Essays on writing

on the craft of writing and rewriting.

September 11, 2026

Ray Ozzie and the Optimism of Being Early

“It wasn’t like I had a choice, you know?”

Imagine you’re Ray Ozzie, born half a decade after Turing outlined his Test to see if a machine is truly intelligent. You’re lucky enough to attend a high school with ARPA funding, ARPA of internet forerunner ARPANET fam…

Read essay →

May 7, 2026

The best ideas come from the arena

Start. See. Switch things up.

The company behind the Centurion Club and the Black Card, best known for a concierge service and charge cards without limits, and for turning the card in your wallet into a lifestyle choice, that company started out with…

Read essay →

March 21, 2026

AI as fuzzy search

A modern interview stack

The idea started with Benjamín Labatut’s The MANIAC , a fictional oral history-style narrative about mathematician John von Neumann. What starts as a near-reality narrative about Neumann’s work and genius descends into n…

Read essay →

March 14, 2023

How to write accessibly and make your content better for everyone

Accessibility for Writers

“Two of the most important characteristics of good design are discoverability and understanding.” Don Norman, The Design of Everyday Things Ever stopped to think about how people read your blog posts? They might open the…

Read essay →

February 27, 2023

How to contribute your first UX copy as a writer

The first step from writing to working on technical teams.

Ever been clicking through an app when you notice a typo, an errant space or bit of punctuation, and wished you could jump in and fix it? You could. Copywriting is, perhaps, the best way to make the leap from writing to …

Read essay →

February 23, 2023

The slow death of dot com: Less than half of startups today use a .com

After decades as the default, dot coms are no longer used by most new startups, and alternative TLDs are the new default.

In the beginning, in the early ’90’s when the internet was young and everything seemed possible, there were only a handful of top-level domains (or TLDs). You weren’t starting a non-profit or government, so .com was the …

Read essay →

February 23, 2023

The best domain names are two names. Or three.

You don't need a dot com, or a short name, to build a successful startup.

Last year, I started two companies (great idea, totally recommended, definitely not too much to take on). And in the process, I accidentally ended up stumbling upon the best way to buy a domain and rank first on Google f…

Read essay →

February 1, 2023

You, too, need a copyholder: The art of reading writing out loud to edit it

Copyholder (noun): one who reads copy for a proofreader

I noticed it, first, in the original Chicago Manual of Style , with its Notes to Copyholders tucked in the final appendix after notes to authors, editors, and proofreaders. I thought, perhaps, the editors were referring …

Read essay →

February 1, 2023

Exceptions will constantly occur: Advice from the original Chicago Manual of Style

To fellow gropers in the labyrinth of typographical style...

The first edition of the Chicago Manual of Style wasn’t nearly as imposing as today’s 1,146-page tome. With merely 106 pages of grammar and composition rules—plus another hundred or so pages of typeface samples—it was ac…

Read essay →

January 26, 2023

The Mastodon Guide

How to leave Twitter behind and start a new community—or bring your existing one—on the Elephant Network.

It all started as public SMS, a decade-and-a-half ago when Jack Dorsey posted "just setting up my twttr" and launched perhaps the most influential social network. Facebook has more users, Instagram and Twitter more viral…

Read essay →

Write. Rewrite. Revise.

Reproof is the app to write until you get it right. Free forever for 10 documents. $10 a month or $99 per year for unlimited documents.

Start writing

Essays on writingwriting

Ray Ozzie and the Optimism of Being Early

The best ideas come from the arena

AI as fuzzy search

How to write accessibly and make your content better for everyone

How to contribute your first UX copy as a writer

The slow death of dot com: Less than half of startups today use a .com

The best domain names are two names. Or three.

You, too, need a copyholder: The art of reading writing out loud to edit it

Exceptions will constantly occur: Advice from the original Chicago Manual of Style

The Mastodon Guide

Essays in your inboxinbox

Write. Rewrite. Revise.

Essays on writing

Essays in your inbox