It might be worth considering a mixed or hybrid path -- if you can get a high-paying traditional (software, finance, etc.) job, while being very frugal and saving money (and you don't have much or any debt), you can get pretty quickly to the point of having a very comfortable savings buffer. If at that point you use your savings for living frugally, but not for funding your startups (do that with Other People's Money), I think you'll have more runway and more options than you might otherwise, and should you find that the startup life is not working out you should have a good backup trajectory available where you go back to a high-paying traditional career and retire.
I'm curious why you think (4) seems unlikely -- is this a fact about your personality, or about the world (i.e. you think there will be no normal-ish jobs, and/or the world will not survive to see your retirement?) Considering again high-paying jobs like software and finance, I think the math shows that a very frugal person can effectively retire after very few years in such a job -- perhaps as little as a decade, certainly as little as two, which is similar to your stated startup timeframe -- depending on what your goals are. And once you're in "effective retirement" (i.e. you don't have a problem supporting yourself), then you're in a great position to try to get a startup going.
I'm curious why you think (4) seems unlikely -- is this a fact about your personality, or about the world (i.e. you think there will be no normal-ish jobs, and/or the world will not survive to see your retirement?)
Let me try to clarify. What I'm trying to say is that 1 & 2 seem likely enough that I won't need to worry about saving for retirement. And even if (!1 && !2), it seems very likely that I'll be both willing and able to continue earning money well past retirement age. Given these three things, it seems like pursuing 4 is unlikely to be worthwhile.
I'm 22 years old, just got a job, and have the option of putting money in a 401k. More generally, I just started making money and need to think about how I'm going to invest and save it.
As far as long-term/retirement savings goes, the way I see it is that my goal is to ensure that I have a sufficient standard of living when I'm "old" (70-80). I see a few ways that this can happen:
Median optimistic year (10% likelihood): 2022
Median realistic year (50% likelihood): 2040
Median pessimistic year (90% likelihood): 2075
- http://waitbutwhy.com/2015/01/artificial-intelligence-revolution-2.html
And even if they're wrong and there's no singularity, it still seems to be very likely that there will be immense wealth creation in the next 60 or so years, and I'm sure that there'll be a fair amount of distribution as well, such that the poorest people will probably have reasonably comfortable lives. I'm a believer in Kurweil's Law of Accelerating Returns, but even if you project linear growth, there'd still be immense growth.
Given all of this, I find thinking that "wealth creation + distribution over the next 60 years -> sufficient standard of living for everyone" is a rather likely scenario. But my logic here is very "outside view-y" - I don't "really understand" the component steps and their associated likelihoods, so my confidence is limited.
Anyway, I think that there is a pretty good chance that I succeed, in, say the next 20 years. I never thought hard enough about it to put a number on it, but I'll try it here.
Say that I get 10 tries to start a startup in the next 20 years (I know that some take longer than 2 years to fail, but 2 years is the average, and it often takes shorter than 2 years to fail). At a 50% chance of success, that's a >99.9% chance that at least one of them succeeds (1-.5^10). I know 50% might seem high, but I think that my rationality skills, domain knowledge (eventually) and experience (eventually) give me an edge. Even at a 10% chance of success, I have about a 65% (1-.9^10) chance at succeeding in one of those 10 tries, and I think that 10% chance of success is very conservative.
Things I may be underestimating: the chances that I judge something else (earning to give? AI research? less altruistic? a girl/family?) to be a better use of my time. Changes in the economy that make success a lot less likely.
Anyway, there seems to be a high likelihood that I continue to start startups until I succeed, and there seems to be a high likelihood that I will succeed by the time I retire, in which case I should have enough money to ensure that I have a sufficient standard of living for the rest of my life.