Breaking big tasks into first steps

Hilary Gridley is an entrepreneur, former product leader, and new mom who previously appeared on the podcast discussing AI for managers. She returns to share how she's transformed her approach to personal productivity using Claude Code as her primary tool for managing both professional work and life admin. Hilary demonstrates her "anti-system system"—a philosophy that prioritizes simplicity over complex setup, allowing AI to learn preferences through observation rather than upfront configuration.

What you’ll learn:

1. How to capture to-dos instantly using a simple iPhone back-tap shortcut that requires zero app switching
2. The “10x impact framework” for deciding what tasks to automate versus where to invest your human effort
3. How to use Claude Code’s observation capabilities to build a preference file that improves over time without manual setup
4. Why the “yappers API” (talking about what you’re doing while working) eliminates the need for complex OAuth integrations
5. A workflow for breaking down overwhelming tasks into 10-minute first steps that actually get completed
6. How to create Claude Skills by simply describing problems rather than writing code or following tutorials
7. Techniques for using “recording mode” to demo workflows without exposing personal information

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Brought to you by:

WorkOS—Make your app Enterprise Ready today

Lovable—Build apps by simply chatting with AI

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In this episode, we cover:

(00:00) Introduction to Hilary Gridley

(02:43) The opportunity cost of time as a new mom and entrepreneur

(07:11) Philosophy of the anti-system system

(08:05) Demo: Planning your day with Claude Code

(10:00) Setting up simple iPhone shortcuts for task capture

(11:48) How Claude organizes reminders and learns preferences automatically

(16:19) Breaking down overwhelming tasks into manageable first steps

(23:40) The yappers API: talking to Claude instead of building integrations

(25:28) Daily logging and observation patterns

(27:45) Quick summary

(30:50) The power of screenshots

(32:55) 10x impact framework for automation decisions

(37:51) Applying the framework to different career stages

(39:29) Building a “recording on” skill for anonymizing demos

(44:11) Building a returns tracking skill from scratch

(48:31) Building the muscle memory to reach for AI tools

(50:18) Where to find Hilary

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Tools referenced:

• Claude Code: https://claude.ai/code

• Obsidian: https://obsidian.md/

• iPhone Shortcuts: https://support.apple.com/guide/shortcuts/welcome/ios

• Cursor: https://cursor.sh/

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Other references:

• Figma file Hilary demo’ed: https://www.writerbuilder.com/howiai

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Where to find Hilary Gridley:

Substack: https://hills.substack.com/

Website: https://writerbuilder.com

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Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.