Ask HN: Interesting forks in the road

Recently I read that Andreas Gal became CTO of Mozilla. I realized quickly he used to be my academic project adviser in undergrad, and he tried to recruit me into the comp sci phd program. I did a couple projects pro bono during the summer, but I decided against the phd and went into the workforce.

I kind of now wonder what would have happened if I committed to the phd program and followed his coat tails many years ago.

Does anyone else out there have any interesting stories of forks in the road?