Don't forget that you can talk to me directly for one-on-one advice about travel and running an online business.
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Chris Guillebeau has an excellent collection of guides to help entrepreneurs to start their businesses as well as a great guide to becoming a frequent flyer master. His blog is one of my favourites and I have met him several times in person; he is genuine and knows what he is talking about.
This page has a bunch of products that he has created to help others have the kind of freedom that he, myself and others enjoy.
I'd only recommend his frequent flyer master guide to North Americans (US / Canada) though. Non North Americans will also get the guaranteed 25,000 miles as everyone else, but I find it difficult to apply the rest of the advice as an Irish citizen. His other guides would work for pretty much everybody however!
The empire building kit is a huge project of an email every single day for a year filled with immense detail of how to grow a business and start a movement, slowly but surely!
Travel and health insurance
I move country a lot, so I was very happy to find that World Nomads have a very easy to set-up system for travel insurance. Everything is done online, it works with any nationality. Rather than have one generic price you can specify precisely how many days/weeks/months you will need it and if you'll need it for countries where insurance is expensive (like USA/Canada/Japan) or inexpensive.
You make a claim by logging into the website, so you don't have to carry around any paper that you could lose during your travels.
Just to see how much it could cost for an upcoming trip, fill out this form for an estimate:
Simple & Flexible.