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Why hasn’t independent software design improved over the years?

Sometimes I’m called in to do fun teardowns of various businesses. I’ve done this at MicroConf, BaconBiz, Double Your Freelancing, and elsewhere. And no matter what, I find a lot of interesting things to be poking at:

  • Site design that looks a decade old… for a business that hasn’t launched yet

  • Low-quality copy

  • Too-squishy positioning

Free post
#321
August 18, 2026
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Post-LLM design, again

The idea of “post-LLM design” continues to evolve, balefully. Someone recently wrote a universally correct piece on the emerging dynamic, where slapping “AI” on the thing, making it predictive, is causing buyers to froth. Actually doing the actual work is not. Instead, the work is being doing in secret, under the radar, sometimes even being billed as LLM-generated in order to save face.

Free post
#320
August 11, 2026
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Four times a year

I did a little podcast about why we don’t use social media.

Free post
#319
August 5, 2026
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27 public beta review

“It’s bad,” they said, and you were unprepared for how bad but you installed the thing anyway and hoo boy wow. Icons don’t align. Corners are inconsistent. When you navigate away from a list of items and back, a black band appears on the lower third of the screen. Moving emails from one folder to another, a thing you formerly did several times a day, is now completely broken, showing a blank screen instead and forcing a long press. You think wow, this is really bad, maybe they will fix it on the .1 update. In practice, you end up running alpha-grade software across all of your platforms for the next ten months.

Free post
#318
July 28, 2026
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Benchmarking: progress, questions

As mentioned, we’re creating benchmarks for software funnel performance. The goal is to use it as part of roadmapping for new clients. I’d like to talk a little about how we plan on doing this, and how far we’ve already gotten on it.

Free post
#317
July 21, 2026
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Be weird & specific

I have a standing call with my friend Quinn. I met Quinn at a professional conference before the Bad Times™ began. We became friends, I started using their usability testing platform, we stayed friends. We chat every other month and I look forward to it every time. Lots of laughter. This time we talked about work stuff, of course, as we always do, but we also talked about other stuff. Quinn’s a maker, and she recently went to a conference that had a fun little workshop where you got to make a body scrub, which is comically easy to do, and take it home. Then we talked about how I make my own face mask with a 2:1 blend of bentonite clay & crappy matcha, and I mix with diluted apple cider vinegar. It also works for detoxing your armpits.

Free post
#316
July 14, 2026
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Post-prune perspicacity

We have pruned the bonsai tree. In my conversations with close people about all of this, usually they ask what I’m working on right now, and I tell them that I’m unshipping a lot of the business. I think they expect creation, instead. We are all drawn to newness, to ascendance, to the future-forward. Lord knows I’ve been on the correct side of that one before, but all of this hits different, no?

Free post
#315
July 7, 2026
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Last chance for two books

Just wanted to let you know that it’s your last chance to get a couple of our books:

  • Store Design (buy)
  • Draft Evidence (buy)
  • Or get a bundle of all four of our books.

I’ll take these offline first thing tomorrow morning, so if you want them you’ll need to act now.

Thanks, as always, for your support.

Free post
#314
July 2, 2026
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The unshipping

As part of our repositioning, we’ll be pausing a few more offerings. Towards this end, both memberships & text will conclude this week. For those of you who supported our paid work, we’re deeply grateful for you. If you got charged anytime after June 01, we’ll be refunding your payments.

We’ll continue writing letters every week, of course. In fact, we think our letters will be better going forward, since we’ll be able to put more effort into making each of them amazing.

We’re folding text’s subscribers into this list, and if you’re not interested you can always just part ways. No hard feelings!

Finally, Draft × Sonnenzimmer sales will conclude on Friday, July 17 at 5p CDT.

Free post
#313
June 30, 2026
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How do you experiment inside your product?

Most of your experiments happen on home or pricing. Some on signup. But you can go deeper. In this paid lesson, we’ll be talking about how to run A/B tests behind the login wall of your product.

Free post
#312
June 25, 2026
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On "creative"

As promised, we’ll be concluding our sales of Draft Evidence & Store Design shortly. We’ll accept orders of either book, including bundles, until 5p CDT on Thursday, July 02. At that point we’ll take both books off sale.

We stand by all of our work, of course, but this is a permanent decision. They aren’t coming back after then. We’ll continue to put effort towards supporting our other two works, Cadence & Slang & Value-Based Design.

Thanks for your ongoing support of us, and please let us know if you have any questions!


900 years ago, I worked for ad agencies around Chicago. They’d have a “UX” need and hire me to not research, do wireframes, and hand them off to the people who made it pretty. This sometimes worked, for some definition of “worked.”

Free post
#311
June 23, 2026
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How do you synthesize research to create higher-quality data display?

I’m about to kick off a major project with a client that is turning a handful of interviews into a dashboard uncharitably, and analytics more broadly.

I have spent my whole career, even pre-Draft, circling the topic of data display like a curious leopard. Data should tell a story. Most of it, by default, does not.

Free post
#310
June 18, 2026
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Build slow

Now that we’re sold through most of the year, it’s worth talking about what’s worked for us.

Free post
#309
June 16, 2026
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How to critique: power, psychology

Building on our free letter, in this lesson we’re covering some of the more subtle, consultative aspects of critique. This has shifted over the past few years alongside new technological developments & the urgent necessity to restore design to a consultative position.

Free post
#308
June 11, 2026
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How to critique: process, structure

Announcement 1: Thanks to everyone for your interest in our open consulting slot. We are now sold through late October. Grateful, as always, for your support of value-based design.

For those of you who wish to increase your revenue in 2027, you may begin your application by replying to this email.

Free post
#307
June 9, 2026
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How do you synthesize heat maps over time?

In a paid lesson from way, way back, I talked about how to pull heat & scroll maps every month and analyze how behavior changes over time. Sometimes it changes in response to the improvements you’re making; sometimes it changes alongside the behavioral characteristics of your addressable market. In either case, you should build these changes into a coherent narrative that explain what your customers are really doing.

Recent developments have made it much easier to start with this.

Free post
#306
June 4, 2026
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Same funnel, different day

I was on a fun chat with a fellow consultant recently who does sales. I am unfond of doing sales. It’s nice talking to people who like doing sales, because we have a weirdly symbiotic relationship.

Free post
#305
June 2, 2026
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How do you run & analyze post-signup surveys?

Every software business should ask their customers what drove them to join and how they can help. Post-signup surveys should be a part of onboarding, and they should be periodically analyzed for design improvements & product direction.

In this paid lesson, we’ll walk you through what & how.

Free post
#304
May 28, 2026
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Help us out

I made a mistake recently. I was hanging out with my pal Quinn in Mexico and thanked her for referring a client to us recently. I said I hoped the box full of snacks I sent her was delicious.

“Box?”

Free post
#303
May 26, 2026
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How do you respond to edicts to change tooling?

I am, in some ways, the worst person to answer this question, since we contractually dictate tooling. However, since we have fluency in describing tooling, in knowing the systems that surround tooling, that may provide us with a perspective that could be valuable to you in the present moment.

Free post
#302
May 21, 2026
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