Jun 15, 2026 · 1 hr 3 min · 9 segments
## Show Description How do you estimate how long a task or project is going to take? Is it easier or more difficult with AI's help? Were web components a mistake? What do we think about Cloudflare's…
Dave RupertHost
Chris CoyierHost
Well, you're talking about like how long does certain development tasks take? How much is that changing? How does it change when you have a different role? That kind of thing.
I think that's fascinating because I've been living in it for years because we had this like the hardest project in my life was this 2.0 CodePen editor thing that's... that we were kind of rounding the end of.
Like we can barely guess what little pieces of it take, let alone the whole thing.
It's kind of, yeah, it's kind of like how many whatever pieces uh, Skittles are in this gumball machine or something, you know, you're like, Oh no, man.
well part of it or it's like the classic one of a car where you're like okay somebody needs to design the exterior somebody needs to design the chassis somebody needs to design the engine somebody's like sourcing the glass that we're going to use the windshields they're like very different tasks and each one of them has overlapping people in it and each one of them is hard to estimate so it's like what's the deal you How can we guess the end date when we can barely guess what one of those very complicated things takes? I don't know.
I mean, and then like you need to make sure there's needs to be like an overarching vision to where the guy picking out the glass isn't like, dude, orange glass is super cheap.
Well, you're talking about like how long does certain development tasks take? How much is that changing? How does it change when you have a different role? That kind of thing.
I think that's fascinating because I've been living in it for years because we had this like the hardest project in my life was this 2.0 CodePen editor thing that's... that we were kind of rounding the end of.
Like we can barely guess what little pieces of it take, let alone the whole thing.
It's kind of, yeah, it's kind of like how many whatever pieces uh, Skittles are in this gumball machine or something, you know, you're like, Oh no, man.
well part of it or it's like the classic one of a car where you're like okay somebody needs to design the exterior somebody needs to design the chassis somebody needs to design the engine somebody's like sourcing the glass that we're going to use the windshields they're like very different tasks and each one of them has overlapping people in it and each one of them is hard to estimate so it's like what's the deal you How can we guess the end date when we can barely guess what one of those very complicated things takes? I don't know.
I mean, and then like you need to make sure there's needs to be like an overarching vision to where the guy picking out the glass isn't like, dude, orange glass is super cheap.
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