This is the 500th letter.

So for new year’s, I went to my pal Kathryn’s place and hung out with a few friends. Extremely lowkey. My partner was out of town, so I rolled up solo in my casual suit with a bottle of bubbles, and we all shared tea and ate charcuterie and journaled.

When it got close to 11p, we tried to turn on the ball drop in New York. And since Kathryn is a zoomer (non-derogatory) she does not have any sort of “”””””actual””””””” TV (also non-derogatory). Tech took over TV just like it took over pretty much everything, and since we exist in the slow-motion birth of a horrifying world, truly nothing worked on the streaming tip. After some fustigation we did find something that looked like a stream. Unfortunately, instead of the mass-popular entertainment that was actually happening in Times Square, the actual ball-drop bit was relegated to a tiny thumbnail in the corner, and we just got a supercut recap of everything the fascist regime did to our country this year. Since we live in Chicago, a place that is now thoroughly radicalized, comprehensively unsubscribed, and really, really take-no-shit (CW applies for the aforelinked), this did not come off as terribly fun or enjoyable to those present, especially those who had consumed wine and were laying on the floor under a pile of blankets because gosh who stays up until midnight anymore. So we muted whatever channel we found and looked away, talked about the universe a little, and with one minutes to go the little thumbnail that we found in the corner enlarged and an actual countdown miraculously happened and well gosh the ball looked pretty small this year? The “2026” was in the same old font, and everyday partied with hats that were sponsored by the worst gym chain in America. Happy new year!

This year, we repositioned, said a bunch of universally correct things about the state of our industry, and served our clients with as much grace & aplomb as we could muster. Now it is time to resume our most sacred practice: intermission.

We annually close the public-facing parts of our business for a brief period in order to perform deep work. Posts are usually extant, although sporadic & not guaranteed. Private lessons & calls will continue for members, of course.

Intermission is structurally necessary. By generously & openly saying “no” to the outside world, we protect our field & create the spaciousness that we need to work on the business – which in turn helps us serve you better. In previous intermissions, we came up with our flagship consulting service, rewrote our first book, finished our third book, wrote our fourth book, and planned our successful repositioning, among many other activities.

Intermission is especially necessary right now. We have found the current moment to favor those who are laying low, keeping their heads down, doing the work to protect their close people. One must focus. Acting beats yelling.

Do you run a software business, but don’t know where to get started with value-based design?

Our final paid offering for 2025 is a banger: a wholly updated version of our research & operations calendar for independent software.

You’ll learn when to research, what to improve, and when to time anything for the holidays – assuming you need to, of course. By the end of the year, you’ll come out with a whole new marketing site that converts far better than before.

Link after the jump.

On the research front, we expect to discuss the correct recentering of design as a research practice, with creation existing in subservience to the research. We got a little far away from what design is, right? What you design is only as good as your ability to research.

We’ll also cover some of the more positive ramifications of platform collapse. Their conscious decision to fuck up their software is our opportunity. Look no further than design tooling, where an entire suite was built on the ability to buy it with no subscription. The door is again open there. In fact, there are doors open everywhere.

We’ve talked a little about calm companies before, but now that we’re in a few we can’t get enough of it. In fact, we seek calmness exclusively now. Fortunately, we see it everywhere. And we think calm, high-margin companies will survive what’s coming. We look forward to exploring this idea further.

Finally, we’ll be discussing the global separation of design practices that will continue to occur as American society collapses and is replaced by a broader global relationship. Not enough work is devoted to analyzing this, but we believe it to be essential. Like, century-defining essential. Wild how people are too busy playing defense to notice it happening everywhere.

It feels like every single software business owner makes the same mistake, despite the exhortations & evidence to the contrary.

That’s talking about yourself.

In 2009, I published a book that did well and was immediately out of date. Mobile as an idea was only a year old. I ended up rewriting the book, put out a second edition in 2013, and now that’s almost sold out, too.

In 2019, the spiritual successor to that book arrived in the form of Value-Based Design. Six years later, someone recently asked me if I now have to rewrite it in response to recent developments in my industry.

The answer is no, and that’s not because I’m a tremendously lazy person who is too busy cooking & petting dogs to rewrite their book. Value-Based Design doesn’t need an update because the techniques surrounding value-based design are evergreen. In fact, the reasons designers get hired are evergreen.

Value-based designers are hired for the same reason that anyone else is: to increase revenue, decrease costs, or decrease risk. There are two headwinds facing our acceptance, though. First, our expertise was at one point decoupled from all of this, making it harder for us to prove our existence. And many organizations took the functions of value-based design and internalized them broadly, which is good for design but less good for design experts.

It’s one thing to write good docs. It’s another entirely to maintain good docs. Docs are a continuous organizational function. They are only a sprint-focused activity if the organization accrues documentation debt, and documentation debt is only accrued when docs get ignored.

Updating docs should be an essential component of shipping.

So you should reduce the friction that it takes to write documentation. There are obvious operational benefits for doing so, and it also results in higher-quality docs that speak with a unified voice and help the customer in a more consistent, legible fashion.

Every business should have a style guide for creating new docs. In this lesson, we’ll talk about how to make it happen for businesses of any size.

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.