The New Rules of Business Communication — Jason Fried

Jason Fried, co-founder of 37signals and author of four books, treats writing as communication first and foremost — the goal is to transfer a clear idea from your head to someone else’s, not to produce polished prose for its own sake.

• He writes quickly and throws work away the moment it feels like a struggle, starting over on a blank page rather than pushing through friction.
• He finds a “flow state” — a sense of effortlessness where good sentences emerge intuitively — and stops immediately when that feeling disappears, trusting that contrived effort shows up in the writing.
• He values the visual and rhythmic shape of sentences, looking for lines that “feel good” the way a found branch with lichen looks naturally right.

His writing process is rooted in speech and personality, not formal technique.

• He writes the way he talks, often going for a walk and speaking ideas out loud to find the hook or title before sitting down to write.
• He avoids writing on a schedule, only writing when he has something to say, and uses compressed time frames (like 20 minutes before a meeting) to prevent overworking a piece.
• He rarely shares drafts before publishing, edits as he goes, and is comfortable fixing small errors after publication, comparing the Navajo rug tradition of keeping imperfections to his tolerance for minor mistakes.

He is skeptical of most business writing and traces the problem to institutional habits.

• He blames MBA programs and school assignments that reward length and BS over genuine communication.
• He dislikes the word “content,” preferring “communication,” and argues that most companies write to sell rather than to say something real.
• He sees most business writing as jargony, interchangeable, and driven by SEO rather than a genuine point of view.

His founder letters (for Hey and Once) demonstrate his approach to persuasive writing.

• He opens with a hook that creates mystery — “Something happened to business software” — to pull readers in without asking a direct question.
• He structures letters by first establishing a problem the reader already feels, getting them to nod along, then introducing his product as the alternative.
• He uses rhythm, repetition, and wordplay (alliteration, short punchy endings, “bounce” between contrasting ideas) to make the writing feel alive and playful.
• The name “Once” emerged from writing the phrase “once upon a time” and discovering the double meaning with paying once for software.

He values editing that preserves the writer’s voice and feeling over technical precision.

• His best editing experience was with Rick Hogan on Rework, who made the piece substantially better through deep engagement.
• He prefers talking through edits with an editor rather than receiving a redrafted version, because conversation reveals reasoning.
• He pushes back on editors who “sterilize” his writing by replacing his word choices with technically correct but lifeless alternatives.

He believes in working within natural limits rather than emulating others.

• He compares himself to a 400-meter sprinter — he writes short essays well and has no interest in forcing himself into long-form narrative.
• He argues that knowing your limits and staying within them is underrated, and that copying others’ styles leaves you without the underlying ideas needed to evolve.
• He sees his books as byproducts of being willing to share how they work, inspired by chefs who publish cookbooks rather than guarding secrets.

Writing is central to how his company operates internally and how he hires.

• Every six weeks, team leads write a “heartbeat” — a written summary of their team’s work — which serves as the primary mechanism for disseminating institutional knowledge.
• Good heartbeats have personality, are concise, reference specific people and problems solved, and allow someone unfamiliar with the work to understand what happened.
• In hiring, cover letters are the first filter; generic or buzzwordy letters are rejected immediately because the ability to communicate clearly and personally is the most important skill at the company.

He advocates for a writing class focused on distillation — taking a long piece and compressing it down to one page, one paragraph, one sentence, even one word.

• The exercise forces you to identify the essence of what you’re saying and often produces insights (like a title or core concept) that wouldn’t emerge from simply cutting words.
• He compares distillation to making maple syrup: it takes roughly 40 gallons of sap to produce one gallon of syrup — the end product is fundamentally different from the raw material.

His broader philosophy is to relax your grip — in writing, in business, in life.

• He uses the analogy of learning to play drums: gripping the sticks too hard limits tone, speed, and endurance; relaxing improves everything.
• He avoids industry news and competitive analysis to prevent being influenced by others’ thinking, preferring to find his own way the way an isolated island evolves independently.
• He believes most business writing fails because people take it too seriously, try too hard, and forget they’re just communicating with another human being.