How to Organize Your Files Better Than 99% of People — Transcript

Your external environment is a mirror of your internal state. A cluttered desktop, a downloads folder with 3,000 files, an Obsidian vault overflowing with half-baked ideas that you swore you'd organize later. These aren't just annoyances. They actually start to drain your ability to think clearly and do your best work. That's why every so often I go through a personal process for cleaning the gutters of my physical and digital lives. A three-part process I call the big clean. We'll clean our physical space first, the place where we're doing most of our work. Then we'll clean our digital space, our files, our folders, our desktop. And last, we'll clean our mental space, our ideaverse in Obsidian, so that we can move forward with focus and clarity. Part one of the big clean process is to clean your physical space. It is so much nicer to have a clean physical space around you, wherever you're doing most of your thinking work. If it's messy, it's not going to work well. For me, when I'm here, it's this desk. It's kind of satisfying in a strange peculiar way to just clean parts of your desk and then at the end of it have something that feels so much more calm with so much fewer distractions. And yes, this is feeling pretty good right now. You ready for the digital space? Oh my, this is my desktop. Well, it's not really. It's an example of what can cause great anxiety. And here's the thing, it doesn't have to be this way. We can actually clean things up in a hurry. So, what I'm going to do right here on the desktop is create a new folder. And these are all screen grabs, screenshots that I've taken. And for now, we're just going to put here 2026 screenshots. Not all of them. But now what I can do is let me throw this folder somewhere where I can now select everything else essentially. And it's going to be pretty magical once it happens. So, you ready for this? We select everything and boom. Just like that, our desktop is cleaned up. So, step one, if you do have a messy desktop, go ahead and immediately throw all that stuff in one folder. Then, we'll go over to step two. If you're on a Mac, open Finder. On Windows, open your file explorer. And what I encourage you to do is create a folder called the plus folder. It's just a plus icon. Just create that folder. For me, I have it in Dropbox, but whatever your syncing solution is, go ahead and create a plus folder if you haven't already. Now, in that plus folder, you should create two folders, but definitely one. You do download things from the internet. I know you do. Where do those downloads go? They probably go to some other downloads folder, and it's probably not unified. And if you use multiple internet browsers, it's all over the place. What you want to do is have the single source of download. And that's what I've done here. I actually call my downloads folder with an extra s on the end. That way I'm never confused when I see any internet browser telling me what downloads folder it's going to. We go open this downloads folder and we're going to notice a lot of things here. But looks like 125 items. Here's how I think about organizing all these downloads because this isn't the best use of my time. It's not really going to net me too much unless I'm really feeling the pinch with the space on my computer's hard drive. I shouldn't be spending time here. I should be spending time with my ideas, with my communications, those sort of things. What I like to do immediately is one sort by kind. I want to see what folders I have. And if I do that, I can see, and this is kind of the hint that we're going for, every year the downloads. And you can see going back to 2020 and how many downloads are in each of these folders, how many files I give in parentheses here. So, we could start this if we wanted to for 2026 right now. Now, before we do, there is one other thing that we want to do, and that is sort by size. Now, I said we're not going to spend time manually sorting all this. But what we want to do is look at any file that is over 10 megabytes. That's my threshold. If something is under 10 megabytes, I'm going to let it slide. Too many files to worry about. It's not worth it. But for things that are over 10 megabytes, I want to look at these and ask myself which of these I can delete. Uh, as it turns out, I can definitely delete at least these ones I'm pretty confident in. And already that feels pretty good. Now, we go back to sort by kind. And let's pretend it's the end of the year. That's the time that I would actually then create the new folder. And I would go 2026 downloads. And then I'll give it a number. Then I just simply highlight everything. And then I drag and drop. It looks like 103 items. Next, do you take screenshots? I use an app that I absolutely love. It's called CleanShot X. I've talked about it in a separate video that we'll point to. And I'm taking screenshots throughout the day most days. So, if we go back to the plus folder that I asked you to create, this is also where you should spin up, if you don't already have something like this, a screenshots folder. Now, this place is a mess. Now we see 1,467 items. Again, I'm going to do the same thing. First, I'm going to sort by size and everything. I have one thing that's a video, so that shouldn't be in here, and that's a good catch. And then everything else, my 10 megabyte rule, just these two things. So, that's something that I I'll deal with later. And then we go into kind, sort by kind. If you scroll to the top, you'll see a lot of folders. Right now, there are too many folders, but I'm going to do the same thing where I create the 2025 screenshots folder. And I actually get to now consolidate and archive my 2025 screenshots. The first thing I'll do is clean up all these 2025 folders. I'll just throw those in the 2025 screenshots and start to collapse that. Then because I know that I've already archived 2023 and 2024, all of these screenshots, almost all of them should be in the year 2025. And I can double check this later. I'll just drag and drop. And now we have 1,446 images all going to the 2025 screenshots folder. That feels good. That feels satisfying. And now I have an archive and a record. 1465. That number now goes into parenthesis. 1,465 images. And what's fun is I get to compare the years. So I see that 2024 was a lot more than that. And then 2023 was basically on pace with 2025. And now we can throw in from the desktop the 2026 screenshots. So if you take a lot of screenshots, make sure you have a single source of screenshots just like you have a single source of downloads. And that's how we organize our digital life. But more and more these days, I'm not really organizing these digital files. It's not important. What's important to me are my digital notes, my ideas, and how I can link them together. So, for that, we're going to go into organizing our thinking space of the big clean process. Now, before we go any further, if you want to go even deeper with this process, we walk through all of these steps and more in greater detail inside the Knowledge Academy. Once a year, I go through this entire process and a lot more alongside you hands-on step by step with guidance and we record it and we break down the full details of how you can keep your mind and digital home clean. And by joining the Knowledge Academy, you don't just get the big clean, you also get the February Linking Your Thinking workshop, a live experience connecting ideas together. You get Obsidian Flight School, the world's best jump start to learning the Obsidian app, as well as all my best Obsidian templates, and regular monthly workshops, just like the Big Clean. The Academy only opens for a limited window, so check out the link in the description or the QR code here for more details. Now, we're in my Obsidian vault. I call it my ideaverse. Why that's so important is because an ideaverse is a connected ecosystem of ideas, and that is how we need to organize. We ne

your ability to think clearly and do your best work. That's why every so often I go through a personal process for cleaning the gutters of my physical and digital lives. A three-part process I call the big clean. We'll clean our

physical space first, the place where we're doing most of our work. Then we'll clean our digital space, our files, our folders, our desktop. And last, we'll clean our mental space, our idea verse in Obsidian, so that we can move forward

with focus and clarity. Part one of the big clean process is to clean your physical space. It is so much nicer to have a clean physical space around you, wherever you're doing most of your thinking work. If it's messy, it's not

going to work well. For me, when I'm here, it's this desk. It's kind of satisfying in a strange peculiar way to just clean parts of your desk and then at the end of it have something that feels so much more calm with so much

fewer distractions. And yes, this is feeling pretty good right now. You ready for the digital space? Oh my, this is my desktop. Well, it's not really. It's an example of what can cause great anxiety.

And here's the thing, it doesn't have to be this way. We can actually clean things up in a hurry. So, what I'm going to do right here on the desktop is create a new folder. And these are all

screen grabs, screenshots that I've taken. And for now, we're just going to put here 2026 screenshots.

Not all of them. But now what I can do is let me throw this folder somewhere where I can now select everything else essentially. And it's going to be pretty magical once it happens. So, you ready for this? We select everything and boom.

Just like that, our desktop is cleaned up. So, step one, if you do have a messy desktop, go ahead and immediately throw all that stuff in one folder. Then, we'll go over to step two. If you're on a Mac, open Finder. On Windows, open

your file explorer. And what I encourage you to do is create a folder called the plus folder. It's just a plus icon. Just create that folder. For me, I have it in Dropbox, but whatever your syncing solution is, go ahead and create a plus

folder if you haven't already. Now, in that plus folder, you should create two folders, but definitely one. You do download things from the internet. I know you do. Where do those downloads go? They probably go to some other

downloads folder, and it's probably not unified. And if you use multiple internet browsers, it's all over the place. What you want to do is have the single source of download. And that's what I've done here. I actually call my

downloads folder with an extra s on the end. That way I'm never confused when I see any internet browser telling me what downloads folder it's going to. We go open this downloads folder and we're going to notice a lot of things here.

But looks like 125 items. Here's how I think about organizing all these downloads because this isn't the best use of my time. It's not really going to net me too much unless I'm really feeling the pinch with the space on my

computer's hard drive. I shouldn't be spending time here. I should be spending time with my ideas, with my communications, those sort of things.

What I like to do immediately is one sort by kind. I want to see what folders I have. And if I do that, I can see, and this is kind of the hint that we're going for, every year the downloads. And

you can see going back to 2020 and how many downloads are in each of these folders, how many files I give in parentheses here. So, we could start this if we wanted to for 2026 right now.

Now, before we do, there is one other thing that we want to do, and that is sort by size. Now, I said we're not going to spend time manually sorting all this. But what we want to do is look at

any file that is over 10 megabytes. That's my threshold. If something is under 10 megabytes, I'm going to let it slide. Too many files to worry about.

It's not worth it. But for things that are over 10 megabytes, I want to look at these and ask myself which of these I can delete. Uh, as it turns out, I can definitely delete at least these ones

I'm pretty confident in. And already that feels pretty good. Now, we go back to sort by kind. And let's pretend it's the end of the year. That's the time that I would actually then create the new folder. And I would go 2026

downloads. And then I'll give it a number. Then I just simply highlight everything. And then I drag and drop. It looks like 103 items. Next, do you take screenshots? I use an app that I absolutely love. It's called CleanShot

X. I've talked about it in a separate video that we'll point to. And I'm taking screenshots throughout the day most days. So, if we go back to the plus folder that I asked you to create, this is also where you should spin up, if you

don't already have something like this, a screenshots folder. Now, this place is a mess. Now we see 1,467 items. Again, I'm going to do the same thing. First, I'm going to sort by size and everything. I have one thing that's

a video, so that shouldn't be in here, and that's a good catch. And then everything else, my 10 megabyte rule, just these two things. So, that's something that I I'll deal with later.

And then we go into kind, sort by kind. If you scroll to the top, you'll see a lot of folders. Right now, there are too many folders, but I'm going to do the same thing where I create the 2025

screenshots folder. And I actually get to now consolidate and archive my 2025 screenshots. The first thing I'll do is clean up all these 2025 folders.

I'll just throw those in the 2025 screenshots and start to collapse that. Then because I know that I've already archived 2023 and 2024, all of these screenshots, almost all of them should be in the year 2025.

And I can double check this later. I'll just drag and drop. And now we have 1,446 images all going to the 2025 screenshots folder. That feels good. That feels satisfying. And now I have an archive and a record.

1465. That number now goes into parenthesis. 1,465 images. And what's fun is I get to compare the years. So I see that 2024 was a lot more than that. And then 2023 was basically on pace with 2025. And now

we can throw in from the desktop the 2026 screenshots. So if you take a lot of screenshots, make sure you have a single source of screenshots just like you have a single source of downloads.

And that's how we organize our digital life. But more and more these days, I'm not really organizing these digital files. It's not important. What's important to me are my digital notes, my ideas, and how I can link them together.

So, for that, we're going to go into organizing our thinking space of the big clean process. Now, before we go any further, if you want to go even deeper with this process, we walk through all of these steps and more in greater

detail inside the knowledge academy. Once a year, I go through this entire process and a lot more alongside you hands-on step by step with guidance and we record it and we break down the full details of how you can keep your mind

and digital home clean. And by joining the knowledge academy, you don't just get the big clean, you also get the February linking your thinking workshop, a live experience connecting ideas together. You get Obsidian Flight School, the world's best jump start to

learning the Obsidian app, as well as all my best Obsidian templates, and regular monthly workshops, just like the Big Clean. The Academy only opens for a limited window, so check out the link in the description or the QR code here for

more details. Now, we're in my Obsidian vault. I call it my ideaverse. Why that's so important is because an ideaverse is a connected ecosystem of ideas, and that is how we need to organize. We need to organize for

context. That's what it's all about. The relationships between these ideas. Like why did we save these notes in the first place? So that we could remember them at the right time so that we could use them in this context. So for me, I have guess

what the plus folder. So just like in the file system where we had the plus folder for downloads and screenshots, in my thinking system, I also have a plus folder for any new note that I create that's unsorted. All right. Right. So,

if I hover over this, we can see it says 165 files. I've let this thing build up because I have better things to do. But now I'm feeling a little bit of a cluttered mind and I need to declutter

my thinking space. If I twirl open the plus folder, you can see all sorts of strange types of notes. This is overwhelming. Just looking at this, I'm thinking to myself, what am I going to click individually on one note at a

time? So, I'm going to process 165 notes and try to add context to each one and then file it appropriately. That does not sound like fun, but there's value in doing it. So, how do I make this work

and make it work effectively and efficiently? Click on search and we're actually going to select the path. Now, select whatever that folder is. So, for me, it's the plus folder and then I'm going to delete once and then add a

slash. So that's now targeting the plus folder, that file path, and we can see 165 results. It matches. Did you know in Obsidian you can click right here in these three dots, copy search results.

Now I can actually copy everything. Copy results. Copied it to my clipboard. And now I can paste it right here. That's pretty cool. And we can take it even further. So if I click copy search results this time link style I'm going

to make it a wiki link. Now all these are going to be links. So I can copy results and now when I paste it in we get all of these results. Now 165 is a lot but something is coming really

apparent to me that I have a whole linking your thinking section. So move to light and I can just tell myself anything that's linking your thinking related I can move all of these to linking your thinking. That's a huge

section. So that's going to change this file path really fast if I can move all these. So let's go ahead and now go back to the path here. We're going to organize file name A to Z. And for

everything that's linking your thinking, let's see if I can do this. If I click on this one and then I go and shiftclick over here, rightclick. Now I can just move 25 items. And just like that, I'm going to move it to my linking or

thinking folder. Atlas and light. Now, just like that, we don't have 165 files. We have 140. And that's feeling a lot better. But let's look at some other examples that aren't so simple where we actually want to jump into the note. So,

let's go back to all these things. Now that we've moved them to the light folder, we can remove those. Now, something else that I think would be useful is I have a lot of people. So, I could just start to move around and

group people. So, I'm just going to start to move these people around. When I find another one, I'll add that person. Looks like those are the only ones so far. And just like this, I have a group that I can now say, you know,

move to people. What I want to show you are the notes that we jump into for these. Let's do unlin concepts. This is a fun one. Okay. So, I'm just going to scroll through all these notes. That's a

nice concept. This is a statement idea I like a lot. Three rules of engagement with AI. That's something I want to look at as well. Okay. Now, I'm going to look at one of these and just say, where do I

want to spend my time right now? I like this idea. Billions, trillions are spent on how to best hijack our attention.

Let's open it up into a new tab, which I've done here. Okay, this is cool. Now, I'm thinking to myself, it's actually quite well linked. I know I want to mention it in the book I'm writing. It's a part of a collection that I have

called statements because it's a statement note. I also want to see what else I might have on the topic of attention. So, this is where autocomplete is such a key for you. So, all you have to do is hit the brackets a

couple times and then type a keyword like attention and then I'm going to see is there anything wo grievance-based attention farming. So, this reminds me of grievance-based attention farming.

This is a well-connected note. It's short. It's sweet. It's to the point. It connects to a big effort of mine. I can also find it through the statements. So, that's all I need to do. I don't need to

file this note anywhere. It does not need to exist in any folder, but for my purposes, I'm going to throw it in Atlas. So, let me just go ahead hit move and then I'll just move it to Atlas. So,

now whenever I need to find this note, that's where it will always be in the Atlas folder. You can have subfolders or you don't need subfolders. But if you think to yourself, how am I organizing this by context? That's our whole point

here. How am I organizing this for context so I'll find it again? Will I be able to find billions, trillions? Now, will I be able to find this note? You tell me. I can find it if I look at my

light book note, if I look for statements, or if I look for some other note, or if I just happen to be in the atlas folder. So many different ways to find this note. I feel calm and I feel

relief. But to get there, we started with our physical space, our digital file space, our digital thinking space, so we could get to this mental space of clarity, calm, and focus. If you want to go even deeper with this process, join

the knowledge academy and you can complete all these steps alongside me in real time and also watch the recording.

We go through so much more. Plus, you get everything else included in academy so that you can master Obsidian, you can master link notes, and you can have an idea verse that supports you in every aspect of your life. But if you want to

learn just the most important 80% of Obsidian in just 15 minutes, then check out this video next.