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.

Your funnel is pretty simple when you sell only one thing. Grow your offerings and suddenly it gets complicated. In this paid lesson, we’ll talk about what to ask when you’re reworking your site’s structure to match your product offerings, and what structure makes the most sense for you.

I’m out on a little field trip this week, so let’s keep things light with some notes on reading. Someone once asked me in a Q&A what I read – not knowing, I think, that I read a lot. I read a few dozen articles and around two books every week.

Tools, which are unimportant

For articles I’ve used Instapaper, the greatest iPhone app, since the day of its release in 2008. Now that the consumer web is unreadable, I use archive.today to fix what needs fixing, which is most of it. When I favorite something on Instapaper, it syncs over to a tool that permanently archives the plain text of the web page so I never lose it to link rot.

I’ve used plain text exclusively for all of my work since 1992. Plain text is the only correct format, because it is the only durable format.

When you’re onboarding new customers, you obviously want them to complete whatever steps you’re asking – but you also probably want them to feel like they have some amount of agency. This can happen for a variety of reasons:

• Your customer base exists at a variety of experience levels, and one of those is “just show me the stupid product”

• People might not be ready to provide the information that you want or need them to enter

• There may be many different routes into your product, with onboarding less linear or direct

• Customers behave in all sorts of unexpected ways that might surprise the team; towards this end, a strict onboarding process might be too constraining or even unnecessary

So in this paid lesson, we’ll go deep on how to make your onboarding short and skippable – and what you need to do to make sure your customers are signing up in a way that’s helpful to them and diplomatic for you.

It’s time once again to read things that are not me, even though isn’t why you’re here? Let’s try not to think too much about that.

• I wrote once about Thomas Ptacek’s article where he uses LLM for development. Here is a nice counterpoint to it. Via. Related, clean.
• Give me all of the conversion maturity models that you have, please.
• As I’m sure all of you remember, in 1998 I wrote a brief piece on my blog about how the VC-funded advertising model for free content online was structurally untenable and would eventually come to be replaced by direct payment. Here is someone saying the same thing in 2025, and – no offense to the children, who remain our future – I’m sure they wrote it better than any 16-year-old possibly could.
• Civilization hasn’t collapsed quite yet, but when it does, it will be unsurprising to those who have been paying attention. For everybody else, there is numbness, bypass, and deferral.
• I wrote some text on Hobonichi Techo, Yeti, and some of the principles behind our repositioning. It can get even more meta than this!
• Dating as a head. Relatable.
• And lastly, how to make stirfry.

Over the past few weeks, we’ve covered:

• Common blind spots for independent software

• Home page issues & how to address them

• Baseline design for pricing pages

• Operational issues when designing as an independent developer

And now it’s time to cover our final lesson in this mini-course, which discusses what to do first.

There is the noise outside, and then there is the inner voice telling everything to shut up. We wrote about this recently, telling designers to stay in their lane, focus on the practice, and generate revenue the only way we know how.

This has turned out to be correct. 95% of recent projects fail. A new model comes out; the collective reaction is akin to a deflating balloon.

I can’t blame anyone for not believing the skeptics, though. This cycle was loud. It really did feel like the future for a minute there – maybe by sheer force of will, but it was there. There were moments when even I doubted whether my practice would continue to be relevant.

It turns out that making money is relevant.

In the past few lessons, we’ve talked about blind spots, your home page, and your pricing. But there’s a lot more, of course – like your actual product.

I care less about the final design of your product and far more about the operations that go into its maintenance. Making an amazing comp does not result in good design. High-quality operations result in good design.

And so instead of a lesson about how to teach you taste or aesthetics or even how to research, we’re starting with the bedrock of any good design process. A culture that accepts design is more likely to design well. A system that puts design at the forefront is more likely to remember design when building.

Anyone can design. You design. Every decision you make is a form of design. The goal is not to learn design. It’s to make better decisions.

One of the fun things about serving software again is that I feel like I’m working in a startup. I mean this less in terms of the economic conditions of the business and more in terms of process:

• Prototype fidelity (low, fast)
• Layers of approval (none, do what you can do)
• Process (push fast, QA/test, adapt)
• Consensus & critique (this looks good & I have notes)

Which is especially interesting as a designer. It’s always been the case that the actual design I’m doing matters less than whether & how it ships, but with such a fast turnaround cycle and so few layers of approval, you really can do quite a lot more.

If you’ve been reading these letters for over 6 years or so, you know that I once wrote a lot about how designers will code, and that learning code is how you create higher-quality design. Now the roles have flipped, and I think a lot more about how developers will learn the basic principles of design. Ultimately we’re all making design decisions, and in independent software businesses, many decisions will be made outside of a designer’s influence.

Now that we’ve chatted about some of the biggest challenges facing your business’s home page, we turn to pricing. In this paid lesson, we’ll talk about the specific elements of a pricing page, and how to get to a solid baseline with each of them.

We’re embarking on a small, private research project here at Draft – focused on independent software, of course. Here are the steps behind what we’re doing and what we hope to get from it.

1. Map the market

The short-term goal is to map our addressable market. Who will we offer to serve? In what specific ways are they in need of value-based design?

We’re figuring this out by going to a handful of watering holes & indices, and pulling down every independent business that makes more than $600k and less than $15M (more than that and they’d probably just hire us for a workshop).

Hi! We’re gathering some more topics to chat about over the next few months – and that’s where you come in.

Got any questions about practicing value-based design for independent software businesses? Hit reply and let us know. If we answer yours, we’ll give you a free membership for a month.

Thanks again for your support, and we look forward to hearing from you!

Continuing from last week’s lesson about some of the blind spots that people experience in independent software, we’re now going to move through the most load-bearing parts of your business.

In this paid lesson, we’ll talk about the four biggest parts of your home page, and what you should do instead.

One more note about staying in your lane, building off of last week’s letter.

Recent technological developments have largely occurred because of the growth imperative. We had a big success, then another big success, then a little success, and along the way a bunch of other successes that have rewritten the way that society works now. Then we ran out of ideas for a bit, and so what fills the void? Moreover, what happens when the answer to that question is forced onto customers who don’t actually want it, and are asking for something else?

There will, of course, be a quieter rebellion against that form of technology, and it will come faster than you think. People try to do stuff they like. People seek ease & convenience. And they’re smarter than you think.

In this monthlong course, we’re going to teach you about everything we’ve learned when designing for independent software businesses.

This isn’t a “design for developers” course. There are plenty of those, and learning aesthetics only gets you so far. Instead, we’re going to talk about the real-world issues that independent software businesses face at various stages of growth.

You’ll come out understanding some of the biggest things that people mess up, and you’ll learn both why and what to do about it.

Our first lesson is going to focus on some of the more unintuitive principles or blind spots that we tend to encounter.

Our final office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here.

If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way. Moving forward, we’re offering 30 minute 1:1 sessions for new members. Book your 1:1 here.

Returning back to design for software this week.

First, our final office hours for paid members is coming up! Join us on **Tuesday, August 5 ** to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. August office hours link after the jump!

We’re offering free half-hour calls to new members going forward. Easier than our previous hours, and more value for you. Current members can book a half-hour call with me, too – link’s at the bottom of this letter.

Now that we’ve established that you’ll be posting price, let’s talk about what prices and how. In this paid lesson, we’ll talk about pricing tiers: why they’re important, and how you should create them.

There is much noise right now. I just spent a month discussing it. How do value-based designers stay in our lane and continue to generate outsize impact for our clients?

Your goal now is to find businesses that perceive business like normal people. The rules have not changed and will not change. Here, for those in the back, are the rules:

• A business exists to serve its customers, not the other way around.
• A business needs to make more than it spends in order to survive.
• A sustainable, durable business makes its money directly from its customers – not from investors or shareholders.

That’s it. Those are the rules.

In software businesses, we post price. We post price in almost all circumstances. We post price for B2C, we post price for B2B. We post price.

In this lesson, we’ll discuss why we post price, why you will post price, and what it means for businesses to post price.

Two brief updates to membership:

• We changed billing systems the other week. Our thanks to those who signed up after the change and called out a bunch of old cobwebs that we forgot to clean up. If you were on the old system, we sent you an email that you have a couple of weeks to switch over; we’ll be turning that one off on August 01.
• We’re offering free half-hour calls to new members going forward. Easier than our previous hours, and more value for you.

Now would be a great time to join us as a member, especially if you work in software. We’ve got a lot of great lessons planned over the coming months.

It used to be that you would build something and people would use it. But it’s not enough to just make a tool that works anymore. That’s where positioning comes in, or the process of making your product stand out in a competitive market.

In this paid lesson, we’ll be going deep on how to apply a simple positioning to independent software businesses. If you’ve never gone through this exercise before, start here.

Over the past two weeks, we talked a little about the high-level view of post-LLM design and how buyers view design now. Apparently “the nickd take on LLM” resonates, since all of my opinions are universally correct and many of you are wondering how to move going forward.

I’m going to write a little more today and a little next week, and then we’ll get back to our regular programming, because (despite what you may have heard) there’s quite a bit more to value-based design than how we respond to LLM. In the meantime, I might package some of my thoughts on post-LLM design into a smaller offering. Hit reply if you might be interested.

“Post-LLM value-based design” is a bit of a mouthful, and it’s also inaccurate, because value-based design is an evergreen principle that responds to conditions.

Presumably, your home page has a masthead, and that masthead has a button for someone to get started using your product. In this lesson, we’ll talk about how to write ones that get a little… wordy.

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here. If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.

In last week’s letter, I wrote about the world we exist in as designers after LLM’s broad-scale introduction. Now I’d like to talk a little bit about the labor aspects of LLM, which are, like it or not, heavily influencing those who buy design as of press time.

There’s a lot of noise out there. Almost all writing on this topic is unreadable. I sort of get why people are getting loud, though, considering western civilization is slowly collapsing and nothing feels remotely safe or permanent anymore. Kinda makes sense why people would think LLM is a cool safety blanket of future-forward manifestation, eh?

First, our monthly office hours for paid members is coming up! Join us on Tuesday, July 8 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!

First, two stories about how social proof can be put in your headline. Then, a lesson about why and when you should do so.

Our prices on new consultative work will change at 5p CDT today. Now’s your last chance to buy a teardown, roadmap, or call with us at our current rate. If you’re an active client, your fees will not change for the duration of your work with us.

A couple of weeks ago, I surveyed everyone about what we should write about next, and “post-LLM design” won by a landslide. I find this to be fascinating, because we’ve positioned ourselves rather firmly as skeptical of LLM, at least with respect to some of the messaging that exists around it.

For the first half of my career, tech was changing the world, and there was a lot of optimism & promise around it. We didn’t really question much. The iPhone came out, then we all made a bunch of apps, then we ruined taxis & hotels. The internet was a place where we could all connect with one another and understand the world’s information. Twitter had infighting, but we thought it was funny.

We already established that design is not dead. In this paid lesson, we’ll discuss the specific ways that design is surviving, alongside some steps for you to take.

No.

Asking for design input from a wide range of stakeholders has its upsides and downsides. One downside is when someone sees a large company or influencer offering a specific solution, and they think “well, we should do that, too.”

On face, this is not a horrible idea. Other people did all of this work and succeeded, so why not us? It’s more efficient, helps us compete.

You know better, so let’s talk about it.

Some business announcements this week, and then a brief note on fiat plays:

• Our repositioning is more-or-less complete. If you find anything on our site that looks off or requires a rewrite, please let us know.
• We’re kicking off a major summerlong project on the topic of onboarding, and I’m doing a small literature review for it. I’m already intimately aware of Hulick’s work, but if you have any other books or resources for me to review, hit reply and point me to ‘em.
• For the first time in five years, we’re going to be changing our fees for new work in a few weeks. Since we could change it all right now, that means a lot of things are on sale as of the conclusion of this sentence. Now would be a very good time to book a roadmap, call, or retainer, if you feel so called. Thanks for your support of us, now & always.
• Lastly, one brief question: what would you like me to write about next?

In last week’s paid lesson, we defined the seam and discussed what you can do to address it. We’re building on that lesson by talking about why a style guide is important, and what makes it different from a design system.

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here.If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.

—

Financially, we have something here called the breakeven point, where we know we’ll be able to live comfortably, meet our expenses, and do what we want to do for the year. This typically comes around late August, when a lot of businesses lock in their strategies for the rest of the year and have chosen to get us involved. A couple of years, it didn’t happen at all. One year, it happened in early June because everybody suddenly invested in our work in response to a global pandemic.

I don’t want to jinx anything, but it’s nonzero likely that we’ll reach the breakeven point soon. Our existing client portfolio has not changed since last September, and a couple of them have chosen to hire us for more expansive work. With one more renewal, we’ll be good for the year.

Have you ever signed up for software that had a lovely-looking marketing page, and the product itself was… lacking? We call the transition between marketing & product the seam, and we think it’s of profound importance for your business.

A prominent seam results in lower retention and higher churn, plain & simple. Competitors can take advantage of it. And it’s just not a good look.

That’s because your marketing page promises something, and so your customers expect the quality of your design to translate, in some form, to the product. When someone goes through a well-designed conversion funnel, joins, pays you, and encounters something that looks like it was built ten years ago, they feel deceived.

In this paid lesson, we’ll discuss what the seam is, where it typically occurs, why it occurs, and what you can do about it.