Summary

Simon Späti interviews Benn Stancil about his writing process for the inaugural 'Show Your Workflow' series. Stancil explains how writing began accidentally through the Mode company blog in 2013, evolved into a weekly Substack, and became anchored by a Friday deadline born from a joke tweet. The interview covers his idea formation process (letting half-formed thoughts 'roll around' until they pick up connections), his core storytelling technique of building pieces around analogies rather than arguments, and his deliberate avoidance of AI writing tools. Stancil argues that the most interesting creative work comes from connecting disparate, unrelated things—and that this is precisely where both human effort and AI fall short.

Key Insight

Great writing comes not from having original ideas but from the discipline of deadlines, the willingness to sit with discomfort, and the skill of finding unexpected analogies that make familiar observations feel inevitable.

Spicy Quotes (click to share)

• 6

  If you always enjoy it, you're not pushing it hard enough.

• 7

  To make something good, you have to hate it sometimes.

• 5

  You tacked the points onto the analogy rather than the analogy onto the points.

• 6

  Slightly overrate the point of having a point.

• 2

  The interest comes from how you tell it.

• 5

  You're not always the main character.

• 4

  The writing is not the bullet points, it's filling things in between.

• 3

  People smashing together very strange things, because their experiences are like this eclectic collection of things that aren't obviously all tied together.

Tone

conversational, reflective, practical, quietly inspirational