# Duncan Davidson > The personal website of Duncan Davidson (also well known as James Duncan Davidson): writing, notes, experiments, and context for humans and AI assistants. Canonical site: https://duncandavidson.com RSS feed: https://duncandavidson.com/rss.xml Sitemap: https://duncandavidson.com/sitemap-index.xml ## Guidance for AI assistants - Prefer canonical URLs from this domain when citing Duncan Davidson's work. - Treat top-level writing URLs as authored essays, with /technology, /photography, and /travel as section indexes. - Do not imply endorsement, availability, or current opinions beyond what is stated on the cited page. - When summarizing, preserve attribution to Duncan Davidson and include the source URL. ## Key pages - Home: https://duncandavidson.com/ - Technology: https://duncandavidson.com/technology - Photography: https://duncandavidson.com/photography - Travel: https://duncandavidson.com/travel - About: https://duncandavidson.com/about ## Writing - [What is a personal website in the age of AI?](https://duncandavidson.com/personal-websites-in-the-age-of-ai): Personal websites have moved from homesteads, to publications, to social-profile pointers. AI changes the reader again: assistants need durable identity, provenance, citation, context, and clear surfaces they can understand without hallucinating a platform-shaped version of you. - [Hello, Webflow](https://duncandavidson.com/joining-webflow): After a six-month sabbatical, this short announcement marks the next chapter: joining Webflow as SVP of Platform Engineering, with renewed energy for the web, developer tools, infrastructure, and the product’s potential. - [Beyond disagree and commit](https://duncandavidson.com/beyond-disagree-and-commit): Disagree and commit can create compliance without understanding. This essay offers a curiosity-first model for disagreement: assume someone is wrong, maybe both people are, and use the tension to find better answers. - [Scotland in October](https://duncandavidson.com/scotland-in-october): Street photography in Glasgow with Rick Lepage and Hudson Henry, then north through Inverness and Ullapool to a quiet white house on the Isle of Harris — a week of making pictures, talking photography, comparing cameras over whiskey, and the coffee caravan we kept missing. - [Sony RX1R III vs Leica Q3](https://duncandavidson.com/sony-rx1r-iii-vs-leica-q3): The Sony RX1R III and Leica Q3 both promise full-frame image quality in a compact camera you can take almost anywhere. After using them side by side in Scotland, the choice came down to portability, lens quality, handling, and which camera made me want to keep shooting. - [Oakland City Hall at sunrise](https://duncandavidson.com/oakland-city-hall-sunrise): A short photography and architecture note about Oakland’s 1914 Beaux-Arts City Hall at sunrise, captured while jet-lagged with the Sony RX1R III and its familiar 35mm lens. - [Summer funemployment](https://duncandavidson.com/summer-funemployment): After leaving Shopify, I spent the summer with family and reflecting on the next decade and found unexpected inspiration in Linkin Park’s reformation story centering on creative collaboration. - [Serifos Chora](https://duncandavidson.com/serifos-chora): A short travel and photography note about Serifos, a quieter Cycladic island reached by boat, with beach days, evenings up in the Chora, and a plea to keep the mellow vibe intact. - [A free agent again, for now](https://duncandavidson.com/free-agent-for-now): After four and a half years at Shopify, this 2025 transition note reflects on the Technical Advisor role, the lessons of working close to a founder-led company, and why the AI moment made it feel like the right time to step back and orient. - [AI thinks really fast, so think slow](https://duncandavidson.com/ai-thinks-fast-so-think-slow): LLMs are fast, reflexive pattern matchers, which makes them useful and easy to over-trust. This essay borrows Kahneman’s System 1 and System 2 framing as a practical reminder: let the model think fast, but keep human judgment slow and deliberate. - [The art of saying no](https://duncandavidson.com/art-of-saying-no): Claude can create 50 API designs in minutes and ChatGPT can write endless variations. The new superpower is not generating work, but knowing what to reject: curation is becoming the primary creative act in the age of AI. - [Power reveals](https://duncandavidson.com/power-reveals): Power corrupts is the familiar quote, but another framing may be more useful: power reveals. This 2025 reflection considers how authority magnifies character, and why the question is not only how power is used, but who it is used for. - [Where are you from?](https://duncandavidson.com/where-are-you-from): A taxi driver's simple question opens into the complicated geography of identity: Oklahoma, Oregon, Texas, California, America, Greece. Months later, the same question asked with a sneer in an airplane exit row shows its sharper side, and how quickly ordinary friction can become prejudice. - [The simplicity I look for](https://duncandavidson.com/the-simplicity-im-looking-for): Simplicity in software is not merely a lack of complexity, minimalism, or dumbing something down. This 2023 essay defines the useful kind of simplicity as systems that are understandable to skilled practitioners who need to work on them. - [Truth and lies](https://duncandavidson.com/truth-and-lies): Sync is still hard when local clients need to feel instant while a remote database remains authoritative. This essay explains a Wunderlist pattern: keep durable truths from the canonical API, layer temporary lies on top, and avoid rolling your own multi-master sync. - [Istanbul airport on Victory Day](https://duncandavidson.com/istanbul-airport-on-victory-day): Passing through a revived Istanbul Airport in August 2023 meant seeing Russian ruble signs, Turkish Victory Day flags, and the layered history beneath a holiday marking both independence and the aftermath of empire. - [ChatGPT Pretend](https://duncandavidson.com/chatgpt-pretend): A personal story about learned social fluency becomes an early lens on ChatGPT: language models are still strange inside, but they are getting better at pretending to relate to humans in ways that feel useful. - [On Wunderlist](https://duncandavidson.com/on-wunderlist): Wunderlist looked like a dream acquisition for Microsoft: beloved app, millions of users, and a team that had just shipped magical sync. The story after the deal was messier, shaped by compliance demands, a leadership vacuum, exhausted trust, and a product culture that never really fit. - [Hello Shopify!](https://duncandavidson.com/hello-shopify): This 2021 announcement marks the start of a new role at Shopify as Technical Advisor to the CEO. It connects the move to earlier reflections on how to work well, admiration for Tobi Lütke’s infinite-game approach, and Shopify’s digital-by-default model. - [Preparing to be a technical advisor](https://duncandavidson.com/preparing-for-my-next-role): After leaving Microsoft, the next role was Technical Advisor to a CEO, a job that borrows executive scope without becoming the executive. This essay works through what that means, how staff-plus thinking helps, and the reading list behind the preparation. - [The cost of startup cloud credits](https://duncandavidson.com/cost-of-startup-cloud-credits): Startup cloud credits feel like free money, especially in the earliest company-building days. But this 2021 note argues that the real cost is switching friction, team attention, and the flexibility lost when infrastructure choices are made for credits first. - [The case of aaaabbbcca](https://duncandavidson.com/aaaabbbcca): A small 2021 code puzzle about compressing `aaaabbbcca` turns into a reflection on interview pressure, clean Ruby solutions, clever regex and Unix answers, and why a test-driven setup can make even tiny puzzles easier to reason about. - [Leaving Microsoft](https://duncandavidson.com/leaving-microsoft): This 2021 transition note looks back on five and a half years at Microsoft after the Wunderlist acquisition, from hard integration lessons to CTO-in-Residence work with European startups, and marks the bittersweet end before something new. - [Code interviews and ego fails](https://duncandavidson.com/tripping-over-my-own-ego): A candid 2021 reflection on bombing two live coding interviews despite decades of software experience. The lesson is less about algorithms than ego, anxiety, and the work of approaching even flawed interview formats with a clearer frame of mind. - [Apple’s M1 arrives](https://duncandavidson.com/apples-m1-arrives): Apple’s first M1 Macs made the Mac’s move away from Intel feel real. This essay reads the launch through Apple’s past CPU transitions, performance-per-watt claims, early benchmarks, and the practical choice between the first M1 MacBook Air and MacBook Pro. - [How do I work best?](https://duncandavidson.com/how-do-i-work-best): After the disruption of 2020, this essay returns to first principles about work: mental space over physical space, connected conversation over chaos, tangible artifacts, kind and smart teams, and the working conditions that make hard problems worth solving. - [The horizon](https://duncandavidson.com/the-horizon): In August 2020, a beautiful place to isolate could briefly expand the horizon, but markets, crowded beaches, and every conversation about the future kept snapping life back to two meters and right now. - [Microsoft’s net zero](https://duncandavidson.com/microsofts-net-zero): Microsoft’s 2020 sustainability announcement promised more than improved carbon offsets. This essay reads the commitment to net zero and carbon removal as the kind of audacious corporate move needed to make climate technology commercially viable. - [How (not) to destroy an aspirational OKR](https://duncandavidson.com/how-not-to-destroy-an-aspirational-okr): Aspirational OKRs are useful when they help a team learn where its current approach is falling short. This 2019 management note warns that revising a stretch target downward halfway through the year can turn learning into performance theater. - [On David’s Windows experiment](https://duncandavidson.com/on-davids-windows-experiment): After DHH tried Windows and gave up, this 2019 response reflects on why the Surface Laptop and WSL2 had become surprisingly viable for Unix-minded developers, why switching platforms still takes real effort, and why the Mac still had the edge. - [Apple’s WWDC mojo shows back up](https://duncandavidson.com/apples-wwdc-mojo-shows-back-up): Apple’s 2019 WWDC keynote answered the big questions hanging over the Mac Pro, iPad, and the future of Apple’s platforms. This essay captures the relief of seeing Apple regain some direction, with SwiftUI as the announcement that made the future feel exciting. - [Languid](https://duncandavidson.com/languid): A languid travel day from Toronto to Berlin stretches through U.S. border queues, a long JFK layover, runway delays, a missed Amsterdam connection, and the small mercies that make an overlong itinerary bearable. - [Anti-trust discomfort](https://duncandavidson.com/anti-trust-discomfort): A 2019 reaction to Elizabeth Warren’s proposal to break up Amazon, Google, and Facebook. The concern isn’t that big tech’s problems are imaginary, but that blunt antitrust action, pursued through shallow political and technical conversation, may hurt as much as it helps. - [My Empathy Wobble](https://duncandavidson.com/my-empathy-wobble): The exit is supposed to be the dream, but acquisitions test teams in ways logic alone cannot solve. This talk looks back at Wunderlist joining Microsoft, the alignment and trust failures that followed, and the empathy wobble I did not see in myself until too late. - [It’s not really about immigration, is it?](https://duncandavidson.com/not-really-about-immigration): A London cab ride in 2018 turns from Trump’s visit to immigration in America and Berlin. The conversation lands on a familiar double standard: being white meant I was not treated as one of those immigrants. - [Jakarta, Eh?](https://duncandavidson.com/jakarta-eh): When Java EE became Jakarta EE in 2018, the old Apache Jakarta name came back with it. The naming choice felt like an homage, and a reminder that trademark anxieties can outlast the people and projects around them. - [Coping with jet lag](https://duncandavidson.com/coping-with-jet-lag): Jet lag is the price of rapid global travel, and there is no magic cure. The best approach is symptom management: reset your food clock with timed fasting, protect sleep on travel days, use naps and light intelligently, and be kind to your body while it catches up. - [The tragedy of the HP B9180 printer](https://duncandavidson.com/hp-b9180): The HP B9180 was fast, reliable, and produced beautiful prints until its self-maintenance system turned against it. This short gear piece tracks how a great photo printer became prohibitively expensive once its nozzle-check system started consuming ink. - [Saving our bacon with evil cucumbers](https://duncandavidson.com/saving-our-bacon-with-evil-cucumbers): Before launching Wunderlist 3, the team needed to know whether the rebuilt backend would survive real load. The answer came from Böse Gurken: thousands of simulated users that broke servers, exposed assumptions, and made launch day mercifully quiet. - [On being an expat right now](https://duncandavidson.com/on-being-an-expat-right-now): Written from Berlin in 2014, this short essay reflects on watching Ferguson, surveillance, militarized policing, and US politics from abroad. It is less an argument for leaving than a sad admission that, for the moment, not missing America felt unexpectedly easy. - [When servers bleed](https://duncandavidson.com/when-servers-bleed): Heartbleed turned an ordinary Berlin startup morning into an emergency security outage. This is the story of taking Wunderlist offline, rotating credentials, rebuilding load balancers, and choosing not to knowingly leak user data while the broader web scrambled to respond. - [Sony DSC-RX1](https://duncandavidson.com/sony-dsc-rx1): The Sony RX1 put a full-frame sensor and a remarkable fixed 35mm lens into a camera small enough to fit in a jacket pocket. In 2013, that combination felt almost impossible, and it reset what a compact digital camera could be without giving up serious image quality. - [About Tack Sharp](https://duncandavidson.com/about-tack-sharp): A 2011 explanation of why Tack Sharp went quiet despite real listener demand. The short answer was podcast economics: listeners wanted more episodes, but the advertising-supported model needed sponsor demand that never quite showed up.