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How do you analyze a redesign?

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.

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#282
March 12, 2026
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Design for not-you

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.

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#281
March 10, 2026
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How does copy manage expectations in contemporary software design?

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.

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#280
March 5, 2026
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Two bits (one you, one us)

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.

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#279
March 3, 2026
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How do you create business diagnostics?

On the consultative tip, one of the most valuable things you can provide to businesses is your own set of proprietary diagnostics. It’s important for businesses to know how they fit into their wider industry, and where their strengths & weaknesses lie. But this is often a blind spot for them, since they’re too busy actually running the business to know what’s wrong with them or how to improve.

This role is impossible to automate, and it’s essential to outsized consultative impact.

It must be consistently applicable across your client portfolio. And most importantly, you need to create the diagnostic yourself, because if you adopt anybody else’s you’re not fulfilling the goals of your own consultancy’s positioning. This also allows you to become irreplaceable. Helpful, yes?

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#278
February 26, 2026
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Where it comes from

Tech has always introduced new elements as if they aren’t optional. Imagine working in the industry for 10 years, taking one look at the iPhone, and saying no, that isn’t for me. Now imagine having really good reasons to nope it. That’s what things feel like right now, when we’ve run out of new ideas and so have resulted to forcing things on people.

And so it’s been very interesting watching people react to it, and what they stand to gain or lose out of reacting to it. I follow someone who runs a successful independent business. They answer to no boss and have no incentive to use new technology in their job. And they just hate the new thing. Hate it to hell, y’all. Won’t stop posting about how it’s bad. It is bad, of course, at least in the way that everybody is using it, but it’s also bad in that it’s a labor issue.

Speaking out about the thing is very liable to cost a person their future in the industry. Or at least that’s how it’s framed by capital, which makes people afraid to do it, regardless of how true that may be. Wouldn’t you be afraid? So instead you use it, and talk about using it, and you conveniently ignore all of the problems with it, because you are convinced you have to.

As a result, I’ve been asking myself a handful of questions whenever I see someone talking about the thing. What do they stand to gain out of it? What do they stand to lose by following their ethical center? Is their interest in it genuine, or is it forced by capital? Are they addicted? (People can get addicted to it. I forgot to mention that. I know this is very complicated.)

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#277
February 24, 2026
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What are the design requirements for onboarding & support emails at scale?

When you’re onboarding new customers, you’ll be sending welcome emails, how-to emails, and anything else transactional that helps them get value from your product.

Obviously, those emails will be designed. But we frequently see companies either screwing up the initial designs, or letting the emails go stale over a long period of time – making for a bad first impression.

Let’s talk about how to do it better.

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#276
February 19, 2026
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How to train

In response to a letter from a couple of weeks ago, someone asked:

How in the world is a junior designer meant to get a consultant position?

This is an excellent question. If you handed a consultative role to me in 2006, I would not have done a good job with it. Hell, I was barely competent as a designer back then. I know I’m not alone.

You don’t make junior designers into consultants. You make junior designers into senior designers. Then those become consultants.

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#275
February 17, 2026
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How does pricing influence positioning?

In software, the short answer is “a lot.”

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#274
February 12, 2026
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What will fill the design leadership gap?

When I first started in design, I would sit at the table and get a client brief, and they would frequently ask me for the iPod of X. (I’m old, thanks.) Later, I would watch as clients asked for other Apple devices, or for their product to be “like Apple.”

This is external design leadership, affecting the broader world. You’re a company known for design, and your design is broadly desirable, so those who buy design want to seem cool and hence similar to your thing.

Back then, Apple were design leaders internally, too, in our own industry. When they launched new features, the industry followed. When they offered interface guidelines, we all listened. When they put out new redesigns of their software, we redesigned our own software, too – not only to follow the normative context of their platform, but also to follow the broader trends that they were setting as leaders in design.

Obviously, Apple’s design leadership has concluded, possibly for the rest of our lives. There is now a vacuum. Who will our industry follow, instead? Who will others follow to understand what design is and how it can benefit us?

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#273
February 10, 2026
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How do you design plan upgrades?

Building off our previous lesson on plan limits, we now turn to the baseline for upgrade messaging, including the form itself.

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#272
February 5, 2026
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The higher design is

I enjoyed this podcast where two design managers talked about the state of the industry. They speak, correctly, of the primacy of consultative work, and the consultative imperative within design:

But in the last couple of years, not that the business has been super healthy for design firms, but if you, as a designer, especially coming out of school or earlier in your career, if you as a designer can get a job in a consulting environment you will feel better about your work. I just think that has now become true again. You’ll feel better about your work. You’ll be able to do better work. You’ll be able to engage in your practice with more depth and rigor. On the flip side, you’ll probably get paid less.

Designers get into their field in order to have an impact. And you can only have an impact if you manage to leverage your power. There are only two ways to do this: work in an organization that is run by a designer, where design is given the power to perform its work correctly; or consult.

They get sort of close to discussing power:

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#271
February 3, 2026
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How should you design a blank state?

When you start using software, the blank state is what you see when no data has been loaded, and you still have yet to do something. There is usually some sort of exhortation, alongside a corporate memphis comic that implies your ongoing failure.

Let’s talk about a better way.

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#270
January 29, 2026
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Away from craft, towards something deeper

On January 26, 2012, I walked out of my final job. Thanks for your support these past 14 years.


As you get more fluent with design, you find a progression from tool use to insight generation. In order:

  1. Tool use. You become really, really good at whatever design tools are in vogue at the time. Doesn’t matter which. Underneath that is a solid understanding of the basic principles of color, typography, layout, and behavior.
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#269
January 27, 2026
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How do you consult in down economies?

The news is not great. In this paid lesson, we talk about what this means for team dynamics and our ongoing consultative work.

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#268
January 22, 2026
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How to read

One of the best interview questions I ever got was the first question of an AMA, and it was: what do you read?

I don’t talk about my reading much, but I probably should, because I think it’s low-key becoming a superpower of mine. I say this because I’m currently writing to you from a jurisdiction where people very obviously read. There are multiple bookstores in every neighborhood; there’s a magazine newsstand at the end of my block. Cafés dot the parks with people quietly reading.

Every time you read, you’re not looking at your phone, which makes reading both a victory and an act of resistance. But reading is always more than that, because it has always been more than that. Reading is how you make sense of the world – and it’s maybe the most important thing you can do as a consultant.

It is cliché to say this. If your education was anything like mine, you were told, in no uncertain terms, to read, often & well. You don’t need me to tell you that, right? And yet I couldn’t help but notice that people aren’t reading much anymore, at least in America. And so there is urgency, and exhortations, etc.

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#267
January 20, 2026
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How do you message when someone hits a limit?

Oh, diplomacy. On the one hand, someone used your product a lot, which is kind of a good problem, right? On the other, now they have to pay you more.

Let’s talk about the best places to place messaging for plan limits.

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#266
January 15, 2026
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They don't tell you

Early in my career, I was like many other designers. I thought Apple was the second coming. I cared about typefaces too much, enough that it became a bit of a personal brand at parties. And in my work practice, I’m certain I was insufferable.

This is a big problem with design. We feel that we’re right, and we’re ostensibly hired for our expertise. But a few things are true:

  • Other people can and do practice design.
  • Actually designing something is 1% of the work. Basically no work.
  • Other team members have their own motivations for how and why something ships.
  • Snobbery isn’t a good look.
  • Nobody tells designers any of this.

And so we go on thinking we’re the most important part of the organization, and we wonder why others simply don’t understand us.

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#265
January 13, 2026
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Ask them

We’re going to ease back into our paid lessons with a fun one about asking people. This is more about the mindset of a value-based designer than any specific tactics. At the beginning of a new year, I hope it’s helpful.

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#264
January 8, 2026
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Watching TV

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!

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#263
January 6, 2026
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