Oct 6, 2026 · 29 min · 11 segments
Most leaders think being busy means they need better systems, better priorities or more discipline. Sometimes that's true. Sometimes the real problem is that you've built a working life around being…
And if you've ever worked in a fast-growing technology company, you understand the environment I'm talking about.
We had a phrase of, "We are building as we are flying," so therefore, priorities were changing on a regular basis.
Teams change, products change, the market change, the environment and culture struggle to keep up 'cause the rate of change was incredible.
So you can start the week thinking one thing was important, and end the week working on something completely different.
It was also absolutely mad, chaotic, frantic, and that rate of change, hey, it built character for sure.
So what happens? You have a meeting, and then you have another meeting, and that meeting becomes weekly.
And then someone else needs to attend that meeting, and then there's another pre-meeting.
Nobody sits down one day and says, "Do you know what would make this company better? Thousand more hours in meetings." It just happens, one reasonable decision at a time, well, feels reasonable at the time anyway, until eventually the exception becomes the default.
See, in January 2023, Shopify saw this and they did something that was very radical, very extreme, essentially took a giant eraser to the company's calendar.
And if you've ever worked in a fast-growing technology company, you understand the environment I'm talking about.
We had a phrase of, "We are building as we are flying," so therefore, priorities were changing on a regular basis.
Teams change, products change, the market change, the environment and culture struggle to keep up 'cause the rate of change was incredible.
So you can start the week thinking one thing was important, and end the week working on something completely different.
It was also absolutely mad, chaotic, frantic, and that rate of change, hey, it built character for sure.
So what happens? You have a meeting, and then you have another meeting, and that meeting becomes weekly.
And then someone else needs to attend that meeting, and then there's another pre-meeting.
Nobody sits down one day and says, "Do you know what would make this company better? Thousand more hours in meetings." It just happens, one reasonable decision at a time, well, feels reasonable at the time anyway, until eventually the exception becomes the default.
See, in January 2023, Shopify saw this and they did something that was very radical, very extreme, essentially took a giant eraser to the company's calendar.
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