I've been using local LLMs for a good while now, which has been an exciting journey, but means I haven't really spent much time on how commercial models have evolved. Claude, for example, has turned from a coding curiosity into a powerhouse of agentic precision, as I discovered recently by putting Claude Code into Obsidian to organize notes for me. Sure, that's the equivalent of using a V12 engine to drive to the corner store, but it showed me how much I'd been missing.

I think I was hung up on thinking Claude was only for developers, and I'm no developer. I can understand pseudocode logic and follow along with coding language documentation, at least enough to know what a script or applet is doing, but creating something with that code is a skill I'd never mastered. It's funny, really, considering I have a background in Comp Sci, Psychology, and AI, but the landscape was drastically different nearly three decades ago.

Plus, Claude can actually do things on my PC, while asking for confirmation every step of the way, unlike some cheeky codebases that are now owned by OpenAI. I've been using Claude to digitally reassess and organize my messy file structures, and the only question I have is, why the heck is this not possible with Copilot?

Claude has one feature that beats everything else for me

Cowork is a revelation

I've always struggled with two things: organization and accountability. The latter has improved over the years through practice, but I still work better when I have a second person around, even if they're not actively doing anything to help. The former is still an unmitigated disaster, whether it's my physical desk drawers or the digital ones that hoard my documents and other files.

And that's where Claude comes in. Or to be more exact, Claude Cowork, a new agentic feature that lets me chat to Claude and get real work done on my PC. The only limitation on my Windows desktop is that it won't work outside the C: drive, as some measure of sandboxing is required to keep my PC safe.

I've been using this new agentic ability to organize saved files, screenshots, photography, and my disastrous downloads folder, and it's been one of the most impactful additions to my workflow. I don't have to tediously rename individual files, or move them by hand, or even think about the folder structure — Claude does it for me and I couldn't be happier.

You'll need a Pro or Max plan for this

Unfortunately, those who might want to try Cowork for free can't. You'll need the Pro, Max (or Team, Enterprise), and it costs $17 a month for the Pro plan, so it might be worth it. I know for a fact I spend more than an hour a month reorganizing my files as they build up, and I'm more than that per hour, so the math checks out.

Time to make sense of my digital clutter

I hate organizing anything

The problem with getting my system organized is that without an imposed structure, everything falls into chaos. My brain is not a well-ordered machine, and neither is my working environment. As below, so above, or however the saying goes.

And it's not like I haven't tried. Oh, how I've tried. I have file structures in OneDrive, Dropbox, the other hard drives in my PC, on my NAS, and everywhere else I have data. The problem is, once it goes out of view my brain forgets it exists, so if (okay, all the time, so when) I move files and don't name them correctly or into the correct folders, I can't find anything.

Claude Cowork is the only tool I've found that can organize photos and screenshots, add descriptive names, and put them into organized folders ready for later use, without me actively doing anything. And that's the whole point: a tool to organize my files should not take more time to set up and use than it would for me to manually move those files. Every other tool I've tried fails at this.

Claude's the intern I always wanted

So, I ask Claude to organize my screenshots at the end of the day, in case I need to keep them for future use. I don't particularly like automating tasks like this because I don't always check whether they actually ran, and I've lost files because of it. But asking Claude, it'll scan the folder, figure out appropriate folder bins to sort things into, and then ask me before it moves anything.

Drafts/
 screenshots/
 auto-claude/ ← 13 files moved here
 claude-cowork/ ← 4 files moved here
 ipad-home/ ← 6 files moved here
 youtube-tv/ ← 5 files moved here

It also gives me a sense of agency, which makes me feel more productive, and that momentum carries over, getting me pumped to finish the more substantial tasks in my life.

Claude Cowork is more capable on Macs

There is one problem. Most of the extensions are written for Mac users, and Claude is somewhat limited in what it can do in Windows. I was planning on moving to a Mac for productivity tasks, and keeping my Windows machine for games, so I suppose this is the clarion call to actually do that, but I do want to be clear that Claude isn't the reason I'm about to buy a shiny new Mac, only part of the overall reasoning.

Claude Cowork handles my scut work, so I can focus on creation

I'm sure there is a ton of other things that Claude Cowork can handle for me. Maybe I'll explore those one day, but for now, reducing the tedium of organizing my PC files is plenty enough to warrant the Pro subscription fee.