Rainy Day in Tahiti Fund

We have not yet had the luxury of not working, so working for pay is normal. Railroad Tracks

In addition to our corporate careers, we have earned side gig money to fund out travels.  Saving for a rainy day just seems more fun if the rainy day is on a tropical island! Here are some perspectives on ways to create more income for travel.

Fence-post painting –This was probably the first paid job that I had on the farm.  I remember wanting money to spend at a State Fair and the going rate was a nickel per post and a quarter for a gate.

Fenceposts in rural Mississippi

Fenceposts in rural Mississippi

These metal posts and gates had to be fully brushed down with a wire brush to remove any rust before painting with a thick silver-colored paint. It was messy and the days were long but I had money for a few rides at the State Fair that year!  Those hours working the fences taught me to work hard and save money–the experience has value in my life even today.

Travel Agency –John and I owned an online travel agency for a couple of years. We learned the challenges of business ownership and the rewards of a client well-served.

Carnival Triumph

Our Carnival Triumph Cruise 2008

With our interest in cruising, we joined CLIA and were certified as destination specialists for Hawaii. The travel industry is both complex and fascinating.   As business owners, the commissions earned were minimal but the experience gave a unique viewpoint to the industry.

Online Greeting Card Reseller

This is a fun job that we have continued to enjoy!  SendOutCards is an MLM organization with a super-useful product!  Instead of standing in a store searching for the perfect greeting card, we use the SendOutCards website to select and customize our greeting cards. When we click “send”, the fine folks in Salt Lake City will print, envelope and mail our personalized cards (including photos and personal notes) through the US postal service!  When on the road, it’s not always convenient to go into a store to shop for or mail a greeting card, but this system really works and saves time and money. I was a customer for a couple of years before becoming a distributor.  Using the online tool as a customer is free (no sign-up fees), but you will pay for postage at USPS rates and for your selected cards (about $.50 each for beautiful greeting cards).  Send a FREE CARD today and brighten someone’s day!

Retail Store and Grocery Clerk

While not as charming as being on the front line of exotic vacation planning, operating a cash register, bagging groceries and understanding retail are excellent skills for “on-the-road” income sources.  Retail skills are in our toolkit for times when we plan to be in one place for several months, particularly in the US, where our citizenship avoids the bureaucracy of obtaining work certifications.

Custom Embroidery Retail Store

Custom Embroidery Retail Store

The CoolWorks website is our go-to resource for these types of jobs. The website and forums are consistent with our way of thinking about the travel lifestyle. The Older and Bolder forum brings a solid perspective to our thinking and is good for brainstorming on destinations.

Telephone/Call Center

I worked as a call-taker for a virtual call center, taking calls for the infomercials on television.  Do you ever hear the “Operators are standing by” commentaries on television?  Yes, I was one of the operators through liveops.com.  With a computer, land-line connection, headset and a few hours of training, I was making money from home during odd hours of work and getting ahead financially towards our dreams. The pay averaged $10 per hour for the months that I was working, so I set a monthly goal and then tried to improve on it each month.


Writing and photography are great hobbies, but can also provide income for travel.  For several years, I wrote articles for a pay-per-click site with revenue sharing.  There have been a lot of changes to the site in recent years, the most notable is that the company is now owned by RR Donnelly, Inc and has expanded to more than a publishing platform. In addition to revenue sharing income, I was successful in selling an article for publication and in generating income from contests.

As the first step in our “how to” series, this article has a few of the many ideas that we have used successfully to generate travel money. These skills are marketable and are ways to supplement the travel piggy bank, both now and in the future.

The Retirement Project

This is the core of what this blog is all about.  Is it possible to set a timeline for retiring and starting our dream of international immersion travel?  We vote YES!

Natchez Trace Parkway, Mississippi

Natchez Trace Parkway, Mississippi 2010

After all, if Gretchen Rubin can cram happiness into a one year experiment, we can use the same approach with retirement planning. Right?

So, starting points and ground rules – only two at this point.

We must work our current career fields diligently and with focus. Daydreams of retiring during the workweek will surely send us off course to the path that we have chosen.  We are very fortunate to both have interesting careers and reliable income.  Daydreaming on weekends and during long commutes is perfectly allowable (and encouraged!).

Practice traveling together and find the groove for our travel experiences.  This is beginning to come together. Gwyn is the “planner” and John is the voice of reason and problem solver when we are “in the moment” and the plan falls apart.  Good fit!  This understanding of our strengths is crucial as we move into different cultures and new experiences.


As we start The Retirement Project, the goals are vague. They will become SMART goals over time, with structure and specific actionable events to ensure the key milestones are achieved.

Cover living expenses with one income source and build new income streams for travel and hobbies.  We have never had the luxury of not working, so working for pay is normal.  In addition to our careers, we have dabbled in a variety of enterprises which include travel agency, retail store, custom embroidery, classroom teaching, telephone order taking, genealogy research, woodworking, crochet, sewing and crafting, to name a few. These skills are marketable and are ways to supplement the travel piggy bank, both now and in the future.

One trip each month – Go Somewhere and Do Something!  This goal is about not becoming stagnant in our quest for a nomadic future.  It is easy to become an armchair traveler or to spend the day in front of a television filled with adventures of other people. That is not the story we desire to live.  Having recently relocated to central Mississippi, there is a land to be explored just outside the door!

Learn from the experts.  This is the time to seek the wisdom of other world travelers and fine-tune our list of adventure locations.  We well-know the frailty of life and our time on this earth.  Our plan may not be the plan that plays out for our future, but to choose not to dream into the future is akin to quitting.

So, there we have it.  Two rules and three goals. The journey begins.

Join the conversation! What’s your dream and your plan to get there?  Is there a “Retirement Project” or “Happiness Project” in your future?