Anticipation: how planning trips can boost happiness in Retirement
Many retirees find themselves facing a schedule lacking purpose, despite years of hard work. This sense of restlessness often isn’t tied to financial concerns, but rather a lack of engaging activities.

Certified Financial Planner Wes Moss, author of *The Retire Sooner Method*, suggests embracing adventure to combat this. He emphasizes that the joy of an upcoming adventure begins long before the actual trip, citing the psychological phenomenon of “anticipatory happiness” – the pleasure derived from looking forward to something exciting.
Moss explains that planning a trip can provide more enjoyment than the trip itself. “What’s more fun, planning your vacation or being on vacation?” he asked in an interview. The months spent researching, booking, and anticipating a trip far outweigh the brief duration of the experience. A five-day trip booked four months in advance provides four months of anticipation, whereas a last-minute booking yields little build-up.
He notes that even enjoyable trips can leave retirees feeling ready to return home, highlighting the diminishing returns of extended vacations. The key lies in proactive planning, with multiple shorter trips spaced apart generating more anticipation than a single, hastily arranged excursion.
Moss’s research comparing happy and unhappy retirees revealed a significant difference: happy retirees engage in an average of 1.9 adventure-related activities, compared to just 1.2 for those who are unhappy. A concerning 57% of unhappy retirees reported having zero such activities, leaving their calendars devoid of anything to look forward to.
Adventure, Moss emphasizes, is personal and can take many forms. While travel, RVing, and exploring national parks are common choices, simpler activities like fishing, boating, horseback riding, kayaking, or even a motorcycle ride can provide the same benefit. “Adventure is personal. It’s a blank page for you to fill however you like,” he states.
To incorporate this principle into retirement planning, Moss suggests booking dates several months in advance and reserving specific details like campsites or charters. Spreading out shorter trips throughout the year and even including planning time as part of the adventure itself can further amplify the anticipatory joy. He also recommends booking the next trip before the current one concludes, preventing a sense of emptiness.
Ultimately, Moss believes that “Retirement is not simply a vacation, and that distinction can be the difference between discontent and fulfillment.” The positive effects begin the moment a date is set.
Source
“Bored in Retirement? Wes Moss Says Planning the Trip Can Make You Happier Before You Even Leave”
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