When you get older, several things work against you to jump into SV culture:
- You are not as easily impressed by or eager to try new technologies. (many of which are new spins on old ideas you've seen before.)
- You fail to see the appeal of the types of technology younger people are using. Or, you see the switching costs as too high to move away from what you are using now.
- Your lack of ignorance leads you to (often correctly) identify that an idea will lead nowhere. The problem is sometimes you are wrong.
I think the best way to fight against ageism is to make an effort to retain an open mind and curiosity. Try new things, even if you think they are going not be worth your time. Try to see the novelty in things that may seem to be a rehash of old ideas. Realize that no matter how stupid an idea sounds, sometimes it's worth trying, because you can't always predict the future, no matter how much you've seen.
Just think of the number of people on HN who have posted about how they don't understand Facebook, Twitter, or shoot down some whiz bang new technology. I've done it sometimes myself. Engineers are naturally skeptical, but this skepticism can grow out of control. It's fine in moderation but there's a tendency for this type of perspective to grow with age naturally, and that can ultimately undermine your ability to recognize and execute on genuinely novel, good ideas.
If I could hire someone who had both extensive experience but did not have a chip on their shoulder and lived on the edge of the curve like a 20 year old I'd do it. But it's pretty hard to not have a chip on your shoulder in this industry after a decade or two, and it's hard to continue to adopt the latest technology and not just settle in at some point along the way.