One problem I have is determining my personal life expectancy. I had one grandmother die at 94, the other grandmother died at 96, one grandfather died at 90, and one grandfather died at 63 one month after a car accident where a blood clot went to his brain. My mother is still alive and living unassisted at 80, my dad died at 78 but was a heavy chain smoker (always lit a cigarette with a cigarette, then would get up in the middle of the night to go smoke). His lungs finally gave out and then he died.
I have no medical issues at this time and I always get a clean bill of health from my doctor at my yearly physical. I don't smoke, drink alcohol (I'm not a prude, I just never acquired the taste for beer or hard liquor) or take any medications (I sound kind of boring).
I know I'll have to find another job before I turn 60 for the simple fact that my company's pension plan penalizes you by reducing your pension benefit every month after age 60. So I'll find another job and start drawing the pension before I retire. It's one way my company can legally get rid of older workers.
I know the earliest you can start taking SS is 62, so I should factor this in as well.
My biggest problem though is not having a clue how much health insurance costs will be from when I retire to when I can start getting Medicare. Also, how to determine what Medicare will cost me when I'm fully retired.
If I could get a good grasp on this, I think I could get a better idea of when I can retire.