Acing the Family Vacation

When Kathleen Westcoat, CEO of Healthcare Access Maryland, turned 40 she made a resolution: to take an annual family vacation. “I decided, come hell or high water, we are going to do this every year,” she says. “It’s critical for busy families to spend concentrated time with one another—and to do that, you have to make it a priority.”

That sentiment was echoed by all of the CEOs we spoke to for this article, each of whom makes a concerted effort to block out time to travel as a family—and each of whom admits that arranging those escapes is no easy feat. “The whole notion of a vacation has changed,” notes Peter Orrell, CEO of Junior Sports Corporation. “With all the connectivity we have now, it’s virtually impossible to disconnect; but in my view, you can’t be optimally effective in your professional life if you aren’t optimally effective in your personal life and vice versa. So you have to balance that out.”

The Connectivity Conundrum

Ironically, the technological advances that provide 24/7 connectivity around the world both enable and hamper downtime. The trick, say vacationing CEOs, is to find ways to leverage your accessibility without letting it take over your time away. Orrell, for example, finds it impossible to go completely dark, so he sets aside a few hours to check email and handle urgent business while away and also makes sure to choose destinations offering the dedicated landlines and high-speed Internet that allow him to do that efficiently.

“My goal is to get work done during the first three hours of the day so that I can spend the afternoons with my family,” he says. “Dropped calls and intermittent connections make me crazy. We even put in high-speed, satellite Internet at our vacation home, which is in a remote area of Ontario.”

Connectivity can be more challenging for CEOs who enjoy remote venues. Steve Cody’s travels with his son Chris are typically spent 15,000 feet in the air clinging to the face of a rock—not exactly an ideal position from which to field a call from the office. However, that’s more or less the point, says the CEO of Peppercomm, who goes rock climbing with his son several times a year. “It’s the single best way to relax I’ve ever found. Sitting on a beach, I end up thinking about work, whereas being in a position where every step is critically important tends to force you to cleanse your mind of everything else.”

Like many CEOs, Cody plans ahead for stretches of inaccessibility by prepping his team and creating a contact plan in the event of a crisis. “When Chris and I were climbing the Andes in Ecuador, I was off the grid for three to four days at a stretch, so I alerted my business partners and my clients. We also put in place a way for them to reach our climbing guides who, in turn, can always reach me in a crisis.”

For time-pressed CEOs, sometimes the complexities of planning to be away seem trickier than travel planning itself. Yet, navigating vacation venues can be a significant source of pressure. After all, you’ve got to pick the perfect place, where you can realize an ambitious goal: to relax, recharge and reconnect as a family in one week flat—or maybe less.

Something for Everyone

For families fortunate enough to share interests, weighing travel options is simple, lighthearted fun. For example, the Orrells enjoy any destination that offers activities like horseback riding and swimming. Families like the Codys, however, must tread more carefully around the destination dilemma.

“We look for places where Chris and I can go climbing, while my wife and daughter can sightsee and do the things they like to do,” explains Cody, who also takes short climbing trips with Chris throughout the year. “Then, we regroup over dinner and a show.”

“My sister and my mother don’t really understand why we are so into climbing,” agrees Chris Cody, who enjoys vacations most when the whole family goes on outings together. “Whenever we can convince the girls to go hiking with us, that’s always when we have the most fun.”

Since the need to address divergent interests often escalates as children enter their teens, a family’s ideal vacation tends to evolve over time. For the Westcoats, beach vacations when the kids were small evolved into skiing, kayaking and hiking trips. “It gets harder to keep everyone happy,” asserts Westcoat, who says the family is now shifting toward more urban venues.

“We’ve been taking a trip to New York City every year for my daughter’s birthday; and this year, I’m planning to take them to Ecuador to give them exposure to life outside of the U.S. Your plans have to evolve with your children’s interests and ability to appreciate things.”

Parental abilities may also factor into that evolution, laughs Cody, who figures he has maybe a decade left scaling the likes of Mt. Kilimanjaro, which the father-son team climbed to celebrate Chris’s college graduation. In the meantime, the climbing ventures are clearly serving the sought-after “recharge and reconnect” family-vacation goal.

“Those climbing trips with my dad are the highlight of my month,” reports Chris Cody. “Each one is a new climb and I’m doing it with my dad, who is my best friend. It doesn’t get much better than that.”