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ThrustVectoring comments on On not getting a job as an option - Less Wrong Discussion
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Now that would be an interesting topic: The rationalist hobo.
I am actually considering something similar. There is the extremely early retirement community where the general suggestion is to earn much money in very short amount of time, to live below means in that time, to invest as much of it as possible and to then live from the interest gathered. Driven to extremes the necessary base capital can be quite low, such as in the low hundreds of thousands.
As interest is mobile and I can relocate to a country that almost does not tax capital interest I am free to roam the world. Additional income can come from local work or donations as I intend to still work some amount of time in theoretical research which essentially is just time consuming without need for capital expenditure.
For some time at least this would be very interesting.
Edit: The availability of so much free learning material online makes this even more viable. The only issue will be maintaining a good exercise regimen and good eating habits.
Edit 2: If you can learn remotely, you can work remotely. Being on the road does not preclude doing analysis or similar stuff to stil learn an income.
There is a huge amount of risk involved in retiring early. You're essentially betting that you aren't going to find any fun, useful, enjoyable, or otherwise worthwhile uses of money. You're betting that whatever resources you have at retirement are going to be enough, at a ratio of whatever your current earning power is to your expected earning power after the retirement decision.
No, you're betting that you aren't going to find enough such uses for enough money to outweigh the benefit of having hugely more leisure time.
I can think of pretty good uses for a near-unbounded amount of money (more than I am ever likely to have, alas). I can think of pretty good uses for a near-unbounded amount of time (more than I am ever likely to have, alas). Working full-time, working part-time, and not working at all (note: by "working" here I mean working for pay) make different trade-offs between time and money; none of them implies not having any use at all for time or not having any use at all for money.