May 18
263: The Tyranny of Thirty —
My piece in Medium on the artificial deadline that’s ruining a generation
May 11
262: Diminishing Returns on Merit Badges —
On the pursuit of external markers of success
May 02
261: Making Gut Calls —
What no one ever explains about building your gut intuition
Apr 26
260: Fraught Conversations —
3 proven techniques for getting through messy disagreements
Apr 05
259: Off Track at 30 —
A 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 Out —
Using 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 FAQ —
5 Questions & answers about my new book and the future of this newsletter
Jul 05
213: Two tech interviews that are four decades apart —
Steve Jobs in Playboy (1985) & Threads/IG chief Adam Mosseri in Platformer (2024)
Jul 03
212: Writing a book in 30 days —
Never 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 Everyone —
On finding an audience for your work
Jun 18
208: There is no penalty for asking —
On 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 Hunt —
On accountability and team culture
Jun 09
205: A smarter way to make friends in a new city —
You gotta shoot your shot
Jun 01
204: A simple way to jumpstart your creative process —
Remake the things you love
May 29
203: Why are most people so stubborn about certain ideas? —
On persuasion and weird talents