Sept. 30, 2025, 9 a.m.

Working with what we have

Draft's Letters

Some sundry administrivia before we get started today. On Buttondown’s blog, I wrote a little bit about how I created onboarding for them and plan on adapting it into the future. Take a look!

I visited City last week, and am posting a two-parter about my experience this week on text.

I didn’t write this piece on airports, but wish I had. Did you know that there are no good airports in North America? It’s true.


I think often of the pace of change in an industry. It is all over the map, and there’s seldom a way to figure out a decent pattern.

I’ve used the exact same tissue brand for my whole life, buying the same stuff my parents did and never thinking about it. The box is the same, and the experience appears not to have changed.

My garden tools are not only the same as the garden tools that my ancestors bought, some of them literally are. My shovel was bought by my great-grandfather at the beginning of the industrial revolution. It still shovels.

The knife I use is perhaps a new model, but it’s made by a company who has made knives using the same methods for over 400 years. They switched to kitchen gear after the abolition of the shogunate.

Technology is not like this. The whole point, we’re told, is change. We’ve always talked like this: ten years of experience is “like a century,” new developments coming out that “change everything.” If the tech industry made my tissues, I would not recognize the box that I buy every time I run out.

And for my whole life, this really was true. We were on a roll there, right? The one-two of the internet & smartphones truly did change everything for everyone. Some other things came out and those were good too. You might have the watch. I’m writing this on a tablet.

At one point, though, about a decade ago, the innovations started to dry up. And we cast about for… something. We crave newness because tech always embraces the future, right? So you come out with some big new thing and then do the thing until the next new thing comes along. You are, in fact, always working on a new thing.

And we used to always roll out new things and have them land. Everybody owns a smartphone. Everybody uses the internet. Then we dropped some bricks and tried to make them shiny.

What I find most confusing about my industry these days is why we can’t simply be content with what we already have. I could be perfectly happy working on mobile design & customer happiness for the rest of my life. Heck, I could spend the rest of my career thinking exclusively about the psychology & power dynamics inherent in shipping software, and I’m certain I would never hit bottom. Instead of trying desperately to embrace newness, why aren’t we looking around and working with what already sits in front of us?

I find that this question tends to stop people. Nobody knows how to answer it. Perhaps they believe it’s built on the unfounded premise that new developments are in fact less desirable, which: fair, desirability is subjective. But you use “old” stuff all the time. It helps you live better, you pay real money for it, and you never think twice about it.

This is an industrywide version of the conversation that I typically have with executives. I talk to customers for a living. When a team is spinning their wheels about what the customer might think, I pipe up: we could ask them. Everyone falls silent, turns ashen, looks at me like I just slaughtered a goat in front of them. After a few rounds of stammering, they conclude: ok, fine, I could ask them.

So I do, often, and I find that people don’t really care about most big things that the tech industry has done in the past ten years. Or what they care about is not what we tend to care about, or emphasize. In fact, they often work hard to route around what we’ve done in the past ten years. They are fixing our mistakes, cleaning up our messes, and sidestepping the whole thing. They are working in ways that surprise us, constantly. This mismatch has never been more prominent, in my experience, after a decade of interviewing people.

And so I come bearing two invitations in this moment.

First, when customers tell you what they are trying to do, and how they are trying to get value from you, I invite you to believe them. They have no reason to lie and every reason to tell the truth.

Second, I invite you to look around our industry, see what we built prior to this shift in customer attitudes, and work with what we have. Some of it remains. Most of it is amazing.

You just read issue #239 of Draft's Letters. You can also browse the full archives of this newsletter.

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