If everything goes my way, I'm going to retire in April 2021, at the age of 51. Years down the road, if I'm sitting on a lot more money than I thought I'd ever had, I might start regretting a bit, that I didn't retire earlier. But, at this point I figure I'd rather have too much, instead of not enough, and end up having to go back to w*rk or worse, having it run out when I'm too old to really be employable.
There actually is a good chance that I'll end up in the "too much money" side of things. I'm the sole beneficiary of my uncle's estate, as he has no kids of his own, and I'm also set to receive a pretty good inheritance from my Mom and stepdad. I'm an only child and he never had kids, but they set it up so that I get half of everything, his sister gets a quarter, and his brother gets a quarter. I don't use either of these inheritances in any financial planning, though. My uncle isn't all that healthy, and I could see him running up some pretty big medical bills, although he's been pretty good so far. And, anything could happen with my Mom and stepdad. She could die first and then he changes the will, or they could end up hitting some big medical bills, as well. All I know, though, is that they actually have more saved up now than they did when they retired back in 2011. They don't even spend all of their pension checks, so they're still accumulating even in retirement!
But, again, I'd rather err on the side of caution, rather than count on something that may or may not happen.
Also, if I fall victim to one more year syndrome, and go out at 52 instead of 51, but then look back and realize I didn't need to, I don't think I'd regret it too much. But, with each passing year, I think I would regret it a bit more.