Wei_Dai comments on Academia as a career option, its social value, and alternatives - Less Wrong Discussion
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See this comment of mine. While it was posted as a "ridiculous munchkin idea", it's essentially what I did, and seems to have worked out well at least for me. So I suggest adding "self-supported independent researcher" as another alternative to your list.
To answer one of your questions, I considered going into academia, but didn't for a number of reasons (some of which are just personal, but I'll mention for completeness).
What I ended up doing was working for a couple of Internet startups in succession, and taking a year off in between to develop a software product which I handed off to a partner to sell and to continue developing. I was hoping that one of these would make enough money for me to "retire". Eventually my stock options in the startups proved worthless but the software product started earning enough money that I could quit my job.
BTW, since you are advising high school students and undergrads, I suggest that you mention to them that they can start being independent researchers before they graduate from college. For example I came up with my b-money idea (a precursor to Bitcoin) as an undergrad, and was also already thinking about some of the questions that would eventually lead to UDT.
Do you have thoughts on the degree of risk involved, or on conditions that would reduce risk?
Many people endorse goals that lead naturally to "make money, retire and do X".
Do you mean 1) the risk of not making enough money to retire, or 2) the risk of failing to make progress on your chosen topic, or something else?
For 1, I'm not sure what the start-up stats are, but as you can see my personal experience was one success out of three tries. Looking back, I think what I did right was to diversify, not put all of my eggs in one basket, and what I could have done better was to choose employers based more on a level-headed analysis of their business prospects rather than just how cool their technology was. (Although to be honest I'm not sure how to do the former, so I'm glad I don't have to anymore. :)
Also, I should note that while I was hoping to quickly make enough to retire, I was also saving most of my regular income aside from the stock options so that I could do early retirement even if I wasn't able to "get rich quick".
For 2, I think the key is to pick a topic that you're really curious about and that's important but neglected by academia/industry/government for some reason (so there's more likely to be low-hanging fruit for you to pick). I'd also suggest striking a balance between being persistent and being opportunistic, but again that's easier said than done and I don't know what practical advice I can give here. Oh, almost forgot, it helps to find or build an online community around your chosen topic.