I'm in the awkward middle area I think where I'm almost a digital native, and what you said maps perfectly to my experience. In middle school and high school I got pretty good at the first type of search you mentioned. I was young enough that I was almost learning how to "speak" google and it came easily, I was fluent. Throughout the end of high school and into college I had more and more issues finding what I wanted and one day after I had failed to search several times I thought to myself "Fuck it. I'm just going to type in exactly what I want in plain English, as if I was a moron, and see what happens." And it worked, and that day a lightbulb went off in my head.