How to Write Essays That Spread

Everything I’ve learned about writing on the internet

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Since we started Every three years ago, I’ve published over 230,000 words. Google claims that the average business book has roughly 50,000–60,000 words, so by that metric I’m somewhere around my fourth or fifth book.

It’s been… a journey.

If I take a deep breath and close my eyes, I can place myself back in my San Francisco apartment where my wife and I were living when Divinations first launched. We had a nine-foot bookshelf that stretched to our ceiling, and I moved our kitchen table next to it so I could soak in some calming vibes while I twisted my brain into knots, trying to find the right sequences of words that would make this crazy dream of becoming a “real writer” come true.

We were running on fumes financially, so we had to move out of that place and in with my in-laws to keep the dream alive. In retrospect it was a pretty wild bet. There were many late nights in my office—a garage filled with boxes of all our stuff, my desk, a space heater, and that bookshelf—that lasted until 2, 3, even sometimes 4 a.m.

Thankfully, it worked out. When I hit publish on this piece, it will get delivered to around 75,000 inboxes. The business is in a great place. My co-founder Dan and I were able to find enough of the right sequences of words to grow a respectable audience and, more importantly, attract some wonderful kindred spirits along the way to write with.

I won’t lie: I’ve made a lot of mistakes over the past three years. I am a deeply flawed writer. But I do feel confident that I’ve learned some useful things about writing essays that spread on the internet. Now that I’m starting to focus more on Lex, I figure it’s a good time to spill the beans.

Here are the frameworks, metaphors, aphorisms, and various other forms of advice that I find myself returning to when I struggle with writing.

Why essays spread

Every article has thrust and drag. The thrust of a piece is what motivates readers to invest the energy necessary to extract its meaning. It is the reason they click. Drag is everything that makes the reader’s task harder, such as meandering intros, convoluted sentences, abstruse locution and even little things like a missing Oxford comma.

When your writing has more thrust than drag for a group of readers, it will spread and your audience will grow. Achieving this takes practice and experimentation.

The idea of thrust and drag may seem obvious, but it helps to decompose the problem of growing an audience into its component parts. Do you know what people want to read about? Can you channel that knowledge into compelling writing? These are independent variables, so work on one at a time.

Sources of obsession

How can you know what people want to read about? This is the hardest part about writing, at least for me.

My theory is that most people read deep non-fiction writing in order to cultivate an obsession. Some obsessions last weeks, others last decades. People are willing to skim and graze random articles, but that’s not the kind of readership you want to attract. You want people to care.

The best advice I have for finding these people is to not try too hard. We’ve all seen the writers who are pandering to a recent trend or copying a “proven” format. It usually doesn’t work, because in order to feed someone’s obsession you need to be able to go unusually deep. This takes a lot of energy, and the benefits from writing are sufficiently uncertain to make it a bad bet to do so if you’re only doing it to grow an audience.

A better (and more fun) strategy is to work unusually hard to cultivate your own obsessions. Run experiments! Do research! Try things! And, of course, write about it. When you’re pursuing your own curiosity, it matters less if others immediately care. The work becomes its own reward.

Angles, not topics

I asked GPT-3 for a list of article ideas for me with the prompt: “My name is Nathan Baschez. Use what you know about me to suggest topics of articles I should write.” This is what it came up with:

  1. Strategies for successful startup growth and scaling
  2. Analysis of emerging trends in the technology industry
  3. The importance of brand storytelling in marketing
  4. The role of effective leadership in building high-performing teams
  5. The future of work and remote collaboration
  6. Lessons learned from your experience building companies such as Substack
  7. Innovation and disruption in media and journalism industries
  8. The impact of social media on modern society and the changing nature of communication
  9. Personal development and career growth strategies
  10. The role of empathy and emotional intelligence in business success.

These are great topics, but none work as a starting point for an article. To start writing, I need a sharp angle.

For example, last week I was thinking about why ChatGPT broke out now when the underlying AI model is a couple of years old. I realized that the success of DALL-E 2 and Stable Diffusion helped spread a narrative that AI is exciting right now, which helped prime people to be excited about a new product like ChatGPT. This, to me, is a good angle. It’s a specific question with a specific answer—not a general topic area like “the rise of AI.”

But what makes a compelling angle?

Made to STIRC

Angles that spread usually check the following boxes:

  1. Surprising — presents unexpected new information or theories
  2. True — we actually believe it
  3. Important — has an impact on our behavior
  4. Relevant — related to domains we care about
  5. Cool — we think we’ll look impressive for sharing it

It’s hard to come up with angles that fit all of these criteria. You’re not going to be able to do it every week. But at least you know what you’re looking for.

Find the central question

To sharpen your angles, ask yourself early in the writing process what the central question is. Once you can frame this, the rest of the piece becomes much easier to write.

“If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and five minutes thinking about solutions.” — Not Albert Einstein

For this piece, the central question is, “How can I write essays that spread online?” It seems obvious, but it was only something I figured out about halfway through the first draft. When I started writing, all I had was a fuzzy idea that I would write about the frameworks and theories about writing I’ve developed over the past three years. The original placeholder title was “writing advice.” Most essays start this way.

Once you’ve found the central question, you can go back and re-orient everything you’ve written to provide answers as logically as possible.

Plot a logical through-line

Readers are more logical than most writers think. They’ll bail on a piece if it meanders aimlessly, and they’ll stick with it if it seems like most ideas follow logically from what came before, even if those ideas aren’t terribly compelling.

I learned this lesson when I worked at Gimlet Media. When I sat in on meetings where editors would give the podcast producers and hosts feedback on rough cuts of episodes, I couldn’t believe how logical their advice was. I thought the creative process was about hand-wavy, inexplicable, personal, and perhaps even emotional decisions. False! Logic also matters. You can’t move people if they’re confused.

The most common mistake when I’m editing is when a writer jumps from one idea to another without explanation or transition. You can reduce 50% of the drag in your writing if you edit yourself so that each line follows logically from what came before.

Use an organizing principle

So how do you ensure a logical flow of ideas? You could take it one sentence at a time, but that’s hard. Especially when you’re writing the first draft, if you don’t have a foundational structure you can return to, you’ll often have no idea what to say next.

My best-performing essays often have an organizing principle that makes the structure easy to follow. For example, this essay starts at the beginning of the creative process and follows in more or less chronological order. My most popular essay, “Why Content is King,” goes over each of Hamilton Helmer’s 7 Powers in order, and shows how they apply to media. If you look at each of my most popular posts, you’ll probably be able to identify a clear organizing principle.

Ask for feedback

Good feedback from the right kind of reader can transform an essay. Without the help of my colleagues at Every my writing wouldn’t have spread nearly as far.

There are two types of people from whom you can get good feedback:

  1. Professional editors
  2. Readers in your target audience

Each has unique value to offer.

Professional editors who aren’t familiar with your world won’t have a nose for what your audience cares about, so they won’t be able to add much thrust, but they can reduce drag and help you articulate your thoughts more clearly.

Readers in your target audience probably won’t have the editorial prowess to improve sentences or help you structure a piece, but they can help you identify what works and doesn’t about a draft. Because readers aren’t used to giving feedback, I ask them to look out for anything that triggers the following reactions:

  1. Awesome
  2. Boring
  3. Confusing
  4. Disagree/don’t believe

The acronym is ABCD, which is nice and memorable.

Set and meet sacred deadlines

I didn’t set deadlines until last year, and it was by far my best and most prolific year as a writer. Once I committed to publishing weekly, everything improved. The numbers went up, sure, but more importantly I learned to control my creativity. I no longer need to wait for inspiration to strike, I just sit down and start working and I know eventually something good will come out.

When you’re starting out, especially if you’re writing on your own outside the context of an editorial organization, it will be hard to make a deadline feel sacred. The best way to do it is to start a newsletter where you promise you’ll publish on a certain day of the week, every week, rain or shine. This is painful, but necessary. The best way to improve your writing is to publish a lot of writing. Hoarding drafts teaches you little. 

Writing on the internet is like playing Battleship. You don’t know how a piece will land until you put it out there. Over time, the more shots you take, the more you can form a map in your mind of what works and what doesn’t.

Regard public recognition with bemused detachment

Never let the scoreboard (likes, views, subscribers, etc.) affect your motivation. This is impossible, of course, but it’s worth striving toward. If publishing essays starts to feel like pulling the lever of a slot machine, you’re in trouble. Writers do awful things when they become addicted to public recognition. It becomes a sort of game where they try to make the numbers go up, and they lose touch with the reason to write in the first place. This eventually has the perverse effect of making the numbers go down, because readers don’t want to be pandered to.

I learned this the hard way. In the first year of Divinations, the growth metrics were all up and to the right. Gradually I began to feel as if I was on a high wire—one mediocre essay away from alienating my audience. The stress consumed me, and I stopped having fun writing. The numbers suffered, and I started writing less often so I could “focus on building the business.” In retrospect, almost everything I did besides write or edit was a waste of time that cost the company significant momentum.

At some point early in 2022, I pulled myself out of this funk. I committed to a weekly publishing schedule. This structure did not make my anxiety disappear, but it did force me to confront it. I read a book called Big Magic by Elizabeth Gilbert that taught me an important lesson: writing can and should be fun. You should do it because you get a thrill out of it. Sure, it can also be hard, but so can everything. Focus on the parts you like. When you sit down to write, remind yourself that you’re doing so in order to experience those fun, joyful moments. This taps into—and even expands—a much more durable form of motivation than public recognition: intrinsic satisfaction.

When you publish, of course you’ll be happy if you get a good response. But the balanced reaction is more along the lines of “Huh, you liked that? Interesting…,” rather than, “OMG they like me!!! I am not worthless after all!”

If I’m being honest, the hopes and dreams of that guy sitting under the bookshelf in the San Francisco apartment were closer to garnering the latter reaction than the former. I wanted to write so I could learn about business strategy, partly because I found the subject valuable and interesting, but also so I could become a Smart Guy™ in the eyes of tech Twitter. Now I’m not so sure how much that matters to me. I’m more attuned to the work that gives me joy and brings genuine value into the world. I still have an ego and perform my little routines to try and fortify it. But the ego has less of a death grip on me now. I can set it aside, and allow feelings like curiosity and joy take over when I write. It is and always will be a work in progress—a bit of a mess at times. But it’s me. I’m learning to feel okay with that.

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josh spilker over 1 year ago

This is good about the process itself but I’d love for you to tackle the distribution question. You yadayadayada’d it in the section about getting to 75k inboxes. That didn’t happen overnight & takes more than a few well received posts

Nathan Baschez over 1 year ago

@joshspilker you're right that it didn't happen overnight and took more than a few well received posts, but honestly there was no distribution trick! literally just posted essays to twitter and hacker news every week for 3 years.

To the extent there was something unique it was the fact that Every is a shared audience where it's not just my writing that helps grow the list, but also all the other writers we work with. The other thing is probably relationships with prominent folks. We've experimented with cross-promo (aka "list swaps") and even paid acquisition, but nothing has mattered nearly as much as just writing and publishing consistently for years.

@nishit over 1 year ago

@nbaschez Love the honesty here.

@aalnuaimi over 1 year ago

Something is missing.

Nathan Baschez over 1 year ago

@aalnuaimi ha, what?

Matt Ellsworth over 1 year ago

Now I want to write great essays and also play frisbee.

@imdorn over 1 year ago

The following from your message, according to my teachers, is a run-on sentence, has a comma too many after "and" and it ends with "with". "My co-founder Dan and I were able to find enough of the right sequences of words to grow a respectable audience and, more importantly, attract some wonderful kindred spirits along the way to write with."

Eliminate those commas after the "and" word. Change those "with" endings. Like this, "... along the way with whom to write." Trust me, I became a school teacher too. :-)

At least you know you make errors.
I won’t lie: I’ve made a lot of mistakes over the past three years. I am a deeply flawed writer.

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