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.
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![258: Manager Initiative [Ask Jason]](https://storage.ghost.io/c/ee/b5/eeb51aed-5fc9-48e8-80b2-2499ce01cf7d/content/images/size/w400/2025/03/jason.shen_In_the_style_of_a_knife_palette_painting_A_stressed__0ac1f4d0-87ea-44a5-9eb7-282049e2a027.webp)
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.
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.
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.
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.
213: Two tech interviews that are four decades apart
Steve Jobs in Playboy (1985) & Threads/IG chief Adam Mosseri in Platformer (2024)
212: Writing a book in 30 days
Never let a good deadline go to waste
211: "Good writing is the Grammarly fixes you ignore"
On good writing and good characters
210: How come some longtime couples get divorced when they’re old?
On Frustration in Relationships
209: Your Talents Will Not Be Appreciated By Everyone
On finding an audience for your work
208: There is no penalty for asking
On going after what you really want
207: "Your body language reflects your mental state"
What judo and gymnastics can teach us about mental fortitude