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Are Some Countries Really Happier Than Others?

One possible consideration for your five flags plan, or any long-term international plan for your life, is to consider how happy the people are in the country (or countries) you intend to live. The problem is that there is a huge amount of bullshit when it comes to...

Looking for a House and Office In A New Country

As most of you already know, in January of 2021 I am finally moving out of the Collapsing USA for good. My current plan is to live in my primary home in either Australia or New Zealand for six months, then be in Hong Kong for approximately three months, then spend...

Living Abroad When You’re Younger

A reader (I don’t remember who, sorry!) recently asked this question: Caleb, you said in one of your podcasts that your biggest life regret was that you didn’t live in Asia for 2 years when you were in your 20s. Could you make a post about traveling on another part of...

My Five Flags Plan as of December 2018

This is an update of exactly where I stand with all the countries I’m working with on my five flags plan to permanently move out of the United States, save myself a shitload of money on taxes, increase my freedom, and increase my income. As always, this plan is still...

Staying 100% Legal With Five Flags

Is offshoring your business or finances legal? Is having multiple passports legal? Is having multiple residencies legal? Yep. It’s 100% legal (unless you do it incorrectly). Is reducing your tax down to microscopic levels legal? Won’t you get in trouble? The answer...

Overview of How Five Flags Works

Above you’ll see a handy dandy flowchart (click it to zoom) that I actually had to set up for myself to keep my thoughts straight on all this stuff as I implement it. Five flags is a way in which you can minimize your taxes, maximize your freedom, and maximize your...