Jack Kerouac was a famous writer from 1950's, but he referred to his own practice as "sketching." Like a painter, he'd look around slowly to soak in and reflect on the details. As images and memories bubbled up, he'd scribble them into flowery, never-ending sentences. When Kerouac writes, it feels
“At what point should I share my essay with editors? Should I ask for feedback as soon as possible, or should I wait until it’s a coherent draft?” Both! The biggest misconception about feedback is that it’s a singular event. You don’t have to write in isolation
“Regarding pseudonyms, how do you promote your blog? Since your family and friends don’t know your writing identity, how do you spread the word about it?" One challenge with starting an account from scratch is The Cricket Effect. Whether you start under a pseudonym or not, it’s frustrating
What are the benefits of writing under a pseudonym? Even when we find the courage to publish our ideas, we often get tripped up by our audience. The idea that our parents, co-workers, or clients could potentially read our essay is enough to scare the life out of our writing
"How do I actually translate my personality onto the page? I know the vibe I want to get across, but when I sit down and write, it feels flat." Some would say, “Voice is just something you have. Don’t think about it. It’s natural. It just comes out.
"This newsletter fires me up! I feel like I have permission to explore my interests, and I have faith my Personal Monopoly will emerge over time. How can I create a theme that runs through all of my writing?" Great question. An underrated way to link all of your essays
I need to decide how I'll distribute my logs through email. The simple route is 3-5 per week. But there's a certain wonder in peaking into someone's unedited mosaic of thought. It's hardcore, but it's distinct. It stands out from the wave of filtered, curated tidbits.
"Big Red Son," is an outrageous David Foster Wallace essay about a 1998 adult film conference. By dissecting it, we'll learn some (non-vulgar) tricks to help our writing jump through the page. Use relatable metaphors. Make unlikely associations. Look behind the scenes.
“I have so many interests and they don’t all fit under a single brand. Do you recommend multiple websites so each one has a clear value pitch?” The pain of the polymath is real. When you’re starting out, keep all your interests under one personal website. Maybe you
Hello world! This is the inaugural edition of Dean's List. I've decided to transplant both my website and newsletter into Ghost (this will surprise those who know me as "the Notion guy.") Sounds drastic. It is, but let me explain.
We're in a newsletter arms-race. What happens when everyone has one and they all sound the same? Overwhelm, skimming, and email fatigue. The old tricks around niches & weekly streaks are becoming predictable. What makes a newsletter exciting to open each time?
A long-term horizon around "the note" leads us to worship inputs. We often feel the need to create perfect constellations of notes before we start. Instead of notes to serve us in 5-10 years, what if we accept that they expire in 3 weeks?
Every week day, we host a WOP "Feedback Gym." After 1:1 breakout sessions, we come back and share insights on writing and editing.
I went into the city on Saturday to meet up with Isabel in person for the first time. On a walk from Penn Station to Bryant Park, I decided to write down everything I experienced. Eight blocks north, and then a few more east. It’s a great exercise to practice, “placemaking.”