How to Plan a Working Vacation

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A working vacation may sound like an oxymoron, but taking meaningful time to recharge your batteries without going on a full digital detox is a more realistic and modern approach for many burnt-out professionals. You certainly don’t want to come back to a bursting inbox and stressful scenarios that completely wipe out the relaxation and peace of mind you just achieved, but taking a step back from work is important for your health and well-being. You’ll return to your work routine feeling refreshed and possibly even more inspired, as natural environments can help nurture creativity. 

“Leaving the stressors of daily life to take a break can help reduce stress and anxiety,” says Alyssa Mairanz, licensed counselor and executive director of the New York-based Empower Your Mind Therapy. “Physically leaving the home and office can be an emotional and mental release. This allows your mind to take a break and wander to imaginative ideas and inspiring thoughts.” Who knows? You might just come up with a brilliant solution to a challenging problem during a meditative paddle boarding trip. 

With a little advanced planning, even the busiest entrepreneurs can take a much-needed vacation without letting your business fall apart. The key is prepping colleagues and clients, choosing a destination conducive to balancing work and play and setting boundaries for yourself.

Prep for your working vacation

Inform any partners, clients and colleagues of your travel plans and only commit to the most important meetings while you are away. Everyone in your organization should be aware of your schedule and hopefully help you pick up some slack while you’re gone. Have clear directives written up for colleagues and assistants, to minimize the chance that you’ll be contacted on vacation for business as usual.

“It is important to plan itineraries with the client’s work schedule in mind and keep the rest of the family entertained while the client is working,” says luxury travel adviser Stacy Fischer-Rosenthal, CEO of Fischer-Rosenthal Consulting and president of Fischer Travel. Fischer-Rosenthal also recommends booking refundable accommodations and services whenever possible, just in case your travel plans change with short notice.

Double check if there is Wi-Fi on the flight if you need it—but remember that in-flight Wi-Fi is not the most reliable. 

Choose the right working vacation destination

If it’s critical that you are available in case of emergencies during business hours in your home city, traveling more than a couple time zones away may not be wise. If you’re traveling to a different time zone, always double check your calendar to make sure any meeting times are correctly noted. A location that’s too remote may not work if Wi-Fi and phone service are not up to par. On the flip side, a vacation on the Las Vegas strip might be far too distracting with noisy neighbors and late-night partying.

Selecting the right hotel for your working vacation is as important as the destination. Several hotels beefed up their remote work and working vacation amenities during the pandemic to appeal to remote workers and longer stays. Free high-speed Wi-Fi and a well-lit dedicated workspace with readily accessible outlets are the baseline minimum, but resorts such as Four Seasons Resort Scottsdale have added ergonomic chairs, an “Express Lunch” menu and shorter 30-minute spa services with their new “Work at Leisure” program. The Hilton Aruba Caribbean Resort & Casino offers “special Power Palapas on the beach complete with power and USB charging station, a laptop cooling pad, sunshade privacy cover, bottled water and power bowl with hydrating aloe juice or coconut water,” according to their website.

When booking longer stays, especially during low season, hotels may offer a discount off the standard rate. For example, Shangri-La The Shard, London is offering a fourth night free when booking three nights until Dec. 22 and Shangri-La Bangkok is offering a discount of up to 25% for guests booking five consecutive nights or longer until April 30. This is where a travel advisor like Fischer Travel can be especially helpful, vetting hotels based on personal experience through the lens of a traveler on a working vacation and helping to secure perks to enhance your stay. “Sometimes, while a discounted rate is not offered, we are able to negotiate the inclusion of other amenities for longer stays, such as spa treatments or food and beverage credit,” Fischer-Rosenthal says.

Consider an executive lounge

Fischer-Rosenthal always reviews floorplans of accommodations prior to her clients’ arrival to understand where the client should set up to work, without impacting their travel companions. Sometimes she even confirms a suite or extra accommodation with ample workspace, away from the primary bedrooms. 

Executive or club lounges like those offered by Fairmont, Shangri-La, Langham and Ritz-Carlton can also be great options for work space during a working vacation. Many have quiet nooks and conference rooms available to conduct meetings, although these may need to be reserved in advance. “Our clients who work while traveling often have time restraints and they especially appreciate the all-day access to culinary presentations and grab-and-go food,” Fischer-Rosenthal says. “This is also beneficial for families, as it provides easy access to food, which is great for children.”

Respect work/time off boundaries

Vancouver-based luxury realtor Nick Neacsu recently took a two-week vacation to Bali. He chose to travel during early January because it’s normally a slower time in his line of business and the only time of year he could plan a longer vacation. To set healthy boundaries while on his working vacation, Neacsu told his clients that he would be in Asia and while they could contact him if needed, he would not be able to immediately respond to emails and phone calls. Because of the time difference, he would get calls, texts and emails throughout the night, which he would check first thing in the morning. 

“I think high performers tend to forget how much you’ve depleted your battery,” Neacsu says. “It doesn’t have to be one or the other. Give yourself permission to spend a day without talking to your clients. Generally, people who like you want the best for you.” There were only a couple instances when he needed to be up late for an urgent call, but for the most part he felt like he could relax and said his clients were supportive and respectful of his vacation time.

Savor every moment of your working vacation

Fischer-Rosenthal recommends that her working clients take some time to enjoy the spa, as a chance to decompress after working. “We try to carve out special, privatized moments with families and arrange for activities that will appeal to our clients’ passions and everyday interests to ensure that our working clients do stop to enjoy the moment while traveling,” she says.

Neacsu loves fishing and one of the highlights of his Bali vacation was going on a full-day fishing trip with two local guides. He didn’t have access to his phone or computer the whole day, but he caught a giant trevally on a handline that the chef at his boutique hotel, Alila Manggis, prepared for dinner that night. Neacsu says it was an unforgettable experience and completely different from salmon fishing back home in Vancouver.

“Coming back from vacation, I felt reinspired to work,” he says. “Sometimes you work so hard that you forget to enjoy it. A proper vacation reminds you why you work so hard.”

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