My smokin' hot Puerto Rican girlfriend and I were discussing this (again) the other night.
She retired from NASA a few years ago (she's literally a rocket scientist). While I'm free to come and go as I please, work-wise, we're wondering if it's getting close to the time when I should just finally call it a day for good and embark on our well-earned life of leisure.
As it is, over the last year or so I've been spending less time at the office and more time working at home. We're fortunate that our hard work has put us in this position. One of my businesses is in a very niche market (which is why I've never shared what it is here), and if I elected to sell it I know I would get pretty much what I ask for it. That said, it would provide a nice revenue stream in retirement, too, and it's something I would have to pass down to my daughter.
We want to travel, we've got the Viking (which I'm considering selling), a vacation home and passports. I'm 60, my smokin' hot Puerto Rican girlfriend will be 53 in January, and we're still active and healthy enough so that we could enjoy life away from the workplace.
The current thinking is that I give my self a nice birthday present in 2024, when I'll turn 62, and finally hang up my key for the executive washroom one last time...