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gjm comments on Persistent Idealism - Less Wrong Discussion
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The following two strategies seem (to me) roughly equally plausible but (unfortunately) exactly opposite.
Establish a ruthless Schelling fence like "never keep more than $X of income in a year" where X is a rather small number.
Accept that you are likely to be unable to maintain a really unspendy lifestyle when surrounded by spendy rich people, and instead decide from the outset on a level of self-indulgence that you are likely to be able to keep up.
If forced to guess, my guess is that the former is probably easier to keep up for longer but may lead to a more drastic failure mode when it fails. But I have no reason to trust my guesses much on this. I'd be interested in others' opinions.
How about practicing nonconformism as a skill so you're comfortable being frugal even with spendy friends?
"instead decide from the outset on a level of self-indulgence that you are likely to be able to keep up."
For example, by setting a percentage to donate.
Schelling fence idea is interesting. However, as you indicated, I think that if it is too restrictive, your future, morally-compromised self is likely to abandon it. If you can outsource the enforcement, then maybe you’ve got a chance, but will banks fund a charitable trust with money you don’t have yet? Maybe you could take out a huge loan today and give the proceeds to charity, forcing your future self to pay it down. Of course, access to capital, cost of borrowing, and income growth rates need to be considered.
Or perhaps a less intense alternative would work: set up a relatively small, pre-scheduled, automatic bank draft to charity before you are corrupted. If the committed amount is more than you would have contributed otherwise, yet small enough to avoid being cancelled by your future self due to the “default effect”, then you’ve made progress.