Newsletter

227 posts


May 18
263: The Tyranny of ThirtyMy piece in Medium on the artificial deadline that’s ruining a generation
May 11
262: Diminishing Returns on Merit BadgesOn the pursuit of external markers of success
May 02
261: Making Gut CallsWhat no one ever explains about building your gut intuition
Apr 26
260: Fraught Conversations3 proven techniques for getting through messy disagreements
Apr 05
259: Off Track at 30A high achieving reader struggles in the messy middle of startup life
Mar 29
258: On Fostering Managerial Initiative [Ask Jason]A frustrated CEO asks how they can get their "Head of" to take more responsibility
Nov 09
226: Write It OutUsing letters to work through severe cofounder conflict
Aug 23
215: "You Have to Be a Little Delusional"Sharing my talk and Q&A from Medium Day 2024 on pivoting and the smarter way to revive a struggling startup
Aug 10
214: A Weirdly Brilliant FAQ5 Questions & answers about my new book and the future of this newsletter
Jul 05
213: Two tech interviews that are four decades apartSteve Jobs in Playboy (1985) & Threads/IG chief Adam Mosseri in Platformer (2024)
Jul 03
212: Writing a book in 30 daysNever let a good deadline go to waste
Jun 28
211: "Good writing is the Grammarly fixes you ignore"On good writing and good characters
Jun 26
210: How come some longtime couples get divorced when they’re old?On Frustration in Relationships
Jun 20
209: Your Talents Will Not Be Appreciated By EveryoneOn finding an audience for your work
Jun 18
208: There is no penalty for askingOn going after what you really want
Jun 15
207: "Your body language reflects your mental state"What judo and gymnastics can teach us about mental fortitude
Jun 12
206: Babe wake up I got a text from the founder of Product HuntOn accountability and team culture
Jun 09
205: A smarter way to make friends in a new cityYou gotta shoot your shot
Jun 01
204: A simple way to jumpstart your creative processRemake the things you love
May 29
203: Why are most people so stubborn about certain ideas?On persuasion and weird talents