It does, because we’re talking about the total lifespan instead of remaining lifespan. A person who is 120 may have a 10% chance of living another year; but a 50 year old probably has less than a 1% chance living 71 more years. Of course the 50 year old probably has more than a 99% chance of living another year. So the older you are, the older your expected total lifespan is, even if your expected remaining lifetime is shorter.
You’re absolutely right, stats are a very misunderstood subject. It’s difficult to contextualize stats like this when the population is so large. My measurement for when I got old was when I started to meet old friends and at some point in the conversation we begin talking about other friends who we both knew who’ve passed away since the last time we’ve talked.