What happens when someone generates a front-end comp for you and says this must be the way? Of course this hasn’t happened with any of our clients, since this is unallowable into the field. But we’ve noticed this happening in other organizations, and we read this post about the survivor of a toxic workplace recently, so we feel called to speak out.

In my 20s I had a bunch of chances to move out to the bay area or New York, work at a big company, play the startup lottery. I never did, clearly. One company approached me with a creative director role and I said I’d love to accept, and then asked them to move the company to Chicago. They did not reply to my inquiry.

I have regretted nothing about this decision. Chicago is one of the best food cities in America, and it’s also the best large city for community in America. I like both of these things enough to orient my life around them. I was once wandering a different city with a local there, and they said something that stuck out to me: “this is going to sound like I’m dissing [CITY NAME], but the people are unambitious here.” I instantly got it. Chicagoans have ambitions to throw the best barbeques and go to every street festival during the summer. They do not have ambitions about their jobs, only to do good work and vibe.

In short, I log off at precisely 5:01p every single day, and then I cook, garden, go to shows, and hang out with my friends. Which is exactly what being a Chicagoan is supposed to be. My friends frequently tell me that they have to remind themselves that I’m a very different sort of person in my day-to-day job. Good. My colleagues sometimes get invited to my big parties, and they’re shocked at the vibes. Good.

Besides the obvious quality-of-life elements, there is a fringe benefit to my job about doing all of this. None of my friends are early adopters of anything except for bike lanes and locally native fruits. Their phones are five years old and their screens are cracked. Every single one of them is pausing new tech purchases because Apple is a fascist company now. Some of them are asking about screen repair.

One of the big themes I had in the hallway track of MicroConf a couple of weeks ago surrounded A/B testing, which I guess I’m a little known for here. It looks like everyone is running A/B tests now. They’re building their own frameworks with LLMs, feature-flagging new ideas, and going off the results.

I actually love this. One of my favorite clients home-rolled their framework. Another one of my old clients built a whole Rails gem for experimentation back in the day. Most contemporary frameworks are too heavy-handed and too expensive to justify for the price.

But this also creates a lot of methodological questions.

If you’re an independent publisher – meaning you print & ship directly from your place of business, and don’t contract it out to a third party – can you please hit reply to this email? Got a question about international shipping that is best served by those who have similar infrastructure. Thanks!

I enjoyed reading this piece from Elizabeth Lopatto about the current technological conditions, and wanted to write a little bit about its ramifications for value-based design.

When we think of innovation in technology, what arrives? Maybe big developments like the iPhone. Maybe “disruptive” businesses like Uber. Machine learning – the purest expression of the technology – is, admittedly, on the list.

At MicroConf this past week, one of the best talks was by Amanda Natividad on the topic of inbound traffic.

You probably know that we specialize more in what happens after someone comes to your site. But inbound matters, because the quality of traffic that you get matters. And we find that people want to know everything that they can about their inbound traffic. They want to test cross-device. They want precise attribution.

None of this is possible right now, possibly ever.

In this lesson, we’ll talk about what to do about it.

With the benefit of one year of critical distance, we’ve overhauled our website. We:

• Pared back all content & offerings that do not structurally serve our positioning.
• Used as few words as possible.
• Added surgically. New speaking page. New bit about text.
• Swapped our former three-page application monstrosity with a simpler front door. Our previous positioning required high walls, a lot of boundaries, and deep field protection. Not so much in software. Kindred spirits. We belong here.
• Fixed a few cosmetic things in the nav.

The funnel now goes Roadmap → Revise → Retainer. Growing businesses who don’t yet fit into this funnel can pick up our books or get a teardown or call.

We will be concluding sales of two of our books soon. We love Draft Evidence & Store Design, but they no longer serve our positioning and are unallowable into the field. It’s best to call time on those while they’re still getting an impact. If you run a store or library and want copies, please get in touch – we love leaving giant crates of books on our front porch for our hardworking delivery logistics system.

In a recent paid lesson, I wrote:

When you’re moving from free to paid, there are still high objections on the customer’s part, and they may not be fully convinced as to your product’s value. They may also be forced to upgrade out of necessity, creating emotions of frustration or resentment.

This poses an interesting design challenge, because it effectively acts as the first point of conversion in the funnel. Free signups are not conversion. Conversion is an economic activity.

So in this lesson, we’ll go into the baseline design for a paid upsell, and what you should avoid.

We’d like to speak at more conferences & on more podcasts in 2026, so we’ve put together a little page showing what we could do for you, what we’ve done in the past, etc. Hit reply if you’d like us to make your event one to remember. In a good way. In a good way!

We also finally answered a question you may have had.

Last week we discussed tooling: specifically how tools are generally irrelevant, and adaptability to new tools is a strong signal of longevity in the industry.

Call it the Curse of Knowledge: a difficulty in imagining what it is like for someone else not to know something that you know. They price their assets as if their customers knew as much about their quality as they do.

— Steven Pinker, The Sense of Style

In this lesson, we’ll go into how to write for customers – even though you aren’t one of them.

I read a fun thing recently where someone said that the recent flood of designers in our industry learned how to use a specific tool. Now the tool is becoming obsolete, they said, and the designers are, too.

Whether the tool is becoming obsolete isn’t terribly relevant. I personally think there will always be some demand for hands-on making, for craft, for sitting in the thing and pushing pixels a little.

But the long-arc spirit of the argument is true. Tools become obsolete all the time. Do you know of any designers who still do everything in Photoshop? Visio? Right.

Progress comes for every design tool. They change every few years. If you associate design with using a specific tool, you will very shortly cease to be a designer.

A little of column A, a little of column B.

I’m currently providing a little offering to the people who attend my talk in Portland in a few weeks, and in doing so I am writing.

Writing is best defined as four days of total psychic heat death, followed by three hours of writing the first draft in an absolute fugue state, concluded with four weeks of editing it into a fine paste. This writing is 1,200 words, so of course it’s taken over 100 hours to edit. I don’t have 100 hours to edit anything in 2026, so I’m editing it on the train, while I wait for the doctor, while I wait for my food at restaurants, while I walk the dogs. It has filled the cracks of my existence. Yet this will not make for writing that is necessarily good, because the writing may just be for me and not for you. Is the writing useful? Unclear. The writing talks about us. Writing is seldom useful when it’s about the author. Too ego-filled, ungenerous. But this writing acts as a bit of a business card, as a nice little way of planting our flag in the sand. Remember us, it says. We once met a client who saw us speak, said hello, they liked our talk and wanted to talk later but they had to run, and we handed them our business card and went about the rest of the conference. We ended up working together for almost four years. That was the only time we ever met in person.

The writing also plays to our strengths. We do both flag-plants and zines well. Zines are distinctive. Few others do them well.

The first draft is always muddy, and writing is imprecise even when it’s “good.” The idea of clarity in writing. How is writing clear? We’re not lawyers or mathematicians. The more we get into the weeds of design, the more we lean on vibe & emotion. We work well in that space and feel like our older work is a bit of an away game. When we have to print a thing now, we retreat back into an intellectual space, and so we have to edit from that angle, which feels unfamiliar and weird, a muscle you flex after a long time off.

You want to feel like you’re in control, no? Let’s math it out. Any one of these scenarios could happen, or a blend of them. Choose your own adventure!

New case study! We helped sleep accessory brand Manta Sleep through a 10% ARPU bump, a redesign, two product launches, and their best BFCM ever.

Is usability testing ever not chaotic? You’d expect a research method that generates outsize value to be relatively stable. It is not, and that is largely because of recruitment.

Your tests are only as good as the people who take them, no matter how well-written the script may be. So it’s hard finding quality people to take your tests. Platforms know this, and usually things go as follows:

One of our biggest clients recently redesigned, so we did a teardown for them. Then we had to figure out what to do with it. In an era where most people are communicating professionally via video snippet, this may be relevant to you, too.

So in this lesson, we’ll talk about what happens when someone smart records a video for you, and you need to turn it into actionable design decisions.

Some popcorn-fun things are happening in technology. Two articles, very different, worth discussing.

Fun thing 1

The first is this summary from Simon Willison about LLM’s role in “clean room coding”, as applied to a recent – and, as of this writing, still very much unsolved – open source fracas.

To sum, a famous person made a widely used open source library that was LGPL-licensed. Future versions of LGPL-licensed code also need to be LGPL-licensed. Famous person retired two years later, handed the code base to others, and those others did good by it for 15 years until a new point version came out that was a complete LLM-assisted rewrite under a new license. Famous person unretired, said “hey, that’s illegal,” and the new head of the project wrote something very, very long in response that amounted to “no.” (It also looked LLM-assisted, which I think is very funny; and it got ratioed, which is funny in a more objective sense.)

One of our clients redesigned recently, and it’s been fun looking at how things have changed. As a value-based designer, you need to know that a redesign is coming, and you need to come up with a plan for approaching it. New research is needed, and a lot of your old plans will no longer work.

I’m gonna be leading a little talk at MicroConf in April. We don’t do many public appearances anymore, so I am excited and mildly terrified to be taking the stage at the most important event in independent software. If you’re going to MicroConf, please come through and ask softball questions, thank you.

Preparing for this talk, I’ve thought a lot about where good creative ideas come from. For us, we research because we are actually extremely uncreative and hence need to punt to evidence to do some of the work for us. This has the added benefit of our coming up with ideas that actually work.

There is definitely the genre of human who comes up with something brilliant and never needs any sort of research to justify their decisions. These humans are very, very rare and if you’re reading this, you are absolutely not one of them. You are not one of them because you would be off creating the future, not reading a newsletter that is about generating better ideas.

Lately I’ve been doing a few internal teardowns for one of our clients, and in-between the groaning and forehead-pinching, there has been one common thread: copy.

There’s a deep relationship between copy and usability. That’s because interfaces are written. They have a narrative. The words they contain defines our expectations with them.

Lately I’ve thought about the prospective client who used to come in the door, look around, see a bunch of qualitative research, and ask for quantitative research, instead. Doing so is kind of the equivalent of walking into a hardware store and asking for a finished house. Like, yes, that’s the point, but we don’t sell houses. We sell the tools to build them. If you want a finished house, there are other places for you to go, instead.

Yes, there is demand for finished houses. Of course there is. But there is also demand for architects, no? Someone’s gotta figure out what to do and how to do it.

I don’t think recent technological developments will change this. You need to know what to write in your prompt. No automation will ever change that for you.

I said “used to” in that first sentence. What happened to them? We pause conversations with those who don’t understand our work. After all, you’re in a hardware store. We sell hardware here. If we didn’t think it had value, we wouldn’t be selling it.