Five Questions With Non-Conformist Chris Guillebeau
October 11th, 2008
Would you like to travel the globe while financing those trips solely through your online efforts and income? How about attempting to visit every country that the world has to offer?

Right around the time we started to make final preparations for the launch of Train for Humanity, I came across the aptly titled website, The Art of Non-Conformity, which belongs to Chris Guillebeau.
His site’s tagline is:
“Unconventional ideas for remarkable people. Along the way, I visit every country in the world and profile other nonconformists.”
Certainly after starting a business in the Caribbean, all of my travels, and a pre-mature escape from the corporate world I thought that I led a somewhat non-conformist life…but I don’t have anything on Chris.
After going through his archives and reading about various travels and adventures, one thing that immediately struck was the fact that Chris had lived and worked on the ground in Africa as an aid worker.
Before the launch of Train for Humanity I decided to email Chris to see if he would provide some feedback on TFH. Almost instantly I received a reply with some solid input and I have been following his adventure ever since.
I think most readers of MyTropicalEscape are living, or are working towards living, a life that is outside of the traditional norm and to that end, Chris has recently published an ebook, The Unconventional Guide to Working for Yourself, which is intended to help people create personal freedom via a very small business.
Below, Chris answers five questions that I had for him regarding the direction he has chosen for his life and how he funds his travels.
1. Does nonconformity run in your family? If no, what started you on your path…?
I wouldn’t say it runs in the family, but my dad was really good at encouraging me to do whatever I wanted. He encouraged me to try new things and not be afraid of failure. I think those are essential prerequisites for any unconventional lifestyle.
2. Wouldn’t life be easier if you just got a 9-5 desk job, earned a steady paycheck, and lived like a lot of other people?
No. At least not for me — some people are happy to embrace the 9-5 life, but I would be miserable doing that. Most self-employed people I know would gladly trade money for freedom. Obviously you have to make a living to some degree, but once you’ve had the freedom to make your own choices, it’s hard to go back to the cubicle lifestyle.
3. How do you fund your travels?
I support myself entirely through my own work. I create information products and occasionally consult for other small businesses.
4. What has been your favorite country to visit so far and why? What place will you never return to and why?
I don’t have a single favorite. I especially liked South Africa, the Netherlands, Ghana, Macedonia, and Hong Kong — but there’s usually something to appreciate (as well as something not to like) about anywhere you go. As to where I will never return, well, that’s a long list. It can be unpopular to say so, but there are a lot of countries that are deeply impoverished in large part because they lack good governance or because the foreign aid system has let them down. When I go to Africa, for example, I’m usually reminded that there are some things I really love about being there and other things that are a lot easier in North America.
5. What inspired you to write your latest ebook, “The Unconventional Guide to Working for Yourself?”
All of the emails! People ask every day about how I got started and what they can do to create a lifestyle that allows them to pursue their own goals and dreams. I don’t claim to have all of the answers — one of the things I try to be clear about is that there is no quick-fix system to any of this — but I hope the product will help get some people going in the right direction.
What is your ultimate job (or life) description?
October 1st, 2008
If you could do anything to make a living, what would you do? And why?
It’s a lighthearted (and somewhat trite) question, but a serious one too. Unfortunately, I think people struggle with this emotional inquiry everyday.
I am NOT talking ninth grade, school guidance counselor crap…e.g., “Billy, what do you want to be when you grow up?” No. I am talking about the real deal. You have lost your job, or something inside of you has clicked and you decide - now is that time, I am going to pursue the life/job that I have always wanted.
With the present economic and financial situation (ruin?) happening in the USA I started to think about what would happen if I had to get a real job and what the heck would I do? Don’t get me wrong, owning the Palmetto Guesthouse B&B here in Culebra is a REAL job seven days a week.
What are your goals for this week? And Surprise Pre-Launch Announcement
September 8th, 2008
I hope that you all had a very nice weekend! Last week’s post on “goals for the week” seemed to resonate fairly well with some of you and it drew a pretty good response and discussion, so I thought that I would do it again this week.
However, before we go any further, I wanted to mention, if your goals for this week (or anytime in the future) include “self-branding” or online reputation management, then you need to get yourself over to Chris Brogan’s website. Chris, who just happens to be a Boston guy, is a social media guru and all around super nice person and he has just released an eBook, “Personal Branding for the Business Professional” that is well worth your time. It’s available for FREE so do yourself a favor and go download it now!! OK back to the post. :)
Today I actually have two questions for you:
- What are your goals for the coming week?
- Beyond this week, what are you really working towards in your life?
image source: bulldog1
What are my goals for the week and what am I working towards?
How Did You Do With Your Goals Last Week? And an Announcement
September 6th, 2008
Hey Everyone - on Monday I put up a post asking, “What are your goals for the week?” The natural follow-up question at the end of the week is, how did you do?
The following people dropped by and posted some of their goals: Brian Monahan, Expert in the Rough, kelly, kazari, Glen Allsopp, Diana, Jarkko Laine, Ulla Hennig, Becky, Kelly@SHE-POWER, Success Professor, Susan, Cath Lawson and Al at 7P.
Did you complete all of the tasks and goals you listed?
Escape the Cubicle NOW! Five Tips to Help You Get Started
September 4th, 2008
Do you long to be your own boss? Work from home as a freelancer? Or, perhaps travel the world?
image source: carter comics
Don’t worry, I toiled away in a cube for many a year working for the man, but still managed to free myself. And you CAN too!
There is absolutely nothing wrong with the cube life, but for some reason I found it to be stifling. In fact, at the same time we were looking to purchase our business in the Caribbean I was offered a very good federal job in the states. I even went so far as to go (read: fly) to the interview at largely my own expense.
Obviously, you know the outcome because I am in the Caribbean. However, I must say that the clincher for me, when I really knew I would not take the job, came during the interview process. While getting the tour around the office they took me by (and specifically pointed out!) what was to be my cubicle and I knew right then and there that there was no way in hell I would take the job.
What about you?
What a nice surprise to be featured in Islands Magazine this month in their “Ten Best Islands to Live On” article. Almost exactly one year ago Terrie and I purchased the Palmetto Guesthouse after living overseas for many years.
We are both originally from Massachusetts and we had the dream of owning our own business for many years and finally saw that goal come to fruition with the purchase of the Palmetto here on Culebra.
Our travels have taken us to Europe, Central and South America, the South Pacific, and of course, the Caribbean.
Let me ask again – Does passion guarantee a successful venture?
NO! But, passion, combined with vision, hard work, and tenacity can certainly help to ensure that your project or venture will continue beyond the “thought” stage.
image source: marioragona
When I originally started the make money online challenge I was quite excited to see if I could earn some additional “passive” income online, which would help to increase my capacity to continue pursuing personal freedom and designing my life. Though I was passionate about my self-imposed challenge I think I was lacking motivation in certain areas.
So, ultimately I have failed with my goal and plan because I have not taken any action towards monetizing my site or creating new niche sites.
Open Source SOCIAL Entrepreneurship and a Guest Post
May 6th, 2008
First, apologies for the lax posting schedule and server issues recently!
Last week I had the chance to take a mini-surf trip down to Tortola in the British Virgin Islands for a few days and with the end of the north swell season upon us I could not refuse.
As far as my self-imposed AnyWired-Middlebrook Make Money Online Challenge goes, I think I am about to shift gears. During the past year I have been given a LOT! I quit my job, purchased a small business, etc… As such, I began to feel a little greedy when reading the category “Make Money.”
So my plan as it stands now will be to investigate some online [SOCIAL] entrepreneurial ideas that I have. In that way I can pay forward some of the good karma that I have received and learn about the ins and outs of making money online while generating funds for some humanitarian agencies that I would like to support. I have NO idea where this will go, or if anything will get off the ground but will certainly keep everyone posted!
