Apple Designer Kare Details How Pixel Limits Built Original Mac UI
Y Combinator
Enduring user interfaces rely on simple, abstract metaphors rather than hyper-specific hardware depictions that quickly become obsolete.
AI-assisted summary of Susan Kare: Designing Icons & Graphics For the Original Mac — original source. Check the original for full context.
Source published:
Key ideas
- Susan Kare designed the visual language of the original Macintosh by treating severe 1-bit display constraints as creative prompts, hand-sketching initial pixel grids in a notebook now held in MoMA's permanent collection. (1:51)
- Following Paul Rand's maxim to make designs 'meaningful and memorable,' Kare prioritized universal abstraction over literal hardware representation, creating enduring icons like the Happy Mac and Chicago system font. (15:26)
- Steve Jobs eliminated keyboard shortcut clutter by banning repeated Apple logos—which he derided as an 'Apple farm'—prompting Kare to discover the Nordic looped heritage symbol for the Command key (⌘). (22:15)
- Kare's post-Apple work showed that digital metaphors must favor emotional resonance over literal physical skeuomorphism: Facebook virtual gifts proved that 'cute trumped everything,' with kisses and penguins vastly outselling luxury status items. (29:56)
Detailed notes
## Background This talk was published by the Y Combinator channel on YouTube on August 14, 2026. Captured at Startup School 2026, the presentation features iconic graphic designer Susan Kare sharing the origin stories of the original Macintosh's visual identity—including the Happy Mac, Chicago typeface, and Command key—alongside enduring design philosophies learned from working with Steve Jobs, Paul Rand, and early Apple engineers.
## TL;DR Art historian turned pioneer iconographer Susan Kare recounts entering Apple with no computer background and sketching bitmap fonts and icons onto graph paper to humanize early personal computing. She details the creation of landmark interface elements like the Chicago font, MacPaint tools, the Happy Mac, and the Borgholm Castle-inspired Command symbol, highlighting how tight hardware constraints fueled enduring visual shorthand. Kare traces her post-Apple trajectory through Windows 3.0, General Magic, and Facebook virtual gifts, illustrating why simplicity, universal metaphors, and iterative discipline consistently outperform ornate realism. She concludes with candid reflections on startup culture, pitching strategies for Steve Jobs, and design wisdom from mentors like Paul Rand on embracing resilience and letting go of preciousness.
## Atmosphere & style The presentation carries a warm, self-effacing, and deeply nostalgic tone, blending fireside reminiscence with practical masterclass insights. Kare speaks with relaxed humility and dry wit, chuckling over early design missteps like the literal bomb crash icon while recounting legendary episodes like hoisting a pirate flag over Apple headquarters. Listening feels intimate and grounding, stripping away the tech industry's self-important veneer to reveal personal computing's foundational breakthrough as an earnest, human-scaled craft project driven by empathy, curiosity, and playful experimentation.
## Bulletin - [01:51](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=111s) Susan Kare designed the visual language of the original Macintosh by treating severe 1-bit display constraints as creative prompts, hand-sketching initial pixel grids in a notebook now held in MoMA's permanent collection. - [15:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=926s) Following Paul Rand's maxim to make designs 'meaningful and memorable,' Kare prioritized universal abstraction over literal hardware representation, creating enduring icons like the Happy Mac and Chicago system font. - [22:15](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1335s) Steve Jobs eliminated keyboard shortcut clutter by banning repeated Apple logos—which he derided as an 'Apple farm'—prompting Kare to discover the Nordic looped heritage symbol for the Command key (⌘). - [29:56](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1796s) Kare's post-Apple work showed that digital metaphors must favor emotional resonance over literal physical skeuomorphism: Facebook virtual gifts proved that 'cute trumped everything,' with kisses and penguins vastly outselling luxury status items.
## Key takeaways - [00:07](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=7s) Effective iconography begins with a strong conceptual idea rather than visual embellishment, adhering to Paul Rand's rule to keep work meaningful and memorable. - [01:51](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=111s) Kare transitioned from sculpting to computing without technical training, borrowing typography books from the library and sketching bitmap concepts on graph paper before interviewing at Apple. - [05:01](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=301s) The early Mac software team focused on immediate accessibility, replacing confusing labels like 'Do it' with 'OK' and restricting early icons to 16-by-16 and 32-by-32 pixel grids. - [08:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=506s) Chicago introduced proportional screen typography on low-resolution displays, eliminating monospaced compromises and visually foreshadowing the physical layout of the first Apple iPod. - [11:47](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=707s) Andy Hertzfeld's interactive Icon Editor replaced paper sketching by allowing bit-toggling on an enlarged grid with a live 72 DPI preview that automatically outputted hexadecimal code. - [15:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=926s) Applying Scott McCloud's comic theory, stripping an icon of granular detail transforms it into a universal vessel that any user can relate to, whereas excessive detail limits resonance. - [18:22](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1102s) Designing icons based on literal contemporary hardware, such as the ImageWriter printer with tractor-feed holes, leads to premature obsolescence compared to broader metaphors. - [22:15](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1335s) Steve Jobs rejected menus cluttered with Apple logos as an 'Apple farm,' leading Kare to research symbol reference books and adopt the Swedish roadside marker depicting Borgholm Castle for the Command key. - [25:20](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1520s) Bitmapped interface design sits on a historical continuum with ancient pixel-like media, drawing structural parallels from Egyptian hieroglyphs, mosaic tiles, and needlework samplers. - [27:32](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1652s) Introducing color in Windows 3.0 required pixel dithering across a restricted 16-color palette to create textured, muted tones and reserve stark red for critical system alerts. - [29:56](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1796s) General Magic's ultra-literal skeuomorphic office metaphors, including virtual hallways and literal 'jars of text,' failed to anticipate how quickly digital abstractions would outpace physical office objects. - [29:56](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1796s) Facebook's digital gift store demonstrated that human purchasing behavior favored emotional symbols like lipstick kisses and penguins over high-status items like diamond earrings and Rolex watches. - [37:18](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2238s) Paul Rand rejected Steve Jobs's proposed spec-work design contest for NeXT, demanding $100,000 to deliver a single logo that integrated the concept directly into the company's name. - [44:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2664s) Alan Kay's concept of nested hierarchy guided the Mac UI team to tuck technical complexity away so that initial interactions remained clean and effortless. - [45:54](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2754s) The Mac team embraced Steve Jobs's countercultural motto that 'it's better to be a pirate than join the navy,' prompting Kare and Steve Capps to hoist a hand-painted pirate flag atop Apple's Bandley 3 building. - [48:25](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2905s) Andy Hertzfeld taught Kare never to pitch Steve Jobs a single design concept, as Jobs would reflexively reject it; presenting multiple alternatives allowed him to critique weaker options while approving the preferred design. - [48:25](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2905s) Early startup teams operate most effectively below a threshold of roughly 15 people, beyond which consensus hiring and single-room cultural alignment inevitably require formal trade-offs. - [49:46](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2986s) Dennis Hwang's early Google Doodles proved that breaking orthodox brand guidelines to alter a corporate logo can generate deep audience engagement rather than brand dilution.
## Detailed walkthrough ### [00:07](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=7s) Introduction and Paul Rand's Guiding Advice
Susan Kare introduces herself as an iconographer and designer who has worked on numerous tech projects over decades. She frames her experience working on the Macintosh team inside Apple as being effectively part of a tech startup, noting that many of the core issues and themes resonate directly with modern tech developments like artificial intelligence.
Looking back at her career, Kare highlights a foundational design philosophy she received from legendary graphic designer Paul Rand (creator of the UPS, IBM, and NeXT identities), with whom she was fortunate to work. Rand advised her to focus on making things "meaningful and memorable." For Kare, the essence of that maxim is simple: start with a strong idea, and the visual form will naturally follow.
[01:51](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=111s) From Welding Sculptures to the Apple Interview
Kare entered personal computing from an entirely non-technical background: she was a fine art major with a PhD in art history who knew nothing about computers. Immediately before joining Apple, she had been working out of her garage welding a life-sized razorback hog sculpture for an Arkansas museum. While building the sculpture felt like living a creative dream, the solitary routine grew lonely and left her eager to collaborate with a team.
An opening presented itself through Andy Hertzfeld, her high school friend from Pennsylvania who was working as a system software programmer on the nascent Macintosh project at Apple. Hertzfeld reached out because he remembered she loved art and had worked on their high school yearbook. He showed her a bare Macintosh display chassis without a plastic casing and asked if she would interview to design small screen symbols and digital typefaces.
Prior to that point, Kare's typographical background consisted of hands-on mechanical tasks: operating a label-making machine at Philadelphia's Franklin Institute Science Museum and working with Letraset rub-down dry-transfer lettering, where she had developed an eye for spacing and kerning. To prepare for the interview: - She visited the Palo Alto public library to borrow font specimen books and typography volumes, bringing them under her arm to the interview so she would look like she knew the field. - Following Hertzfeld's advice, she bought a grid notebook and hand-sketched early bitmap concepts using graph paper, sketching out items like a pond with a boot, sheets of paper, and prototype letterforms. - The interviewers never asked her a single technical question about font design, and she got the job. - Her original graph paper sketch notebook was later acquired by the Museum of Modern Art (MoMA) for its permanent collection—prompting her advice to designers to "hang on to your stuff."
[05:01](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=301s) First Days on the Mac and Designing Under Constraints
On her first day at Apple, the team showed Kare a prototype system screen and told her it was her job to improve it. The interface displayed early five-and-a-quarter-inch floppy disk graphics with rounded rectangles ("round rects") that users could click and drag with a mouse. Even in that primitive state, the tactile interaction felt magical to her.
```mermaid flowchart TD accTitle: Early Mac Interface Evolution accDescr: Progression from primitive system prototypes to refined friendly bitmap UI
subgraph Primitive ["Early System Prototype"] P1["Rough jagged display fonts"] P2["Button text: 'Do It' (misread as 'Don't' / off-color)"] P3["Crude floppy disk icons"] end
subgraph Refined ["Susan Kare's UI Overhaul"] R1["Chicago proportional system font"] R2["Button text: 'OK' (clear, unambiguous)"] R3["Standardized 16x16 & 32x32 tool icons"] end
Primitive --> Refined ```
One immediate editorial change was replacing the confirmation button label "Do it" with "OK"—"Do it" struck people as slightly off-color and users frequently misread it as "Don't."
The Mac software team was driven by a sincere, evangelical desire to create an approachable computer that anyone could use without ever opening an instruction manual. Kare appreciated this ethos because she herself was a complete novice. Rather than chafing at hardware limitations, she embraced them as creative prompts, comparing it to making art out of found beach trash: - Icons were initially constrained to tiny 16-by-16 black-and-white pixel grids. - Working pixel-by-pixel, she crafted foundational tool symbols like the lasso tool (designed to surround irregular screen regions) and various art implements. - Kare observed that these early 1-bit icons have lived on in popular culture, noting that the French mosaic street artist Invader (Space Invader) has liberally incorporated early Mac iconography into his public street art across Paris.
[08:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=506s) The Invention of Chicago, City Font Names, and the First iPod
The default screen text Kare encountered was uneven and jagged. She realized legibility could be improved by designing a system font adhering strictly to horizontals, verticals, and clean 45-degree angles. This resulted in Chicago, a bold, sans-serif typeface with a nine-pixel cap height. Although she admits she still winces when looking at Chicago's lowercase "x," the typeface solved the readability problem across early low-resolution displays.
Crucially, the Macintosh supported proportional spacing, moving beyond the ugly compromises of monospaced screen typography where the letter "M" was squished and the letter "I" floated in excessive whitespace. Chicago was deployed throughout the Mac OS title bars alongside horizontal structural lines. Looking back at the Mac's modular onscreen calculator application, Kare points out that its graphical layout and Chicago typography effectively previewed the physical design of the original Apple iPod two decades later.
Kare also developed a range of companion typefaces: - **New York and Geneva**: Proportional bitmap equivalents designed to serve the roles of Times New Roman (serif) and Helvetica (sans-serif). - **Ransom**: A novelty font styled after ransom notes made from mismatched letters clipped out of newspapers. - **Naming the fonts**: Kare and Hertzfeld originally named the fonts after suburban stops along the Pennsylvania Railroad's Paoli Local commuter line near their hometown (such as Bryn Mawr, Rosemont, and Wynnewood). When Steve Jobs dropped by the software area during his regular end-of-day walkthrough, he approved of using city names but declared they needed to be "world-class cities"—prompting the pivot to names like Chicago, New York, and Geneva.
[11:47](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=707s) MacPaint, the Icon Editor, and 32x32 Pixel Portraits
Kare worked closely with Bill Atkinson, the lead programmer behind MacPaint, which became her favorite application. She collaborated with Atkinson on creating tools, visual brushes, and fill patterns. Atkinson also built an early flatbed-style scanner mechanism, which the team used to digitize an authentic Japanese geisha woodcut print owned by Steve Jobs.
To help users understand system configurations without reading text, Kare designed a graphical Control Panel. It used animated icons, sound, and visual speed indicators to demonstrate slider settings so the interface would work internationally without localization text changes.
```mermaid flowchart LR accTitle: Bit-Toggling Icon Editor Workflow accDescr: The feedback loop inside Andy Hertzfeld's custom icon editing tool
A["Andy Hertzfeld's Icon Editor"] --> B["Toggle bits individually"] B --> C["Simultaneous views: Enlarged grid + 72 DPI preview"] C --> D["Auto-generated Hexadecimal code"] D --> E["Implemented into System Software"] ```
Moving away from paper sketches, Hertzfeld built a dedicated Mac-based Icon Editor that allowed Kare to interactively toggle pixels on and off. The tool displayed both a magnified pixel-editing grid and an actual-size 72 DPI live preview, automatically outputting the corresponding hexadecimal code to paste into system builds. The ability to iterate endlessly on screen without an eraser felt revolutionary to her.
Outside of standard UI work, Kare used the 32-by-32 pixel canvas to create digital portraits of colleagues and visitors who sat for her, as there was no straightforward way to capture or import photos. She remarks that it remains astonishing how recognizable a human face can become in a grid of just over 1,000 dots (1,024 pixels) with enough iteration—a craft she still enjoys, pointing to a recent 32x32 portrait she made of Pharrell Williams.
[15:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=926s) The Genesis of the Happy Mac and Universal Simplicity
One of the very first icon assignments Susan Kare tackled was the startup screen for the original 128K Macintosh. Because the hardware was limited and took a noticeable amount of time to boot—audibly "sitting there kind of grinding while it started up"—the team needed an image to reassure users that everything was functioning normally. Kare was constrained to a tight 32-by-32 pixel canvas. Wanting to communicate that "everything was okay," she settled on a smiling face, drawing inspiration from her childhood memory of a smiley button she owned around age fourteen. Her instinct favored warmth: "I like smiling and happy things."
Kare connects the philosophy behind the Happy Mac to Scott McCloud’s seminal book *Understanding Comics*, published a decade after the Mac's launch. While ostensibly about comic books, McCloud's work offers profound insights into user interface design. As McCloud demonstrated, when a human face is rendered with high detail, it represents a specific, external person; when stripped down to basic lines, it becomes an abstract vessel onto which any user can project themselves. The fewer the details, the more universal the icon becomes.
To Kare, this principle explains why a humble pencil drawing represents the act of writing far better than a rendering of a high-end chrome pen complete with polished reflections. The ornate pen is simply too particular to resonate universally. Her design philosophy has always leaned toward choosing "a salient detail or two, but don't lard it with a lot of extra stuff." She likens effective iconography to municipal street signs: a school crossing sign depicts a clean silhouette of two children holding hands. Technically, an illustrator could add plaid lunchboxes, visible shoelaces, or render them singing, but such details would only distract the viewer and erode the split-second clarity the sign must convey.
[18:22](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1102s) Glitches and Misunderstandings: The Bomb, Wristwatch, and Over-Detailed Icons
Alongside the Happy Mac, Kare was tasked with designing visual states for failure, under the assumption that these states would practically never be witnessed by the public. Told that in the "extremely unlikely event" something went wrong there should be an alternative, she designed an Unhappy Mac that looked sickly and "a little hungover." Operating under the belief that she could be irreverent because "no one was going to see this," she drew an icon for total system crashes: a cartoon bomb with a burning fuse reminiscent of Bugs Bunny.
That irreverence backfired when system crashes inevitably occurred in the real world. One afternoon, working inside the glass-walled "fishbowl" where the software group sat, Kare witnessed the Apple receptionist field a frantic call from an upset customer. The user insisted on speaking directly to the software team because she was staring at a bomb on her screen and was terrified that her computer was literally about to explode, leaving Kare with lingering design guilt.
Beyond handling errors, the team needed to establish a visual architecture for the Mac's applications. With only about half a dozen programs slated for release, Kare designed an intuitive paired system treating applications as verbs and files as nouns. She created an active, process-oriented icon for MacPaint, which was then mirrored in the document icons it generated. Other system assets pushed against legacy physical metaphors:
```mermaid flowchart TD accTitle: Mac Application and Document Pairing Model accDescr: Diagram showing how applications representing actions pair directly with corresponding document nouns. subgraph ConceptualModel["Visual System: Action & Result"] Verb["Application Icon (Verb)<br/>e.g., MacPaint in active state"] --> Result["Document Icon (Noun)<br/>Visually mirrors the tool"] end subgraph Metaphors["Everyday Metaphors"] Alert["Alert Dialog Icon<br/>Tightly cropped, ageless & genderless"] Wait["Wait State Cursor<br/>Modern wristwatch replacing hourglass"] end ```
- **Alert Figures**: Instead of drawing an explicitly detailed person, Kare tightly cropped a generic face into the frame, obscuring age, gender, and hairstyle to prevent any specific demographic bias. - **The Wristwatch Cursor**: Rather than using a traditional hourglass—which she only ever associated with boiling eggs—Kare decided personal computing in the 1980s called for an update, replacing the sand timer with an analog wristwatch. - **The Pitfall of Product Specificity**: For the print icon, Kare meticulously drew an ImageWriter printer complete with tractor-feed sprocket holes and a side platen knob. She considers this a misstep: capturing ephemeral hardware quirks severely shortens an icon’s shelf life. The same obsolescence struck the 3.5-inch floppy disk save icon, proving that enduring interface design requires broad metaphors rather than literal representations of contemporary gadgets.
[22:15](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1335s) Steve Jobs and the "Apple Farm": Discovering the Command Symbol
The Macintosh user interface originally relied heavily on Apple's corporate silhouette. Drop-down menus were filled with keyboard shortcuts that featured the Apple logo beside individual letters. Steve Jobs walked into the software room at the end of a workday and immediately banned the layout, deriding the cluttered menu screen as an "Apple farm." Jobs insisted, "Our logo is precious and we have to respect it. So, you know, we just can't have a bunch of apples."
Given the task of replacing the logo on what was designated the Command or Feature key, Kare initially brainstormed literal concepts of commanding, but found them harsh and militaristic, noting that depicting the Ten Commandments felt like an absurd visual pun. Turning to an art and symbol reference book in the library, she spotted an ancient looping motif labeled simply as a mark for a "feature."
```mermaid flowchart LR accTitle: Command Key Symbol Evolution accDescr: Flow showing the evolution from Steve Jobs rejecting repeated Apple logos to Susan Kare discovering the Swedish feature symbol. A["Initial Menus:<br/>Apple logo shortcuts"] -->|"Jobs: 'Apple farm'<br/>Devalues precious logo"| B["Redesign Mandate:<br/>Find abstract symbol"] B -->|"Library Research"| C["Looped Nordic Sign:<br/>Cloverleaf / Feature"] C -->|"16x16 Grid Adaptation"| D["Command Key (⌘)"] D -->|"Later Swedish Visit"| E["Origin: Borgholm Castle<br/>Four-turret ruin aerial view"] ```
The looped design felt promising: rendered in the restricted 16-by-16 pixel space, it suggested a lucky four-leaf clover or an aerial view of a highway cloverleaf interchange, evoking speed and navigation. Although she worried that its abstract nature lacked an intuitive metaphor to help users remember its function, the team adopted it, and it remains on Apple keyboards to this day.
Years later, Kare flew into Gothenburg, Sweden, and was stunned to spot the exact symbol on local roadside markers. A Swedish companion explained that the symbol had marked cultural heritage and sightseeing monuments across the Nordic countries for centuries. It directly depicts a top-down aerial silhouette of the four-turreted Borgholm Castle, an architectural ruin dating back to roughly 1200 AD. Decades after shipping the keyboard, Kare was delighted to learn her abstract graphic was an architectural depiction after all.
[25:20](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1520s) Ancient Grids: From Stone Carvings and Samplers to 1984 Emojis
Reflecting on her art history doctorate, Kare observes that visual interface design sits on a historical continuum: "there's not much new under the sun. People have been making little symbols for a long time." Bitmapped typography and constrained icon sets closely mirror Egyptian hieroglyphics, stone tablets, and centuries-old cross-stitch samplers.
Historical embroidery and mosaic patterns frequently solved the exact pixel-grid puzzles digital designers face. Kare highlights early historical examples where craftspeople constructed legible, proportional alphabets within tiny grids—such as capital letter heights restricted to a mere seven or ten units—more than two centuries before personal computing arrived. She jokingly traces her own comfort with coordinate grids back to childhood crafting kits where children were encouraged to assemble ceramic mosaic ashtrays for their parents.
This appreciation for symbolic shorthand led directly to her work on decorative fonts like Cairo for the 1984 Macintosh. Long before modern smartphone text messaging popularized emojis, Kare embedded hieroglyphic-inspired dingbats directly into system typography, enabling users to intersperse pictures with standard text. For Kare, the heart of digital design has never been the technical grid of pixels itself, but rather the underlying metaphor, intention, and clarity embedded within the marks.
[27:32](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1652s) Design Iteration at Swatch and Introducing Color in Windows 3.0
Icon design is far from an exact science; it requires relentless, exploratory variation. Illustrating her iterative process, Kare reviews a suite of concept sketches created for a Swatch digital device interface alarm function. Her initial instinct was an analog alarm clock face, which she steadily modified to look louder by layering vibrating sound waves. Realizing a clock icon displayed on a physical watch face was redundant and "way too self-referential," she pivoted toward alternate metaphors for waking up, testing everything from acoustic horns to roosters. She emphasizes that good UI ideas often emerge from taking a client's offhand suggestion or an engineer's crude temporary placeholder graphic and systematically refining it.
Following her tenure at Apple, Kare was hired by Microsoft to design the iconography and graphical elements for Windows 3.0. Stepping into the PC ecosystem introduced the challenge and opportunity of color. While the palette was initially constrained to sixteen standard system shades—many of which were harsh and unflattering—color offered powerful functional benefits. Red could finally be deployed specifically for critical warning dialogs, enabling instant visual prioritization.
Rather than allowing the Windows interface to resemble a "garish jet chessboard" of clashing primary tiles, Kare applied subtle dithering techniques, blending complementary pixels across the 16-color palette to create textured, subdued tones that were far easier on the user's eyes.
[29:56](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1796s) Life After Apple: Metaphors at General Magic and Facebook Virtual Gifts
Reflecting on her career after the Macintosh, Susan Kare notes how early digital graphics unexpectedly entered popular culture. In the 1990s, countless people spent hours playing Windows Solitaire—for which she designed the original pixel-art cards. Kare laughs that she eventually had to delete Solitaire off her own machine because it was too addictive, recalling that *Slate* once remarked the game had truly "made a dent." Moving through decades of client work that ranged from playful to corporate, she points out how design metaphors evolved over time.
One prominent post-Apple project was creating the identity and interface graphics for General Magic. The team attempted an ultra-literal desktop metaphor where users navigated virtual hallways lined with doors, opened virtual filing cabinet drawers to store documents, and encountered literal "jars of text" on shelves—an idea she looks back on with amusement: "the very worst thing we had was jars of text, because why?" While the interface relied on familiar physical tropes like Rolodexes, desk phones, and postcards, it failed to anticipate how quickly email and abstract software paradigms would render those physical office objects obsolete.
```mermaid flowchart LR accTitle: Evolution of Kare's Digital Metaphors accDescr: Progression from General Magic physical skeuomorphism to Facebook microtransaction digital gifts. subgraph General_Magic["General Magic (Physical Analogies)"] A["Hallways & Doors"] B["Filing Drawers & Rolodexes"] C["Jars of Text"] end subgraph Facebook["Facebook Virtual Gifts (Digital Economy)"] D["Daily Midnight Launches"] E["Predictable 15-Minute Velocity"] F["Emotional / Cute Micro-Goods"] end General_Magic -->|"paradigm shift"| Facebook ```
Later, Kare spent nearly four years designing virtual gifts for Facebook. Users could purchase small graphic illustrations for one real dollar to display on friends' profiles. Operating essentially as a digital gift shop, the team released a new gift daily at midnight Eastern Time. They could reliably predict whether an item would become a runaway bestseller within the first fifteen minutes based on sales volume. While Kare initially theorized that status items like diamond earrings or Rolex watches would feel more valuable for a dollar, human behavior proved otherwise: - **"Cute trumped everything"**: Teddy bears, heart-shaped items, and kiss marks consistently outsold luxury symbols. - **The Lipstick Kiss Mark**: The all-time bestselling virtual gift on the platform. - **The Power of Penguins**: Kare jokes that if her life ever depended on selling a drawing for a dollar, she would immediately draw a penguin, as every limited-edition run sold out instantly. - **Collaborations**: The project featured high-profile partnerships, including custom drops with Britney Spears and other entertainers, before Facebook shut the gift shop down to avoid competing with third-party app developers.
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[34:13](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2053s) Diverse Graphic Work: From Subtly Animated Pins to Amtrak Maps
Kare's portfolio in the decades following Apple spanned small consumer devices, web platforms, and editorial illustrations. At Pinterest, she collaborated with a skilled animator to build icons with gentle, looped motions designed carefully so they "wouldn't get really irritating over time." For stealthmil.com—a project dealing with waste—she crafted an interim logo featuring a "trash panda" (raccoon) before their permanent identity launched. Editorial work included a commission for Amtrak's quarterly magazine, *The National*, where artists were asked to reimagine train route maps; Kare embraced the opportunity to return to her pixelated roots, crafting discrete 8-bit vignettes representing rail destinations across the United States.
Her enthusiasm extends naturally to play, games, and hardware customization: - **Game Logos**: Developing the branding for *Magic Puzzle*—jigsaw puzzles designed to perform an optical magic trick once assembled—as well as logo studies for Niantic's *Pikmin Bloom* and *Paradot*. - **Avatars**: Designing avatar suites remains a favorite pursuit because of their open-ended representational freedom: "Avatars are so freeing because they can stand for anything." - **Hardware Badging**: Designing retro-styled collectible badges for a Ledger hardware crypto wallet, engineered to snap directly into a front-facing slot on the physical device. - **Outdoor VC Branding**: Designing a fast-turnaround visual identity over a single weekend for a venture firm organized by Dave Morin, built around the philosophy of escaping corporate cubicles to work outside in the mountains.
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[37:18](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2238s) Paul Rand and Steve Jobs: The NeXT Logo Story
Turning to enduring advice from creative mentors, Kare highlights the legendary graphic designer Paul Rand, who began illustrating magazines around age 15. Rand was famously brusque about modern design trends, especially the explosion of digital type: "You don't need that many fonts. You just have to know how to use them well." Kare found comfort in his disciplined palette and typography, noting that whenever she designs, "if PMS 354 green is good enough for Paul Rand, it's good enough for me."
When Steve Jobs departed Apple to found NeXT, Kare was eager to bring in Rand, her design hero. Jobs was initially unfamiliar with Rand's stature and proposed holding a spec-work contest—offering five different designers or agencies $15,000 each, after which NeXT would pick a winner. Kare reached out to Rand anyway, who delivered an uncompromising ultimatum: > "You will pay me $100,000. I will do one logo and you will like it."
Jobs agreed, NeXT paid the fee, Rand delivered the iconic tilted cube logo, and Jobs loved it. Rand strongly advocated integrating the concept directly into the product's actual name rather than relying on detached visual marks. He criticized the contemporary AT&T globe mark as an example of what *not* to do, arguing that unless a corporation has limitless money to artificially burn an arbitrary shape into the public consciousness, logos should clearly express an intrinsic idea. He illustrated this through his own masterworks: the rising sun in Morningstar, the crisp business pinstripes of IBM, and his classic UPS shield. When Rand tested the UPS logo on his six-year-old daughter Catherine, asking her what she saw, she answered: "It's a present, Daddy." To Rand, that unprompted recognition was the ultimate proof of clarity. Kare laments that UPS later modernized the mark to strip away the string-tied package because executives wanted to signal they did more than just ship boxes.
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[41:40](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2500s) Creative Philosophy and Wisdom from Mentors
Kare draws continuous inspiration from maxims shared by colleagues, family, and collaborators across various disciplines: - **Paul Saffo (Futurist)**: Reminded her about the persistent fallacy of estimation. Kare admits she always falls into the trap of assuming a visual problem can be solved in a single hour, when genuine design exploration invariably requires generous runway. - **Dr. Morley Kare (Father & Director of the Monell Chemical Senses Center)**: Directed Philadelphia's premier research institute on taste and smell. Kare introduced her father to Paul Rand, who designed Monell's corporate mark. From her father's demanding fundraising campaigns, she absorbed pragmatic, unvarnished advice on resilience and coping with rejection when hearing "no." - **Daniel Nord (Architect)**: An architect who worked under the Mayor of London, Nord grew weary of committee meetings where teams talked in circles. His guiding rule was simply to force visual alignment: "Make it visual... do the drawing... show, don't tell." - **Jean-Paul Goude**: The boundary-pushing French graphic artist, photographer, and early digital enthusiast whom Kare met through Steve Jobs.
[44:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2664s) Lessons in Simplicity from Alan Kay and the Mac Pioneers
Susan reflects on the camaraderie and wisdom shared across the original Macintosh team, highlighting a photograph featuring Andy Hertzfeld, Bill Atkinson, Bud Tribble, Steve Jobs, and computer science pioneer Alan Kay. She recalls a foundational user interface philosophy that Bud Tribble often quoted from Alan Kay: the importance of nesting and hierarchy. Rather than flattening every control and command onto the same visual level, interfaces should tuck complexity away so that things surface only when needed, making true ease of use feel attainable to the user.
Beyond interface architecture, Susan cherishes a personal validation she received from Alan Kay regarding her typographic work on the Mac. Looking at the system's screen typography, Kay remarked to her with genuine surprise, "Yeah, it's like, who knew? Proportionally spaced fonts can actually look pretty good." Coming from a foundational figure in modern computing, the compliment brought her tremendous joy, confirming that moving beyond rigid monospaced terminal fonts was well worth the effort.
- **Interface Tenet**: Keep interface complexity nested rather than exposing everything on a single level, ensuring that initial interaction feels intuitive and effortless. - **Proportional Fonts Validation**: Alan Kay’s affirmation that proportional screen typography could look visually refined helped validate Apple's departure from traditional monospaced computer type.
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[45:54](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2754s) Flying the Pirate Flag and the Spirit of the Mac Team
Showing an image of Steve Jobs lounging casually inside her Apple cubicle, Susan recalls his advice during the 1980s to appreciate the present moment and savor the rare energy they shared. At the very first offsite retreat she attended, Jobs presented three guiding tenets to the team. The second of those goals—championing the rebellious counterculture ethos that it was better to be a pirate than to join the navy—inspired an immediate, practical response from the group.
Teaming up with software engineer Steve Capps, Susan helped turn Jobs's pirate metaphor into tangible team folklore. Capps sewed a large black fabric flag, and Susan hand-painted a skull and crossbones across it, substituting a rainbow-striped Apple logo for the traditional eye patch. Under the cover of darkness, taking advantage of Apple’s relatively relaxed 1980s security, the two climbed onto the roof of the Bandley 3 building in the middle of the night and hoisted the flag overhead. It remained flying as a proud rejoinder to the rest of the company that the Mac group operated by its own rules.
Susan explains that this same empathy shaped how they tested and demonstrated the computer. When introducing the Mac to newcomers, the team took deliberate care with framing: rather than boasting that anyone could instantly master the machine, they presented it gently so that testers who struggled would never feel foolish, and those who succeeded felt empowered and genuinely smart.
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[47:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2844s) Steve Jobs' Advice: Bits, Stock, and NeXT
While Jobs offered many visionary insights, Susan candidly notes that not all of his guidance was infallible. When it came to financial matters, Jobs once gave her what turned out to be terrible stock advice, expressing skepticism about Apple stock that led her to follow his lead and refrain from buying shares herself—reasoning that if Steve was not investing, he must know best.
Jobs also pushed her on career ambitions, warning her against staying too close to low-level craft: "Susan, you can twiddle bits and never make more than $20,000, or it's better to be a creative director." When Jobs founded NeXT, Susan joined him as Creative Director, which gave her the invaluable opportunity to collaborate directly with legendary graphic designer Paul Rand. Yet despite the prestige of creative leadership, she discovered where her true passion lay:
> "Ultimately I was a bit twiddler at heart, and I went back to it—and maybe not always bits, but..."
She also recalls Jobs's idiosyncratic cultural tastes, noting that he would regularly take visiting business executives out to watch *Flashdance*—a film Susan herself enjoyed primarily because the main character was a welder.
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[48:25](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2905s) Startup Culture, Team Scale, and How to Present to Steve Jobs
Working conditions during the crunch of the Macintosh software rollout bore little resemblance to contemporary notions of work-life balance. Jay Chiat, the founder of Apple's iconic advertising agency Chiat/Day, set a blistering pace, and virtually every software engineer in Susan's group kept a sleeping bag stashed inside their cubicle for overnight coding marathons. Susan observes that early startup teams operate best at a specific threshold: up to about 15 people, an entire company can fit in a single room, preserve consensus hiring, and maintain shared alignment. Once headcount expands beyond that magic number, organizational trade-offs inevitably emerge.
Susan also recounts a crucial survival tactic taught to her by Andy Hertzfeld for pitching design work to Steve Jobs. Hertzfeld warned her never to present Steve with only a single design option, because Jobs's instinct would be to reject it outright to force another iteration. By presenting several alternatives, Jobs could vent his critical instincts on the weaker options while still feeling ownership over selecting the best one.
```mermaid flowchart TD accTitle: Pitching Steve Jobs Decision Strategy accDescr: Comparison between showing Steve Jobs a single design option versus presenting multiple options to guide approval.
subgraph Trap["The Single-Option Trap"] A["Present 1 Design Concept"] --> B["Jobs rejects it automatically"] B --> C["Designer sent back to iterate"] end
subgraph Strategy["The Hertzfeld Rule"] D["Present 3-4 Distinct Concepts"] --> E["Jobs critiques & dismisses weaker drafts"] E --> F["Jobs feels involved in the process"] F --> G["Selects preferred winning design"] end ```
---
[49:46](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2986s) Breaking the Rules: From Google Doodles to Moving to the Next Idea
Looking across tech generations, Susan highlights lessons from subsequent design leaders, including Pinterest co-founders Evan Sharp and Ben Silbermann, as well as Dennis Hwang, who began illustrating the very first Google Doodles while still an undergraduate at Stanford University. Classic design dogma dictated that corporate logos must remain pristine and uncompromised, cautioning designers against ever altering a brand mark's colors or backgrounds until the company achieved decades of household familiarity. Hwang and Google disregarded that conventional wisdom early on, playfully reshaping the search engine's identity for holidays and historic anniversaries with immense success.
Concluding her talk with a photograph of an accordion player, Susan shares a favorite piece of life advice from a friend's father about creative persistence. When an idea fails to take root, rejection should not be seen as a cue for despair or a reason to quit trying altogether. Instead, it serves as a straightforward, practical prompt to let go of preciousness and move forward to the next idea. She wraps up with heartfelt appreciation for Y Combinator and Startup School, noting the infectious energy of the founders in the room and expressing admiration for everyone building new projects.
- **Consensus Scaling**: Small teams under 15 people can operate on complete consensus and shared cultural context; growing beyond that size requires formalizing communication. - **Brand Heresy Turned Staple**: Dennis Hwang proved that breaking sacrosanct branding rules by altering the Google logo created deep emotional resonance rather than brand dilution. - **Creative Resilience**: Rejection of a creative concept is not a verdict on talent—it is simply the signal to pivot quickly toward the next iteration.
## Notable quotes > [00:07](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=7s) meaningful and memorable — Paul Rand
> [01:51](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=111s) hang on to your stuff. — Susan Kare
> [15:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=926s) I like smiling and happy things. — Susan Kare
> [15:26](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=926s) a salient detail or two, but don't lard it with a lot of extra stuff. — Susan Kare
> [22:15](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1335s) Our logo is precious and we have to respect it. So, you know, we just can't have a bunch of apples. — Steve Jobs
> [25:20](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1520s) there's not much new under the sun. People have been making little symbols for a long time. — Susan Kare
> [29:56](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=1796s) the very worst thing we had was jars of text, because why? — Susan Kare
> [37:18](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2238s) You don't need that many fonts. You just have to know how to use them well. — Paul Rand
> [37:18](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2238s) You will pay me $100,000. I will do one logo and you will like it. — Paul Rand
> [44:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2664s) Yeah, it's like, who knew? Proportionally spaced fonts can actually look pretty good. — Alan Kay
> [47:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2844s) Susan, you can twiddle bits and never make more than $20,000, or it's better to be a creative director. — Steve Jobs
> [47:24](https://www.youtube.com/watch?v=YEvLKzsEwMw&t=2844s) Ultimately I was a bit twiddler at heart, and I went back to it—and maybe not always bits, but... — Susan Kare
## Mentioned Susan Kare, Steve Jobs, Paul Rand, Andy Hertzfeld, Bill Atkinson, Bud Tribble, Alan Kay, Steve Capps, Jay Chiat, Scott McCloud, Dennis Hwang, Evan Sharp, Ben Silbermann, Paul Saffo, Dr. Morley Kare, Daniel Nord, Jean-Paul Goude, Pharrell Williams, Britney Spears, Invader, Apple, Macintosh, MacPaint, Happy Mac, Unhappy Mac, Chicago (font), Geneva (font), New York (font), Cairo (font), Ransom (font), Command Key (⌘), ImageWriter, iPod, NeXT, Windows 3.0, Windows Solitaire, General Magic, Facebook, Pinterest, Google, Google Doodles, Swatch, Ledger, Amtrak, Y Combinator, Museum of Modern Art (MoMA), Franklin Institute Science Museum, Borgholm Castle, Understanding Comics, Flashdance
## Video description Susan Kare joined Apple as an art history PhD who barely knew anything about computers. She went on to design many of the icons, typefaces, and symbols that helped make the original Macintosh feel understandable and human, defining a visual language for personal computing that still influences software today.
At Startup School 2026, Susan shares the stories behind the Happy Mac, Command key, Chicago font, and more, along with the design lessons she learned from Steve Jobs, Paul Rand, and the original Mac team: make things meaningful and memorable, embrace constraints, iterate constantly, and use just enough detail to make an idea instantly clear.
Transcript: https://www.ycrootaccess.com/p/susan-kare-on-designing-the-original
Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs
Chapters: 00:00 — Making Things Meaningful and Memorable 01:51 — How Susan Joined Apple 05:01 — Designing the Original Macintosh 06:35 — A Computer Anyone Could Use 08:26 — Creating Chicago and the Mac Typefaces 11:47 — MacPaint and the First Icons 14:45 — The Story Behind the Happy Mac 17:08 — Why Simple Icons Work Better 18:25 — The Icons That Didn’t Work 21:23 — Designing Symbols That Last 22:44 — How the Command Key Got Its Symbol 25:20 — What Ancient Symbols Can Teach Designers 30:18 — Designing After Apple 36:32 — Lessons From Steve Jobs, Paul Rand, and More
[Source](https://www.youtube.com/watch?v=YEvLKzsEwMw)