May 18
263: The Tyranny of Thirty —
The pressure to 'make it by 30' has become a cultural epidemic. Jason Shen examines how the Forbes 30 Under 30 list and early-success myths created an artificial deadline that's ruining a generation.
May 11
262: Diminishing Returns on Merit Badges —
After your first few prestigious credentials, the returns on more 'merit badges' diminish fast. Jason Shen explains when chasing validation stops serving you and what to pursue instead.
May 02
261: Making Gut Calls —
Your gut intuition is only built when you actually follow it. Jason Shen shares a founder coaching story about trusting instincts over sunk costs and social pressure.
Apr 26
260: Fraught Conversations —
When disagreements get tangled with emotions, they become 'fraught conversations.' Jason Shen shares three practical tools for resolving conflicts with cofounders and close collaborators.
Apr 05
259: Off Track at 30 —
A reader writes in panicking about turning 30 with a failed startup and dwindling savings. Jason Shen responds with hard-won wisdom about 'established adulthood' and the surprises your thirties hold.
Mar 29
258: Manager Initiative [Ask Jason] —
When managers won't take initiative, the problem is usually the founder's transition from doer to delegator — not the manager's competence. Here's how to fix it.
Nov 09
226: Write It Out —
When cofounder conflicts get emotionally charged, face-to-face conversations often fail. Jason Shen makes the case for letter writing as a powerful tool for resolving deep business partnership disputes.
Aug 23
215: "You Have to Be a Little Delusional" —
A talk on startup pivoting from Medium Day 2024: why founders need productive delusion, and how the Double Loop Pivot framework helps struggling startups find their next direction.
Aug 10
214: A Weirdly Brilliant FAQ —
Jason Shen answers the most common questions about his book Weirdly Brilliant — a guide for ambitious outliers who want to swing big, own their genius, and play a different game.
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