July 31, 2026 ยท by David Gilbert ยท 3 min read ยท Flashback Friday

Flashback Friday: 25 Years of Tech, From Dial-Up to AI

This feels like the right note to close out a month of Flashback Fridays on: a proper look back across roughly twenty-five years of doing this, from a screeching dial-up handshake to AI tools quietly drafting my emails. It's been a genuinely wild stretch of change, and yet somehow, sitting here writing this, the actual job feels remarkably continuous.

What's Completely Different

The list is enormous if I actually sit and total it up. Floppy disks to cloud storage. Dial-up to fibre. Phones that made calls to phones that are more powerful than the desktop tower I built with my own savings and nearly set on fire as a teenager. A handful of niche hobbyist tools to AI assistants embedded in nearly everything. Physical cart machines and cassette archives to cloud-scheduled digital radio. Chain emails about bad luck to algorithmically optimised social feeds about, depending on the day, very similar things dressed up considerably better.

What Has Not Changed at All

Someone walks in with something broken, worried, and wants to know honestly if it can be saved. That sentence was true in the kitchen-table Nokia 3310 era. It's exactly as true today, just with a different device and a more sophisticated diagnostic process behind the answer. The actual emotional core of the job โ€” being useful to someone who's a bit stressed about something they don't fully understand โ€” hasn't shifted by a single degree in twenty-five years, and I'd genuinely wager it won't shift in the next twenty-five either.

The Pattern I Keep Noticing

Every single "this changes everything" technology I've lived through โ€” the internet going mainstream, smartphones, social media, and now AI โ€” has followed roughly the same arc. Wild hype, real disruption somewhere underneath the hype, genuine new risks nobody saw coming attached to genuine new benefits nobody saw coming either, and eventually a new normal that the next generation will take completely for granted, the same way nobody under thirty today is remotely impressed by broadband. I'd bet good money AI follows that exact same arc, and that in another twenty-five years someone will be writing a "remember when AI tools felt new and exciting" nostalgia post of their own.

What I'd Tell My Kitchen-Table-Repair Teenage Self

Keep being curious enough to pull things apart just to see how they work โ€” that instinct is the actual foundation everything else got built on, more than any specific skill or tool I picked up along the way. Don't get too attached to any particular piece of technology, because every single one of them, no matter how permanent it feels in the moment, eventually becomes someone else's nostalgic Flashback Friday post. And the people skills matter at least as much as the technical skills, the whole way through โ€” that's the bit I genuinely wish someone had told me clearly and directly, right at the start, instead of letting me figure it out slowly over a couple of decades.

Here's to the Next Twenty-Five

I genuinely have no real idea what this job looks like by 2051, and if I'm honest, that's most of the fun of it. Thanks for reading along through this first month of posts โ€” there's plenty more where this came from, and I'll keep showing up here roughly the way I keep showing up on air every second Sunday: a bit imperfect, genuinely curious, and hopefully useful more often than not.