AND make great money.
For credibility: I have generated over $1,000,000 in revenue from multiple of the Career Paths I am going to present here. So, at a minimum, I know these paths are possible from personal experience. Others, I have studied fastidiously.

Now, onwards!

Writer Career Path #1: Literary Writer

When most people say, “I want to become a successful writer,” that phrase is usually grounded in Literature.

What is Literature?

Novels
Novellas
Short Stories
Writing for The New Yorker
Winning literary awards
Etc.

But here’s the only barbell you need to understand about Literature:

High Status / Low Income

Plain and simple.

If you win a Pulitzer or a Nobel Prize, you achieve a tremendous amount of status, niche industry fame, approval, etc., but you (most likely) are not living in a mansion in the Hollywood Hills.

Why?

First of all, literature books (almost) always sell less than Genre Fiction and/or Non-Fiction. Literature is dense. Literature is hard. Literature, despite its high status and acclaim, is more of a “mental workout” than it is entertainment. For this reason alone, the market for literature readers is inherently smaller—which is why Literary Writers are typically high status but low earners.

Second, literary writers are notoriously bad at business. They are the ultimate archetype of “the artist who only cares about their art,” and then signs ridiculous publishing contracts that ensure the publisher makes all the money. I wish this weren’t true, but it is—and there’s a reason why you don’t hear of very many (any?) literary writers buying $20M homes or flying in private jets.

The other thing you have to keep in mind, if this is the path you want to take (and if you care about Status more than Money—which is fine, just know that’s the trade-off), your Time Horizon has to be very long.

It’s very, very rare for a writer to achieve any sort of Literary notoriety within the first 10 years of their career. And if it happens, it’s often a buzzy young novelist coming out of a nationally-recognized MFA program (like the University of Iowa’s Writer’s Workshop).

The only literary writer I know of who is achieving “fame” in the literary world but also unlocking new levels of income is George Saunders. There are probably others, but they are few and far between. And based on my napkin math, George’s Substack is likely earning him more money than his entire library of books. (And it’s worth pointing out his Substack is probably considered very low-status to people in the literary world—despite it earning him anywhere from $20,000 - $100,000+ per month.)

So, want to become a Literary Writer?

Be prepared to play the long game (10+ years).
Be prepared to trade Money for Status.

Writer Career Path #2: Genre Fiction Writer

Literature and Genre Fiction are, in many ways, opposites:

Literary Writers pride themselves on “quality.” Genre Fiction Writers (typically) pride themselves on “quantity.”
Literary Writers focus less on plot, more on style, voice, and structure. Genre Fiction Writers focus less on style, voice, and structure, and more on plot & pace.
Literary Writers are applauded by the New York elite writing world, but make mediocre money. Genre Fiction Writers are shunned by the New York elite writing world, but are the one of the ONLY tiers of writers who have the potential to generate hundreds of millions of dollars for themselves. (There are 0 Literary Writers worth $100M+ or $1B+, but there are dozens of Genre Fiction Writers worth $100M+, and several worth $1B+.)

Want proof?

In 2003, critically-acclaimed Genre (Thriller) Fiction writer, Stephen King, was awarded the National Book Award Medal for Distinguished Contribution to American Letters.

In his acceptance speech, right out the gate, he addresses the fact that when he was announced as the winner, a large number of people in the literary world did NOT think he deserved the award. Why? In a nutshell: because they didn’t view him as a “real writer.”

It’s worth taking this to heart:

There is a massive difference between writers who go the Literature route and writers who go the Genre Fiction route—both in terms of Status and Money.

And you need to decide which one you want to optimize for.

The catch is, even though Genre Fiction Writers have the potential to out-earn Literary writers by a factor of 100x or even 1000x, it still takes just as long to see any success. You should NOT think, “Oh, I’ll write 1 novel, hit publish, and make millions of dollars!” The chances of that happening are <1%.

However, if you extend the time horizon (and more importantly, if you create & dominate a new category of fiction for yourself), then the more stories you write, the higher your likelihood of success.

So, want to become a Genre Fiction Writer?

Be prepared to play the long game (10+ years), but realize moderate success can happen as quickly as 3 years.
Be prepared to trade Status for Money.
Be prepared to pick a specific genre and write within that genre for decades.

If you want to get into the weeds, there’s an amazing study from 2017 that found writers earning $100,000 per year or more from their book sales “..have on average 30.3 books in their catalog! Emerging authors had around 7 on average.”

Volume wins.

Writer Career Path #3: Non-Fiction Writer

Becoming a Non-Fiction Writer can mean a LOT of different things.

For the sake of simplicity though, I’m going to define becoming a Non-Fiction Writer as someone who primarily wants to write, share, and monetize their knowledge through Non-Fiction books, first.

In Non-Fiction, however, it’s very common for these types of writers to ALSO monetize that same or tangentially related knowledge in a variety of other ways—such as having a personal blog, a newsletter, an active social media following, a podcast, a suite of courses, merchandise, etc.

I’ll give you a few examples:

James Clear, author of Atomic Habits. But on his site, he also has: a blog, a newsletter, speaking inquiries, and he even sells journals and pens.
Ryan Holiday, author of The Obstacle Is The Way. But on his site, he also has: a blog, a newsletter, speaking inquiries, courses, and a Daily Stoic store where you can buy Marcus Aurelias medallions & such.
Mark Manson, author of The Subtle Art of Not Giving a F*ck. But on his site, he also has: a blog, a newsletter, and a suite of courses.

(Noticing a theme?)

All 3 of these Non-Fiction authors (and many others) also have giant social media audiences, and more importantly are known for a very specific category/niche. And their success in the world of Non-Fiction has everything to do with their dominance in that category/niche. (But if Ryan Holiday decides, tomorrow, he wants to pivot to Dating Advice, his publisher is going to have a heart attack.)

Quick context: This is the path I took early on in my writing career. To date, I’ve written & published 10 Non-Fiction books, and have generated multiple 6 figures in Non-Fiction book revenue.

However, there are 3 big differences between Non-Fiction Writers and Literary or Genre Fiction Writers:

Difference #1: Non-Fiction Writers almost always make more money (and/or more “predictable” money) on their newsletters/courses/etc., than they do their books. Even authors like James Clear and Mark Manson, both of whom have sold millions and millions of copies of their flagship books, monetize in other ways besides just book sales. Why? Because a) book sales are lumpy, unpredictable, and even if a book surges in sales in the first few years, it’s unlikely to sustain over the long term. And b) because in Non-Fiction, you can almost always make the same or more money selling “the education” in other more lucrative mediums (like courses, for example).
Difference #2: Non-Fiction Writers can find success sooner than Literary or Genre Fiction writers. Again, outliers aside, it’s significantly easier to write a “How To” book or an “According To Research” book than it is to write a really great story. It just is. (So if you want to “make money NOW,” you may consider the Non-Fiction route, first.)
Difference #3: More Non-Fiction Writers find some form of monetary success, sooner—but with a significantly lower ceiling. There are quite a few Non-Fiction writers (Ryan Holiday, Seth Godin, etc.) who have made >$10M (and that’s WITH monetizing in other ways). But there are 0 Non-Fiction writers who have crossed $100M from book sales alone.

Here’s the hierarchy you should internalize:

Highest Status, Lowest Paid: Literary Writers
Second-Highest Status, Second-Highest Paid: Non-Fiction Writers
Third-Highest Status, Highest-Paid: Genre Fiction Writers

So, want to become a Non-Fiction Writer?

You can achieve success sooner—but you have to dominate 1 specific niche.
Be prepared to still be lower-status than Literary writers, but higher-status than Genre Fiction writers.
Be prepared to still out-earn Literary writers, but never out-earn the top-tier Genre Fiction writers.
Be prepared to monetize your knowledge in other ways besides just books (newsletter, podcast, courses, speaking, etc.), since your book sales alone likely won’t be able to “fund your life.” (And even if they can, you will still have too many other lucrative opportunities to monetize—which shouldn’t be ignored.)

Writer Career Path #4: Newsletters

Despite the “Status Hierarchy” I laid out above, the brutal reality is: if you pursue Career Paths 1, 2, or 3, you are still in the upper-echelon when it comes to “status” in the writing world.

That’s because you’re an author, first. And it has only been in the past ~20 years that OTHER lucrative career paths for writers have really emerged and proven themselves to be viable—of which being an author is not a pre-requisite.

(For example: Telling your mom you signed a publishing contract will make her cry tears of joy. But telling your mom you’re going to pay rent with your paid newsletter will likely yield a confused look and maybe tears of fear for you and your future.)

So while some of the following career paths will not give you the same looks of approval and validation Career Paths 1, 2, and 3 may bring, they can be just as lucrative (and in some cases, even more so).

Now, there are 2 different types of newsletters:

Free
Paid

If you have a Free newsletter, the way you monetize is either directly via ads or indirectly via selling your own books, courses, products, etc.

If you have a Paid newsletter, the way you monetize is directly (via subscription)—but you can ALSO monetize again by plugging your own books, courses, products, etc.

Quick context: I have built multiple paid newsletters to 6 figures in yearly subscription revenue, as well as several free newsletters that direct people to our courses & products—which do 7+ figures in revenue. So I have experienced both.

For this reason, I like thinking about newsletters through the following mental model:

If you are a Genre Fiction writer, it’s very unlikely you are going to be able to launch a paid Fiction newsletter. Few reasons why: first, the vast majority of paid newsletters are focused on either making the reader’s life better or making the reader more money. “Entertainment” (in a world where YouTube, TikTok, and Instagram are all free) is harder to make paid. Second, if you DO want to try to launch a paid Fiction newsletter, it needs to be serial: short, quick stories that an audience can consume & you can create quickly and consistently each week. Otherwise, there’s a reason why most Fiction writers who have a newsletter focus it around Non-Fiction in some way (how they think about publishing, their own writing frameworks, etc.).
If you are a Non-Fiction writer and have other products/courses to sell, you’re better off making your newsletter free. A free newsletter that monetizes indirectly via courses, products, services, etc., is much easier (and oftentimes more lucrative) than trying to launch a paid newsletter.
If you are a Non-Fiction writer but REALLY want to launch a paid newsletter, there are 2 big rules you need to follow: first, it has to in some way a) make the reader’s life better and/or b) make them more money (otherwise they won’t be able to rationalize the subscription fee). And second, it has to be in a specific category you can write about often—wherein you have significant domain expertise. This Substack of mine is a good example, as is my previous business & paid newsletter, Category Pirates.

So, want to become a Newsletter Writer?

You have to pick a niche and dominate it.
If you want to hit 6 figures ASAP, make your newsletter free and monetize indirectly by directing readers to other paid products, courses, etc.
If you want to hit 6 figures slowly (but make it to The Holy Land of subscription revenue), start a paid newsletter in a niche category where you help readers lose less money or make more money.
If you want to hit 7 figures, I recommend going the free newsletter route and focusing on monetizing indirectly by selling other products, courses, services, etc.
If you want to hit 7 figures with a paid newsletter, be prepared for a 5-10+ year run. Stratechery is a good example of a 7-figure paid newsletter, but it took nearly a decade to get there.

Writer Career Path #5: Content Writing

The next few career paths are all about making money NOW.

If you are broke, or burned out from your 9-5 and desperately want to earn a living through writing—but need to start generating cash A.S.A.P—then the single easiest way to get the money machine running is by providing a service.

Why?

Because a service solves an immediate problem.

And anything that solves an immediate problem tends to get paid immediately as a result.

(Whereas the other Career Paths we’ve talked about so far are Vehicles that compound, but compounding takes time.)

Content Writing encompasses all sorts of writing jobs:

PR writing
Website writing
Blog post writing
Newsletter writing
Social media writing
Etc.

Basically, any COMPANY that hires you to write *something* can be lumped into the bucket of Content Writing.

The pro here is: this is the fastest way to start earning a few thousand dollars per month as a writer. It’s way, way easier to get 1 company to pay you $3,000 per month than it is to write a $20 book and sell 150 copies every month.

The con here is: you can get to $5,000 or even $10,000 per month as a content writer, but then you’re stuck. There are hundreds of thousands of content writers on Upwork, and all of them “do the same thing” and are positioned the same way. As a result, you are essentially a commodity—which means you have very little pricing power. (You also have no ownership, and no compounding Vehicle, which means you’re stuck in a game of trading hours-for-dollars).

So, want to become a Content Writer?

This is one of the fastest ways to start making a few thousand dollars per month as a writer. And you can get up to as high as $10,000 per month as a Content Writer.
But then you’re stuck. You have a very low earnings ceiling, and no compounding Vehicle.
Being a Content Writer is low status, and in the grand scheme of things, also low money.
You are a commodity—until you find a way to niche down & specialize in some way.

Writer Career Path #6: Ghostwriting

If Content Writing is a catch-all bucket for different writing services, Ghostwriting is one of the “specialization” paths you can choose when you’re ready.

I talk about all the nuances between Freelance/Content Writing and Ghostwriting in my book, The Art & Business of Ghostwriting. But in a nutshell: Content Writers typically write on behalf of “companies,” whereas Ghostwriters typically write on behalf of “individuals.” (Think: writing for Walgreens the brand vs writing for the CEO of Walgreens.)

Quick Context: I built the first Ghostwriting Agency for founders, CEOs, investors, etc., back in 2017. I scaled that agency to 23 full-time employees and $2M in annual revenue, and to-date I have generated over $5M in ghostwriting revenue.

Ghostwriting is how you start to unlock Premium Pricing as a writer.

Anytime you “specialize” as a writer, you make more money. It’s very rare that a generalist out-earns a specialist (in any domain).

Similar to Content Writing, Ghostwriting is another “generate-money-NOW” Career Path—because again, you are providing a service that solves an immediate problem for a client.

The difference is you can get all the way up to $20,000 or even $30,000 per month as a Premium Ghostwriter. (I have a free email course explaining how, if you want to check it out.) But then, you’re stuck again (because services are not compounding Vehicles) and in order to get above $30,000/mo, you will likely have to change Vehicles and find a different way to scale—getting you out of trading hours for dollars.

So, want to become a Ghostwriter?

This is one of the fastest ways to start making a few thousand dollars per month as a writer. And you can get up to as high as $20,000 or $30,000/mo.
But then you’re stuck. And at $30k/mo, you will likely have to change Vehicles in order to get to the next tier of income.
Ghostwriting is both higher Status and higher Money than Content Writing. (It’s sexy to say, “I’m a ghostwriter for startup founders,” etc.)
Ghostwriting is also an amazing playground for you to get paid to practice your craft.

Writer Career Path #7: Copywriting

Ah, the last of the 3 writing services buckets:

Content Writing
Ghostwriting
Copywriting

I get a lot of questions about the differences between these three Career Paths, and in a nutshell: all of them share similar writing fundamentals, but have very different perceptions (Status) and financial trajectories (Money).

The correct use of the term “copywriting” has to do with “sales copywriting,” as in writing words with the singular goal of increasing customer conversions (aka: sales). If you are getting paid to re-write a company’s home page, that’s Content Writing—not really “sales copywriting,” despite the fact that the underlying skills are extremely similar.

Copywriting examples:

Writing ads that drive click-throughs, opt-ins, and purchases.
Writing landing pages that drive/increase purchases.
Writing sales emails that drive/increase purchases.
Writing Video Sales Letter (VSL) scripts—to drive/increase purchases.
Etc.

Copywriting is a highly specific “world” of writing—and, from my experience, a very “insider” community. If you’re in the Copywriting world, everybody knows everybody and it’s a competitive & lucrative space to be in. But if you’re NOT in the Copywriting world, chances are you have no idea this community of writers exists—and if you were to step inside of it (especially if you were, say, a Literary writer), you would be shocked at how *differently* Sales Copywriters think about language, persuasion, and human psychology.

Quick Context: I have generated millions and millions of dollars as a Sales Copywriter—both for myself and my own businesses, as well as for other businesses. I have also been mentored directly by some of the most successful sales copywriters in the world, and have been “in the room” at some of the most insider-y Sales Copywriting masterminds.

Copywriting is the most lucrative of the 3 writing services.

In the short-term, Content Writing, Ghostwriting, and Copywriting all earn you about the same amount of money. (There are tons and tons of writers who provide these services and all hover in the $5k/mo - $25k/mo range.)

The difference with Sales Copywriting, however, is that the best copywriters in the world can negotiate revenue share deals—which is where you’re able to jump out of trading hours-for-dollars and into a more scalable & lucrative Vehicle.

For example: There’s a little-known book in the Sales Copywriting world called The 16-Word Sales Letter. The author, Evaldo Albuquerque, was a highly successful copywriter within Agora Financial—one of the most well-known publishing companies in the world and the pioneer of the “paid newsletter” category way back when. (Their yearly revenues exceed $1 billion.) And in this book, Albuquerque explains how he has generated hundreds of millions of dollars for Agora Financial through his sales letters—of which he was paid a percentage.

When I discovered this world of Sales Copywriting, I also found myself offered the same deal by an incredibly successful company. If I could write something that converted customers (in a specific product funnel), I would be compensated a % of the upside.

So, want to become a Copywriter?

This is the 3rd service path that allows you to start generating money NOW.
You can easily get up to $20,000 or $30,000 per month as a Copywriter.
In Copywriting, you will spend far more time studying human psychology and persuasion than you will novels or any conventional writing style or structure. Copywriting is a completely different language, with completely different rules.
There is a big gap between Copywriters in the $20k-30k/mo range and the copywriters who unlock rev share deals (and get paid upwards of $500k-$1M+ per year). Plan on it taking 5-10 years to acquire the necessary skills & connections in order to unlock this higher level.
Copywriters are typically lower status (some uneducated people even call them “slimy!”) but very, very highly compensated. Copywriters & Genre Fiction writers are the only 2 Writer Career Paths with the potential to cross $100M. (Legendary sales copywriters like Gary Halbert and Gary Bencivenga built tremendous fortunes increasing company revenues & sharing in the upside.)

Writer Career Path #8: Writerpreneur

The next career path, despite being extremely lucrative and accessible to the average person (including beginner writers), is actually one of the lowest Status Career Paths.

It’s what I like to call being a Writerpreneur.

These are writers who spend the vast majority of their time writing on social build & building digital audiences, and who may or may not have a free newsletter (but most do), but have very few aspirations of becoming a Literary Writer, a Genre Fiction Writer, or even a Non-Fiction Writer.

(Although, there is a growing trend of publishing houses discovering these digital-first Writerpreneurs with large audiences and offering them book deals. But the vast majority of the time, the Writerpreneur writes 1 big Non-Fiction book, maybe makes it to the NYT best-seller list, and then never writes another book again. Sahil Bloom, Ali Abdaal, Tiago Forte, etc., are all good examples of Writerpreneurs.)

The business model of a Writerpreneur is every simple:

Write online
Drive traffic to your free newsletter
Nudge email subscribers to buy some sort of product or service.
(And on occasion, Writerpreneurs may also monetize their free newsletters with ads and/or affiliate partnerships.)

One of the biggest benefits of being a Writerpreneur is that you don’t need to ask anyone’s permission to get started. There are no gatekeepers—no publishing houses you have to make happy, or magazines you have to ask for approval. You just start writing online, start figuring out who your ideal readers are, start doubling-down on proven topics, and start launching products.

The other big benefit of choosing the Writerpreneur path is that, aside from services, it’s the next-fastest way to start generating cash. You do NOT need millions of followers (or even hundreds of thousands of followers) to start selling digital products. For example: most people don’t realize that we started Ship 30 for 30 back when I only had 2,000 Twitter followers and Dickie had 800 followers. The barrier to entry is very low, and the potential to start making money is high.

Some Writerpreneurs only monetize through ads, but the most profitable ones almost always monetize by selling some sort of education product:

A book or eBook
A cohort-based course
A course (text or video or both)
A template (or compilation of templates)
A paid 5+ day Educational Email Course
Etc.

However, not all Writerpreneurs play in the same price point of product.

A helpful way of thinking about it (which will dictate what sort of product you want to build & sell) is to think in terms of pricing tiers:

Low-Ticket: Anything $150 or less (an “impulse purchase”), and usually an asynchronous course, digital download, etc.
Medium-Ticket: Anything $150 - $999 (not quite an “impulse purchase” but not quite a “I need to talk to my partner about this” purchase either), and usually a text & video course or cohort-based course & experience.
High-Ticket: Anything above $1,000, but usually more in the realm of $3,000 - $20,000. Absolutely falls in the category of “This is a big investment in myself,” and usually a text & video course with some sort of network and hands-on training component.

They all work. But some Writerpreneurs prefer creating Low-Ticket products, while others love creating Medium or High-Ticket products. It really just depends on what you want to do, and where your skills can be best leveraged. (Although it is worth acknowledging that in order to maximize your earnings as a Writerpreneur, you’ll want to eventually have all 3—and reach customers at every level of the buying curve.)

Quick context: I have generated millions of dollars as a Writerpreneur. And as an example of reaching customers at various levers of the buying curve: My book, The Art & Business of Ghostwriting, is low-ticket. Our Premium Ghostwriting Academy is medium-ticket. And our Premium Ghostwriting Mastermind is high-ticket. 3 different offers, 3 different price points, allowing us to help ghostwriters at every stage of their career trajectory. This is the goal.

A few examples of Low-Ticket Writerpreneurs:

Justin Welsh: Justin writes about Solopreneurship on Twitter & LinkedIn, drives readers to his weekly newsletter, The Saturday Solopreneur, and then nudges readers to buy one of his $150 products—like The LinkedIn OS.
Dan Koe: Dan writes about Modern Mastery on Twitter & LinkedIn (and also has a very successful YouTube channel), drives readers to his weekly newsletter, The Koe Letter, and then nudges readers to buy one of his $150 products—like The 2-Hour Writer.
Steph Smith: Steph writes about technology & remote work, drives readers to her weekly newsletter, and then nudges readers to buy one of her $150 products—like her ultimate guide/eBook Doing Content Right.

Notice a pattern?

A few examples of Medium-Ticket Writerpreneurs:

Dickie & Cole: Dickie and I both write about Digital Writing, drive readers to our Start Writing Online newsletter, and then nudge readers to join the next cohort of Ship 30 for 30 ($800).
Tiago Forte: Tiago writes about digital productivity & organization, drives readers to his weekly newsletter, and then nudges readers to join the next cohort of his Building A Second Brain program ($999).
Ali Abdaal: Ali is a YouTuber, but fits all the criteria to also be called a Writerpreneur. He writes about productivity, nudges readers to his weekly newsletter, and then nudges readers to buy the async recordings of his previous cohort-based course, Part-Time YouTuber Academy ($995).

A few examples of High-Ticket Writerpreneurs:

David Perell: David writes about writing, drives readers to his weekly newsletter, and then nudges readers to join his writing program, Write Of Passage.
Codie Sanchez: Codie writes about how to make money buying & owning “boring cash-flowing businesses,” drives readers to her weekly newsletter, and then nudges readers to join her high-ticket business coaching program.

Obviously there are TONS more examples, but I just wanted to give you an idea of what these different tiers & offers look like—so you can decide which one you want to create for yourself as a Writerpreneur.

Also, Dan Koe has a great YouTube video breaking down how this Writer Career Path works, and how he made over $800,000 in a single year as a “Writerpreneur” (although he doesn’t use this language).

So, want to become a Writerpreneur?

You have to be entrepreneurial.
This is one of the fastest paths to 6 or even 7 figures as a writer. However, it requires a) focusing on a specific niche, b) an astonishing level of consistency and Practicing In Public, and c) being OK with low-status work for a very long time. You only begin to unlock “status” in this Career Path if/when you start crossing 300,000 - 1,000,000 followers. And even then, you are still seen as “lower status” than, say, an author in Career Paths 1, 2, or 3. (Even though you might be making more money!)
Be prepared to master the art of writing online, love spending time on social media, and building/interacting with your audience.
Be prepared to also write a weekly (free) newsletter—so you can build trust with your most loyal readers & continuously nudge them to buy your education products.
Be prepared to give away 99% of what you “know” in a particular category/niche for free, and monetize the last 1% either in a low-ticket education product, or some sort of medium-to-high ticket course, training program, etc.

And so that’s the trade-off:

Writerpreneurs tend to be low Status (some “authors” may even go so far as to call them “not real writers!”). But Writerpreneurs also tend to make a lot more money, a lot more consistently than their higher-status “author” counterparts.

Writer Career Path #9: Category Copywriter

Finally, the last Career Path to $1,000,000 as a writer is what I like to call being a Category Copywriter.

This is different than being a “Sales Copywriter,” in the sense that Category Copywriters tend to get paid (very, very well) to “think” and give strategic messaging advice—opposed to just churning out ads and landing page copy.

Said differently, Category Copywriters help creators & companies Name & Claim new and different categories using new and unique language. (Note: This is building on my work with Category Pirates, and many of the more general Category Design ideas we’ve written about there.)

Quick Context: I have generated millions of dollars as a Category Copywriter, both helping companies and individuals Name & Claim new categories, but also get “in the weeds” and help them deploy that new language into all their marketing materials, etc.

Category Copywriting can encompass all sorts of different things:

Company name & tagline
Company messaging strategy
Company PR & marketing “lightning strike”
Company offer construction & pricing/language strategy
Etc.

In short, Category Copywriting is you leveraging your talents as a writer at the HIGHEST level. 90% of the time, you aren’t even getting paid to “write.” You’re getting paid to THINK, deeply, about which words a company (or an individual) should use to pioneer new ground—and get that language to “stick” with customers, readers, listeners, etc.

The way I like to describe it is: as a ghostwriter, I got paid a decent amount of money to write lots of words. As a Category Copywriter, I get paid a lot of money to write 2 or 3 words—but those 2 or 3 words dictate the entire direction & category of the company.

And it’s harder than it sounds.

How Category Copywriters make money:

Since Category Copywriters can have such a huge impact on a company (because the language they create becomes the North Star of everything the company does & stands for), it’s hard to measure their value in terms of cash.

For example: if I help a startup Name & Claim a new category, and their new positioning in that category is what allows them to raise $100 million, and then that category grows into a multibillion-dollar category, and then the company exits for $8 billion five years later (with every other company using the same language that I helped them create), how much should I get paid?

Exactly.

As a result, Category Copywriters tend to get paid in stock, or stock + a bit of cash. And the only way a fast-growing, venture-backed, or publicly traded company is going to give you stock options and/or millions of dollars in cash is if you have a) clear expertise in a specific niche, and b) 10+ years of pattern recognition they can leverage strategically.

So, that’s the pro-con here as a Career Path: becoming a Category Copywriter is rarely something you start doing early in your career. Instead, it tends to be the tier of opportunities you unlock after 10+ years of being a writer and achieving success elsewhere. Because once you achieve success in one of these other Career Paths, that’s usually when companies and industry leaders start poking around asking, “Hey, can I pay you to do what you do, with us?”

(Fiction writers included! Tech companies hire sci-fi and fantasy writers all the time to help them brainstorm strategic new initiatives. Who would have thought?!)

So, want to become a Category Copywriter?

Don’t be in a rush. Trust you will be able to monetize the strategic side of your craft later in your career.
In my opinion, don’t pursue this Career Path until you’ve made a few million dollars and are financially stable. Category Copywriters who get paid in stock are trading cash NOW for potentially-lots-of-cash LATER. (But there’s also a chance your stock is worth $0 as well, so you have to be prepared to take that time/effort risk.)
Be prepared to have to learn a LOT about business & company structures if you want to get paid well. Category Copywriters almost always get paid in stock, and this requires a different level of financial literacy.
Be prepared to also change the way you think about “writing,” in the sense that you aren’t getting paid to “write” anymore—you’re getting paid to THINK about how a company’s entire marketing department should be writing.

Lastly, being a Category Copywriter is both high status and high money. It’s high status because you’ll get to talk directly to some of the most powerful, well-connected, and successful people in business. And it’s high money because, if your skills help move the needle for a company, your upside can yield you millions of dollars.

But again, these aren’t the sorts of outcomes you unlock Day 1 of your career.