It was a Tuesday in 2018, and I was sitting in a cramped glass-walled conference room in Chicago, feeling like a total genius. I had just convinced our VP of Operations at the logistics firm where I worked to sign off on a new “visual project management” tool. We already had Jira for the dev stuff and Slack for talking, but I insisted we needed this third thing—I won’t name it yet, but it rhymes with ‘Sunday’—to bridge the gap. I spent three weeks setting up the boards. I color-coded the labels. I felt productive as hell.
Two months later, the whole thing was a graveyard. Half the team was still using spreadsheets, three people were stuck in Jira, and I was the only one moving cards around in my shiny new tool just to make it look like we were hitting milestones. We had created three different versions of the truth. I felt like an idiot. I had spent thousands of dollars of the company’s money to buy us more work.
The problem isn’t that we don’t have enough tools. It’s that we have too many.
The Notion cult and the death of actual work
I know I’m going to get heat for this, but I have to say it: I hate Notion. Well, I don’t hate the software itself—it’s actually quite pretty—but I hate what it does to people’s brains. It’s a cult. I’ve seen teams spend more time “building their second brain” or tweaking the padding on a database gallery than actually shipping code or closing deals. It’s vanity work. We’ve reached a point where the tool is the destination, not the vehicle.
What I mean is—actually, let me put it differently. We’ve traded the messiness of real collaboration for the aesthetic of organization. If you spend four hours a week maintaining your workspace, you aren’t a high-performer. You’re a digital janitor. I used to think flexibility was the most important feature in software. I was completely wrong. Flexibility is just a rope you use to hang your own productivity. Give a team a blank canvas, and they’ll spend forever choosing the right brush instead of painting the damn fence.
That’s it. That’s the whole trick.
142 minutes of wasted life
A couple of years ago, I got obsessed with why I felt so tired at 5:00 PM even when I hadn’t done much. I started tracking my context-switching with a stopwatch (I know, I’m fun at parties). I did this for exactly 11 workdays. I found that I was losing an average of 142 minutes every single day just to “tool friction.”
- Finding the right login (12 minutes)
- Searching for a document that could be in Google Drive, Dropbox, or the Slack history (45 minutes)
- Updating the same status in two different places (30 minutes)
- Getting distracted by a notification while trying to open a specific app (55 minutes)
That is over two hours of life gone. Every day. If you multiply that by a team of fifty, you’re basically setting a pile of money on fire in the parking lot every morning. But we keep doing it because saying “we bought a new AI-powered platform” sounds better to the board than saying “we actually learned how to use the software we already have.”
If a piece of software requires a “certified implementation consultant” just to get your team to use it correctly, it shouldn’t be allowed in the building.
Anyway, I was looking at mechanical keyboards the other day—those clicky ones—and realized I spend way too much time thinking about the tools of my trade rather than the trade itself. But I digress.
The unfair truth about “Digital Transformation”
I might be wrong about this, but I’ve started to believe that most “Digital Transformation” initiatives are just a way for middle managers to look busy. It’s much easier to buy a new SaaS subscription than it is to fix a broken culture. If your team doesn’t communicate well on Slack, they aren’t going to communicate better on a specialized video-messaging-hologram-app. They’re just going to be silent in more places.
I’ve developed a very biased, probably unfair rule: I refuse to recommend Monday.com to anyone. I don’t care if it’s the best tool on earth. The colors are too bright, the interface feels like a preschool, and every time I see an ad for it, I feel a physical twitch in my eye. It’s not rational. I don’t care. I’m sticking to it.
We’ve become addicted to the “New Tool Smell.” We think the next feature will be the one that finally makes us organized. Total lie.
Why your IT department should be meaner
We need more people in companies who are willing to say “No.” We’ve empowered every department head to go out and buy their own little stack of specialized tools. Marketing has their thing, Sales has theirs, and HR has three things that don’t talk to each other. It’s a mess of silos.
I used to think the “shadow IT” people were the heroes—the ones getting stuff done despite the red tape. Now? I think they’re the ones making everything harder for everyone else. We need a return to the boring, monolithic systems. I’d rather have one mediocre tool that everyone actually uses than twelve “best-in-class” tools that require a map and a compass to navigate.
Stop adding. Start deleting.
I don’t have a five-step plan for you. I don’t have a framework. I just know that every time my company adds a new button to the sidebar, a little piece of my soul dies. Does anyone actually feel more productive than they did ten years ago? I genuinely don’t know the answer to that, but my gut says we’re just spinning our wheels in more expensive mud.
Go delete a Chrome extension today. It’s a start.