For someone like me, for whom "leaving documents" is a habit in both work and personal life, Dropbox Paper has become indispensable.

  • When I want to organize complex information "in my own words"
  • When I want to share information with "someone who isn't here right now"

When these two conditions are met, document-based communication is remarkably effective. It removes the risk that important information will "be forgotten in a verbal handoff or stay unorganized in my head."

Conversely, ideas that don't satisfy the above two go into the iPhone Notes app as quick fragments. Any idea, any discussion — I never skip leaving it as text. Since thought is made of words, anything that doesn't remain as words = text is "as good as nonexistent."

Dropbox Paper

I've tried various document tools over the years, but Dropbox Paper — which I started using at the end of 2016 — is head and shoulders above the rest in two dimensions: "ease of writing" and "ease of reading."

Why it's easy to write, why it's easy to read — that's something you need to experience rather than hear about, so I'll leave a sample document below.

My relationship with documents

Working with documents well requires some knack. Here's what I'm careful about:

  1. Write the conclusion at the top. Most people only need the conclusion.
  2. Most important: articulate the reason and intent.
  3. Freshness of information matters. Include the date you started writing. Most documents have their highest value "the moment they're written."
  4. Don't assume "maintenance." Rather than revising an old document, create a new one. Don't hesitate to let them accumulate.
  5. Don't work hard at management. Don't make management a job. As long as you know where to look, you'll manage. Keep directory management to a level where you can reach any document in 2 clicks or fewer. Don't create folders.

The "don't work hard at management" in practice

Nearly 500 documents fit into essentially 3 folders. I don't put folders inside folders (with the exception of daily/weekly/monthly reports), so documents can be found flat.