How can I manage to maintain affordable health care coverage and travel a lot?

Question - Date: 2007

I'm 58, my wife is 57. We own our home and have a few investments, no debt, no kids. We travel a bit (6-8 weeks per year) but are still tethered to the health benefits derived from my wife's job. So my question is: How can I manage to maintain affordable health care coverage and travel 12-16 weeks per year. Assume that my wife's employer might have a problem with that schedule. I would consider buying health care coverage outside the U.S. if it were of comparable quality.

Answer Paywizard:

Certainly concerns about affordable, accessible, high-quality, portable health care are shared by countless Americans today, so you and your wife are not alone there.  Your challenge, however,  is a more complex one since  you hope to travel 12-16 weeks a year, something that is simply prohibitive financially or temporally for most workers.  Even in Europe, 4-5 weeks is the norm, with only a few countries such as France allowing more, so your current 6-8 weeks’ holiday is already extremely impressive, given traditional US employers’ vacation or leave benefits.

Nonetheless, if you are in a position to be able to create opportunities for even more travel, let’s see what we can do.  This Paywizard always welcomes a challenge!  For starters, given your current financial situation – owning your home, having some investments, not being beholden to debt or children’s college funds, for example – you two are in a wonderful position to perhaps embark on some further travel adventures together.  If in recent decades you’ve planned and prepared well, why not enjoy reaping what you’ve sowed?

If you have been resourceful enough to allow yourselves the travel opportunities described above, perhaps you will be open to some creative options for the “end game” you mention.  It is somewhat difficult for me to give you as concrete career guidance as I would like since I do not know what either you or your wife do for a living (or have done until now).  Even understanding your training, abilities, interests, etc. would be helpful.  Nevertheless, I can at least provide a few ideas to get you started…

Have you considered starting your own firm or nonprofit well-suited to your past decades’ experience and expertise?  While starting one’s own organization is a challenging and daunting for many, perhaps you have expertise here and would enjoy working together to start something anew.  While you may find yourselves working some long hours when you are stationary, depending on your organization’s mission or business focus, perhaps you are in a position to do contract work or dial hours up or down?  Maybe you have something to offer that can be conducted online from afar?  For information on  providing for your own health care in this way, the US Small Business Administration provides online resources and supports local Small Business Development Centers.  Both will serve as helpful guides if you decide to join the ranks of the self-employed and secure health coverage on your own.

As an alternative, have you considered seasonal work that will provide you with benefits?  Anything from tax preparation to snow plowing to fall harvesting may be well an option for you if you are so inclined and are open to the training required (or perhaps already have this under your belts).  Maybe you have a great deal to offer your local community college and would be open to teaching courses in between travel adventures, or you might enjoy teaching online to allow yourselves greater geographic flexibility.  Would you be interested in joining the Peace Corps together or exploring other meaningful opportunities to help others throughout the world while also working with an organization that affords you the travel adventures and freedom you both crave?  See Idealist.org for ideas.  Have you considered tying your extracurricular interests more closely with the security of income and benefits, perhaps by becoming travel writers?  It sounds as if you can offer a wealth of experience in this area and may be able to offer insights for other boomers in particular.

Whatever you decide, please be sure to research your new path thoroughly so that you can make informed decisions and know what to expect in the years to come.  For example, if you decide to pursue the travel writing route, learn from articles such as The New York Times’  recent article, “A Job With Travel but No Vacation.”  Similarly, the Bureau of Labor Statistics’ Occupational Outlook Handbook is an invaluable resource to help you learn about not only salary but also benefits, working conditions, job responsibilities, etc. 

Good luck!