Today I Learned

• Work, Structures, Design
  • Good Design
  • Must-reads
  • Other book recommendations
  • Working
• Topics
  • Design
  • Design Leadership
  • Design Systems
  • Strategy
  • AI
  • Audio, Video, Disco
  • Random

Work, Structures, Design

Good Design

An evolving list of design principles:

• Elimination over addition: remove every non-essential element, interaction, and decision point. Question every piece of text, button, and visual element. If it doesn’t directly serve the user’s goal, eliminate it.
• Focused: One primary action per state. Minimize secondary options that create decision paralysis. Clear visual hierarchy with emphasis on the primary action, with clear outcomes.
• Confident messaging with a bias toward action: Focus on what the user will do, not the system.
• Better: There are many ways to solve human problems, and good design does it better.
• Aesthetic: Create visual clarity and beauty through excellent use of typography, negative space, layering, and color.
• Ethical: Good design respects user agency, promotes well-being, and considers its broader impact on society and the environment.

While it’s important to ground good design in principles, it’s also important to understand how good design comes to life and what needs to exist to create great products. My README shows more about creating that environment.

Must-reads

• Design Form and Chaos
• Making Music: Creative Strategies for Electronic Music Producers
• Understanding Context
• How Artifacts Afford. This is my “getting started” recommendation that is superior to The Design of Everyday Things.
• Thinking in Systems. This book broke my brain.
• Systems of Systems
• Resilient Management. My go-to for new managers.

Other book recommendations

• Set Boundaries, Find Peace. Breaks down different types of boundaries and how to assert them.
• Activist Affordances. The entire design of the world works against people with disabilities. This book shows how disabled people navigate their world with creativity and ingenuity.
• Creative Leadership: Born from Design. I did not love this book as a total product, but it has transformed what I view as my (and other design leader’s) superpower: creativity.
• Dilla Time. This book fundamentally changed how I create art, embracing imperfection and humanization.

Working

• 8AM Monday is my ceremony for setting up my week.
• The Importance of Talking Points. The most important thing I learned leading a 45+ person team was the role of shared talking points.
• Structured. I’m trying this daily planner app out to help plan my days.
• Mouseless. I learned to write code without a mouse, and I realized this is how I approach working with all tools (Figma, Coda, etc). It helps me be hyper-efficient when building stuff.
• How to Build Anything Extremely Quickly. I love this approach to working: breaking up big tasks into smaller ones, knocking them out quickly, and returning to refine them when the MVP is done.
• Better designer-developer collaboration for an Agile world. Breaks down how Jira and Figma can work together to facilitate production.

Topics

Design

• Essential Design Principles. Apple’s Essential Design Principles are simple: Wayfinding, Feedback (including Visibility, Consistency), Mental Model (Proximity, Grouping, Mapping), Affordance (including Progressive Disclosure, 80/20 rule), Symmetry. This list misses Aesthetic, though the linked talk definitely talks about the role of aesthetic in design. I’ve used these principles to baseline on good design foundations for digital apps.
• Mobbin is a neat tool for screenshot inventories of apps/websites. It’s helpful for quickly critiquing particular flows, like onboarding. I used their Figma plugin to run a critique on “consumer grade” design.
• Benny Safdie on The Curse - Episode 10. Spoilers. “If you have a drawer and there’s no handle on the drawer, how would you open it? Would you tip it forward so the drawer falls out? Would you use a knife to get into the crack and open it? Would you take some tape, stick it to the front, and pull it out that way. You’d come up with a lot of different ways to open that door. And what you’d find inside is the same information. But the way you got that information was your own. If you put a handle on the drawer, you open it right up and find your information. So you lose a little bit of that process and that searching, which I think is important.”
• Inside the design decisions of how initials should display in avatars. When showing default initials in an avatar, there are some small and big decisions when it comes to different names and titles.
• Modern iOS Navigation Patterns. A few navigation patterns in mobile based on different objectives and outcomes.
• Good Typography, Better Apps. Breaking down V for Wikipedia’s typography-driven approach to a more readable article experience, broken down by text size, horizontal rhythm, line length, and vertical rhythm.
• Multi-edit in Figma. Multi-select in Figma now grabs similar layers based on name and allows you to apply the same edits across multiple frames.
• Design Patterns Catalog. A guide to building trustworthy products.
• Air Travel Design Guide. An excellent breakdown of air travel design decisions, like how baggage tags are designed.
• How long should objects last? The half life of designed things.
• Visual design rules you can safely follow every time. I like practical, compact principles like these, and it’s also important to break them.
• Swiss Design: Iconic and Influential. A brief history to the Swiss post-war design movement.
• Navigation design for iOS. Work project has our team deep into information architecture for mobile contexts.
• WWDC 2024 sessions I watched:
  • Add personality to your app through UX writing
  • What’s new in Wallet and Apple Pay
  • Steamline sign-in with passkey upgrades and credential managers
  • Enhance your UI animations and transitions
  • Design great visionOS apps
  • What’s new in UIKit
• Config 2024 Playlist:
  • Eames & teamLab: crafting for the physical space
  • Beyond the hype: a critical look at design systems
  • Enhancing product experiences with AI
  • Design quality and brand
  • From keyframes to keycaps
  • Advocating and designing for human needs
  • Lost Found in the details. I’m a huge fan of Jessica Hische and have seen a few of her talks over the years. The Periodic Table of Branding and detail in lettering/logotypes is incredible, and Hische has a ton of use cases and before/afters that are very inspiring.
• Copying is the way design works. The role of copying in design and art.
• Japanese web design: weird, but it works. Here’s why. When in Japan recently, I noticed that the information architecture of Japanese ecommerce sites very much reflected more maximalist designs of the 2000s. The source material seems a little under-researched, but it’s an interesting dive into how culture impacts UI design.
• Corporate Memphis When conducting a design evaluation, we noticed the ubiquitous tech style of flat geometric illustrations not knowing it had a whole name.
• Mindsets. An interesting alternative to personas.
• CSS Property. CSS is evolving to do some cool things!
• Commit: Online Groups with Participation Commitments. Cool paper on designing engaging communities.
• Microsoft Desirability Toolkit. An interesting set of words that can be used to describe software, modular for testing responsiveness and aesthetic (but maybe not together).
• Creating the Glass Surface. Using SVG filters to create the liquid glass effect using pure CSS. I’m not sure this is worth the performance hit (native or CSS).
• Web interface guidelines. Vercel’s AGENTS.md for agentic coding of web interfaces.

Design Leadership

• 🔥 Katie Dill: Building beautiful products.
  • Beauty and delivery are not at odds. Don’t underestimate the role of sentiment in how people perceive products.
  • Gotta have the courage to say: this doesn’t meet our standard of quality.
  • Essential journeymaps. Create 10-15 critical journeymaps for your product and Walk the Store regularly to keep leadership and teams close to how people use your product.
  • Great product companies have an “editor”–a person in power who is somewhat opinionated about product design upholding the standard-of-quality.
  • In hiring, look for judgment and taste in addition to design skills.
• Most HR Data is Bad Data. The processes for assessing performance are rife with bias and fundamentally broken.
• $400,000 a year and 10 hours a week at Google. The bar to get promoted is very, very high, but the bar to get fired is very, very low. Because HR data is broken, you can easily game the system to do as little as possible without getting fired.
• 9 - I am involved in the planning of the work that affects me. The Ritz-Carlton service values comprise 12 “I” statements that allow them to fulfill their service promise to themselves, each other, and guests to create an elevated experience.
• Managing Someone Who’s Too Collaborative. Great distinctions between leaning on collaboration when faster (and more autocratic) decision making is needed, considering how this presents different for women and men in the workplace.
• The myth of Servant Leadership. Explores the religious and patriarchical roots of Servant Leadership through a feminist/gender neutral lens. I noticed a rise in Servant Leadership’s popularity during COVID-19 (perhaps related to burnout and mental health in the workforce). However, I have always felt some tension between S-L theory and application.
• Staying hands-on: how designers can lead without waving the work behind. Examining the false narrative of leadership meaning you leave design and designing behind.

Design Systems

• Porsche has a Design System. Besides the regular hits of a modern design system, it includes some interesting content like their Definition of Done. I love the details like “Smallest possible DOM hierarchy.”
• Expressive Design Systems. In the pursuit of consistency and maintainability, design systems risk suppressing creativity by being too rigid. Perez-Cruz proposes flexible design systems that are “expressive,” allowing them to be bent and broken where needed to evolve.
• The broken promises of design systems. Great designs never start with the system.
• Mantine. This is one of my favorite new UI libraries, and might be a good post-Tailwind solution for modern websites.

Strategy

• OKRs are bullshit. I’ve used OKRs extensively in my career and find them challenging as a framework due to their universality.
• An Audacious Plan to Halt the Internet’s Enshittification. Cory Doctorow breaks down the phases of enshittification, which plagues many of the software platforms around us. First, there’s a fight for users in a two-sided marketplace. The switching cost is made artificially low. As profit becomes more lucrative, the business then taxes its seller or business personas in the ecosystem. In the last phase, when it’s not enough to tax the business users, the entire ecosystem is taxed because the cost of switching is too high and everyone is being held hostage. Introduced me to the term “chokepoint capitalism.”

AI

• Language Model Sketchbook, or Why I Hate Chatbots. Getting past the laziness of chatbots and into the real power of LLMs.
• ChatGPT is bullshit. “Because these programs cannot themselves be concerned with truth, and because they are designed to produce text that looks truth-apt without any actual concern for truth, it seems appropriate to call their outputs bullshit.”
• I will piledrive you if you mention AI again. Where does hype end and utility begin?
• Navigating the Jagged Technological Frontier. Lots to unpack here and many references to previous work, but this can help inform approaches to complex task automation and how to create cognitive load when human intervention is needed in task automations that are risky or flaky.
• AI Design Studio. Open-sourced RISD course.
• Project IDX. I’m composing this update to my TIL on Replit, and I love the idea of an integrated, web-based IDE (basically Visual Studio Code on the go) with agentic coding built in. I’ve already edited code on the train, while I was on a trip, and other random contexts. I used to do this via SSH and neovim, but this feels more accessible and fun.
• PBJ Problem. Natural language instructions create challenges for LLMs (and compilers.) To have more command over how LLMs work, we have to be more verbose, descriptive, and directive. For certain tasks, shaping the instruction may be faster than simply doing the work.
• Extracting high-quality claims from language model outputs. Claimify helps detect and verify claims generated by LLMs to ensure they’re accurate and disambiguated.
• Noam Chomsky Speaks on What ChatGPT Is Really Good For. Chomsky’s 2023 read of ChatGPT calls upon unique human faculties (moral and language) that cannot be replicated by AI.
• I Love Generative AI and Hate the Companies Building It. […] A hierarchy of harm where the question isn’t who’s good - it’s who sucks least. = Using AI in services. The UK government’s guide to responsible use in public services.
• OpenAI Is Just Another Boring, Desperate AI Startup. OpenAI is trying to do too much, and it’s critically unsafe.

Audio, Video, Disco

What am I playing? The Hacker @ TheLotRadio

• Remaking the water caustics effect from Blade Runner. Pinhole light into water casts the caustic effect against walls with movement creating the texture.
• The Making of Weyes Blood’s Underwater ‘Titanic Rising’ Album Cover. One of my all-time favorite album covers, done practically in a pool.
• Being Free of Photography Dogmas. “I am poisoned by self. By self consciousness, by self criticism, by some inner grandiosities, all this ego related stuff that I need an escape valve from. You can do it all kinds of ways, but this is the greatest way I’ve ever found.”
• Do The Right Thing - Making Of. Beautiful 16mm-esque behind-the-scenes about the production of Do The Right Thing.
• Stop Shooting At F 1.8. Mostly because I’m guilty of too much bokeh.
• When Leica Met Apple.
• Why Steven Spielberg Avoids Wide Open Apertures.
• Learning to See with Stephen Shore. An interview with Stephen Shore about how his photography has changed over the years, bridging multiple eras and technologies.
• Steve Jobs on Paul Rand. Steve Jobs talks about the logo development process for NeXT, and working with Paul Rand who famously told him “I’ll solve your problem for you. If you want options, talk to another designer.”

Random

• How Complex Systems Fail.
  • Post-accident attribution accident to a ‘root cause’ is fundamentally wrong. The evaluations based on such reasoning as ‘root cause’ do not reflect a technical understanding of the nature of failure but rather the social, cultural need to blame specific, localized forces or events for outcomes.
• The Shirky Principle. “Institutions will try to preserve the problem to which they are the solution.” In systems thinking, I think this maps to the resilience of systems and how they protect and preserve themselves.
• 68–95–99.7 rule. I’m bad at stats.
• Explorations on Single Usability Metrics. Qualifying SUM with threshold selection for subjective ratings - perceived time, perceived ease, and satisfaction. Objective measures move to pass/fail to get a slightly different lens on SUM.
• git column is a thing. Did you know that you can format output into columns using git?
• pkl takes key-pair values and objects and prints them in other extensions like yaml or json. But wayyyy more portable.
• Thinking Fast and Slow: A Meta Scientific Analysis This was one of my favorite books (previously a must-read), but this article changed my perspective and challenged my knowledge model sourced from pop-science books.
• Humane isn’t Apple, no matter how hard they try. Analysis of why the Humane Pin failed so spectacularly.
• Primarium. Shows how handwriting is taught in countries around the world. I’m in a handwriting phase and have added it to a few album covers recently.
• Promote your art. Tyler, the Creator explains why you need to stand on your art proudly.
• The secret of how not to be fooled.
• The 7 Questions For Any Technological Idea.
  • What is the problem that this new technology solves?
  • Whose problem is it?
  • What new problems do we create by solving this problem?
  • Which people and institutions will be most impacted by a technological solution?
  • What changes in language occur as the result of technological change?
  • Which shifts in economic and political power might result when this technology is adopted?
  • What alternative (and unintended) uses might be made of this technology?
• Text clipping in OSX. I’ve been using OSX for a long, long time, and I just learned that you can hold down any piece of text and then drag it to your desktop to create a “scratch” file very quickly. I’ve already used it a bunch.