Writing on the web

TL;DR: I’m going to start blogging again. If you’d like, you can follow along via old-fashioned RSS or get the email.

Following the common pattern for born-again bloggers, let’s talk a bit about writing.

I’ve been writing on this domain since January of 2012. My initial posts included titles like “Three Life Lessons From The Dark Knight Rises.” It was fun and lightweight, but I certainly thought about traffic and numbers. I wrote to draw a crowd.

Around the same time, I began taking on paid writing gigs. First for health and fitness magazines like Men’s Fitness, Greatist, and Outside Online. Later, doing content marketing for brands like Zapier and Doist. I made connections that benefit me to this day. As two key examples, I was later hired at Zapier and subsequently joined Ness, founded by the former CEO of Greatist. My writing also improved dramatically. There’s just no substitute for an editor drilling in for clarity and brevity, questioning every sentence.

My blog naturally followed the trend of my paid writing gigs. More content marketing, less personality. Each post had to hit a certain bar of quality. Success was measured in pageviews and subscribers. As a result, I wrote less and less.

Over the past several months, a few links caused me to rethink my approach.

First, there’s Tom Critchlow’s classic Small b blogging:

So what is big B blogging? I’d contend that too much of what you read on the web is written for large audiences…Instead – I think most people would be better served by subscribing to small b blogging. What you want is something with YOUR personality. Writing and ideas that are addressable (i.e. you can find and link to them easily in the future) and archived (i.e. you have a list of things you’ve written all in one place rather than spread across publications and URLs) and memorable (i.e. has your own design, logo or style).

He goes on to propose a lightweight structure for small b blogging, riffs. The basic premise: Write small, connect some ideas, invite responses, and do it again. Expose the “sawdust” of your thinking.

Next, there’s Sari Azout. From her newsletter:

Where are the spaces where you can share the process of thinking, not just the finished thought? Spaces that are less about projecting authority and more about individuals weaving the threads of their mind and connecting different ideas. More curious and iterative, less defensive and definitive?

And finally, Tyler Cowen (a notorious blogger). In 2018, he described his “personal moonshot” — how he uses the internet as a platform to further his career and his ideas. I highlighted this gem:

One point of the internet is to find an outlet for super-unpopular material.  What’s important right now is to develop internet methods of thinking and communicating, and not to obsess over reaching the largest possible numbers of people.

With these ideas in mind, I began to observe my own reading habits. When plucking items from my read-later queue, I was less inclined to pick the polished “Ultimate Guide” types. Instead, I gravitated towards small b bloggers — Melanie, Dave, Kelly, Om, and Chai to name a few.

My new mental model for writing has two axes: audience (public vs. private) and purpose (think vs. tell). Here’s how they fit together.

If the top right (Tell/Public) is dedicated to building influence, the top left (Think/Public) is like “a search query” to find your people, using an analogy from Austin Kleon. From Austin’s post:

You will write essays that almost no one likes…. Luckily, almost no one multiplied by the entire population of the internet is plenty if you can only find them.

One closing thought — I believe the tool you choose influences the direction of your work in obvious and subtle ways. Obviously, DayOne is a private journaling app with constraints that make entries difficult to share. The business model of Substack is built on taking a cut of subscriber revenue. There’s a subtle push to grow your subscriber count and launch a paid subscription option. Hence, I return to my own domain.

That’s the gist. Look forward to more riffs on building software for humans. Some topics I’m keen to explore further that I believe overlap in interesting ways:

  • Business – The overlap of strategy and operational execution that brings ideas to life.
  • Product – How we bundle these ideas and deliver them to customers in a way that works for the customer and the business.
  • Customers – Ideas around maintaining a maniacal customer focus and serving end users
  • Communication – How to effectively share these ideas publicly and within organizations to get buy-in and build momentum

Photo by Yannick Pulver on Unsplash

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