Circa 2013, had I been asked this series of questions, the answers almost certainly would have been:
1. Spend as much time with my friends and family as possible. Do a bit of traveling. Try to finish off seeing all the MLB parks.
2. Yes. I want to leave a legacy for my children. I figure there are a few ways to do that. Join a very promising mid-stage startup, e.g. Optimizely, Pinterest. Join a very promising late-stage startup, e.g. AirBnB, Dropbox, Stripe. Join a FAANG.
I was super hot on Optimizely back then, so I would have jumped at the opportunity to get in relatively early. With ten years to live, and a family to think of, you can be damn sure I would have given all I had for 3-5 years.
With three years to live, I _might_ have taken a moonshot on a mid-stage like Optimizely. In that case my plan would have been to negotiate a high-equity package, early exercise the first year, then quit and live the next two years of my life however. But, I never would have said that in an interview.
That is a strange assumption.
My answers to #1 and #2 would have been contradictory to you, but with 10 years to live I would see working at Optimizely for 3-5, then doing what I wanted to do for 7-5 years a great tradeoff.
Would I have said that in answer to #1? No. I'd have said "Travel and more time with friends and family", while knowing full-well I had to work, or I would starve.
Would I have said it in answer to #2? Perhaps, but unlikely.
What was the success rate with these two questions?