The Online Writing Roadmap

If you’re ready to start writing, but don’t know where to begin, this page is for you.

It’s a list of the best things I’ve written and read about online writing.

The Basics

The Ultimate Guide to Online Writing: In this post, I outline my entire philosophy of writing online. Writing online is the fastest way to accelerate your career. It’s the best way to learn faster, build your resume, and find peers and collaborators who can create job and business opportunities for you.

Why You Should Write: Writing online is a guaranteed way to shrink the world. A well-written article can change your life because the internet rewards people who think well. Everything you write is an advertisement for the kinds of people and opportunities you want to attract, and if you have a voice, you can build a platform. As Derek Sivers once wrote: “The coolest people I meet are the ones who find me through something I’ve written.”

How to Maximize Serendipity: Writing online is the fastest way to increase serendipity. If you can maximize your surface area for luck, you’ll accelerate your progress and create opportunities for yourself.

Finding Great Ideas

How I Choose What to Read: Information is like food. Any chef will tell you it’s impossible to cook a world-class meal without world-class ingredients. Writing is the same. The quality of your output depends on the quality of your input.

How to Learn on the Internet: Tell me what you pay attention to, and I’ll tell you who you are. In this post, I outline my strategy for learning for the internet.

Where the Wild Things Are: It’s a law of the universe: Creativity always starts at the edge. If you want to find interesting ideas, you have to escape the mainstream spotlight.

How to Maximize Creativity: Creativity can’t be created directly, but it can be cultivated. Turns out, there are a simple set of tricks you can use to maximize your creativity.

Building the Writing Habit

The Magic Moment: This post answers the question: “When should you start writing?” In it, I argue that you should start writing right when you have an epiphany because the moment right after an epiphany is the only moment in the creative process where the rush of enthusiasm trumps the fear of judgment.

How to Cure Writer’s Block: By the time you finish this article, you’ll be done with writer’s block forever. In it, I focus on three strategies for ending writer’s block: (1) gather supplies, (2) talk it out, and (3) start with abundance.

The Craft of Writing

My Writing System: In this post, I outline the system I use to generate articles, organize them, and prepare them for publishing. I share my basic rules for writing and editing, such as switching context and adding a list of banned words.

Robert Caro’s Writing Secrets: Robert Caro’s is the world’s greatest biographer. Never, never, never in a million years did I think I would read a 1,200 page — 700,000-word — window into the politics of New York. But first-rate writing is seductive, no matter the topic. Facts alone aren’t enough. They’re too black-and-white. Readers yearn for images and anecdotes that make the information pop. For facts to stick in the reader’s mind, they must be enriched by colorful stories. Aided by subtle visuals and roller coaster narratives, Caro brings his biographies to life. That’s Robert Caro’s secret: he unlocks the electricity of sight.

Recommended Articles by Other People

Nat Eliason: 21 Tactics to Help You Become a Better Writer (Highly recommend)

Jordan Peterson: Jordan B. Peterson’s 10 Step Guide to Clearer Thinking Through Essay Writing

Paul Graham: Writing, Briefly

Eugene Wei: The Rhythm of Writing

Khe Hy: Create Your Own Luck with a Writing Practice

Ernest Hemingway: The Art of Fiction

Venkatesh Rao: Tips for Advanced Writers

Morgan Housel: Make Your Point and Get Out of the Way

Gergely Orosz: Why Writing Well is an Under-Valued Skill

Morgan Housel: Why Everyone Should Write

Steve Cheney: On How to be Discovered

Tyler Cowen: My Personal Moonshot

Julian Shapiro: Writing Well

Nivi: How to Write Like a Great Entrepreneur

Scott Adams: The Day You Became a Better Writer