I remember discovering HN around 2008 when I was a teenager. I hardly understood anything on the front page. I knew how to program a little bit, but only at a superficial level. Now, it's rare for me to come across something I don't understand unless it is very specialized or about some scientific topic. But I think Slava is right that if you want to stay motivated and stay interested you have to find a way to remind yourself of the bigger picture. Otherwise you get bored no matter how interesting the work is. I know a guy who left a job working on rocket guidance systems because after a few years it got boring to him.