Being able to do something useful makes all the difference in the world when you want to travel the world for free or for almost nothing.
The fact that I can write, edit, work on computers, fix cars, and wash dishes means that I can go just about anywhere and trade my skills for whatever I need.
World Travel for Almost Nothing Tip #5:
Make yourself Useful.
Whether you cook, clean, or practice medicine the skills you’ve 
worked hard to develop will help you to be welcome wherever you go. If you are a carpenter or a mechanic, you can probably find everything you need in return for your skills. If you’re good at eating chips and playing World of Warcraft, well, it might be harder to find someone who is willing to trade food or lodging for those skills…but in this world, anything is possible.
In fact, lots of people opt to take actual jobs that involve travel. Working on cruise ships, airlines, tour guiding, and many more jobs actually pay you to travel…that’s almost better than free.
The key to this is that it takes time. You can’t step off the plane and simply say, here I am! You have to talk with people, you have to interact, you have to let people know that you have something to offer. So if you want to get that free vacation rental in Bermuda for three days, you better work your ass off figuring out who you know has connections there or using the internet to network virtually.
Another skill that has really worked in my benefit is being a teacher and a Native English Speaker. You can usually find someone who wants to trade what you need for language lessons.
This is actually, a very hard list to order – mainly because the particular time and experience I had in each place weighs just as heavily as the place itself. I didn’t realize that ranking these would be so difficult. Not only is it hard to rank the best from the places I’ve lived – it’s equally hard to rank the worst. In the middle, each place had positive and negative qualities that would change the ranking. Perhaps the only way to do this is to rank these places based on whether I would want to move there again with all other things being equal.
I loved living in Seattle. I had been there for the protests that shut down the WTO in 1999. Seattle has great art, music, food, museums, and is surrounded by some of the most epic nature of any city in the world. I probably would have stayed there if the start up I was working for, TechPlanet, hadn’t of been an early crash and burn victim of the dot com crash in 2000. When I first started working there, I was commuting and after that couch surfing during the work week with friends in Shoreline and coworkers in Greenwood. Techplanet sent a bunch of us to Houston to take a crash course and become network engineers and all around tech gurus and after that three of us from the same cohort and office rented a house in Green Lake. We had stock options, we had good salaries, we were working in one of the fastest growing and best funded dot-com startups of that era – and then the venture capital dried up and one day we went to work and the corporate office in Menlo Park, California had simply closed. Suddenly, there weren’t all that many jobs in tech and those with more experience snapped up the jobs at Microsoft and Amazon.
One of my room mates became an insurance salesman, another one teamed up with some of the other guys from our old office to try to build a consulting firm, and I bought a VW van, got a job as a community organizer with ACORN (Association of Communities Organizing for Reform Now) and began attending a lot of anti-capitalist, anti-government rallies and meetings. ACORN trained me in identifying discontent, organizing community members, and working towards legislative and social change (they also trained President Obama in this). I was working in poor communities like White Center and South Seattle and I was mainly working with people who were the victims of predatory lenders. Their neighborhoods were being gentrified and they were being preyed on by companies like Countrywide Mortgage. It was agonizing and horrifying work. It was terrible to see what was being done. These were the early days of what would lead to the Great Recession of 2008 and the robbers were feasting on the flesh of the poor with impunity. I suggested radical action – too radical for ACORN – specifically, a neighborhood group I’d organized in South Seattle said they didn’t want the gentrification to continue AND they wanted the police to have more presence in the community – I suggested they break a window in the new local Starbucks every night. ACORN asked me to leave.
I moved out of my house, moved into my bus and began writing what would eventually become my first book 
Seattle is the largest city in the Pacific Northwest of the United States and while it isn’t the political capitol of Washington, it is the cultural capitol. With a total metropolitan population of about 4 million Seattle has a bit of everything you could want – unless you want more than two months of sunshine a year.
Thinking of Bellingham, Washington always makes me happy. I’m not going to lie and tell you that my life there was always happy, but for me, Bellingham was a magical place. I rolled in during the worst blizzard in decades. I wasn’t worried, I had a huge 4×4 and had first learned to drive on mountain roads in blizzard conditions up in 
I got a coffee at a hippie coffee house on High Street and began looking for work and a place to live using The Echo – a free classified newspaper – it was like Craigslist but in newspaper form. I quickly fell in love with KISM 92.9 FM Independent Rock – the most amazing radio station I’d ever listened to. Great DJs, amazing announcers, absolutely amazing music programming, and superb fun shows. The morning show DJ, Dave Walker, would end every show with his tagline “You live in the coolest place in the world, go out and enjoy it.”
As a painter I made a bunch of new friends. I also made new friends through my new roommate, Alyssa. Every day, I listened to 92.9 FM while I was working. One day, I told my co-worker – I’m going to get a job at that radio station. At a blues festival hosted by the station, I saw my chance. I met the programming director, a guy named Ken Richards who was also one of the DJs – I cornered him in the beer tent and told him “I want to work for 92.9 FM, I don’t care what it takes – I’ll clean toilets if I have to.” He gave me his card and told me to call him the next week. I did. He offered me a job as an producer/intern on ‘The Morning Deal’ – I would have to quit my painting job and it was a serious pay cut, but I took it.
The girl was great but she had two children from previous relationships and I wasn’t ready to be anyone’s dad. Then, one day, I met a girl I fell head over heels for – she was all I could think about for years. I pursued her with a single minded determination that utterly failed. All she ever wanted from me was my friendship, but I wanted more. That desire (the root of all suffering) destroyed me, destroyed my ego, and left me disjointed and dis-satisfied. It left me completely unsettled despite my very cool life, great friends, minor fame, and decent income. I wanted her and since I couldn’t have her, I wanted more from every other aspect of my life.
Back in Bellingham, I started a magazine and co-founded an early internet startup. Once again, there were plentiful opportunities presented to me in work, in life, and in love – but she was all I saw or wanted. It was a sickness, this love and obsession – and whenever I would find myself healing from it – then she would appear – at a party, a call out of the blue, in the street, at a coffee shop, or showing up at my door. She wanted me in her life and yet, the one thing she didn’t want was a romantic relationship with me. It was all I wanted. Finally, I realized, I just had to get away from her. She wasn’t doing it on purpose, but she had eaten my soul.
Bellingham is a treasure. It sits 20 miles south of the Canadian Border and 90 miles north of Seattle. It is sandwiched between the San Juan Islands and the North Cascade Range of mountains. There are about 92,000 people who live in Bellingham and it is the northernmost city in the USA with a population of more than 50,000. There are numerous lakes, streams, waterfalls, and great hiking, mountain biking, and outdoor recreation of all kinds in the area. Summers don’t get hotter than about 90 Fahrenheit and winters can get incredibly cold – well below zero if caught in a Nor’easter. The population of Bellingham has nearly doubled since the time I arrived there – I’ve heard that Fairhaven is now more of a retirement community than a hippie burg – which is too bad. As a side note – I’ve just looked at the cost of buying or renting a family home in Bellingham due in no small part to nostalgia in writing this – it turns out that the increase in population has led to a housing shortage – good old B’ham, which used to be cheap – is now way out of range for nearly everyone with rents nearly as high as in Honolulu and Seattle…All I have to say is it’s a damn shame…