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> The only "wrong" answer to these question was when someone would answer YES to the second question after clearly answering something completely different to the first one. For example, if someone would say travel the world to #1 and yes to #2.

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?




This is something I wanted to say in my response but left it out to avoid taking away from my other thoughts.

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.




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