Archive

Deep rest as slow fade. Senioritis energy. Here & not here.

Plans are made. There’s a lot to trim away & focus on. This will be our first deep rest after our repositioning, and this year we dealt with a lot in the wider world. I’m looking forward to spaciousness. Finessing the pack load. Cooking elaborate meals. Spending time with the dogs.

I always remain deeply grateful for the work I get to do, but this year it hits different. Thanks for all of your support this year. It means the world to us.

First, in July, remember that there are only 150 days until Black Friday, and have a complete panic attack. One for the ages. Total breakdown in front of your family. Start screaming in a grocery store. Get kicked out of the bus. Only then may you schedule your first meeting.

Start early. No, earlier. Call it Black November. First sale happens before Halloween. Black Labor Day. Black Arbor Day. Do not tell people that the actual sale is Black Friday. Call everything “early Black Friday.” Do not listen when they get mad at you for discounting further.

At some point, you snap and drive five hours to a state park. It is Wednesday and nobody is there. You hike a trail alone with 1,000’ of vertical gain, get to the top, and sit on a rock. The view is spectacular; the only sound comes from an occasional gust of wind. You immediately remember a great copy idea for your Black Friday campaign, get your phone out, and write it down.

Email often. 15-part drip campaign. You are Hobonichi with the slow monthlong hypebeast reveal. Black Friday as drop. Release everything. Throw away everything anyone ever thought about you. You are a new store. You start calling your store a brand for some reason.

Walk into any big-name luxury fashion brand and you will see t-shirts. Check the price of those t-shirts and you won’t believe how much they cost. (Here’s Prada, for example.)

Anchoring is the practice of pricing your low stuff high and your high stuff truly unreasonable in order to drive people to choose what you want them to choose. In either case, you’re usually disclosing your anchor first, in order to set expectations. By setting that anchor, you subconsciously telegraph what the rest of your work is worth. This is why our books are $50 and our calls are $500. If just an hour of our time is $500, suddenly $50,000 for fractional design work seems a lot more realistic, no?

So in this lesson, we’ll talk a little about the signals that your pricing page sets, and what you can do to increase average customer value by anchoring properly. By the end, you’ll have a sense of how to change your pricing page – and make sure your changes work.

I was recently reading a group chat with some design pals who were talking about their role given recent technological changes. The expectations are high, and they run largely contrary to what design does.

Despite some people’s best attempts at the contrary, humans use technology. And design is the analysis of the human element in technology.

Design asks: what do you need?

Design asks: what are you doing?

In this paid lesson, we’ll talk about how to start interviewing for your software business.

Nobody interviews customers for the hell of it. You interview for an outcome. Put another way, you never ship research; you ship the results of that research.

Good interviews should be:

My partner & I made holiday cards this year, and they are set in the most festive font that exists: Zapfino. By the time you’re reading this, I’ll have already been to one Thanksgiving party.

Now’s a good time to get your book orders in. They will arrive in time for that big holiday.

Professional tools require professional commitments. The software must be updated. File formats are proprietary, usually, so they need to work for the duration of one’s career, for everyone. And so when there are significant changes to professional tooling, they must be justified with professional outreach, professional language, and above all professional pricing.

Everybody knows that the main headline on your home page’s masthead defines your positioning, establishes the tone, and begins to resonate with the customer. It is the single most important element for conversion that you have.

Your attitude to your headline tells me everything I need to know about how much you embrace experimentation risk. It also tells me how high-quality your executional velocity is.

So let’s assume you want to test the heck out of your headline. You’ve written a bunch of different approaches, but you’re unsure which will “work” the best. How do you test a lot of headlines all at once?

I’m writing a little bit of text right now about establishing right relationship to software. Mostly this is an act of resistance. What’s practical? What’s worth changing? What is possible?

Somebody once took me out to dinner and said I’m “the most unreplaceable by AI ever.” Which implies that someone was evaluating me for replacement, which uh weird but ok. I guess they were referring to how I write weird, or (more charitably) distinctive, and how you could hoover the whole corpus of my writing up and make it riff on various topics for a minute and there would be effectively no difference. Fine.

A few weeks later, someone else called the writing in these letters “metaphysical,” which is hilarious. I don’t talk too much about my spirituality here, as I don’t think it’s terribly relevant to the practice of design. Nobody is gonna read my letters and get the religion, you know? But there is a real person behind all of this, and that person ostensibly has more of a spirit than any server farm could. So you’re probably not wrong there, either. By actually having a spirit and operating from my own intuition, I’m probably establishing an unassailable competitive advantage over the things meant to replace me. Fine.

I’ve spent the past couple of weeks working on a series of “getting started” guides for a client. We pride ourselves on the product being simple & easy to understand, even though the subject domain is far from it. So in putting these together, there is maybe an element of admission that the product is not in fact complex, or all software is terrible and must be written about, or (god help us) the customer is dumb.

None of this is true.

1. I enjoyed Anil Dash’s recent piece on LLM. This matches my own relationship: use it a little, less than you think, and view with suspicion. Frank Chimero’s recent talk is also quite good.
2. Draft will be on our annual holiday break from December 20 until January 04, and our next intermission will take place from January 05 until February 16. During intermission, we will focus exclusively on client work & members, and put the rest of our resources into working on the business for the coming year. New shipments will be paused during both of these periods, so if you want our books, order them now.
3. When the dot-com bubble popped in 2000, an unsustainable, incorrect model of funding tech went away for a bit, then grew, then took over. Now we witness another bubble. Once that pops, will we see the hyped bits of technology take over a few years later? What will we learn from the lessons of the past, if anything?
4. What if I’ve been liberally using em dashes for 20 years prior to a robot infamously doing it? What then?
5. People have been asking how we’re doing after our repositioning. The short answer is “well.” The medium answer is “we had our second best year ever.” The long answer is best experienced in person. We’re honored to perform this work and grateful for your support.
6. On a personal note, thanks to everybody who has reached out about, you know, recent events. It’s very weird in Chicago right now, which is their whole goal, right?
7. We’re opening a slot for consulting work in April 2026. Reach out if you run an independent software business and would like to begin a conversation with us.

We’ve written quite a bit about post-purchase surveys in the past, but things get a little more interesting when you’re in software. In this paid lesson, we’ll talk about what changes – and what to do about it.

As we’ve repositioned, our research practice has shifted. Think about how research typically works:

• You observe existing behavior
• You call some customers
• Do some synthesis
• Prioritize, experiment, profit

A lot of this breaks down when you’re dealing with a relatively small customer base that happens to be on subscription:

• There are more upfront objections about the sale
• Fewer people are signing up every month, making recruitment more challenging
• You have to deal with ongoing relationship management – and churn

I’m currently working on a big project where I’m updating a beloved client’s documentation site. Docs are interesting because they’re both high value (imagine your churn rate & support load by not having them) and hard to measure, making resourcing for them hard for some people to emotionally justify.

Docs are also very easy to build once & leave to seed. If you write a doc about an integration, expect it to go out of date the moment your integration partner updates their product. Ditto your own product – you’re still building, right? And this all tracks as a distraction, especially in businesses that happen to be resource-constrained.

So in this paid lesson, we’ll talk about what we’re doing with docs, why periodic reassessments are necessary, and what you can do to get your docs back up to baseline.

Over the span of a month, I recently wrote a series of universally correct essays about the implications of LLM on value-based design. The short answer is “minimal”, but describing why took a minute.

Since then, LLM has only become more controversial. Some people are very mad about it, and some people are very enthusiastic about it. Candidly, I got a lot less excited about LLM since I wrote those essays. This happened for a lot of reasons, and one of them is because I discovered that they are the primary reason for electric bills spiking in America. In fact, my own electric bills have doubled, despite my overall electrical usage declining year-over-year. That has never happened to me before. In fact, it probably shouldn’t happen at all, right?

I think for a while, a lot of us took one look at the projected climate impact of LLM and shrugged. I think that is considerably less defensible of a position these days. Building a squillion data centers and hoovering up the collected output of the human experiment is something we are allowing to happen by supporting LLM companies. It’s not a good look.

Practically speaking, I don’t feel great about using LLM unless it’s with models that I can run on my own computers – and only for relatively simple tasks. I definitely don’t feel great about LLM replacing search, or LLM being used to do all sorts of crazy sinister things like deepfakes, artistic infringement, or replacing your therapist or girlfriend.

A dead end happens when you reach the bottom of a page or sequence of interactional steps, and you aren’t given a next step to follow. In this lesson, we’ll explain the most common dead ends and what you can do to avoid them.

Busy week, so some more reads:

• Everything that Kevin Kelly knows about self-publishing.
• Ethical design.
• Basic UX texts.
• Attention.
• How to not build the Torment Nexus.
• Wikipedia.
• “Technical”.

That’s it. Take care of yourselves & each other, always.

One of the problems about working with us is that sometimes you end up signing up enough new customers to start slowly, intentionally scaling. That involves hiring people and building process. Some of that is fun! A lot of it is not fun.

So in this lesson, we’ll talk a little bit about how to scale from the very beginning, and what to look out for.

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.

We’re on the brink of reworking a pricing page that needs… clarification. Our current pricing page works, but it doesn’t answer every question & address every objection. In this paid lesson, we’ll walk through the job of a pricing page and outline how to rework yours – so the numbers don’t change.

Apple recently released a series of software updates that are, by most critical & customer impressions, bad. They are bad not because we react negatively to redesigns all the time. They are bad because people rammed decisions through that should not have shipped. They should not have shipped because of the basic principles of cognitive science. They should not have shipped because normative context already works well enough on their platforms. They should not have shipped because context should override consistency. They should not have shipped because Apple has always had taste as its key economic differentiator.

Now we are here, in this place.

On the other hand, the world is a confusing mess right now, so it makes perfect sense that Apple would turn all of their products into one, too.

Discussions of why translucency make for low-quality interface design are well-documented, of course, so I’m going to provide a few examples of obvious failures that have not yet entered the discourse, and then I will offer some next steps.