![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.
🔧 Tactics
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.
142: Ask My AI
💡Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach
141: How to Be a Dark Horse
💡Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach
138: Effortless Essays
How I built an AI-powered workflow to help me turn voice memos into 1st draft essays (and how you can do it too!)
136: How Humans Still Trump AI
2023 is is a year Generative AI really comes for knowledge workers. Here are 10 enduring human traits that can help us stay ahead of the machines. 🧵
135: A Self-Paced Annual Review
I made a self-paced version of my annual review. Plus: learning to have conviction, bike bootcamps, mixing up your workouts, the human need for novelty.
133: Secrets, Extroverts, and Interfaces
This week's concise 🎉🎄holiday edition 🕎❄️ focuses on uncovering secrets to base your startup on, how extroverts can find the social time they need, and opportunities in generative AI for founders.
132: Twelve Ways to Practice Resilience After a Layoff
In my latest piece for on Every, I wrote about how people can use my resilience framework to better navigate the challenges of a layoff. It's been the most "hearted" piece in the series so far.
130: Happiness at Work
My latest piece in The Muse and early faves from OpenAI's ChatGPT
126: 🎬 Push-Up & Ponder
🎬 Why Being a Jack of All Trades Isn't Bad
🎬 Why You Shouldn't Fear Rejection
🎬 Why Founders Need Conviction
125: The Double Loop Pivot
The Double Loop Pivot is a structured framework for startups that have lost conviction, developed by Jason Shen after two pivots — one failed, one leading to acquisition by Meta.