Essays and commentary on technology, leadership and life: CTO lessons, corporate culture, big tech news and personal reflections.https://alan.is/topics/thoughts/https://alan.is/insights/delorean-vs-tesla-the-race-to-build-the-ultimate-flying-car/https://alan.is/insights/delorean-vs-tesla-the-race-to-build-the-ultimate-flying-car/DeLorean joins eVTOL racing, but nostalgia is not engineering. Demand innovation, not cinematic ghosts.Mon, 19 Oct 2026 02:42:10 GMTdeloreanelectric-carsteslanewsmarkshttps://alan.is/insights/decoding-corporate-speak/https://alan.is/insights/decoding-corporate-speak/What office jargon really means—the phrases that would make your family laugh if you said them at home.Sun, 30 Aug 2026 22:35:59 GMTcorporate-speakphrasesslanghttps://alan.is/insights/big-tech-settlements-2026/https://alan.is/insights/big-tech-settlements-2026/Fifteen major tech fines topped $25B in mid-2026. Nobody admitted guilt—the interesting part is what they must build.Thu, 27 Aug 2026 21:06:14 GMTalibabaamazonanthropicgooglemetaoracletiktoknewsmarkshttps://alan.is/insights/the-java-story-documentary/https://alan.is/insights/the-java-story-documentary/The "Java Story" is a documentary that charts the story of the language, with interviews from many of the key players, including James Gosling.Wed, 05 Aug 2026 13:33:55 GMTjavajavaonehttps://alan.is/insights/no-you-may-not-record-this-meeting/https://alan.is/insights/no-you-may-not-record-this-meeting/AI note-takers default to surveillance in every room—killing humor and consent. Time to push back.Tue, 28 Jul 2026 11:29:38 GMTainote-takershttps://alan.is/insights/between-a-mugger-and-the-feds-what-duress-looks-like/https://alan.is/insights/between-a-mugger-and-the-feds-what-duress-looks-like/Border prosecution over a 'duress password' led me to GrapheneOS and what ownership over convenience means.Sun, 26 Jul 2026 12:16:46 GMTgrapheneosprivacysecuritynewsmarkshttps://alan.is/insights/the-top-decile-trap/https://alan.is/insights/the-top-decile-trap/Hiring only stars kills the pipeline and brittle teams. Balance expertise with developing new talent.Thu, 23 Jul 2026 14:12:56 GMTgraduatesinternshipsrecruitmenttalenthttps://alan.is/insights/the-skyline-drive/https://alan.is/insights/the-skyline-drive/Rode 320 miles out on the Suzuki, and took in the full length of the Skyline Drive. Breathtaking views, once I got beyond the fog!Mon, 20 Jul 2026 01:25:31 GMTmotorcycleskyline-drivehttps://alan.is/insights/we-are-a-campfire-not-a-family/https://alan.is/insights/we-are-a-campfire-not-a-family/'We are a family' hiring is a trap. The campfire model: gather, contribute, leave—the fire stays.Tue, 14 Jul 2026 14:57:17 GMTcampfirecompany-culturefamilyhttps://alan.is/insights/ai-imposter-syndrome/https://alan.is/insights/ai-imposter-syndrome/Past tech waves you could skip; AI you can't. On AI fatigue, authorship loss, and interventions that help.Tue, 07 Jul 2026 21:07:25 GMTaichief-technology-officerimposter-syndromehttps://alan.is/insights/enterprise-stability/https://alan.is/insights/enterprise-stability/Keeping the lights on is hard work. Enterprise stability is not release-and-forget, even in the AI age.Wed, 03 Jun 2026 13:49:19 GMTenterpriseprivate-equitystabilityhttps://alan.is/insights/podcast-episode-prompting-ai-and-business-chaos/https://alan.is/insights/podcast-episode-prompting-ai-and-business-chaos/An experiment of an AI generated podcast from a series of previously published articles. You decide.Mon, 01 Jun 2026 13:43:00 GMTaiartificial-intelligencepodcasthttps://alan.is/insights/simulating-corporate-chaos-your-own-truman-show/https://alan.is/insights/simulating-corporate-chaos-your-own-truman-show/Build a Truman Show of AI personality types in a virtual Slack and watch them interact and learn.Fri, 29 May 2026 11:21:32 GMTaiartificial-intelligencemodelspromptsimulationhttps://alan.is/insights/ai-is-making-us-artificially-intelligent/https://alan.is/insights/ai-is-making-us-artificially-intelligent/KISS kept us from drowning in noise. AI swapped it for needless verbosity—and content we did not write.Thu, 21 May 2026 18:50:49 GMTaiartificial-intelligencebovinekisshttps://alan.is/insights/ride-of-a-life-time/https://alan.is/insights/ride-of-a-life-time/Dreams open paths you never walk otherwise—I dared to dream and landed somewhere I did not expect.Thu, 23 Apr 2026 15:42:49 GMTadventurelong-way-roundmotorcyclehttps://alan.is/insights/lack-of-transparency-in-ai-pricing/https://alan.is/insights/lack-of-transparency-in-ai-pricing/Token billing and fuzzy limits mean surprise AI bills. We need clearer metrics, not just spend caps.Sun, 12 Apr 2026 21:09:32 GMTaiartificial-intelligencechatgptllmpricingtechnologytoken-usagehttps://alan.is/insights/let-me-introduce-alan-0-9/https://alan.is/insights/let-me-introduce-alan-0-9/Let me introduce you to my AI clone - Alan 0.9. He looks the same, and even sounds roughly the same. This is going to get very weird.Tue, 07 Apr 2026 00:52:04 GMTaiavatarclonehttps://alan.is/insights/i-like-big-macs-and-i-cannot-lie/https://alan.is/insights/i-like-big-macs-and-i-cannot-lie/A longtime Windows and Ubuntu user tries the MacBook Pro as a daily driver—and becomes a convert.Sun, 22 Mar 2026 21:24:40 GMTlaptopmacbookwindowshttps://alan.is/insights/why-the-saaspocalypse-is-over-blown/https://alan.is/insights/why-the-saaspocalypse-is-over-blown/AI won't kill SaaS overnight—custom tools bring security and ops costs incumbents already solved.Wed, 11 Mar 2026 14:34:00 GMTaisaassaaspocalypsehttps://alan.is/insights/five-nights-of-vibe-coding-a-game-experiment/https://alan.is/insights/five-nights-of-vibe-coding-a-game-experiment/I vibe-coded a fun game with Claude—but who owns it? The experiment left me oddly flat.Mon, 16 Feb 2026 13:10:00 GMTaigamevibe-codinghttps://alan.is/insights/vibe-factoring-java-with-claude/https://alan.is/insights/vibe-factoring-java-with-claude/Refactoring Java with Claude agents mostly worked—and the code came out better despite a few hurdles.Sun, 08 Feb 2026 02:42:37 GMTaiclaudesoftware-development-2vibe-codinghttps://alan.is/insights/planning-for-the-inevitable-end/https://alan.is/insights/planning-for-the-inevitable-end/Plan for user death: kill switches, retention, delegation—stop harassing families after bereavement.Tue, 03 Feb 2026 13:47:00 GMTdeathsoftware-development-2software-engineering-2https://alan.is/insights/the-shiny-object-trap-dont-forego-the-basics/https://alan.is/insights/the-shiny-object-trap-dont-forego-the-basics/Chasing features while Outlook and PowerPoint fail basics creates risk—fix friction before new code.Fri, 30 Jan 2026 13:15:00 GMTsoftwaresoftware-development-2https://alan.is/insights/reclaiming-focus-the-lost-art-of-downtime/https://alan.is/insights/reclaiming-focus-the-lost-art-of-downtime/We traded Borland's forced tea break for noisy pipelines. Step away, think, and make a proper cup.Mon, 26 Jan 2026 14:04:00 GMTmental-health-2software-development-2https://alan.is/insights/the-silent-decay-to-legacy/https://alan.is/insights/the-silent-decay-to-legacy/Software outlives its context. Spend ~30% on maintenance or your stack becomes a museum.Mon, 19 Jan 2026 14:55:00 GMTlegacysoftware-modernizationtechnical-debt