How do people in this industry cope with their age? Okay, maybe that’s not the right question. I know tons of people work in this industry and they do really well at staying up-to-date and current. Maybe the biggest issue isn’t the people in the web industry, it’s those that dabble and play here and there.
I’m not calling myself an expert in the field, but I certainly have been learning a lot the last few years about interfaces and user-friendly development. I’m a fan of Apple products (because that’s supposed to be some badge of honour or something), I mainly create in WordPress, I handle multiple sites, read A List Apart and basement.org, and probably most important – I grew up on the internet! I feel I at least have a basis of knowledge and enough sense to know when something sucks.
The more I work my current job, the more I find that living in this Midwestern bubble affects how people interact with the outside world. Or even perceive it in general. On the topic of web usability, there’s a huge gap between those in charge of the institution’s site and the current trends in web design and usability standards.
It's the people like Brian Niles and his team at TargetX that know what is going on. Those are the groups higher ed developers should be listening to. On second thought, I would think most developers are doing that. It's their bosses that are convinced their methods are the correct and best means.
I'm sure this is true throughout the industry, and probably much broader, but it's why school sites are so hard on the eyes, frustrating to navigate and downright old-fangled. Let your designers and developers do the work you pay them for! A lot of us are young enough to connect with the kids you're trying to attract. Let us be at their level, you can be at yours.