This is an auto-generated transcript of Never Enough Podcast Episode 8. It may contain minor errors.
Andrew: Charlie, what's up? What are you up to?
Charlie: It is a nice sunny day here in Vancouver and 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.
Andrew: 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.
Andrew: Before we dig into all that, do you want to give a little bit of background on yourself?
Charlie: 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 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 needing to organize yourself before you organize anything else really rung true.
Andrew: 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?
Charlie: 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.
I love walking in the morning and that's usually when I'm thinking about things. 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. 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. 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.
Andrew: 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.
Charlie: 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.
Andrew: So let's break down the system—the library of questions.
Charlie: 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?
Charlie: 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."
Andrew: 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 fiancée 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.
Charlie: 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?"
Charlie: 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.
Charlie: 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.
Andrew: On a good day, how much deep work do you get?
Charlie: On a good day I get 3 to 4 hours of deep work. On a bad day, like zero.
Andrew: 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. Whereas before I'd have to go find the book, sit down, open it up, and be like "ah, what chapter was that on?"
Charlie: 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.
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