Bored in Retirement? Wes Moss Says Planning the Trip Can Make You Happier Before You Even Leave
A trip might last five days, but a retirement expert says most of its joy arrives long before you pack. Why do some retirees get months of excitement from one vacation while others get almost none?
This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.
Monday looks like Saturday. Saturday looks like Wednesday. For a lot of retirees, the freedom they spent decades working toward turns into a long run of empty weekends. The restlessness that follows often has little to do with money.
Wes Moss, a Certified Financial Planner and author of The Retire Sooner Method, says the fix is adventure. The reason he gives is a benefit that starts well before you pack a bag. Adventure activities, he writes, “create what psychologists call ‘anticipatory happiness’: the joy you feel looking forward to something exciting.”
This matters because a retiree with nothing on the calendar gets no anticipation at all. Each week offers only what happens that week, with nothing ahead to lift it.
Planning the Trip Delivers Most of the Joy
Moss has this right, and the reason is time. A trip lasts days, but looking forward to it lasts months. In an interview with 24/7 Wall St., he put the question simply: “What’s more fun, planning your vacation or being on vacation?”
His answer favors the planning. “Let’s say you’re going on this great trip. You get to think about it for two, three, four months, and you get all that anticipatory enjoyment,” he said. “And then [the trip] itself may only be five days or four days.”
Try that on your own calendar. Book a five-day trip four months out, and you get four months of something to look forward to, plus the trip, plus the stories afterward. Book the same trip the week before you leave, and you get the same five days with almost none of the build-up. The destination and the cost are identical. The enjoyment is not.
Moss also hears the other side from retirees all the time. After a long river cruise, he said, people describe a great trip and then add, “But I was ready to get home.” Anticipation doesn’t wear thin the way the tenth day of a vacation can.
The variable that decides your result is how far ahead you plan, and how often. Two shorter trips booked months apart give you two periods of anticipation instead of one. One big trip booked on short notice gives you very little.
Moss’s Survey Shows Who Has Something to Look Forward To
The book draws on Moss’s research comparing happy and unhappy retirees. In Wes Moss’s research, happy retirees average 1.9 adventure-related core pursuits, compared with 1.2 for unhappy retirees.
The more telling figure is at the bottom of the scale. Wes Moss reports that 57% of unhappy retirees have zero adventure-related core activities. For that group, nothing on the calendar creates anticipation. What separates the two groups is whether a next adventure exists at all. How extreme it is matters much less.
Your Next Adventure Can Start at the Local Boat Ramp
Moss’s survey respondents describe adventure in everyday terms. Travel led the responses. One participant wrote, “Traveling whenever possible. It brings me joy.” RVing came up often, usually alongside camping and exploring national parks.
Plenty of answers stayed close to home: fishing, boating, horseback riding and kayaking local waterways. One respondent named his in four words: “riding my Harley.”
Moss is direct about this: “Adventure is personal. It’s a blank page for you to fill however you like.” A day trip to a small town still gives you a date to look forward to. The planning window does the work, so price is a poor guide to how much anticipation you’ll get.
How to Get an Adventure on Your Calendar This Week
Moss, who takes listener questions at wesmoss.com/ask, lays out his retirement framework in The Retire Sooner Method (Greenleaf Book Group). Here is how to put his anticipation idea to work:
- Book a date a few months out. Moss described anticipation building over two, three, four months. Reserve something specific, such as a state park campsite or a fishing charter, so the excitement has a real date to build toward.
- Spread out smaller trips. A long weekend each season gives you several periods of anticipation. One large trip a year gives you one.
- Count planning as part of the adventure. Moss’s research points to at least 2.5 hours per day engaged in activities you love, which works out to 17.5 hours a week. In the book, he describes exploring a new hiking trail or the next RV stop as a way of creating anticipation, so that time belongs on your calendar too.
- Book the next trip before the current one ends. Choosing your next destination on the drive home keeps the calendar from going blank and starts the next periods of anticipation right away.
Moss frames the stakes this way: “Retirement is not simply a vacation, and that distinction can be the difference between discontent and fulfillment.”
Put a date on the calendar, and the benefit starts the day you book it.
Contact [email protected] for any questions or corrections.
Jake has been been working in financial media for almost 15 years. He focuses on all things personal finance for 24/7 Wall St. with high hopes to educate and entertain. Most recently, Jake spent 12 years working various roles at The Motley Fool. He started copy editing fool.com content, worked on premium and marketing campaigns, and helped launch The Ascent, a personal finance brand.
His work has been featured on platforms like MSN, Yahoo Finance, USA Today, and more. He's written about credit cards, social security, ETFs, savings accounts, and just about anything else you can imagine when thinking about money. Jake love to cook, play golf, and tell people he's never had a cavity. (It's true!)
