tiredrod

I don't know if I'm being biased because it's my home or I'm really that lucky to have been raised in a truly multi-cultural and diverse country, but I really love Canada.

I would want my kids to live in a place where the people are kind and are from a full range of backgrounds with wilderness/nature/mountains/lakes just a few hours away.

Picking a country to incorporate your business in is far more important than you think! Singapore is a great country to start a business in with their tax incentives and structures, but I find it to be a poor choice in hindsight given that my business is online-based and that most of my customers are in the US.

I wish I had incorporated it in the US. It's worth paying more taxes just to get the newest and best technologies, tools and services to help out with work. For example, I really really want to use Stripe's payment services, as well as the full feature set from Shopify.

My friends can attest to this. I'm absolutely terrible at keeping in touch with friends. It's gotten much better now that I've installed LINE (IMO a much better alternative to Whatsapp) on my phone and computer. And I know there are a lot of Facebook haters out there, but for someone like me, Facebook is a god-send. It helps so much in keeping up with old and new friends who you've crossed paths with.

Yes, it does get quite lonely sometimes. But all that's needed is to join a local tour, head to hostels or just talk to people on the street!

Dating on the road is very interesting and confusing (and fun)! Sometimes it feels like a very long extended date when you spend days or weeks traveling together, seeing and experiencing some unforgettable things with just the two of you. It gets confusing when you don't know if it's just the lust of traveling that you're feeling or if they're genuine feelings for the other person.

I say I average to about 2 months per country. I try to be as thorough as possible when traveling to a country since I usually have to cross border-to-border (overland) anyways.

My spending on accommodations has increased with time. Sleep is extremely important as it's what keeps you agile for both on the road and business. In the beginning, I would stay in dormitories, which was great fun as you get to meet so many new people, but it turned out to be not so great for doing work at night. Dorms turned into shared rooms at hostels, then to single rooms in the recent quarters. I got a real idea of how sustainable this nomadic way of living is when I lived in a private apartment in Bali via AirBnB. That was a much appreciated comfort!

One thing I noticed in Tim Ferriss' book is that his sports nutrition supplements company must have either been an extremely automated, heavily bootstrapped business that was in a very high profit margin, or that he's over-inflating his income. It's impossible to run a fully functioning and growing online store with a single hire that is the assistant. I know I've tried that model and it was impossible in my experience. I have a couple of employees who are located from all over. We communicate via emails and Skype.

The business was running for nearly a year before I left my country. It's easy to automate a business, but it's much harder to grow it passively. You always need to put in the time to grow a business!

I sort out the visas on the road. I had no idea where I was going to go next when I first landed in my first country, Singapore.

Technology is an amazing thing, especially 3G! Even the poorest countries have some form of mobile data connection these days, so it's always possible to work in a country. There are, of course, some more rural places where there's no signal at all. In those situations, I try to predict the regions beforehand and schedule my offline work for that period of time.

In other words: don't take lightly the country you're going to incorporate in!