Transcript: AI Journaling System: Charlie Grinnell

March 16, 2026

This is an auto-generated transcript of Never Enough Podcast Episode 8. It may contain minor errors.


when we think about AI everyone goes oh like AI is coming it's going to take our jobs I think the benefit for AI first and foremost is like personal productivity when you start to add up that hours saved on an individual level when it comes to personal productivity that's really really exciting what I actually did was I created a prompt that can Shuffle questions each day so in my note when I go for a walk I quickly look down and there's five questions already there I'm able to dump my brain out in a way I can go into my notes and chat about books that I've read and taken highlights from like have I read anything that would be helpful for this and it will like pull things together

Charlie what's up what are you up to it is a nice sunny day here in Vancouver and uh excited to chat with you about the nerdy productivity stuff that you and I talk about in our group text with all of our other nerdy friends yeah so Charlie and I have a group thread with maybe 10 other guys and it's all the most anal retentive productivity nerds that I know and we like exchange tips and stuff and Charlie is the man in this group because he will often share these amazing walkthrough videos of his setup

before we dig into all that do you want to give a little bit of background on yourself yeah I dropped out of University I never went back and I got into marketing so I'm a marketer by trade I worked on the brand side for many many years at Brands like Aritzia and Red Bull and I think as I went through my career and marketing just being chaotic I realized that I just needed to get organized and I think with how the digital world has gone with all these different devices there were all these new tools coming into play

and so it kind of became this like side hobby of researching into these things but then as I started to put them together it allowed me to get more done and I think about now as I build a company this idea of like needing to organize yourself before you organize anything else really rung true so tell us about your typical day how do you structure your day I really like doing deep work in the morning so I try to avoid morning meetings

I wake up every morning and before I start my deep work I go for a walk and I do some journaling I come back home I do some deep work until lunchtime eat some lunch then the afternoon is typically meetings from like 1 to 4 and then 4 to 5 is kind of like clean up and organize for the next day I also really try to do no meeting Mondays which sometimes is very aspirational it definitely doesn't happen but I think just protecting that time is really important

so let's talk about journaling because I have really struggled with journaling I've always wanted to do it and I think everybody loves the idea of being able to note take and remember what happened you have a very interesting system that I've never seen before can you walk us through it I have awful handwriting I'm not a designer like you if you looked at my handwriting it looks like a serial killer

and so writing in a notebook while I really wanted to be able to do that was a pain and the other thing is when you're staring at a blank cursor I notice that when I sit to write something I tend to edit my thoughts I'll start to write something and be like ah is that what you really mean and you stop yourself and so I was like I just want something that's like a natural brain dump

and I love walking in the morning and that's usually when I'm thinking about things and so I landed on a note taking app called reflect it has this really awesome transcription feature so what I started to do was on my morning walks I would just record voice memos and dump my brain into how I'm feeling and so that was the first version just go for a walk and the first few minutes dump how am I feeling what am I anxious about what am I excited about

and then as I started to dig more into journaling I was like oh there are preset questions that you might want to ask yourself so what I actually did was in reflect I created a prompt that can Shuffle questions each day so in my note when I go for a walk I quickly look down and there's five questions already there and they're different questions each day but they tend to repeat every couple weeks

and so I just go for a walk and I answer these questions and I'm able to dump my brain out in a way that I can do while walking it's frictionless for me it's easy and it just all gets captured and then when I get home since I do that on my phone it automatically gets synced to my computer and I have a prompt that formats things quickly it'll clean up format put things in order as the questions and then I'll sit there and read what I've just said and figure out how to take action

so it sounds like you're almost doing a form of self therapy and you're creating like an AI that's trained on you so you've almost got this AI therapist and also a digital person of yourself that can reflect back your thoughts yeah and I think about this concept of building your personal Board of advisers being able to read biographies and pulling that stuff in you can kind of train the therapist to be the way that you want it to be

so let's break down the system the library of questions I think now it's up to 50 things like how was your day today what did you do yesterday what are you excited or grateful for what are you stressed about and why how could you reframe something you're stressed about what kind of person do you want to be when was the last time that you practiced kindness with someone close to you

I do it usually on the Sunday for the next week I'll quickly run the prompt for each day and while I walk it's just a simple hit a button record dump your brain out and then when I get back in front of my computer I highlight that voice memo and run a prompt that cleans it up and organizes it the prompt is like you're a therapist assistant summarize what's being highlighted don't change any of the language remove ums and stutters

let's jump to the Deep work section how do you stay productive I stole one of my best hacks from you which is getting your significant other to set your screen time password and so across all my devices all social stuff and news stuff my fiance has the password I have like five minutes a day and now conveniently she's actually forgot the password so now it's stuck at 5 minutes a day

I'm a big fan of calendar blocking I use a task manager called things that's designed for quick capture and what that is is really a filter of if something's going to get on my calendar or not I have a quick shortcut on my computer on my phone on my iPad so anything that comes to mind goes in there and then I'm able to sit down and go okay does this actually deserve time on my calendar or not

I use a calendar blocking software called reclaim AI it plugs into your calendar and will create events for different tasks based on how you enter it and one of the things I love is when your calendar changes and gets blown up with different meetings you can just delete the event and it will go okay Charlie's day has gone to crap and this needs to be rescheduled and it will find another time for you

in terms of staying focused I use do not disturb focus modes that only let a few people through I've also used brain FM which is AI music designed to get you into flow and then also just curating your environment the room I'm in has no windows it's a little dungeon and I know if I had a window I'd be looking at trucks driving by

on a good day I get 3 to 4 hours of deep work on a bad day like zero what's your favorite type of deep work probably writing more and more or going through my notes to solve a problem where it gets really exciting is you can start to combine journaling with what you're reading and listening to and I've done things where I have an area of business like a people issue and I can go into my notes and chat about books I've read

so I'll describe the situation and then I'll be like hey can you pull have I read anything that would be helpful for this and it will pull things together and I'm like huh that's awesome whereas before I'd have to go find the book sit down open it up and be like ah what chapter was that on

for meetings I record all my meetings using a tool called fathom it has a highlighting functionality built in so let's say you're on a video call and someone says one of our biggest challenges is this I can literally hit a button on the screen that says challenge it will rewind to where you started talking and when you finish it will flag it in the transcription as a challenge

Transcript truncated. Listen to the full episode for the complete conversation.


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