356: ‘An Unranted Rant’, With Rosemary Orchard

Episode Summary

Executive Summary: John Gruber and Rosemary Orchard discuss the frustrations of Markdown errors, the need for practical linting and automation, and why Shortcuts is increasingly central to Apple platform power users. They explore searchability, naming, Siri integration, Automator’s decline, iOS 16/16-era improvements, and how automation empowers both individuals and teams.

Main Topics: Markdown errors and linting as practical automation (Priority: 5/5): Gruber opens with a rant about recurring Markdown typos, especially missing brackets, and explains how he built a personal linting workflow after years of wanting one. The discussion shows how automation can target the actual mistakes users make rather than trying to solve every possible error. The value of books versus search results for learning Shortcuts (Priority: 5/5): Both speakers argue that books still matter because they provide a coherent, end-to-end understanding of a subject. They contrast structured learning with fragmented web searches, Stack Overflow, Reddit, and content-farm SEO noise. Shortcuts as a practical automation platform (Priority: 5/5): Orchard explains that Shortcuts works because it lowers the barrier to automating real-world tasks on Apple devices, from home screen customization to logging health data. Gruber emphasizes that books and documentation are especially useful for understanding the system’s scope and patterns. Naming, searchability, and Siri confusion (Priority: 4/5): A major theme is how Apple’s naming choices affect usability: Shortcuts, Pages, Numbers, and Do all create search and voice-recognition problems. The conversation highlights that unique names help discovery, while generic names and pronunciation ambiguity make Siri and web search less effective. Workflow, Automator, AppleScript, and platform evolution (Priority: 5/5): The speakers trace Shortcuts back to Workflow and compare it with Automator and AppleScript. They argue that Shortcuts is the future on Apple platforms, while Automator looks increasingly legacy, even though some older scripting workflows remain important. Automation as a way to personalize devices and share solutions (Priority: 4/5): They stress that most users won’t create automations, but many will benefit from shared Shortcuts. Orchard notes that automation should serve neurodiversity, regional language differences, and everyday routines, making devices feel genuinely personal. Apple’s growing support for developer-exposed shortcuts in iOS 16 (Priority: 4/5): Orchard highlights improved app action discovery, recommended shortcuts, and better integration between third-party apps and Shortcuts. This makes automation more approachable for new users and more useful for existing ones.

Key Arguments: A good linting tool should focus on the mistakes users actually make, not on theoretical perfection. Books provide a superior high-level understanding of complex tools compared with ad hoc web searches. Shortcuts is valuable because it lets users create useful automations without needing full programming skills. Apple’s naming choices materially affect discoverability, search results, and Siri usability. Shortcuts is effectively the successor to Workflow and is likely to outlast Automator. Most users will consume automations rather than create them, so shared workflows matter more than universal DIY. iOS 16-style app action discovery makes Shortcuts more welcoming and practical for newcomers. Automation should adapt devices to the user’s habits, language, and accessibility needs. Video tutorials are useful but hard to maintain and update compared with text-based guides and books. NFC tags, focus modes, and location/time triggers show how everyday automation can be deeply practical.

Data Points: Year Markdown became public: 2004 - Gruber describes starting Markdown in late 2003 and releasing it publicly in early 2004. Time he spent wanting a Markdown linter: 17 years - He jokes that it took roughly 17 years before he finally wrote a personal linting script. Book timing: Second edition of Take Control of Shortcuts; first edition around late 2019 - Orchard references the updated edition and estimates the first edition appeared in November or December 2019. Podcast episode count: 109 - Orchard notes Automators is about to release episode 109 at the time of recording. iPad keyboard price: $300 - Gruber complains that the Magic Keyboard is expensive for a device showing wear after about two years. Typical iPad Pro + keyboard cost comparison: Higher than many entry-level Macs - The discussion compares an iPad Pro plus Magic Keyboard to the price of base MacBook Air configurations. Podcast recording machine: 2014 MacBook Pro - Gruber says he is recording on a 2014 MacBook Pro whose keyboard remains perfect despite heavy use. Automator/Shortcuts era: Workflow launched roughly 7+ years before the recording - Orchard recalls Workflow becoming popular while she was studying computer science, placing it several years before the current discussion.

Pivotal Quotes: "Why don't I just fix the mistakes I actually make?" — John Gruber: Explaining the breakthrough that led him to build a practical Markdown linting script instead of an exhaustive parser. "The whole point of this whole discussion is to encourage people who are listening to think back to how much you've learned in the past from good books." — John Gruber: Summarizing why he believes book-length explanations still matter for learning Shortcuts and other technical tools. "Apple really has enthusiastically allowed us to turn our iOS devices into customizable, automatable devices." — Rosemary Orchard: Orchard closes the thread by emphasizing the growing power and flexibility of automation on Apple platforms.

Implications: For users, the message is to learn Shortcuts from structured resources and use automation to save time, reduce errors, and personalize devices. For Apple, better naming, discovery, and app action support could make automation mainstream rather than niche.