Embrace the chaos: A messy Windows productivity system is actually perfect

I have a confession: My productivity system is a bit of a mess. When I see people sharing beautifully organized Notion dashboards and using the latest subscription-based productivity tools, I often wince.

Why does my Windows workflow feel like a cluttered desk in software form?

The things I need to keep track of are split between browser bookmarks, a collection of OneNote notes, Microsoft’s To Do app, folders of files in OneDrive, and others in scattered places. My productivity “system” is never going to be Instagram-worthy. (Let’s be honest: Your productivity system probably isn’t about to go viral on social media, either.)

After going down some rabbit holes researching new Windows productivity apps to upgrade my setup, I accidentally achieved productivity enlightenment: If your Windows productivity setup feels like a mess — but you’re actually getting things done — it’s not broken!

If it looks chaotic to someone else, who cares? People waste too much time tweaking and optimizing productivity tools instead of just using them. All that matters is whether your system works for you.

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The myth of the universally ‘perfect’ productivity system

Let’s call a truce in the productivity software wars. Geeks like me have been arguing over the best to-do list app since productivity and software blog Lifehacker launched 20 years ago. People are always trying to find the ideal productivity setup. Maybe the next to-do list app will be the one that’s absolutely perfect, with no friction, and ready to do everything you want.

Or maybe not. Unfortunately, nothing is ever truly perfect for everyone. That’s both freeing and liberating, allowing you to embrace your messy productivity system. In fact, trying to find the perfect productivity tool is a huge productivity trap. In pursuit of perfection, you’ll find yourself constantly researching new apps, migrating data, and getting up to speed on new workflows. Hey, maybe this new to-do app will boost your productivity by 1%! Let’s say it does: Even if so, is it worth spending hours switching systems? If you enjoy it, that’s great. Just don’t mistake it for productivity: It’s a hobby of tinkering with productivity tools. (I’ve had the same hobby. I get it.)

Also, keep in mind: Everything has downsides. Lots of people have impressively organized Notion notebooks, for example, but it takes some setup. Plus, it’s rather rigid compared to a freeform collection of whatever tools happen to work. Even as a Notion power user, you might find yourself adding extra tools for more flexibility. 

My chaotically productive Windows workflow

Here’s what I realized: My unusual collection of productivity hacks is actually quite useful. I’m not paying an extra dime for a productivity tool — no subscriptions. And, since I’m largely using basic tools built into Windows, there’s no risk that a fancy productivity tool I rely on will shut down overnight. It’s robust, simple, and flexible.

So let’s get to my chaotically productive workflow. These are all just things I personally do using a workflow that’s evolved to take advantage of common tools in weird ways that work for me. What works for you will be different, and that’s the key.

Email inbox as reminder tool: If I know I’ll need to reference an email soon, I’ll just leave it in my inbox — possibly with a star. Who needs “inbox zero” or a perfect labeling system? I’ll archive the email when I’m done.

Browser bookmark bar as a scratchpad: I drag links I want to save for later right to the bookmarks bar — no need for extra tools. I’ve used that same setup for reminders, too, such as saving a bookmark named “Birthday on Wednesday” at the left side of the bookmarks bar so it’s always in my face. It’s like a digital sticky note, and I can delete it when I’m done. Chrome, Firefox, Edge, Brave — this works in any browser.

Your browser’s bookmark bar can be a lightweight to-do list, a note-taking tool, and even a reminder system. There are no rules!Chris Hoffman, IDG

Controlled chaos for notes in OneNote: To capture article ideas and other raw writing-related inspirations, I jot them down in OneNote. I don’t worry much about organization. Instead, I make a new section for each month (like “March 2025”), dump notes into that monthly section, and move on with my day. To find the notes later, I can scroll through the monthly section or just use OneNote’s search feature. The key is that I can capture notes fast.

Microsoft To Do as a calendar: I use Microsoft’s tasks app, and I wish it integrated with a modern calendar app. After some digging, I decided to just use it as a calendar, anyway. I have a task list titled “Calendar” in Microsoft To Do, and it’s filled with important dates (appointments, birthdays, shows, and so on). I can quickly see a chronological list of all the events I have planned, and it’s integrated with the “Planned” view so I can see everything upcoming in one place — both tasks and calendar events. Microsoft To Do wasn’t meant for this — not at all — but it works for me.

Microsoft To Do doesn’t integrate with the new Outlook, but it should.Chris Hoffman, IDG

Folders of jumbled files in OneDrive: I don’t obsess over the perfect folder structure for where each file should go. I sometimes sort files into folders, but often I just dump files right into my Documents folder with a clear name. I can find them with search later.

Turning to paper when software is too much: When I was running How-To Geek as editor-in-chief, my digital task lists became overwhelming. I turned to a physical notepad next to my PC. On good old-fashioned paper, I wrote down the most important tasks I had to accomplish each day and checked them off as I went. Something about the physical paper was an antidote to the digital chaos. And it wasn’t a fancy Moleskine notebook, either — just a random pad of paper I had lying around.

The cross-device syncing bonus: Since I’m using built-in Windows tools, they’re always close at hand, and they sync between all my PCs with no extra software. That means I can easily access them on my phone, too.

Aim for organized chaos

That was a weird list, right? I’m sure some of these points sound ridiculous. “Wait, you do what with your browser’s bookmarks bar?”

The point is that this controlled chaos evolved naturally as I looked for the fastest, lowest-friction ways to save, organize, and find information.

That said, not every mess is a good, productive mess. If you struggle to find where you left things, that’s a sign your system isn’t working for you. (Search is key to the efficiently messy approach, though: With good search features, you can dig up web pages, notes, files, emails, and other things without worrying about categorizing them perfectly in the first place.) If the system feels frustrating to use, that’s bad.

On the other hand, if you’re spending lots of time managing your productivity system — making sure every note, email, and file is categorized in exactly the right place — that’s also not optimal. If you’re putting lots of time into finding the right tools rather than getting things done or properly relaxing, that’s not boosting your productivity. That’s draining your productivity.

There’s a sweet spot, and it will evolve over time. That’s what I realized about my setup — it’s always changing. It’s rather chaotic, but I also find myself managing it. I might dump something on my browser’s bookmarks toolbar as a quick way to capture something for later before I move it to OneNote or my To Do app, for example. There’s a sort of organized chaos where you can enjoy the freeform flexibility of your tools while keeping them reasonably organized.

Forget aesthetics — enjoy productivity

The web is full of productivity gurus showing off their beautiful productivity systems on social media. But I’ll bet most people are like me and don’t have an Instagram-worthy setup.

Too many people waste endless hours searching for the perfect productivity system. If you’re getting things done, you can stop searching. If it works, it’s already perfect — for you.

Will it evolve? Sure. Let it. But you don’t have to throw your entire system out and start over again. And you especially don’t have to impress anyone else — you just need to get things done, your way.

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