And it wasn't just surface-level design - the real change was in our personalities. Facebook, Bootstrap, the death of RSS, the rise of streaming music services, etc. The moment when this flipped for me was the iPhone, because unlike Blackberry or Sidekick, this was a device that was meant for both work and play, and it pushed the design boundaries equally together.
And you could clearly tell what was business vs personal. It all had a sort of gaudy messiness that never appealed to the artists and proto-hipsters, but they were the odd ones. WinAmp skins, but also skins in desktops (WindowBlinds), wallpapers (DeviantArt), icons, ringtones, etc. AIM profiles with colors, poems, quotes, and links.