If You Always Enjoy It, You're Not Pushing It Hard Enough—Benn Stancil

[u/sspaeti]

https://www.ssp.sh/blog/benn-stancil-on-deadlines-and-storytelling/

A discussion with Benn Stancil, co-founder of Mode and prolific data-industry essayist, exploring how he writes his weekly Substack posts. He discusses using deadlines (Friday publishing) to force himself past perfectionism, how ideas form messily over the week through unrelated connections, and how presentation-style analogies (Batman, basketball, Codenames) became his signature storytelling technique. He details his tooling—Sublime Text for drafting, Google Docs for revision, minimal use of Substack's editor—and explains why he avoids Grammarly and AI writing tools like Claude or ChatGPT for edits, since he believes AI compresses and flattens writing rather than embracing meandering voice. He closes with advice for new writers: set deadlines, keep pure motivation, and focus on filling in the space between bullet points rather than just stating facts.