It's one of those situations in life in which where you end up makes sense only in retrospect, as all those steps led you to where you are. What would have happened if I didn't go the pre-med/medschool route? I'm not entirely sure. I was a computer science guy in college, so absent pursuing a medical career, I probably would have ended up as a programmer somewhere after college ('96). Maybe I would have gotten rich in the craziness or maybe I would have been a victim of the .com crash.
I do think that if I was in college in the past few years, the startup culture and iphone app opportunities would have infected me, and I probably would have had to make an earlier decision.
Though, if I hadn't gone down the path, I don't think MacRumors.com would exist, as there was a timing/luck element to it. Not that I think success is entirely dependent on luck but a matter of taking advantage of circumstances as they arrive. I got married and had kids during that med school diversion, so certainly have no regrets there.
As for parental pressure/expectations on kids, it's something I've thought about especially after becoming a parent. I think as a parent, in many ways, you try to right the wrongs, fulfill the desires, or fix the challenges when you grew up. For immigrant parents, financial stability is probably the #1 hurdle they had, so they want their kids to go to college, get a white color job. That's what they've been struggling with. As someone who grew up financially stable, and being well off now, my priority for my kids is more of a focus on happiness and doing what they want. But that's a luxury that you can afford once financial stability is a given.