Alan Williamson

  • The Realities of Software Releases: More Than Just a Button

    Releasing software is more than a button click. It is a high stakes moment where code meets the friction of the real world. From the landing gear moment of scale to the clean floor data paradox, here is why going live is complex and why we never release on Fridays. Read Post ⇢

    The Realities of Software Releases: More Than Just a Button

  • Think like a CTO – Japanese Edition

    Think Like a CTO has been translated and published into another language, Japanese. Read Post ⇢

    Think like a CTO – Japanese Edition

  • How AI Agents Will Change Ecommerce

    The rise of the machine customer marks the end of the browser era. To win, platforms must move beyond UI and provide deterministic, AI ready APIs. Making your site agent friendly is no longer optional; it is your new competitive advantage. Read Post ⇢

    How AI Agents Will Change Ecommerce

  • The Flaws in AI Customer Support Systems

    My recent Logitech support experience highlights why context is king. A solid AI speech agent was ruined by a human handover that started from scratch. AI should be a connected workflow, not an isolated silo. If your latest improvement makes the service slower, you have failed the integration test. Read Post ⇢

    The Flaws in AI Customer Support Systems

  • Rock me Amadeus (& Elvis)

    Watching the new Amadeus series led me down a rabbit hole where I found a striking parallel between Mozart and Elvis. Both icons died broke, but their widows, Constanze and Priscilla, became the first accidental CEOs. They professionalized the legacies, cleared massive debts, and pioneered celebrity tourism to save the brands. Read Post ⇢

    Rock me Amadeus (& Elvis)

  • 2025 in review

    With the 1st of January now rolling us into 2026, it’s time for my annual review of the year that has just closed. Another beautiful sunny day here in Virginia, warm and blue skies as I sit down and reflect on some of the stats and journals I have maintained this year. Read Post ⇢

    2025 in review

  • The Inevitable V3 Rewrite

    Software rarely finds its feet until version three. Version one is an idealistic guess. Version two is a survival patch. Version three is the rewrite where you finally delete the noise and build what is actually needed. Real stability comes from subtraction, a lesson every architect learns the hard way. Read Post ⇢

    The Inevitable V3 Rewrite

  • Double NAT, 40 Terabytes, and a Christmas Miracle

    I spent my Christmas downtime replacing a fragile, port-forwarded network with a resilient Tailscale mesh. I managed to overcome double NAT headaches to sync Synology units peer-to-peer, fixed the inevitable MTU “black holes,” and automated the DSM 7 sandboxing hurdles to build a private, encrypted family network. Read Post ⇢

    Double NAT, 40 Terabytes, and a Christmas Miracle

  • “This ain’t no technological breakdown”

    Honoring British rock legend Chris Rea, I recall 1989: a 16-year-old student in Paisley, wrestling with the guilt of spending my living grant on “The Road to Hell” vinyl. Purchased for £5.99 at Woolworths, it became the defining soundtrack of my university years. Thirty-five years later, the joy remains. RIP. Read Post ⇢

    “This ain’t no technological breakdown”

the leg-end that is, Alan Williamson.

For over 20 years, I’ve shared my thoughts whenever the muse strikes. It’s unpredictable, honest, unedited, and occasionally witty. I’m living the best years of my life, working harder than ever, and enjoying every second.