I'm 51, so I figure I'd better get this right pretty soon. :) I think about this a lot, though. The common thread through the last 25 years, though, is that I've worked for myself. That's a lot of years without a safety net, and it's also a lot of years to learn habits that would make it almost impossible for me to work for someone else.
About 20 years ago, though, I put together this list. At the time, I felt like most of my life was ahead of me and that I wanted as many options as possible. So there's very different from each other, and it was just me dreaming one day:
Some people get it. By extension, then, some (most?) people don't get it. Gwen Bell is one of those people who clearly gets it. The first time I read her website, a whole lot of things clicked for me. I'm not prepared (at the moment) to adopt her lifestyle and business model, but I like her presence, how articulate she is, and how key points are explained thoroughly enough to eliminate the frequent response: "Yeah, I've heard of her and read some of her stuff."
When you add someone young to your staff, their primary business goal is to add variety to their experience. That's partly because they believe that doing so will make their next job search easier, but it's also a bit self-serving: more variety means more interesting things to do. Not really because they are forced to do research and become an "expert" overnight on a given subject, but just because there seems to be a genetic A.D.D. affliction among the creative set.
Some thoughts on Saul Bass and his impact on design. He may have been one of the most influential designers of his era.