Editors note: This is a Guest Post from Derek Johanson of Liveuncomfortably.com

Rob: I recently put a tweet out asking if anyone would like to be a guest blogger for this blog.  I received a bunch of great offers, but there was one guy that really stood out above all the rest.  His name is Derek Johanson.  He writes a blog called Live Uncomfortably.  At first, I was like, who the heck wants to do that?  Then, I started picking up what he was puttng down.  In Derek’s own words: “living uncomfortably is doing the unaccustomed everyday to break the cycle of routine and boredom”.

His blog is an experiment in micro testing his philosophy and creating his personal lifestyle design.  I like this guy and I hope you will too. He’s not just talking the talk, he’s walking the walk.  He’s the real deal,  just check out this year’s travel schedule.   In this post Derek will show you how you can create a Jet Set trip simply by taking advantage of a few simple strategies like currency fluctuations and location. Remember, life is about doing exciting things and Derek is an amazing example of that.

Designing A Jet Set Mini-Retirement On A Tight Budget

When I first stumbled upon Jet Set Life seven months ago, I was intrigued.  Hip, chic, and trendy travel is to say the least, extremely appealing.  I was looking to take my first mini-retirement at the time, but quickly realized I didn’t have the cash flow to support the lavish Jet Set lifestyle.

Rob: Not always so lavish- here and here.

It wasn’t until I made my way through Central and South America that I discovered it was entirely possible to live like a king on a tight budget.  If you haven’t yet reached the income level to afford luxury mini-retirements or you’re currently not able to justify the expenses during the recession, don’t fret.  Just because we can’t live like Jet Set rock-stars quite yet, doesn’t mean we can’t get close.  It just takes a little re-designing of our mini-retirements.

Step One:  Take Mini-Retirements That Develop Marketable Skills

Mini-retirements should be about letting loose and relaxing, yes, but also, about personal development and learning new skills.  When you take a mini-retirement to work on a skill-set and not just drinking margaritas at the pool, your costs will be significantly reduced.  In addition, your future money-making potential will dramatically increase.

Most of the skills that you’re likely interested in learning probably won’t cost that much to attain.  For example:  Spanish classes or Salsa lessons are very inexpensive in nearly every Latin-speaking country.  While focusing on a skill you won’t be tempted to constantly spend money on things to pass the time (like alcohol).

When you return home from a vacation you are in the same position as when you left, but with less money.  When you return home from a skill based mini-retirement you come back with something marketable and maybe break even financially.

The new skill that you acquired can be channeled into a money-making opportunity which can even further fuel subsequent mini-retirements.  For example, a friend of mine took his mini-retirement so that he can work on learning Spanish.  He documented his progress, set up a small website to help others learn Spanish and now his site is drawing great traffic and creating affiliate sales.

Step Two:  Rethink Your Destination

It’s possible to live like a rock-star outside of popular high-class tourist destinations.  In a lot of countries, the costs of living have not caught up with the value of living.  Meaning, you can spend half as much in South America as you would on a European vacation equivalent.  Paris, France vs. Buenos Aires, Argentina is a great example of this.

Look into places like South East Asia, Central America, and South America.  You’ll find countless destinations that are beautiful, safe, and best of all, cheap for what you’ll get.

Step Three:  Rethink the Tourist Off-Season

We all know hotels, airlines, and other tourist related businesses jack up their prices during the high season.  You simply can’t get around it. But, there’s a perceived down season in many countries that is really not that much different from the high season.  You can start taking advantage of this.

In Central America, the high season (the dry season), is from Nov-Feb.  During this time you’re going to pay a lot more for accommodations. In many areas the difference between the rainy season and the dry season is only 1-2 hours of rainfall in the late afternoon which is hardly enough to ruin a trip.

A lot depends on the region.  Costa Rica and Panama are so small that people think, “Well it’s the rainy season in X city, so it’s probably the rainy season in Y city”.  The climate can change drastically even within a small geographic region.  I enjoyed the low season rates in sunny Bocas del Toro, because I was there during the perceived rainy season in Panama:  September.

These situations arise everywhere (not just Central America).  Avoid the urge to travel during the expensive months and you’ll be rewarded with cheaper rates and not always perfect, but very tolerable weather.

Step Four:  Get Long Term Luxury Accommodation for Huge Discounts

For the Jet Setter – having luxury accommodations is a must and with a little hard work securing it really is not that difficult.  I’ve found that many smaller resorts and hotels will offer their rooms at severely discounted rates if you agree to stay a month or longer.

The best strategy for finding cheap accommodations in hotels or resorts is to hold off on booking a place until you get to your destination.  In Central and South America I’ve been shocked by the quantity and quality of hotels and resorts that simply aren’t making themselves visible on the internet.

Once you’ve arrived in your desired location, spend a day or two searching for the best deals.  Many hotels and resorts that you can’t find on the internet are cheaper but not necessarily lower quality.  Also, you’ll be able to approach the managers and negotiate a price for a long term stay.  If you book online you’re going to ‘get gringo’ prices and could get stuck in a place you’re not too happy with.

In Panama, my friend and I were able to secure a cabana at a hotel/resort in the mountain town of Boquete for $18 per night.  The cabana included a full kitchen, laundry services, maid-service, WiFi, and access to organic fruit on the property.  The normal prices were $80 per night, but since we agreed to stay for 2 months, we got more than a 75% discount!

You don’t have to stay in hostels and you don’t have to live like a poor backpacker to take cheap mini-retirements.  It’s extremely possible to live like a Jet Set millionaire on a tight budget.  You’re just going to need to re-think the- what, where, when, and why of your mini-retirement.

For more info on what Derek is up to contact him through his website Liveuncomfortably.com

#######

Kim and I are off to Los Angeles to shoot a video and create our L.A. Hit list- if you have anything that you think we should hit in L.A. please let us know through Twitter here.