#47 My Digital Workplace Is a Mess

My digital workplace is a mess. Not the charming kind you can romanticize as “creative chaos”, but the kind that slows me down. 

I can no longer easily find what I was writing a week ago. Not because the text is gone, but because it’s buried in a pile of loose notes in different applications and services. Whatever system I thought I had, I clearly haven’t maintained. What makes this even more ridiculous is that I know I have started on this exact text before. I’ve had these sentences in my head. I’ve written them down before. Yet, here I am, doing it all over again.

In my everyday work, as a CEO and board member, I try to help businesses move in the right direction. It sounds lofty. In practice, it’s a steady loop of researching, listening, writing, facilitating, emailing, talking, and then writing some more. And a lot of it depends on being able to capture my thinking as I go, and find it again when I need it.

A couple of years ago I moved from Evernote to Notion in the hope that I would increase my efficiency. I didn’t. Notion has its merits, and I understand why people love it, but for me it hasn’t worked as a primary writing tool. I found myself spending more time organizing and navigating than writing, and it became harder to pick up a thread I’d started earlier. Next up: Obsidian. But that’s a story for another day. What I really wanted to talk about here isn’t Notion vs Evernote vs the next shiny thing. It’s the need for continuously “sharpening” your tools and improving our processes, and what happens when you don’t.

There’s something comforting about looking at crafts where “the work” is visible. A chef does small things constantly, a quick sharpen, a wipe-down, putting things back where they belong. Then there are the regular routines, like restocking, cleaning properly, making sure tools and equipment are reliable. And once in a while there’s the bigger reset where s/he is changing the setup, replacing gear, or improving the process. The same goes for a painter, a carpenter, or a mechanic.

The “real work” isn’t only the moment where you write, cook, paint, cut, or repair. A big part of the job is readiness. The thing that makes the visible work reliable, fast, and good. 

I used to be good at this. Really good. Especially when I worked as a designer. I used to have time booked in my calendar for regular cleanups. Structuring files, updating tools, evaluating new ones, refining the workflow. It wasn’t something I looked forward to, but it made everything else smoother. It reduced friction. It gave me a sense of control. It made it easier to start, and easier to continue. 

This is my attempt at getting back into shape. Not by obsessing over the perfect tool, but by reintroducing the habit of “sharpening” as something that is part of the job, not something I do “when I have time.”

I’m going to keep it simple. 

First, I want small daily resets. 15 minutes at the end of each day to make sure whatever I was working on is findable again. Make sure my drafts are where I want them. Remove files I’m no longer working with from the desktop. Close all the tabs and the apps that I’m not actively working with. The point isn’t a spotless computer. The point is that future-me shouldn’t have to be a detective to pick up where I left off.

Second, I want a weekly block (one hour) in the calendar that is explicitly for maintenance. This is where I clean up active project folders and archive what’s done. This is also where software updates happen. Not when I’m trying to finish something, and not when I’m already stressed. The weekly block becomes the place where I keep the system reliable, and where I reduce the small frictions that otherwise spread across the entire week.

And finally, every quarter, I want a bigger reset. Review folder structures. Evaluate new tools and settings, and remove tools I’m not using. If the system is a garden, this is the pruning. Without it, the weeds take over. This will probably take a day, but it will be worth it.

Yes. This issue is mostly therapy (so thank you for listening), but it’s also a reminder. Sharpening your tools is an essential part of the job, no matter what that job is. It’s a real activity with real value, not something you do in panic when the mess becomes unbearable. 

If you have a setup that works, I’d genuinely love to hear about it.