Designing Your Digital Mind: Charlie Grinnell's AI Journaling System

Never Enough

About the episode

In this episode, Andrew chats with Charlie Grinnell, the productivity-obsessed Co-CEO of RightMetric. Together, they get into his foolproof system for getting things done and how AI has revolutionized his workflow.
Tune in to learn how to boost your productivity and achieve more with less.
We go over

1. AI and Journaling: Charlie uses Reflect to transcribe his thoughts while he’s on his morning walk. It’s helped him reduce the friction of journaling.
2. Deep Work: “ I go for a walk and I do some journaling, which we'll talk about in a little bit here. I come back home. I do some deep work until I get to lunchtime.”
3. Keeping Track of Meetings, Book Quotes, & Interesting Podcasts: The Readwise app helps Charlie keep track of everything he reads and listens to.
4. Interesting AI Use Cases: Chatting with notes, journal prompts, and speech to text
And so much more.
Resources Mentioned

- Readwise
- Superwhisper
- EightSleep
- Lomi: Smart Waste Kitchen Composter
- Text
- Things
- Reclaim AI
- Basecamp
- Fathom
- Clay
Chapters

00:00 Intro
00:33 Getting to Know Charlie
3:17 Charlie’s Typical Day
5:15 Charlie’s Journaling Routine
11:56 Charlie’s Library of Journaling Questions
13:48 Facilitating Deep Work
15:39 Dealing With Low Priority Tasks
20:09 Avoiding Distraction While in Deep Work
21:19 Time spent in Deep Work
21:47 Charlie’s Favorite Type of Deep Work
23:19 Meeting Recordings, Transcripts, & CRMs
26:48 Charlie’s System for Reading
31:35 Keeping Track of Interesting Podcast Tidbits
34:22 Dealing With AI’s Recency Bias
35:57 How Charlie Keeps Consistent With His System
38:11 What Drives Charlie to Create Systems
42:18 Broken Parts of Charlie’s System
44:00 What Charlie’s Looking Forward to With AI
45:55 Other Interesting Ways Charlie Uses AI
49:30 Products Charlie Really Loves
🔗 Find Charlie On:

LinkedIn: @charliegrinnell
Twitter/X: @CharlieGrinnell
Instagram: @charliegrinnell
🔗 Find Andrew on:

Twitter/X: @awilkinson
LinkedIn: @awilkinson
Website: https://www.neverenough.com/
Sign up for Andrew's newsletter