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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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Intermission

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.

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#262
December 19, 2025
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Get Draft’s 2026 research roadmap

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.

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#261
December 18, 2025
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What will we focus on in 2026?

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.

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#260
December 16, 2025
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What’s the first thing you can do to improve your home page’s copy?

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

That’s talking about yourself.

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#259
December 11, 2025
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What is it you’d say you do here?

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.

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#258
December 9, 2025
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How do you create a style guide for your software product’s documentation?

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.

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#257
December 4, 2025
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Make it click

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.


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#256
December 2, 2025
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