You know, eventually you will get too old to enjoy skiing. I think you should immediately take some vacation time and GO. You need to enjoy this now, while you still can! So what if it delays ER by a couple of weeks. I can tell you that for me, age 66 (my present age) would be way too old for this sort of thing.
Can you do that? Maybe you could make up some sort of excuse to make it seem more urgent to your management. Tell them you are feeling extremely burned out and having panic attacks related to work issues, or something like that.
I could, as finances and PTO time wouldn't be an issue (I have 6 weeks of PTO time built up). However, because I'm in a critical role in Support, people would continue contacting me even though I tell them I'm not checking email, or even turned off my phone. And as much fun as the break itself might be, coming back to a weeks' worth of BS that would pile up in my absence wouldn't be worth it.
I'd rather just suffer through the home stretch I'm in until I'm fully vested and can quit (which will be early next year), and then I can do what I want, when I want, with no boss or job hanging over my head.
As far as health, I'm in my late 40's and (thank God) in good health. My knees are a little wonky, but no more so than when I was in my 20's and skiing. I just avoid bumps (always hated moguls anyway) and go more for nice green and blue runs. I'm more of an easy going cruiser - I just like to get out on the mountain.
I'll say to you what I said to him then, just as a warning. If you have so much of your net worth in your company stock that it controls your choices, you might want to reallocate (if you're allowed to).
Valid point, and yes, I do need to diversify, but I'm going to let what I have ride a little bit more before I do, because I do truly believe there's more upside where I'm at. I'm not just saying that because I "drank the Kool-Aid", but because I see both the good and the bad, and still believe there's upside. Once I leave, I will probably take anywhere from 30-50% out and diversify. I still want a significant amount in the stock because I do think it will continue to do well over the next few years.
During college I took off a year and was a ski bum in Vail. Unfortunately it wasn't a very good snow year but taught me that ski bum wasn't the career I wanted ;-)
I wouldn't want to do it unless I'm FIREd. But one thing I've always wanted to do is spend a season in Vail with no job or boss hanging over my head. Maybe "bum" is the wrong word - think "man of leisure" instead