Retirement, at best, can be problematical even with the most well-intended plan because of unforeseen circumstances such as health and the economy.

But those issues aside, many retirees find themselves in a quandary about what to do with their time after leaving a structured career and venturing into a routine of limitless possibilities and a myriad of ideas and people tugging at them.

With the influx of retiring Baby Boomers, a niche was born and quickly filled with the birth of the “Vocation Vacation.” You can book a retirement how-to vacation trip or retreat offering suggestions and insights about maximizing your time, talent and pleasure while transitioning into retirement. A typical participant in “Vacation Vocation” offerings is age 57; one-third are single or divorced, and the other two-thirds are couples, with most still employed.

The “Vocation Vacation” concept began in 2004 when Brian Keith arranged a short apprenticeship in Portland, Ore. His company Vocation Vacations, Inc., now offers 160 selections costing $649 to $2,000 (plus lodging) with one- to three-day options. This includes on-site mentoring / coaching with follow-up sessions, a Myer-Briggs personality test with report, and lunch daily with your assigned mentor.

Baby Boomers have historically searched for the true meaning or purpose for their lives since adolescence. Most never found it and settled for something tolerable and financially productive in order to succeed and establish a solid platform for later life. Boomers now desire assistance in figuring out how to do something that’s completely different than in their professional lives, some retirement life basics, while concurrently learning how to contribute to the world in the process. I call it the “Woodstock Syndrome.”

A retirement vacation or life retreat teaches people in their 50s and 60s about later life, a phase they heard their parents and grandparents discuss but never believed would affect them. Boomers crave a renewed sense of purpose and the vocation vacation offers an opportunity to interact with others sharing their sense of self-discovery along with field testing their plans and ideas while receiving real-time guidance from “Transition Guidance Counselors,” another newfound occupation.

Vacations range from mundane classroom discussions to hands-on workshops specializing in beer-brewing, winemaking, meditation and yoga. For those adventurous and physically fit, there are photography safaris to distant lands, backpacking into rugged wilderness and mountain climbing.

These intense personal explorations are pricey, but the current economic downturn hasn’t caused many wannabe participants to scale back on what they consider to be essential life-planning exploration and discovery initiatives. These adventurers have lost interest in leisurely vacations, stating these aren’t meaningful or appealing. They’re also avoiding cost-intensive, golf-focused retirement communities with lavish clubhouses because of the perpetual financial drain and demand to participate in repetitive activities at the same location. Boomers still want it their way, consider themselves to be the current groundswell of economic and societal influence, and embrace a freewheeling lifestyle with limited, streamlined material and financial encumbrances as paramount to their overall happiness and well being.

The unconstrained Boomer mindset generated a new wave of college courses such as “Paths to Creative Retirement” at the North Carolina Center for Creative Retirement. This classroom experience focuses on helping people clarify what they want to do next in life using a range of case-study offerings, condensed lectures and small group discussions. The cost is $750 including group meals but no room. Another popular workshop offers detailed exploration of the advantages and disadvantages of living in one’s home town or relocating. Fifty somethings are optimistic about moving; those in their 60’s are reluctant to replant their roots in a strange location. An introspection process is also involved focusing on the subject of time and how to fill it after retiring. Many 50-year-olds anticipate working part-time; 60-year-olds prefer avoiding work unless it becomes essential for maintaining a comfortable quality of life.

Another retirement planning option, “Retirement Boot Camp,” occurs one weekend per year at the Kripalu Center for Yoga and Health in Stockbridge, Mass. It’s overseen by a life coach focusing on teaching people to stay positive during retirement. Participants prepare an extensive list of what they don’t want in later life because this is the hardest part of sorting out retirement. Upon completing the list, the focus shifts to exercises that generate contemplation about rediscovering old dreams and unfulfilled goals and interests. Optional yoga and meditation classes are offered during free time. Tuition cost is $250; room and board ranges from $182 to $702 depending upon dorm style or luxury suites.

For improving health consider the “Wellness Vacation” in Point Lookout, a 380-acre resort overlooking Penobscot Bay in Northport, Maine. This venture highlights “active aging.” Program offerings include high-tech wellness assessments, later life career planning sessions, driving tests and assessments using a street and highway simulator, cognitive-screening tools, and numerous measurements of physical strength, vision and hearing. There’s no mention of having trained / certified medical personnel available.

Have you decided which option is most suitable for you? Your retirement “Vocation Vacation” is waiting.

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