I went to an ivy league college, learned an economically scarce skill (IT security), found contract positions that paid a high hourly wage with no clause to continue the work. I was otherwise frugal.

I am not conventionally attractive or charismatic. Louie is. He will find it easier to find work as a bartender without a resume or reference than I will.

Self promotion is a form of sales. Had this been posted directly on Tim Ferriss's blog, I'd have not noticed a difference in writing style.

I'd like to raise a "dark arts" objection here. This article is written with a lot of presuppositions, strawman attacks, appeals to character, and other interpersonal but non-rational attempts to convince social humans.

For example, the article leads with "You're young, smart, and hoping to have a positive impact on the world." While that may be true of the majority of less wrong readers, the article does not discuss why these qualities are relevant. In fact, the article suggests ways to have less impact on the world - working through a service position - than other careers (such as existential risk reduction). This leads me to believe that this opening line is nothing more than a compliment intended to endear the reader.

The following wording reads like a sales pitch and is highly suspect: "And it is possible to find easily obtained, low-stress jobs with flexible hours that allow you to save as much money as someone in the USA making $100,000/yr... if you leave the USA to look for them."

A classic promise - easy money, with a small catch. Can you rewrite this is as a description of the work you personally experienced, rather than an ambiguous promise?

You disarm objections without providing evidence via, "Your instinctive reaction is probably that there’s no free lunch, so I must be mistaken or dishonest." and follow up with a reiteration of the sales pitch and another appeal to the reader's character in "And while you may have the right prior, I hope to persuade you that these jobs exist and tell you how to get one if you're interested."

More sales-ish writing: "This, I think, is a special opportunity ..." followed by a reiteration of the sales pitch. Why not say, "Act now! Limited supplies available?" It has the same content and validity, absent evidence or justification WHY this is a special opportunity. If anything, rationalists are not the best target market here: low income, low skill US wage earners are.

You fail to discuss your personal experience (other than providing a smiling picture of an attractive young male engaging in the activity you propose - another sales tactic). You don't discuss why you can easily get a job as a bartender (likely that you're a charasmatic, attractive young person) but instead imply that the entire area is somehow 'easier.'

As a personal example for credibility, I made $44,000 in the United States last year working only 5 months out of the year. I was able to save $19,000 of that, after taxes, living expenses, and several luxuries like months-long trips abroad.

There are many ways to optimize one's income and savings rates.

You haven't addressed the main issue:

I prefer to work on things that interest me intellectually. This is worth more to me than any wage. Service labor does not interest me. How does this economic disparity aid a rationalist who has desires other than money?