How to Craft a More Fulfilling Vacation Using Insight from Business and Investing

Been there, done that. You’ve visited the tropics, the mountains, the lake. You’ve sailed on a cruise and made the pilgrimage to Disney, perhaps each twice or more. Most were fun, restful—maybe even restorative or memorable.

But something was lacking. Something was missing. As you dream up your next vacation, it’s hard to find something sufficiently tempting, beyond more of the same. Yes, it’s a good problem to have, but a problem nonetheless.

Faced personally with this conundrum, I found insight in an unlikely place: corporate consulting from Bain and Co. and the investment concept of risk and reward.

Getting Out of the Bubble

“Please just be careful!” Most of our friends and family invoked some iteration of that sentiment as we departed for our recent family vacation. To Nicaragua.

It was not intended to be a vacation in the traditional sense. Our primary purpose was not rest and relaxation, however valid those objectives are. Those elements were indeed present, but the foremost aim of our trip was to expand our mental, physical, and spiritual horizons through the pursuit of adventure and acts of service.

Such a trip has felt increasingly necessary over the past few years, as our healthy, well-adjusted boys, now 15 and 13, have been privileged to grow up in one of many amazing towns and neighborhoods across the U.S. not so affectionately termed a bubble.

We inhabit these bubbles with the good intention of achieving a high quality of life—good schools, nice houses in safe neighborhoods, cultural proximity, and all the personal and professional perks that tend to accompany these benefits.

These are places where genuine hardship does occur, but an Instagram-worthy veneer shrouds much of its pain. External suffering appears irregularly enough here that the greatest challenge many kids endure on an average day is the quest to acquire an iPhone charging cord long enough to allow them to rise from a comfortable couch without suspending a game.

Don’t get me wrong. I love the bubble. The bubble isn’t inherently bad, but living in one—and especially growing up in one—can create a sense of entitlement. It can also generate an unhealthy distance from more troubling realities of life that often are hidden inside of the bubble but all too visible in the rest of the U.S., and especially in the Majority World.

We had to get out of the bubble.

Surf and Serve

The two avenues through which I hoped to find a more fulfilling vacation were surfing and service, and this trip, organized by the Charleston-based nonprofit OneWorld Health, delivered on both.

Every morning, a core group of surfers would meet for strong Nicaraguan coffee at 5:15 a.m. before departing our paradisiacal home base, Surf Sanctuary. A couple pros from Christian Surfers would split up the group based on ability, arm us with the appropriate vessel, and nudge us toward a surfing spot that sufficiently stretched but didn’t entirely overwhelm our capabilities. Meanwhile, two local Nicaraguan surfing legends, Jimmy and “Goose,” gave us the in-water guidance—and timely pushes—to ensure that we came away from every session feeling like we could walk on water (if only for a few precious seconds).

Following a quick rinse, our entire team would pull together for a locally inspired breakfast prepared and served with loving hands by the Florida ex-pat owners of the Sanctuary, Tony and Nancy, before reviewing the day’s service plan.

The plan typically included hopping on a souped-up school bus and meeting the OneWorld Health mobile medical unit at a nearby church or school, where we set up a daylong medical clinic staffed by Nicaraguan and American medical professionals. Unskilled but willing aides, like my family and me, helped in a non-medical capacity.

After serving between 110 and 145 Nicaraguans each day, many of whom struggle to gain access to quality medical care, our drives home were marked by satisfied exhaustion and endeavors to process the day’s activities. The passing landscape was so starkly distinct from our vantage point inside of the bubble.

Each night’s communal dinner was preceded by a second surf session, a purge in the pool, or a nap in a perfectly placed hammock. The meal was followed by a round of “shout outs,” intentional affirmations offered by team members who observed something exemplary in one of their teammates, and “life stories,” where fast friendships already accelerated by the trip’s unifying purpose were further cultivated.

Toward the end of the week, our family could agree on two things. First, this really wasn’t a “vacation.” But second, it just felt better. Surprisingly, the explanation for this deeper sense of satisfaction and fulfillment comes from an unlikely source—corporate consulting research.

The Elements of Value 

In a Harvard Business Review article on research into what they call “The Elements of Value,” Bain and Co. offered insights that apply both to consumer-to-business and business-to-business relationships and the degrees to which the value exchanged by these partners can be enhanced.

The insight has been compressed in the form of a Maslow-inspired, four-tiered pyramid infographic that barely requires translation to see its application in building a truly fulfilling personal experience or vacation. Each tier acknowledges the elements of value that address four ascending kinds of needs:

  • Functional – At the base are requirements necessary for any positive experience. These are “table stakes,” like quality, variety, sensory appeal, and hassle avoidance.
  • Emotional– One level up addresses the emotional elements that motivate any vacation and represent the standards most of us would use to determine if the experience was a positive one. These include measures like fun, therapeutic value, anxiety reduction, and the generation of nostalgia.

But please pay special attention to the top to tiers of the Elements of Value pyramid, because this is where the magic comes in:

  • Life changing– Wait, is life-changing too much to ask of a vacation? I think not, and it becomes clear why as we address each of the respective requirements in the pyramid’s penultimate tier:
    • Affiliation and belonging– Like being invited into a group or team.
    • Heirloom– Something beyond nostalgia, an experience one feels inspired to pass down to the next generation.
    • Motivation– “Spurring people to achieve their goals,” like learning how to say, “Please follow me,” in Spanish, perhaps. (“Por favor sígame,” as it turns out.)
    • Self-actualization– “Providing a sense of personal accomplishment or improvement,” like high-fiving your Nicaraguan surf instructor who, despite somewhat of a language barrier, just taught you to surf “down the line” for the first time.
    • Provides hope – When you’re filled with a sense of optimism.
  • Social impact– A single, elusive requirement lies at the top of the pyramid—”self-transcendence,” defined simply as “helping other people.”

Should we really be surprised? As Daniel Pink shares in his book, Drive, while we certainly are motivated by self-interest, a sense of others-interested purpose increases our level of personal motivation and satisfaction. When it comes to our professional lives, Adam Grant has proven that giving is a greater predictor of success than taking, and that it leads to more fulfilling work. Why not a more fulfilling vacation?

But What About the Risk?

OK, back to the “Please be careful!” admonitions. Is there more risk inherent in going to a developing country and directly interacting with its people, food, and landscape for vacation than in the typical alternative?

Yes, it is true that it’s riskier to drive from the Managua airport to the southwest coast of Nicaragua than it is to drive from the Jacksonville, Florida, airport to the Amelia Island Ritz. But in Nicaragua we met a skilled driver and a welcoming, bilingual host at the airport who were able to introduce us to each of the cities and towns on our three-hour journey to the resort.

Yes, I suppose it’s possible there is inherent danger in vacationing in any place where poverty is so systemic that it creates a sense of desperation among a populace earning an average $2 per day and who could view presumably wealthy tourists opportunistically. But we were well trained to explore the area in pairs and to avoid trumpeting our relative affluence with conspicuous watches or jewelry. Our overwhelming experience was that the people of Nicaragua are welcoming, hospitable and grateful for visitors, whose presence helps fuel a burgeoning eco-tourism industry that spurs economic growth.

The greatest risk affecting anyone on our trip was that of intestinal discomfort, a seemingly unavoidable travel companion common among trips to every country in the Western Hemisphere other than Canada and the U.S.

Yes, of course I’m making the case that the rewards of a more adventurous trip with elements of service built in are worth the risks.

But more importantly, I believe the less-visible risks of life in the bubble—insularity, entitlement, indulgence—are simply too high not to venture out.

Build Your Own

So, what could this concept look like for you? Most of the people I’ve talked to before and after our trip, despite their hesitation, ultimately have said, “Gosh, that sounds amazing,” or, “I’ve been wanting to do something like that.” If you fall into that category, you have a couple options:

1)  Go all-in. As our host and surf instructor, Tony, said, “My advice on dropping into waves is to drop into every wave.” Build your own Surf and Serve trip and replace the “surf” element with whatever source of adventure appeals to you, and with whatever recreation-to-service ratio you prefer. Build up anticipation in the months ahead by learning about the culture beforehand, talking to various nonprofits in the region who serve needs closest to your heart, and practicing enough of the language to make your way around.

For the service part of your trip, I’d like to offer one caveat that I detail further in this post. Not all forms of help are actually helpful, and we Americans, in particular, historically have been guilty of paternalism and the creation of cycles of dependency in efforts to help that, while well-intended, are really more about the helpers than those in need. Therefore, in addition to educating yourself about these nuanced challenges, I encourage partnering only with nonprofits geared toward the creation of long-lasting, sustainable change.

2)  Take a transitional step. If you’re not ready for the all-in proposition, consider taking a single step or two, adding features from the upper two tiers of the Elements of Value pyramid and considering their impact. Facilitate belonging by vacationing with another family. Create a benchmark trip that becomes a rite of passage for your children, grandchildren, nieces, or nephews. Add a goal to your trip that’s enough of a stretch that it feels like an accomplishment. Or, better yet, make that goal to touch base with a local nonprofit you could serve, even for a day or half-day. (Or better yet, stick with Option 1.)

The Power of Moments (Thank you Chip and Dan Heath)

At the close of our week, everyone had a completely free day. No service, just surfing—or horseback riding, ziplining, or lazing. After partaking in some of those activities in the morning, my wife and I took the afternoon to walk down the beach to another resort I’d visited before, Rancho Santana.

We wandered through the postcard setting, hardly able to get 50 feet before pausing to jaw drop or taking a picture. We took a seat in the outdoor restaurant perched over the Pacific Ocean, watching a few surfers squeeze in a last sets of the day. We ordered food and drinks in broken Spanish while our bilingual waiter visibly appreciated the attempt.

“I get it,” my wife said.

While this was my third trip to Nicaragua, it was the first for her and the boys, and naturally, she had been anxious about it. She confessed that it took a few days for her to settle in, but as we recalled the series of meaningful memories we had made throughout the week, in that single moment they accumulated into a deeper sense of fulfillment than we could recall feeling on any trip we’d taken previously.

Fortunately, I didn’t ruin the moment by talking about Maslow or the Elements of Value or any other hierarchical pyramid. But I do think insights gained from these sources can help us build better experiences—vacations, trips, adventures, and even life-long pursuits that transcend rest and relaxation and point us to a greater sense of significance.

This commentary originally appeared July 14 on

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The opinions expressed by featured authors are their own and may not accurately reflect those of the BAM ALLIANCE®. This article is for general information only and is not intended to serve as specific financial, accounting or tax advice.

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