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All Newsletter Articles 🐚 Stories Book Notes ♟️ Strategy 🔧 Tactics Togetherness 🫶 Courage / Risk ⚡️ startups
14 Jun, 2025
Newsletter
267: Snake Oil
14 Jun
Newsletter

267: Snake Oil →

The most capable people often struggle most with self-promotion. Jason Shen reframes the fear of being a 'snake oil salesman' by exploring the surprising history of actual snake oil.
08 Jun, 2025
Newsletter
266: Making a Real Difference
08 Jun
Newsletter

266: Making a Real Difference →

Most nonprofits focus on feeling good or looking good rather than doing good. Jason Shen explains why a theory of change matters for anyone trying to create lasting impact.
31 May, 2025
Newsletter
265: What's the Point?
31 May
Newsletter

265: What's the Point? →

When ambitious people lose their sense of purpose — whether from struggle or success — things go sideways fast. Jason Shen shares two coaching stories about rediscovering what matters.
25 May, 2025
Newsletter
264: Signaling Quality
25 May
Newsletter

264: Signaling Quality →

Before you can prove your substance, you have to signal your quality. Jason Shen explains why presentation determines whether you get the chance to demonstrate what you can really do.
18 May, 2025
Newsletter
263: The Tyranny of Thirty
18 May
Newsletter

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.
11 May, 2025
Newsletter
262: Diminishing Returns on Merit Badges
11 May
Newsletter

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.
02 May, 2025
Newsletter
261: Making Gut Calls
02 May
Newsletter

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.
26 Apr, 2025
Newsletter
260: Fraught Conversations
26 Apr
Newsletter

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.
05 Apr, 2025
Newsletter
259: Off Track at 30
05 Apr
Newsletter

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.
29 Mar, 2025
Newsletter
258: Manager Initiative [Ask Jason]
29 Mar
Newsletter

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.
22 Mar, 2025
♟️ Strategy
257: Threshold Checkpoint Goalsetting
22 Mar
♟️ Strategy

257: Threshold Checkpoint Goalsetting →

Smart founders get stuck overthinking strategy. Jason Shen introduces Threshold Checkpoint Goalsetting — a framework for making decisions under uncertainty without constant second-guessing.
14 Mar, 2025
256: I'm Your Daddy
14 Mar

256: I'm Your Daddy →

A raw, week-one snapshot of new fatherhood. Jason Shen shares what surprised him about having a newborn — from the naturalness of caregiving to the surreal moment of hearing 'daddy's here.'
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Jason Shen
Jason Shen © 2026. Published with Ghost & Rand